CN100463666C - Skin topical composition - Google Patents

Abstract

A composition comprising a compound represented by the following general formula (1) and a specific ingredient. In the general formula (1), R<1> represents -CH2OH or COOR<6>, wherein R<6> represents hydrogen, C1-3 alkyl, or a cation capable of forming a salt with COO-; R<2> to R<5> each independently represents hydrogen or methyl; and ...A... represents =C(CH3)-, -C(CH3)=, -C(=CH2)-, -CH(CH3)-, or -C(OH)(CH3)-.

Description

Skin topical composition

technical field

The present invention relates to a skin external preparation containing a physiologically active component of a specific compound and a specific medicinal agent and having excellent whitening effect and anti-aging effect.

Background technique

At present, in order to impart a certain medicinal effect to skin external preparations such as lotion, cream, lotion, beauty cosmetic cream, toilet products, dispersion, ointment, liquid, aerosol, paste, poultice, liniment, etc., in their Various medicinal ingredients are added in the middle.

For example, whitening agents such as ascorbic acid, placenta extract, glutathione, hydroquinone, etc. are added in order to prevent or improve skin darkening due to sun exposure, brown spots or freckles due to pigmentation, and the like. On the other hand, vitamin A and cell activators such as soybean extract and seaweed extract are added to prevent or improve skin wrinkles and sagging, decrease in tension and elasticity due to aging, exposure to ultraviolet rays, etc.

In addition, hot water extracts such as stems, branches, and leaves of Cistus ladaniferus L., Cistus creticus L., Cistus monoperiensis L., Cistus salvifolius, etc. belonging to the family Pinaceae, or extracts such as ethanol and hexane, have been found to have strong The action of inhibiting the production of melanin, cell activation, and antibacterial action is based on the activity of labdanic acid, and further, it was discovered that the extract or crude labdanic acid was obtained by molecular distillation of the labdanyl-7-ene-15 -acid, laudanyl-8(17)-en-15-acid, and laudanyl-8-en-15-acid have a strong effect of inhibiting the production of melanin, cell activation, and antibacterial effect. Further, their salts or methyl and ethyl esters, and their reducing agents have also been found to have the same activity. (Japanese Patent Laid-Open Publication No. 11-302219, etc.)

Contents of the invention

The purpose of the present invention is to provide an external preparation for skin with excellent skin beautification effect, especially excellent whitening effect and/or anti-aging effect.

A form of the present invention is: (A) with the following general formula (1)

(In general formula (1), R ¹ represents —CH ₂ OH or COOR ⁶ , R ⁶ represents hydrogen, a lower alkyl group with 1 to 3 carbons, or a cation capable of forming ^COO- and salt, R ² to R ⁵ are respectively Independently represents a hydrogen atom or a methyl group, ...A... represents =C(CH ₃ )—, —C(CH ₃ )=, —C(=CH ₂ )—, —CH(CH ₃ )— or —C(OH) 1 or 2 or more compounds represented by (CH ₃ )—), and

桲籽提取物、甘草提取物、薏苡仁提取物、黑穗醋栗(黑房须具利)果实提取物、旋覆花(小车)提取物、蔓越桔果实提取物、鸡血藤提取物、白桦树液、矢车实提取物、仙人掌提取物、罗汉果提取物、虾黄质及其衍生物和芸香苷衍生物。Contains one or two or more compositions selected from the following medicinal agents: (B) asparagus extract, Japanese angelica extract, Morus alba extract, Chuanxiong extract, rosehip extract, raspberry Extract, sophora flavescens extract, acanthus bark extract, coffee extract, rice bran extract, wheat germ extract, asarum extract, hawthorn seed extract, white lily extract, peony extract, tea leaf extract, molasses Extract, Grape Extract, Hops Extract, Rose Flower Extract, Papaya Extract, Scutellaria Baicalensis Extract, Seaweed Extract, Dibutyl Hydroxytoluene, tert-Butyl p-Hydroxyanisole, Mannitol, Beta-Carotene , quercetin, quercetin, rutin, vitamin E and its derivatives, geranium extract, saxifrage extract, lentil extract, bee flower extract, glycyrrhizic acid and its derivatives, licorice Acid and its derivatives, vitamin B and its derivatives, gentian extract, Houttuynia cordata extract, peony extract, aloe vera extract, arnica extract, forsythia forsythia extract, yellow tiller extract, honeysuckle Extract, sage extract, white birch extract, perilla extract, mugwort extract, chamomile extract, daisy extract, Burnet extract, watercress extract, big calendula extract, elderberry Wood extract, cattail pollen extract, sapinberry extract, eucalyptus extract, milk vetch extract, vitamin A and its derivatives, tartaric acid, malic acid, glycolic acid, succinic acid, serine, glutamic acid , hydroxyproline, theanine, pyrrolidone carboxylic acid, cordyceps extract, soybean extract, carrot extract, barley extract, beech bud extract, ginkgo extract, centella asiatica extract, yeast extract, lactic acid bacteria Extract, Lactobacillus Extract, 2-Hydroxy-4-methoxybenzophenone, 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2-Hydroxy-4-methoxy Benzophenone-5-sodium sulfonate, p-methoxycinnamic acid-2-ethylhexyl, 4-tert-butyl-4'-methoxydibenzoylmethane, marshmallow root extract, calamus extract, Rehmannia glutinosa extract, chestnut tree extract, mallow (medicinal marshmallow) extract, apricot extract, lime extract, raspberry extract, almond extract, tomato extract, phospholipid and its derivatives, sweet tea extract , coltsfoot extract,

Quince Seed Extract, Licorice Root Extract, Coix Seed Extract, Blackcurrant (Black Ridge) Fruit Extract, Inula Inula (Trolley) Extract, Cranberry Fruit Extract, Millipeda Spatholobus Extract , birch sap, cornflower extract, prickly pear extract, monk fruit extract, astaxanthin and its derivatives and rutin derivatives.

桲籽提取物。前述(B)中，(B2)包括：甘草提取物、薏苡仁提取物、黑穗醋栗(黑房须具利)果实提取物、旋覆花(小车)提取物、蔓越桔果实提取物、鸡血藤提取物、白桦树液、矢车实提取物、仙人掌提取物、罗汉果提取物、虾黄质及其衍生物和芸香苷衍生物。As one aspect of the present invention, the above-mentioned (B) provides a composition selected from one or two or more of the above-mentioned pharmaceutical agent groups respectively selected from (B1) and (B2). Among them (B1) includes: asparagus extract, Japanese angelica extract, Morus alba extract, Chuanxiong extract, rosehip extract, raspberry extract, Sophora flavescens extract, Acanthopanax bark extract, coffee extract , rice bran extract, wheat germ extract, asarum extract, hawthorn seed extract, white lily extract, peony extract, tea extract, molasses extract, grape extract, hop extract, rose extract, papaya Extract, Scutellaria baicalensis extract, seaweed extract, dibutyl hydroxytoluene, tert-butyl p-hydroxyanisole, mannitol, β-carotene, quercetin, quercitrin, rutin, vitamin E and its derivatives Extract, geranium extract, saxifrage extract, lentil extract, bee flower extract, glycyrrhizic acid and its derivatives, glycyrrhetinic acid and its derivatives, vitamin B and its derivatives, gentian extract , Houttuynia cordata extract, peony extract, aloe vera extract, arnica extract, forsythia forsythia extract, yellow tiller extract, honeysuckle extract, sage extract, white birch extract, perilla extract , mugwort extract, chamomile extract, daisy extract, burnet extract, watercress extract, calendula flower extract, elderberry extract, cattail pollen extract, sapinberry extract, eucalyptus extract extract, vitamin A and its derivatives, tartaric acid, malic acid, glycolic acid, succinic acid, serine, glutamic acid, hydroxyproline, theanine, pyrrolidone carboxylic acid, Cordyceps sinensis extract , Soybean Extract, Carrot Extract, Barley Extract, Beech Bud Extract, Ginkgo Biloba Extract, Centella Asiatica Extract, Yeast Extract, Lactobacillus Extract, Lactobacillus Extract, 2-Hydroxy-4-Methoxy Benzophenone, 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, p-methoxycinnamic acid -2-Ethylhexyl, 4-tert-butyl-4'-methoxydibenzoylmethane, marshmallow root extract, calamus extract, rehmannia root extract, chestnut tree extract, mallow (medicinal marshmallow) extract Extract, apricot extract, lime extract, raspberry extract, almond extract, tomato extract, phospholipid and its derivatives, sweet tea extract, coltsfoot extract,

Quince Seed Extract. In the aforementioned (B), (B2) includes: licorice extract, coix seed extract, black currant (black currant) fruit extract, inula inula (small car) extract, cranberry fruit extract , Spatholobus extract, birch sap, cornflower extract, prickly pear extract, monk fruit extract, astaxanthin and its derivatives and rutin derivatives.

The composition of the present invention is excellent as an external preparation for skin, especially as an external preparation for skin whitening or an external preparation for preventing skin aging.

The term "beautifying skin" in this specification needs to be interpreted in the broadest sense including inhibiting pigmentation, dull skin, skin darkening caused by sun exposure, preventing and improving brown spots and freckles, and preventing and improving wrinkles. It is understood that "whitening" and "anti-aging" are included in its scope.

As a form of the present invention, it is provided that the compound represented by the above general formula (1) is selected from Cistus ladaniferus L., Cistus creticus L., Cistus monoperiensis L., and Cistus salvifolius in the Heliophyceae. A compound extracted from one or more than two plants of the group; or the above-mentioned composition for preparing the compound for the compound; Creticus L., Cistusmonoperiensis L., and Cistus salvifolius composed of one or more compounds extracted from the plants of the plant group, mixed into the above composition.

Viewed from another aspect, the present invention also provides a method for inhibiting melanin production comprising applying the above composition to the skin; a skin whitening method comprising applying the above composition to the skin; A method for skin aging; a method of using the above composition as an external skin preparation; a method of using the above composition for producing an external skin preparation; improving the efficacy of one or more compounds represented by the above general formula (1) The use method of selecting one or more than two kinds of medicinal agents from the above-mentioned (B); improving the ability of one or more than two kinds of compounds represented by the above-mentioned general formula (1) to inhibit melanin production from the above-mentioned ( The use method of selecting one or more than two kinds of the pharmacodynamic agent group of B); improving one or more than two kinds of cell activation ability of the compound represented by the above-mentioned general formula (1) from the above-mentioned drug effect of (B) One or more methods of use of selecting one or two or more of the above-mentioned pharmacodynamic agent groups selected from the above-mentioned (B) group; one or two of the compounds represented by the above-mentioned general formula (1) more than one drug effect enhancer.

Detailed ways

Next, an embodiment in which the composition of the present invention is applied to an external skin preparation will be described in detail.

The external preparation for skin of the present invention contains one or two or more physiologically active components (hereinafter referred to as "(A) component") of the compound represented by the following general formula (1).

In the above general formula (1), R ¹ represents -CH ₂ OH or COOR ⁶ , and R ⁶ represents hydrogen, a lower alkyl group having 1 to 3 carbons, or a cation capable of forming COO ^- and a salt. The lower alkyl group having 1 to 3 carbon atoms may be linear or branched. Examples of the above-mentioned alkyl group include methyl group, ethyl group, n-propyl group and isopropyl group. On the other hand, cations capable of forming ^-COO- and salts include cations such as Na ⁺ , K ⁺ , and NH ₄ ⁺ .

In the above general formula (1), R ² to R ⁵ each independently represent a hydrogen atom or a methyl group, ...A... represents =C(CH ₃ )-, -C(CH ₃ )=, -C(=CH ₂ )- , -CH(CH ₃ )- or -C(OH)(CH ₃ )-.

The compound represented by the above general formula (1) can be extracted from plants. In addition, plant extracts are commercially available (purified gum labdanum, manufactured by Jibodan Co., Ltd., etc.), and commercially available products can also be used in the present invention. Furthermore, as an extract, it is also possible to use ^R1 as the (A) component after obtaining -COOH acid and converting it into an ester agent such as a methyl group or an ethyl group, a reducing agent or a salt.

Regarding the plant species from which the compound represented by the above-mentioned general formula (1) is extracted, there is no limitation if the plant containing the compound is used, however, Cistus ladaniferus L., Cistus creticus L., Cistus monoperiensis L., Cistus salvifolius (half-day Flowers) plants are more beneficial. They can be used alone or in combination of two or more.

The extraction part of the plant is not particularly limited, and it can be extracted from leaves, branches, and bark. Extraction may be performed immediately after collecting each part, or may be performed after drying each part after collecting. The extraction method is preferably carried out with one or two or more solvents selected from water, lower alcohols, petroleum ether and hydrocarbons. Here, the term "lower alcohol" refers to an alcohol having 1 to 4 carbon atoms, and methanol, ethanol, and the like are particularly preferable. As the petroleum ether, well-known ones can be used, and commercially available ones can also be used. Examples of hydrocarbon solvents include aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic hydrocarbons that are liquid at normal temperature, and particularly preferred are aliphatic hydrocarbons and aromatic hydrocarbons that are liquid at normal temperature, and among them, more preferably Hydrocarbons such as hexane and toluene.

Although the extraction operation varies depending on the type of the above-mentioned plants and the solvent used, it can usually be carried out by soaking the cut plants in the above-mentioned solvent at a temperature from room temperature to 50°C. The solvent may be properly stirred during immersion. Furthermore, well-known devices such as a Soxhlet extractor can also be used. The time required for extraction is usually between 3 hours and 48 hours. It can also be extracted by steam distillation or boiling in hot water after pulverizing the leaves, branches or stems of the above-mentioned plants. In this case, the gum fraction floating on water in steam distillation or hot water extraction is taken out, and it is obtained by separating it from insoluble matter in the above-mentioned solvent for extraction. The extract obtained in this way contains 25 to 35% by mass (hereinafter only expressed by "%") of labdanoids.

The crude extract or commercially available extract extracted from the above-mentioned plant body can be directly used as (A) component, but it is also possible to further extract the above-mentioned general formula (1) from the crude extract or commercially available extract The compound is purified and used as (A) component. Next, the crude oil containing the mixture of laudanyl (ラブど)-7-en-15-acid, laudanyl-8(17)-en-15-acid and laudanyl-8-en-15-acid Extracts or commercially available products, methods of purifying each component are described as representative examples, but the present invention is not limited to the following methods.

For crude extracts or commercially available extracts, carry out molecular distillation under a reduced pressure of 0.1 to 0.5 mmHg, and collect fractions at 160°C to 230°C, which contain labdanyl-7-en-15-acid , Laudanyl-8(17)-en-15-acid, a mixture of Laudanyl-8-en-15-acid. As (A) component, these acid mixtures may be used as it is, and may use these mixtures after preparing ester agents, salts, or a reducing agent, such as a methyl group and an ethyl group, as needed.

It is also possible to further separate the three acids from this acid mixture. Specifically, this acid mixture was dissolved in ethanol, reacted in the presence of catalytic sulfuric acid as an ethyl ester, and then subjected to silica gel chromatography using silver nitrate-treated silica gel. The column was washed with hexane, followed by eluting with 1% ethyl hexane acetate. Firstly, ethyl labdanyl-8-ene-15-acid is precipitated, followed by ethyl labdanyl-7-ene-15-acid and ethyl labdanyl-8(17)-ene-15-acid sequential precipitation. The solvent was distilled off to obtain pure ethyl ester agents respectively. The free acid can be obtained from the obtained ethyl ester agent by hydrolysis. Furthermore, the free acid can be reacted with diazomethane to obtain the methyl ester.

Extracts of stems, branches, leaves, etc. of Cistus ladaniferus L., Cistus creticus L., Cistus monoperiensis L., Cistus salvifolius, etc. belonging to the family Pinaceae thus obtained, and acids, methyl esters, ethyl esters or their derivatives obtained from the extracts A mixture of two or more types can be used as (A) component of this invention. That is, as an embodiment of the present invention, (A) component includes (i), (ii), (iii), and (iv) skin external preparations. (i) hot water extracts or organic solvent (ethanol, hexane, etc.) extracts of stems, branches, leaves, etc. of Cistus ladaniferus L., Cistus creticus L., Cistus monoperiensis L., Cistus salvifolius, etc. belonging to the family Pinaceae; (ii) The extract selected from the above (i) or crude labdanic acids obtained after molecular distillation is selected from the group consisting of labdanyl-7-ene-15-acid, labdanyl-8(17)-ene-15- One or more of acid and labdanyl-8-ene-15-acid; (iii) the acid salt or methyl or ethyl ester of the above (ii); (iv) the above (iii) the reducing agent.

In the external preparation for skin of the present invention, the content of the compound represented by the above general formula (1) is preferably 0.00001 to 5%, more preferably 0.0001 to 2%, in terms of dry solids. If it is within this range, the plant extract can be mixed stably, and excellent skin beautification effects (especially whitening and anti-aging effects) can be exhibited. In addition, when the extract is used, the concentration of the solute, that is, the content of the dry solid part, is within the above range, and the concentration of the extract is not subject to any limitation.

In this invention, (B) component mix|blended with (A) component is 1 type, or 2 or more types selected from the agents shown below. Furthermore, esters and salts are included in "derivatives" in the following specific examples.

桲籽提取物、甘草提取物、薏苡仁提取物、黑穗醋栗(黑房须具利)果实提取物、旋覆花(小车)提取物、蔓越桔果实提取物、鸡血藤提取物、白桦树液、矢车实提取物、仙人掌提取物、罗汉果提取物、虾黄质及其衍生物和芸香苷衍生物。Examples include asparagus extract, Japanese angelica extract, Morus alba extract, Chuanxiong extract, rosehip extract, raspberry extract, Sophora flavescens extract, Acanthopanax bark extract, coffee extract, rice bran extract extract, wheat germ extract, asarum extract, hawthorn seed extract, white lily extract, peony extract, tea extract, molasses extract, grape extract, hop extract, rose extract, papaya extract, Scutellaria baicalensis extract, seaweed extract, dibutyl hydroxytoluene, tert-butyl p-hydroxyanisole, mannitol, β-carotene, quercetin, quercetin, rutin, vitamin E and its derivatives, old Stork grass extract, saxifrage extract, lentil extract, bee flower extract, glycyrrhizic acid and its derivatives, glycyrrhetinic acid and its derivatives, vitamin B and its derivatives, gentian extract, fish smell Grass extract, peony extract, aloe extract, arnica extract, forsythia extract, yellow tiller extract, honeysuckle extract, sage extract, white birch extract, perilla extract, mugwort Extract, Chamomile Extract, Daisy Extract, Burnet Extract, Watercress Extract, Greater Calendula Extract, Elderberry Extract, Cattail Pollen Extract, Sapinberry Extract, Eucalyptus Extract, Violet Veitin extract, vitamin A and its derivatives, tartaric acid, malic acid, glycolic acid, succinic acid, serine, glutamic acid, hydroxyproline, theanine, pyrrolidone carboxylic acid, cordyceps sinensis extract, soybean extract Extract, Carrot Extract, Barley Extract, Beech Bud Extract, Ginkgo Biloba Extract, Centella Asiatica Extract, Yeast Extract, Lactobacillus Extract, Lactobacillus Extract, 2-Hydroxy-4-Methoxybenzidine Ketone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, p-methoxycinnamic acid 2- Ethylhexyl, 4-tert-butyl-4'-methoxydibenzoylmethane, marshmallow root extract, calamus extract, rehmannia root extract, chestnut tree extract, mallow (medicinal marshmallow) extract, apricot Extract, lime extract, raspberry extract, almond extract, tomato extract, phospholipid and its derivatives, sweet tea extract, coltsfoot extract,

Quince Seed Extract, Licorice Root Extract, Coix Seed Extract, Blackcurrant (Black Ridge) Fruit Extract, Inula Inula (Trolley) Extract, Cranberry Fruit Extract, Millipeda Spatholobus Extract , birch sap, cornflower extract, prickly pear extract, monk fruit extract, astaxanthin and its derivatives and rutin derivatives.

桲籽提取物。One aspect of the present invention is an aspect in which one, or two or more kinds selected from the following (B1) extracts are contained as the above-mentioned (B) component. (B1) is asparagus extract, Japanese angelica extract, Morus alba extract, Chuanxiong extract, rosehip extract, raspberry extract, Sophora flavescens extract, Acanthopanax bark extract, coffee extract, rice bran Extract, Wheat Germ Extract, Asarum Extract, Hawthorn Seed Extract, White Lily Extract, Peony Extract, Tea Extract, Molasses Extract, Grape Extract, Hops Extract, Rose Extract, Papaya Extract , Scutellaria baicalensis extract, seaweed extract, dibutyl hydroxytoluene, tert-butyl p-hydroxyanisole, mannitol, β-carotene, quercetin, quercetin, rutin, vitamin E and its derivatives, Geranium extract, saxifrage extract, lentil extract, bee flower extract, glycyrrhizic acid and its derivatives, glycyrrhetinic acid and its derivatives, vitamin B and its derivatives, gentian extract, fish Houttuynia cordata extract, peony extract, aloe extract, arnica extract, forsythia extract, yellow tiller extract, honeysuckle extract, sage extract, white birch extract, perilla extract, mugwort Artemisia extract, Chamomile extract, Daisy extract, Burnet extract, Watercress extract, Calendula officinalis extract, Elderberry extract, Cattail pollen extract, Sapinberry extract, Eucalyptus extract, Milk vetch extract, vitamin A and its derivatives, tartaric acid, malic acid, glycolic acid, succinic acid, serine, glutamic acid, hydroxyproline, theanine, pyrrolidone carboxylic acid, cordyceps extract, soybean Extract, Carrot Extract, Barley Extract, Beech Bud Extract, Ginkgo Biloba Extract, Centella Asiatica Extract, Yeast Extract, Lactobacillus Extract, Lactobacillus Extract, 2-Hydroxy-4-methoxydiphenyl Methanone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, p-methoxycinnamic acid-2 -Ethylhexyl, 4-tert-butyl-4'-methoxydibenzoylmethane, marshmallow root extract, calamus extract, rehmannia root extract, chestnut tree extract, mallow (medicinal marshmallow) extract, Apricot extract, lime extract, raspberry extract, almond extract, tomato extract, phospholipid and its derivatives, sweet tea extract, coltsfoot extract,

Quince Seed Extract.

Among the ingredients (B1) above, asparagus extract, Japanese angelica extract, Morus alba extract, Chuanxiong extract, rose hip extract, raspberry extract, Sophora flavescens extract, Extract, rice bran extract, wheat germ extract, asarum extract, hawthorn seed extract, white lily extract, peony extract, tea extract (green tea, black tea, oolong tea and other extracts), molasses extract, grape extract Extract, hop extract, rose extract, papaya extract, scutellaria baicalensis extract, and seaweed extract (these are called (C1) components), although they are mainly used as whitening agents alone, but due to the above-mentioned (A) component Used in combination, they have excellent whitening and/or anti-aging effects that cannot be obtained when used separately. More preferable examples include wheat germ extract, white lily extract, Morus alba bark, tea leaf extract (green tea, black tea, oolong tea, etc.), grape extract, scutellaria baicalensis extract, and seaweed extract.

Among the above ingredients (B1), dibutyl hydroxytoluene, tert-butyl p-hydroxyanisole, mannitol, β-carotene, quercetin, quercetin, rutin, vitamin E and its derivatives (dl- α(βγ) tocopherol, dl-α-tocopherol acetate, dl-α-tocopherol niacin, dl-α-tocopherol linoleate, etc.), geranium extract, saxifrage extract, lentil The extract and bee flower extract (these are called (D1) components) mainly exhibit medicinal effects as antioxidants alone, but when used in combination with the above-mentioned (A) component, they have excellent whitening and / or anti-aging effect. More preferable ones include vitamin E and its derivatives, dibutylhydroxytoluene, β-carotene, rutin, and saxifrage extract.

Among the ingredients (B1) above, glycyrrhizic acid and its derivatives, glycyrrhetinic acid and its derivatives, vitamin B and its derivatives, gentian extract, Houttuynia cordata extract, peony extract, aloe extract, arnica Carnation extract, forsythia extract, yellow tiller extract, honeysuckle extract, sage extract, white birch extract, perilla extract, mugwort extract, chamomile extract, daisy extract, Burnet extract, watercress extract, big calendula extract, elderberry extract, cattail pollen extract, sapinberry extract, eucalyptus extract, milk vetch extract (these are called (E1) ingredients), Although it exhibits medicinal effects mainly as an anti-inflammatory agent alone, it exhibits excellent whitening and/or anti-aging effects that cannot be obtained when used alone, when used in combination with the above-mentioned component (A). More preferable examples include glycyrrhizic acid and its derivatives, glycyrrhetinic acid and its derivatives, aloe extract, yellow tiller extract, honeysuckle extract, perilla extract, chamomile extract, daisy extract, Burnet Extract.

Among the ingredients (B1) above, vitamin A and its derivatives (retinol palmitate, retinol acetate, etc.), tartaric acid, malic acid, glycolic acid, succinic acid, serine, glutamic acid, hydroxyproline, tea Amino Acid, Pyrrolidone Carboxylic Acid, Cordyceps Extract, Soybean Extract, Carrot Extract, Barley Extract, Beech Bud Extract, Ginkgo Biloba Extract, Centella Asiatica Extract, Yeast Extract, Lactic Acid Bacteria Extract, Lactobacillus Extract (These are called (F1) components), although they mainly exhibit medicinal effects as cell activators alone, they exhibit excellent whitening and/or anti-aging effects that cannot be obtained when used in combination with the above-mentioned (A) components, respectively. More preferable examples include vitamin A and its derivatives, hydroxyproline, carrot extract, barley extract, beech bud extract, ginkgo extract, centella asiatica extract, and yeast extract.

Among the above components (B1), 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2-hydroxy-4-methoxydiphenone Benzophenone-5-sodium sulfonate, p-methoxycinnamic acid-2-ethylhexyl, 4-tert-butyl-4'-methoxydibenzoylmethane (these are called (G1) ingredients), although It mainly exhibits medicinal effects as a UV protection agent alone, but when used in combination with the above-mentioned component (A), it exhibits excellent whitening and/or anti-aging effects that cannot be obtained when used alone. More preferably, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sodium sulfonate, p-methoxycinnamic acid-2-ethyl ylhexyl, 4-tert-butyl-4'-methoxydibenzoylmethane.

桲籽提取物(这些称为(H1)成分)，虽然主要单独作为保湿剂显示药效，但是由于与上述(A)成分并用，却起到分别单独使用时不能得到的优良美白及/或防老化效果。更优选的可以举出磷脂及其衍生物、甜茶提取物、锦葵提取物、款冬提取物、

桲籽提取物。Of the ingredients (B1) above, marshmallow root extract, calamus extract, rehmannia glutinosa extract, chestnut tree extract, mallow (medicinal marshmallow) extract, apricot extract, lime extract, raspberry extract, almond Extract, tomato extract, phospholipids and their derivatives (such as soybean lecithin, hydrogenated soybean lecithin, hydrogenated soybean chlorinated lysozyme lipid, hydrogenated egg yolk lecithin, egg yolk lecithin, egg yolk lysophosphatidylcholine, etc. ), sweet tea extract, coltsfoot extract,

Quince seed extract (these are called (H1) components) mainly exhibits medicinal effects as a moisturizer alone, but when used in combination with the above-mentioned component (A), it exerts excellent whitening and/or anti-aging effects that cannot be obtained when used alone. aging effect. More preferably, phospholipids and derivatives thereof, sweet tea extract, mallow extract, coltsfoot extract,

Quince Seed Extract.

In the form containing the above-mentioned (B1) component, a skin external preparation containing one or two or more selected from the following components is excellent as a skin external preparation for whitening: white lily extract, Morus alba extract, natural Vitamin E, dipotassium glycyrrhizinate, yeast extract, hydrogenated soybean lecithin, and 2-ethylhexyl p-methoxycinnamic acid. In addition, skin external preparations containing one or more of the following ingredients are excellent as skin aging prevention external preparations: butylated hydroxytoluene, carrot extract, green tea extract, Burnet extract, p-methoxyl Cinnamon-2-Ethylhexyl, Retinol Palmitate, Coltsfoot Extract.

In the skin external preparation of this form, although the compounding quantity of the said (B1) component differs with a kind ((C1) component - (H1) component), it is preferable that it exists in the range shown below. If it is within this range, when combined with component (A), the preparation and the stability of component (A) in the preparation over time will not be affected, and it will be able to exert a stronger skin beautifying effect (especially whitening and/or prevent aging effects).

In the external preparation for skin of this aspect, the blending amount of the above-mentioned (C1) component is preferably 0.00001 to 10%, more preferably 0.0001 to 5%. When the extract is directly used as an extract, it is sufficient as long as the dry solid content is within this range. If it is within this range, a more excellent whitening effect can be exhibited, and an external preparation for skin with a good usability can be obtained.

In the external preparation for skin of this aspect, the blending amount of the above-mentioned component (D1) is preferably 0.00001 to 5%, more preferably 0.0001 to 3%. When the extract is directly used as an extract, it is sufficient as long as the dry solid content is within this range. If it is within this range, it is found that there is a more excellent anti-oxidation effect, an excellent whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

In the external preparation for skin of this aspect, the compounding quantity of the said (E1) component is preferably 0.00001 to 5%, more preferably 0.0001 to 3%. When the extract is directly used as an extract, it is sufficient as long as the dry solid content is within this range. If it is within this range, it is found that there is a more excellent anti-inflammatory effect, an excellent whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

In the external preparation for skin of this aspect, the blending amount of the above-mentioned (F1) component is preferably 0.00001 to 5%, more preferably 0.0001 to 3%. When the extract is directly used as an extract, it is sufficient as long as the dry solid content is within this range. If it is within this range, it is found that there is a more excellent effect of improving rough skin, exhibiting an excellent whitening and/or anti-aging effect, and an external preparation for skin with a good feeling in use can be obtained.

In the external preparation for skin of this aspect, the blending amount of the above-mentioned component (G1) is preferably 0.001 to 30%, more preferably 0.01 to 25%. If it is within this range, it is found that there is a more excellent ultraviolet protection effect, an excellent whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

In the external preparation for skin of this aspect, the blending amount of the above-mentioned component (H1) is preferably 0.001 to 25%, more preferably 0.01 to 20%. When the extract is directly used as an extract, it is sufficient as long as the dry solid content is within this range. If it is within this range, it is found that there is a more excellent moisturizing effect, an excellent whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

Another aspect of this invention is the aspect which contains 1 type or 2 or more types selected from (B2) as (B) component. (B2) is licorice extract, coix seed extract, black currant (black room mustard) fruit extract, inula inula (small car) extract, cranberry fruit extract, Milletah extract, Birch sap, cornflower extract, prickly pear extract, monk fruit extract, astaxanthin and its derivatives, and rutin derivatives.

The licorice extract that can be used in the present invention is obtained by extracting the roots and rhizomes of Glycyrrhiza glabra (Glycyrrhizaglabra L.) of the genus Glycyrrhizae of the leguminous genus or plants of the same genus (the Chinese herbal medicine name is licorice). Oil-soluble extracts extracted from licorice produced in China and Russia with hydrophobic organic solvents are more ideal.

The coix seed extract that can be used in the present invention is obtained by extracting the seeds of Coixlacryma-jobi L.var.ma-yuen Stapf (Coixlacryma-jobi L.var.ma-yuen Stapf) with the seed coat removed with a suitable solvent. acquired.

须具利、法文名加西斯(カシス)、Ribes nigrum L.)的果实，用适当的溶剂提取而获得的果实提取物或经压榨而获得果实榨取汁液。Black ear currant fruit extract is the black ear currant (Japanese name

The fruit of Ribes nigrum L., whose French name is カシス (カシス), Ribes nigrum L.), is the fruit extract obtained by extraction with a suitable solvent or the fruit squeezed juice obtained by pressing.

The extract of Inula britannica (Inula britannica L.) that can be used in the present invention is obtained by extracting the head of Inula britannica (Inula britannica L. in Chinese herbal medicine) with a suitable solvent. of.

The cranberry fruit extract that can be used in the present invention is the fruit of the cranberry (Japanese name Vaccinium macrocorpon Aiton or Vaccinium oxycoccus) of the genus cranberry of the Heatheraceae family, which is obtained by extracting the fruit with an appropriate solvent. or squeezed to obtain juice from the fruit.

The Caulis Spatholobus extract that can be used in the present invention is the dried seeds of the leguminous plant Spatholobus suberectus Mucuna birdwood iana (Mucuna birdwoodiana Tutcher), the dried seeds of Mucuna birdwoodiana Tutcher (Chinese name It is obtained by extracting the stems of Milletia dielsiana, Milletiadielsiana Harms) or Milletia nitida Benth (Chinese herbal name Milletia nitida Benth) with an appropriate solvent.

The white birch sap that can be used in the present invention is white birch (Betula platyphylla Sukatchuv var. japonica Hara, B. platyphylla Sukatchuv), mountain birch (B. Ermani Cham.), dog volt birch (ジゾウカンバ) (B. globispica Shirai) , Wang Hua (B. Maximowicziana Regel), European white birch (B. pendula Roth) and Western white birch (B. lental L.) before the tree blooms and long leaf period, the liquid that flows out of the tree perforation.

The cornflower extract that can be used in the present invention is obtained from Oobayashayabushi (Alnussieboldiana Matsum.), Alder tree (Alnus firma Sieb.Et Zucc.), Alnushirsuta Turcz. (Alnushirsuta Turcz.) and the fruits of the same family of plants (Yashashi, Yashashi) obtained by extraction with an appropriate solvent.

The cactus extract that can be used in the present invention is the cactus plant extract, such as the stem node of Indian fig (Opuntia ficusindica (L.) Mill, or Opuntia dillenii Haw), オプンティアストレプタカンサ (Opuntia Streptacantha) etc. , roots, fruits, etc. are obtained by extracting with appropriate solvents.

The Luo Han Guo extract that can be used in the present invention is obtained by extracting dried fruit (Momordica grosvemorii Swingle) of Cucurbitaceae Momordica grosvemorii Swingle with a suitable solvent.

The astaxanthin and its derivatives that can be used in the present invention can be obtained by extracting or chemically synthesizing natural products such as krill, salmon, trout, alfalfa, and red yeast. For example, add extraction solvent to krill (Euphausia similis G.O., etc.) After chemical reactions such as decomposition, it can be deodorized and refined by means of molecular distillation or column chromatography or high-speed liquid chromatography to use refined astaxanthin. Astaxanthin is a carotenoid represented by the following formula. Examples of derivatives thereof include monoesters selected from fatty acid esters of astaxanthin, and diesters of the same or different species.

The rutin derivatives that can be used in the present invention may be those in which the water solubility of rutin contained in natural products such as Sophora japonica L. flower buds of the leguminous family and buckwheat (Fagopyrum esculentum Moench) of the Polygonaceae family has been improved. For example, it is best to use starches such as dextrin mixed in rutin, which are converted into glucose, maltose, maltotriose, maltotetraose, etc. in rutin through enzyme reaction, expressed by the following general formula Alpha-Glucorutinoside. Among them, the content of rutin is preferably 10-80% of rutin derivatives. One of them can be used alone, or two or more can be used in combination.

In the formula, R represents glucose, maltose, maltotriose or maltotetraose.

Examples of extraction solvents used to prepare the components belonging to the (B2) group include water, lower monovalent alcohols (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, etc.), liquid Polyvalent alcohols (glycerol, etc.), hydrocarbons (benzene, hexane, pentane, etc.), ketones (acetone, methyl ethyl ketone, etc.), ethers (diethyl ether, tetrahydrofuran, dipropyl ether, etc.), Acetonitrile or the like, one or more of them can be used. As an example of a preferred extraction method, it is possible to use ethanol with a water content of 0 to 100 vol%, or 1,3-butanediol, extract at room temperature, or within 1 to 5 days after heating, filter, and then extract A method in which the obtained filtrate is left to age for about one week, and then filtered again.

Among the ingredients (B2) above, licorice extract, coix seed extract, black currant (black currant) fruit extract, inula inulae (Prunus chinensis) extract, cranberry fruit extract, chicken blood Rattan extract, cactus extract, Luo Han Guo extract, astaxanthin and its derivatives, and rutin derivatives (these are called (C2) components), although they can also show their efficacy as a whitening agent alone, but due to the above The ingredients (A) are used in combination to achieve excellent whitening and/or anti-aging effects that cannot be obtained when they are used alone.

Among the above-mentioned (B2) ingredients, licorice extract, Caulis Spatholobus extract, Cynocarpus extract, Luo Han Guo extract, astaxanthin and its derivatives, and rutin derivatives (these are called (D2) ingredients), although It can also exhibit its medicinal effect as an antioxidant alone, but when used in combination with the above-mentioned component (A), it exerts excellent whitening and/or anti-aging effects that cannot be obtained when it is used alone.

Among the ingredients (B2) mentioned above, the licorice extract and the extract of Caulis Spatholobus (these are referred to as ingredients (E2)) can exhibit their efficacy as an anti-inflammatory agent alone, but when used in combination with the ingredient (A) above, However, they have excellent whitening and/or anti-aging effects that cannot be obtained when they are used alone.

Among the ingredients (B2) above, cactus extract, Luo Han Guo extract, astaxanthin and its derivatives, and rutin derivatives (these are called (F2) ingredients), although they can also exhibit their medicinal effects as cell activators alone, However, when it is used in combination with the above-mentioned component (A), it exerts excellent whitening and/or anti-aging effects that cannot be obtained when it is used alone.

Among the ingredients (B2) above, licorice extract, coix seed extract, black currant (black currant) fruit extract, inula inulae (Prunus chinensis) extract, cranberry fruit extract, chicken blood Rattan extract, white birch sap, cornflower extract, cactus extract, and Luo Han Guo extract (these are called (G2) components), although they can also show their efficacy as a moisturizer alone, but because of the above (A) The ingredients are used together, but they have excellent whitening and/or anti-aging effects that cannot be obtained when they are used alone.

The ideal blending amount of the aforementioned component (B) in the external preparation for skin of the present invention varies depending on the type (components (C) to (G)), but is usually preferably within the range shown below. Or make it match with (A) component within this range, the preparation and the stability of component (A) in the preparation will not be affected over time, which can make it play a stronger skin-beautifying effect (especially whitening and/or anti-aging) aging effects).

Furthermore, among the ingredients (B2) that show multiple medicinal effects, the ingredients (C2) to (G2) are repeatedly exemplified, and the ingredients that are repeatedly exemplified are within the respective preferred mixing amount ranges. The widest range becomes the preferable range of the mixing amount.

The compounding quantity of the said (C2) component in the external preparation for skin of this aspect is preferably 0.00001 to 10%, more preferably 0.0001 to 5%. When the extract is directly used as the extract, it is sufficient as the dry solid content within this range. If it is within this range, a good whitening and/or anti-aging effect can be exhibited, and a skin external preparation with a good usability can be obtained.

The compounding quantity of the said (D2) component in the external preparation for skin of this aspect is preferably 0.00001 to 5%, more preferably 0.0001 to 3%. When the extract is directly used as the extract, it is sufficient as the dry solid content within this range. If it is within this range, it is found that there is a more excellent antioxidant effect, a good whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

The compounding quantity of the said (E2) component in the external preparation for skin of this aspect is preferably 0.00001 to 5%, more preferably 0.0001 to 3%. When the plant extract is directly used as an extract, it is sufficient as a dry solid component within this range. If it is within this range, it is found that there is a more excellent anti-inflammatory effect, a good whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

The compounding quantity of the said (F2) component in the external preparation for skin of this aspect is preferably 0.00001 to 5%, more preferably 0.0001 to 3%. When the extract is directly used as the extract, it is sufficient as the dry solid content within this range. If it is within this range, it is found that there is a more excellent effect of improving skin roughness, a good whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

The compounding quantity of the said (G2) component in the external preparation for skin of this aspect is preferably 0.001 to 25%, more preferably 0.01 to 20%. When the extract is directly used as the extract, it is sufficient as the dry solid content within this range. If it is within this range, it is found that there is a more excellent moisturizing effect, a good whitening and/or anti-aging effect is exhibited, and an external preparation for skin with a good feeling in use can be obtained.

The skin external preparation of the present invention can be prepared by mixing the above-mentioned component (A) and the above-mentioned (B) component, which are essential components, in various types of bases familiar as usual skin external preparations according to a conventional method.

Examples of the mixing form of external skin preparations are not particularly limited, and examples include emulsion, cream, lotion, cosmetic cream, detergent, cosmetics, dispersion, ointment, liquid, aerosol, paste, poultice, paint, etc. Cosmetics in any form, such as medicaments, can be used, and external medicines, etc. can also be used.

In addition, in the skin external preparation of the present invention, in addition to the above-mentioned essential ingredients, various ingredients commonly used in cosmetics, non-drugs, and external medicines, that is, water, alcohol, oil agents, surfactants, thickeners, powders, etc. , chelating agents, pH adjusters, various medicinal agents, extracts derived from animals, plants, and microorganisms, fragrances, etc., can be appropriately added within the range that does not affect the effects of the present invention. Wherein, specifically, the following ingredients are used as examples.

As the alcohol, monovalent alcohols such as ethanol and polyvalent alcohols such as glycerol and 1,3-butanediol can be used for the purpose of dissolution, cooling, preservation, moisturizing, etc. within the range that does not overlap with essential components.

The oil agent can be used regardless of its source, usability of properties, and good feeling of use. Examples include liquid paraffin, triacane, triglyceride oil, ester oil, waxes, fatty acids, higher alcohols, silicone oils, fluorine-based oils, and various waxes.

Anionic, cationic, nonionic, and amphoteric surfactants can be used for emulsification and dissolution of oils and the like.

As a thickener, carboxyvinyl polymer, carrageenan, agar, xanthan gum, dextrin fatty acid ester, organically modified clay mineral, etc. can be used regardless of whether they are chemically synthesized or natural. These components can be used not only for such viscosity adjustment but also for gelation, moisturizing, film formation, and the like.

As a powder, regardless of the shape and particle size, the presence or absence of porosity, and crystal structure, in order to improve usability and usability, compounding and surface treatment can also be performed. Inorganic powders such as talc, mica, sericite, and anhydrous silicic acid can be used according to the application; organic powders such as nylon cement; ??? light scale powder, bismuth oxychloride and other particulate pigments; iron oxide, carbon black, ultramarine, etc. Inorganic pigments; tar pigments and their precipitated pigments, natural pigments, titanium oxide, particulate titanium oxide, zinc oxide, particulate zinc oxide, etc. In particular, when particulate titanium oxide and particulate zinc oxide are contained, the effect of the present invention can be further enhanced, so it is preferable.

In order to prevent the quality deterioration of these components, chelating agents such as EDTA and buffers such as lactic acid-sodium lactate can also be used as pH regulators.

Examples of medicinal agents include various ingredients including vitamins, hormones, extracts derived from animals, plants, and microorganisms. For example:

Antibacterial agents are used for the prevention and improvement of acne, and examples include benzoic acid, sodium benzoate, p-hydroxybenzoic acid esters, p-chloro-m-cresol, chlorinated hemlock, phenoxy ethanol, isopropyl cresol, etc. The combination of these ingredients can suppress pigmentation caused by bacterial skin inflammation such as acne, and further exert more effective whitening and/or skin beautification effects and anti-aging effects.

Active oxygen scavengers are used to suppress the generation of lipid peroxides caused by ultraviolet rays, and examples include superoxide dismutase, catechin, and derivatives thereof, thiamines (thiamine hydrochloride, Thiamine sulfate), riboflavins (riboflavin, riboflavin acetate, etc.), pyridoxines (pyridoxine hydrochloride, pyridoxine dicaprylate, etc.), niacin (nicotinamide, nicotinic acid benzil, etc.) and other B vitamins. Due to the mixture of these active oxygen scavengers, it can suppress dull complexion, exert more effective whitening and/or skin beautification effect and anti-aging effect.

桲提取物、粘蛋白、矢车菊提取物、熏衣草提取物、苹果提取物、龙胆提取物等。Further improve the effect of the present invention with other ingredients, the following ingredients can be enumerated, protein and derivatives thereof or hydrolysis products and their salts (collagen, elastin, keratin, etc.), mucopolysaccharides and derivatives thereof (hyaluronic acid , chondroitin sulfate, etc.), amino acids and their derivatives (histidine, serine, glycine, theanine, aspartic acid, arginine, pyrrolidone carboxylic acid, etc.), sugars (sorbitol, erythritol , trehalose, inositol, glucose, xylitol, sucrose and its derivatives, dextrin and its derivatives, honey, etc.), D-pantothenic acid and its derivatives, glycolipids, ceramide, salty grass Extract, Avocado Extract, Hot Spring Water, Medicinal Marshmallow Extract, Wild Sesame Extract, Formoniole Root Extract, Oat Grass Extract, Gardenia Extract, Bamboo Extract, Burdock Extract, Wheat Extract extract, soapwort extract, spirea extract, ginger extract, peppermint (peppermint) extract, thyme (thyme) extract, camellia extract, vellinga erecta extract, parsley extract, Peppermint extract, witch hazel extract, rose extract, Japanese cypress extract, sunflower extract, genistein, benzenesulfonine extract, loofah extract, linden extract, pine extract,

Quince extract, mucin, cornflower extract, lavender extract, apple extract, gentian extract, etc.

In addition, as a preparation that has a compacting effect on the skin surface, mixing the following oils, etc., can also exert a higher whitening and/or skin beautification effect, and you can expect to achieve a transparent skin (alias names of plants, Chinese herbal medicine names in parentheses) wait). Jojoba oil, macadamia nut oil, olive oil, almond oil (パ—シツク oil), safflower oil, sunflower oil, avocado oil, mango flower seed oil, camellia oil, almond oil, perilla oil, sesame oil , borage (ルリジサ) oil, cocoa resin, shea butter.

Blood circulation-promoting preparations are used to promote skin blood circulation and melanin discharge. Examples include capsicum tincture, γ-oryzanol, etc., and enzymes include lipase and papain. Mixing these products can achieve better whitening and/or skin beautification effects.

Example

Hereinafter, reference examples, test examples, and examples are given to describe the present invention in more detail, but the present invention is not limited by these in any way.

[Example 1] Manufacture of Cistus ladaniferus L. extract

Use 20Kg of pulverized leaves and twigs of Cistus ladaniferus L. to remove oil by steam distillation. Then, the extract obtained by extraction in 200 Kg of n-hexane was subjected to vacuum distillation to remove low boiling point substances, and 150 g of a solid to paste-like extract was obtained.

[Example 2] Preparation of labdan acids and their methyl and ethyl esters

10 g of commercially available pure labdanum (manufactured by Jibotan Co., Ltd.) was molecularly distilled under reduced pressure (0.1 mmHg), and fractions (4.3 g) at 180° C. to 220° C. were collected. This fraction contains Compound 1 (Laudanyl-8-en-15-oic acid), Compound 4 (Laudanyl-7-en-15-oic acid), Compound 7 (Laudanyl-8- (17)-en-15-acid) (this mixture is hereinafter referred to as acid mixture). 1 g of this acid mixture was dissolved in 2 mL of ether, and the diazomethane ether solution was added dropwise to obtain 0.96 g of methyl ester (this methyl ester is hereinafter referred to as methyl ester mixture). Similarly, 10 g of this acid mixture was dissolved in 100 mL of ethanol, and esterified with a sulfuric acid catalyst to obtain 9.5 g of ethyl ester (this ethyl ester is hereinafter referred to as ethyl ester mixture).

Next, the above ethyl ester mixture was subjected to silica gel chromatography to separate the three acids. Specifically, 10 g of the ethyl ester mixture was dissolved in 100 mL of hexane, injected into a silver nitrate-treated silica gel column, and then injected with a solvent to dissolve and separate out. The solvent injected was first hexane, followed by a mixed solvent in which 1 vol% ethyl acetate was added to hexane. At the beginning, compound 3 (laudanyl-8-ene-15-acid ethyl ester) was eluted, followed by compound 6 (laudanyl-7-ene-15-acid), and compound 9 (laudanyl-7-ene-15-acid) was eluted. 8(17)-ene-15-acid ethyl ester) was dissolved and separated. The solvent was distilled off from each eluate to obtain each pure ethyl ester (0.83 g, 0.16 g, 0.63 g), respectively. The obtained ethyl ester is hydrolyzed by the usual method to obtain the free acid. Then drop the diazomethane ether solution into the free acid, distill off the solvent, and use it as a methyl ester agent.

Compound 1

Compound 2

化合物3

Compound 3

Compound 4

Compound 5

Compound 6

Dissolve 4.3 g of the ethyl ester mixture obtained in Example 2 in 10 mL of ethanol, add 0.2 g of 5% palladium-carbon catalyst, and carry out hydrogenation reaction to obtain 4.1 g of compound 11. Furthermore, hydrolysis was performed to obtain compound 10.

Compound 7

Compound 8

Compound 9

Compound 10

Compound 11

[Example 3] Cell culture inhibition of melanin production and cell survival test

Cells were cultured using B16 melanoma from mouse mice. An appropriate amount of MEM medium containing 10% FBS was taken on two 6-well plates, seeded with B16 melanoma cells, and placed in 5vol% carbon dioxide at 37°C. The next day, add and mix the sample preparation solution, make the Cistusladaniferus L. extract obtained in example 1 and the labdan acids and methyl ester and ethyl ester thereof obtained in example 2, and the final concentration is 0 (contrast), 5, 10 μg/ mL, whitening agent white lily extract (manufactured by Maruzen Pharmaceutical Co., Ltd.) 0, 100 μg/mL. On the fifth day of culture, the medium was replaced, and the sample preparation solution was added again. On the next day, the culture medium was removed, one plate was washed with phosphate buffer (pH 7), and the cells were recovered. The degree of whitening of the B16 melanoma cultured cells was evaluated according to the following criteria.

In addition, as a comparative example, the same test was performed on the coix seed extract (100 μg/mL), which is known to have an action of inhibiting melanin production.

The coix seed extract is obtained by adding 100 mL of 70 vol% aqueous ethanol to 10 g of coix seed (Japanese Bureau), extracting at room temperature for 3 days, and then filtering. At this time, the dry solid fraction of the coix seed extract was 0.8%.

(judgement standard)

++: Compared with the control, it is extremely white.

+: Compared with the control, it is clearly white.

±: Compared with the control, it is slightly white.

-: Compared with the control, it is also black.

For the remaining plate, fix the cells with formalin and add 1% gentian violet solution for staining. The cell survival rate corresponding to each reagent concentration was measured with a monolayer culture cell densitometer (manufactured by Olympus Corporation). The above results are shown in Table 1-1.

Table 1-1 (Results)

Sample final concentration (μg/mL) Lily Lily Extract Concentration (μg/mL) degree of whiteness Cell viability (%) Cistus ladaniferus L extract^*1 10 100 ++ 105 Acid Mixture^*2 5 100 ++ 120 Methyl ester mixture^*2 5 100 ++ 98 Ethyl ester mixture^*2 5 100 ++ 89 Compound 1^*2 5 100 ++ 92 Compound 4^*2 5 100 ++ 94 Compound 7^*2 5 100 ++ 95 Coix Seed Extract^*3 100 100 ++ 94 Cistus ladaniferus L extract^*1 20 0 + 100 Acid Mixture^*2 10 0 + 92 Methyl ester mixture^*2 10 0 + 90 Ethyl ester mixture^*2 10 0 + 90 Compound 1^*2 10 0 + 94 Compound 4^*2 10 0 + 93 Compound 7^*2 10 0 + 98 Coix Seed Extract^*3 200 0 ± 100 White Lily Extract^*4 0 200 ± 100

^* 1 Manufactured in Example 1

^* 2 Manufactured in Example 2

^* 3 Manufactured in Example 3

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

As can be seen from the results in Table 1-1, the Cistus ladaniferus L. extract and the labdan acids and their methyl and ethyl esters, even alone, have the function of inhibiting the production of melanin, and for B16 melanoma cultured cells Weak toxicity. Furthermore, by further using the whitening agent Lilium albicans extract in combination, a whitening enhancement effect was obtained compared with the case of a single treatment. Therefore, Cistus ladaniferus L. extract, labdanic acid and its methyl and ethyl esters are combined with white lily extract and applied to the skin to play an extremely good role in inhibiting melanin production. It can be expected to effectively inhibit skin damage caused by sun exposure. Whitening and skin beautifying effects such as darkening, brown spots, and freckles.

[Example 4: Cream]

Various creams with the ingredients shown in Table 2-1 were prepared.

First, the components (1) to (6) and (12) were mixed, heated, and the component (16) kept at 70°C was added to the mixture kept at 70°C. Furthermore, after mixing components (7)-(11) and (13)-(15), it cooled and obtained a cream.

For each of the obtained creams, whitening and skin-beautifying effects were investigated by the following test methods. (experiment method)

For each test cream, 15 women aged 27 to 54 were evaluated by a special group. Twice every morning and evening, after washing the face, smear an appropriate amount of test cream on the face, try it for 12 weeks, and press the button below The standard evaluates the whitening and skin beautification effect. Evaluation results are expressed in terms of the number of people in each evaluation panel.

(evaluation standard)

<Evaluation> <Content>

Effective The dullness of the skin visibly disappeared.

Slightly effective Dullness of the skin is less noticeable.

Void No change from before use.

As shown in the results of Table 2-1, compared with the comparative product, the cream of the present invention using the Cistus ladaniferus L. extract and various components of the (B) component of the present invention (components (8) to (13)) in combination, When used on the skin, it can more effectively prevent and improve the dullness of the skin and achieve the effect of beautifying the skin. [Example 5 Cell activation test using cell culture]

Neonatal fibroblasts NB1RGB were used. Take an appropriate amount of culture medium on a 24-well plate, sow fibroblasts NB1RGB, and place it statically in carbon dioxide with a concentration of 5 vol% at 37°C. The next day, add the mixed reagent preparation solution so that the final concentrations of the Cistus ladaniferus L. extract obtained in Example 1, the labdan acids and their methyl and ethyl esters obtained in Example 2 are 0 (control), 5, 10 μg/mL; cell activator carrot extract (manufactured by Maruzen Pharmaceutical Co., Ltd.) 0, 100 μg/mL. On the fourth day of culture, the medium was replaced, and the reagent preparation solution was added again. On the next day, the medium was removed, the cells were washed with phosphate buffer, and collected. The number of fibroblast NB1RGB cells propagated in each reagent preparation solution was used as a control, and the cell proliferation rate after comparison was evaluated.

In addition, as a comparative example, the same test was performed on a soybean extract (100 μg/mL), which is known to have a cell-activating effect. The soybean extract was obtained by adding 100 mL of 70 vol % hydrous ethanol to 10 g of soybean seeds, extracting at room temperature for 3 days, and then filtering. At this time, the dry solid content of the soybean extract was 0.5%.

(evaluation standard)

Various reagent adjustment solutions were added, and the number of proliferated cells was compared with that of the control, and the cell proliferation rate was used as an index to evaluate the cell activation effect. The number of cells was also counted with a hemocytometer.

Table 3-1 (Results)

Addition concentration of sample (μg/mL) Concentration of carrot extract (μg/mL) Cell activation rate (%) Cistus ladaniferus L. extract^*1 10 100 250 Acid Mixture^*2 5 100 320 Methyl ester mixture^*2 5 100 310 Ethyl ester mixture^*2 5 100 345 Compound 1^*2 5 100 329 Compound 4^*2 5 100 322 Compound 7^*2 5 100 333 Soybean Extract^*3 100 100 170 Cistus ladaniferus L. extract^*1 20 0 120 Acid Mixture^*2 10 0 130 Methyl ester mixture^*2 10 0 125 Ethyl ester mixture^*2 10 0 135 Compound 1^*2 10 0 128 Compound 4^*2 10 0 130 Compound 7^*2 10 0 135 Soybean Extract^*3 200 0 108 Carrot Extract^*4 0 200 110

^* 1 Manufactured in Example 1

^* 2 Manufactured in Example 2

^* 3 manufactured in Example 5

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

As indicated by the results in Table 3-1, it was confirmed that the plant extract has cell activation ability on neonatal fibroblast NB1RGB. When combined with the cell activator carrot extract, it has a stronger cell activating ability. Therefore, since the cell activator of the present invention uses Cistus ladaniferus L. extract, labdanic acid and its methyl and ethyl esters in combination with carrot extract for skin, it has extremely good anti-aging effect, and its anti-aging effect is expected. It can effectively improve skin wrinkles and skin sagging caused by aging, exposure to ultraviolet rays, etc.

[Example 6: cream]

Creams with the ingredients shown in Table 4-1 were prepared respectively.

First, components (1) to (6) and (10) were mixed and heated, and a part of component (15) heated and maintained at 70°C was added to the mixture maintained at 70°C. Components (7)-(9) and (11)-(14) were mixed therein and then cooled to obtain a cream.

For each of the obtained creams, the wrinkle-improving effect was investigated by the following test method.

^* 1 Manufactured in Example 1

^* Made by 2 Sigma Corporation

^* 3 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 4 Made by BASF Corporation

^* 5 Manufactured by Japan Roche Corporation

^* 6 Manufactured by Maruzen Pharmaceutical Co., Ltd.

(experiment method)

For each cream of the test material, 20 females aged 35 to 59 formed a special group, every day, twice in the morning and at night, and applied an appropriate amount of cream on the face after washing the face for 12 weeks. The wrinkle-improving effect after application was evaluated according to the following criteria.

(evaluation standard)

<Evaluation> <Content>

Effective Skin wrinkles visibly disappeared.

Slightly effective Skin wrinkles become less noticeable.

Invalid No change from before use.

As shown in the results of Table 4-1, it is known that the cream of the present invention, which uses the Cistus ladaniferus L. extract and various components of the (B) component in combination, can improve the "wrinkle" of the skin when used on the skin, compared with the comparative product. "Wait, it becomes elastic and beautiful skin.

[Example 7: facial cleanser]

The following ingredients (1)-(10) were heated and mixed, maintaining at 70°C. It was cooled to room temperature, and (11) to (16) were added and mixed to obtain a facial cleanser.

(Element) (%)

(1) N—coconut oil fatty acid acyl—L—glutamic acid triethanolamine 20.0

(2) Betaine lauryl dimethylamine acetate 10.0

(3) Coconut oil fatty acid diethanolamide 3.0

(4) Coconut Oil Fatty Acid Potassium 5.0

(5) Stearic acid 2.0

(6) Glycerin 20.0

(7) Macrogol 400 5.0

(8) Erythritol 2.0

(9) Propylene Glycol 10.0

(10) Preservatives Appropriate amount

(11) Spices Appropriate amount

(12) Cistus ladaniferus L. extract ^* 1 1.0

(13) Aloe Vera Extract ^* 2 0.02

(14) Chamomile extract ^* 3 0.02

(15) Chuanxiong extract ^* 4 0.02

(16) Distilled water balance

^* 1 Manufactured in Example 1

^* 2 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 3 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

The obtained facial cleanser is a skin-beautifying facial cleanser with long-lasting stability and a sense of transparency when used on the skin.

[Example 8: Emulsion]

The following ingredients (1) to (8) were heated and mixed to 70°C. (9)-(13) and (22) which were heated and mixed at 70°C were added to this mixture, cooled, and (14) and (15)-(21) were added and mixed to obtain an emulsion.

(Element) (%)

(1) Hydrogenated soybean phospholipids 3.0

(2) Cholesterol 0.2

(3) Polyethylene oxide (5) Cetyl ether 0.2

(4) Polyethylene oxide (10) hardened castor oil 1.0

(5) Stearyl cetyl alcohol mixture 2.0

(6) Olive oil triodecane 5.0

(7) Dipropylene glycol 7.0

(8) 1,3-Butanediol 5.0

(9) L-serine ^* 1 0.2

(10) Sodium pyrrolidone carboxylate ^* 2 0.1

(11) Trimethylthyrosine 2.0

(12) Hypromellose 0.1

(13)Carboxyvinyl polymer 0.2

(14) Potassium hydroxide 0.1

(15) Preservatives Appropriate amount

(16) Spices Appropriate amount

(17) Cistus ladaniferus L. extract ^* 3 0.1

(18) Quince Seed Extract ^* 4 5.0

(19) Almond extract ^* 5 0.2

(20) Yeast extract ^* 6 0.2

(21) Marshmallow Root Extract ^* 7 0.2

(22) Distilled water balance

^* 1 Made by Miso Co., Ltd.

^* 2 Made by Miso Co., Ltd.

^* 3 Manufactured in Example 1

^* 4 Manufactured by Hyang Young Industrial Co., Ltd.

^* 5 Made by LABORATOIRES SEROBIOLOGIQUES

^* 6 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 7 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 9: Emulsion]

The following ingredients (13)-(17) were heated and mixed keeping at 70°C. Components (1) to (12) which are also heated and mixed are added to this mixture for emulsification. After cooling it down, components (18) to (25) were added and uniformly mixed to obtain an emulsion.

(Element) (%)

(1) Sorbitan monostearate 0.3

(2) Polyoxyethylene monooleate (20) Sorbitan 0.1

(3) Lipophilic glycerin-stearate 0.2

(4) Stearic acid 0.5

(5) Cetyl Alcohol 0.5

(6)Trakane 3.0

(7) Mobile paraffin 4.0

(8) Glycerin tri-2-ethylhexanoate 2.0

(9)Dimethicone 1.0

(10)Hydrogenated soybean phospholipids 0.1

(11) Acetic acid-dl-α-tocopherol ^* 1 0.05

(12) Preservatives Appropriate amount

(13)Carboxyvinyl polymer 0.1

(14)Sodium hydroxide 0.05

(15) Glycerin 5.0

(16) 1,3-Butanediol 7.0

(17) Distilled water Surplus

(18)Ethanol 5.0

(19)Cistus ladaniferus L. extract ^* 2 0.05

(20) Saxifraga extract ^* 3 0.1

(21) Rose Hip Extract ^* 4 0.1

(22) Sophora flavescens extract ^* 5 0.1

(23) Coffee extract ^* 6 0.1

(24) Cordyceps sinensis extract ^* 7 0.1

(25) Spices Appropriate amount

^* 1 Made by エ—ザイ company

^* 2 Manufactured in Example 1

^* 3 Manufactured by Ichimaru Farcos Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 — Manufactured by Maru Fakos Corporation

^* 7 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 10: Gel cosmetics]

The following ingredients (1)-(5) and (19) were heated and mixed, and cooled to room temperature. To this mixture, (6) to (10) which were heated and mixed at 70° C. were added and mixed, and further, (11) to (18) were added and mixed to obtain a gel cosmetic.

(Element) (%)

(1) Methylcellulose 2.0

(2) Xanthan Gum 1.0

(3) Sodium alginate 0.2

(4) Alkyl modified carboxylated ethylene polymer 0.2

(5) Sodium hyaluronate 1% aqueous solution 2.0

(6) Glycerin 10.0

(7) Macrogol 20000 1.0

(8) Methyl Glucose 2.0

(9) Hydrogenated egg yolk phospholipids 0.2

(10) Phytosterols 0.1

(11) Sodium hydroxide 0.1

(12) Preservatives Appropriate amount

(13) Spices Appropriate amount

(14) Cistus ladaniferus L. extract ^* 1 0.001

(15) Oolong tea extract ^* 2 0.3

(16) Alpinia lentil extract ^* 3 0.3

(17) Sage Extract ^* 4 0.3

(18) Mallow extract ^* 5 0.3

(19) Distilled water surplus

^* 1 Manufactured in Example 1

^* 2 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 3 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 11: Oil gel cosmetics]

The following ingredients (1) to (9) were heated and mixed at 70°C, and cooled to room temperature. Add and mix (10) and (21) to this mixture, and further add and mix (11)-(20) to obtain an oil gel cosmetic.

(Element) (%)

(1) Polyoxyethylene (20) Polyoxypropylene (4) Cetyl ether 1.0

(2) Polyoxyethylene (20) glyceryl triisostearate 0.2

(3) Alkyl modified carboxylated ethylene polymer 0.2

(4) Glycerin 10.0

(5) Dipropylene glycol 2.0

(6) 1,3-Butanediol 5.0

(7) Polyoxyethylene (10) methylglucose 0.2

(8) Glyceryl tri-2-ethylhexanoate 75.0

(9)Trakane 2.0

(10) Triethanolamine 0.1

(11) Preservatives Appropriate amount

(12) Appropriate amount of spices

(13) Stearoyl Glycyrrhizinate ^* 1 0.1

(14) Cistus ladaniferus L. extract ^* 2 0.005

(15) β-carotene ^* 3 0.002

(16) Safflower Oil ^* 4 1.0

(17) Peach Kernel Oil ^* 5 1.0

(18) Niacin-dl-α-tocopherol ^* 6 0.1

(19) Retinol Palmitate ^* 7 0.3

(20) Dibutylhydroxytoluene ^* 8 0.002

(21) Distilled water surplus

^* 1 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 2 Manufactured in Example 1

^* Made by 3 Sigma Corporation

^* 4 Made by Miso Co., Ltd.

^* 5 Manufactured by ENNAGRAM

^* 6 Manufactured by エ—ザイ company

^* 7 Manufactured by Russell Corporation, Japan

^* Made by 8 Sigma

[Example 12: Lotion]

Mix and dissolve the following ingredients (1)~(9) and (12), (17) and add ingredients (10), (11), (13)~(16) and (18)~(24) and mix The dissolved mixture is mixed to form lotion.

(Element) (%)

(1) Macadamia oil 0.01

(2) Borage grass oil 0.01

(3) Cetyl octanoate 0.01

(4) Glyceryl tri-2-ethylhexanoate 0.01

(5) Acetic acid-dl-α-tocopherol ^* 1 0.02

(6) Sorbitan sesquioleate 0.1

(7) Polyoxyethylene monooleate (20) Sorbitan 0.1

(8) Polyoxyethylene (8) Alkyl ether phosphoric acid 0.2

(9) Ethanol 10.0

(10) Sorbitol (70% aqueous solution) 5.0

(11) Glycerin 1.0

(12) 2-Hydroxy-4-methoxybenzophenone ^* 2 0.2

(13) Sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate ^* 3 0.2

(14) Lactic acid (50% aqueous solution) 0.1

(15) Sodium lactate (50% aqueous solution) 0.3

(16) Preservatives Appropriate amount

(17) Spices Appropriate amount

(18) Cistus ladaniferus L. extract ^* 4 0.01

(19) Dipotassium glycyrrhizinate ^* 5 0.1

(20) White Lily Extract ^* 6 0.05

(21) Perilla extract ^* 7 0.05

(22) Raspberry Extract ^* 8 0.05

(23) Chestnut tree extract ^* 9 0.05

(24) Distilled water Surplus

^* 1 Made by エ—ザイ company

^* 2 Produced by Kyodo Pharmaceutical Co., Ltd.

^* 3 Manufactured by Shonan Chemical Industry Co., Ltd.

^* 4 Manufactured in Example 1

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 7 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 8 Manufactured by Esperis Corporation

^* 9 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 13: Lotion]

Components (1) to (9) are mixed and dissolved, and (10) to (20) are added to the mixed and dissolved mixture, and mixed to obtain a lotion.

(Element) (%)

(1) γ-Sucrose linoleate 0.05

(2) Polyoxyethylene Monoisostearate (50) Hardened Castor Seed Oil 1.0

(3) L-Ascorbic Acid Isopalmitate 0.1

(4) Polyoxyethylene (10) alkyl ether phosphoric acid 0.1

(5) Octyl Methoxycinnamate ^* 1 0.05

(6) Glycerin 3.0

(7) N-acetyl-L-glutamic acid ^* 2 0.1

(8) 1,3-Butanediol 5.0

(9) Ethanol 8.0

(10) Sodium citrate 0.02

(11) Citric acid 0.05

(12) Preservatives Appropriate amount

(13) Spices Appropriate amount

(14) Cistus ladaniferus L. extract ^* 3 0.05

(15) Centella asiatica extract ^* 4 0.2

(16) Ginkgo biloba extract ^* 5 0.2

(17) Extract of beech bud ^* 6 0.05

(18) Sweet tea extract ^* 7 0.05

(19) Geranium extract ^* 8 0.05

(20) Distilled water surplus

^* 1 Manufactured by BASF Corporation

^* 2 Manufactured by Kyodo Fermentation Co., Ltd.

^* 3 Manufactured in Example 1

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Tokiwa Institute of Phytochemistry

^* 6 Manufactured by ガテホセ company

^* 7 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 8 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 14: cloudy lotion]

The mixture obtained by mixing and dissolving the following components (1) to (10) was added to the mixed and dissolved components (11) to (21) to obtain a cloudy lotion.

(Element) (%)

(1) Polyoxyethylene (60) hardened castor oil 0.7

(2) Sodium polyoxyethylene alkyl ether phosphate 0.2

(3) Cholesterol 0.01

(4) Hydrogenated egg yolk phospholipids 0.02

(5)Dimethicone 0.05

(6) Acetic acid-dl-α-tocopherol ^* 1 0.5

(7) p-methoxycinnamic acid 2-ethylhexyl ^* 2 0.2

(8) Glycyrrhetinic acid stearyl ^* 3 0.1

(9) Ethanol 15.5

(10) Polyethylene glycol 6000 0.2

(11) Citric acid 0.01

(12) Disodium monohydrogen phosphate 0.2

(13) Rutin ^* 4 0.01

(14) Preservatives Appropriate amount

(15) Spices Appropriate amount

(16) Cistus ladaniferus L. extract ^* 5 0.002

(17) Hydroxyproline ^* 6 0.01

(18) Watercress extract ^* 7 0.1

(19) Coltsfoot extract ^* 8 0.1

(20) Lactobacillus extract ^* 9 0.1

(21) Distilled water Surplus

^* 1 Made by エ—ザイ company

^* 2 Made by BASF

^* 3 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* Made by 4 Sigma Corporation

^* 5 Manufactured in Example 1

^* 6 Manufactured by Kyowa Hakko Co., Ltd.

^* 7 Made by AMI company

^* 8 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 9 Manufactured by Kotobuki Chemical Co., Ltd.

[Example 15: Beauty Serum]

Mix and dissolve the mixture of ingredients (1)-(4), (6) and (7) and ingredients (8)-(13) and (25) at 50°C, heat and mix at 50°C, cool To the mixture after reaching room temperature, the mixing components (5), (14) to (24) were added to obtain a viscous cosmetic liquid.

(Element) (%)

(1) Polyoxyethylene isostearate (50) hardened castor oil 0.2

(2) Hydrogenated soybean phospholipids 0.5

(3) Glycerin 7.0

(4) dl-α-tocopherol ^* 1 0.3

(5) Angelica extract ^* 2 0.2

(6) Cholesterol 0.1

(7) Ethanol 6.0

(8) Sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate ^* 3 0.2

(9)L-Magnesium Ascorbyl Phosphate 0.5

(10) Citric acid 0.01

(11) Sodium citrate 0.1

(12) Xanthan gum 0.1

(13)Methylcellulose 0.1

(14) Seaweed Extract ^* 4 0.1

(15) Acanthopanax bark extract ^* 5 0.1

(16) Wheat Germ Extract ^* 6 0.1

(17) Peony extract ^* 7 0.1

(18) Niacinamide ^* 8 0.05

(19) Yellow tiller extract ^* 9 0.1

(20) Tomato Extract ^* 10 0.1

(21) Morus alba extract ^* 11 0.1

(22) Preservatives Appropriate amount

(23) Spices Appropriate amount

(24) Cistus ladaniferus L. extract ^* 12 1.0

(25) Distilled water Surplus

^* 1 Made by エ—ザイ company

^* 2 Manufactured by Nippon Powder Pharmaceutical Co., Ltd.

^* 3 Manufactured by Shonan Chemical Industry Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 Chenghe Huasei Co., Ltd.

^* 7 Manufactured by Inabata Spice Co., Ltd.

^* 8 Manufactured by Wako Pure Chemical Industries, Ltd.

^* 9 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 10 made by ェスペリス company

^* 11 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 12 Manufactured in Example 1

[Example 16: Sunscreen Lotion]

Components (1) to (10) were heated and mixed at 70°C to disperse into a slurry. Components (11)-(13) and (15)-(22) dissolved and mixed at 50°C were mixed here, and component (14) was added to obtain a sunscreen lotion.

(Element) (%)

(1) Neopentyl glycol dicaprate 10.0

(2) p-methoxycinnamic acid-2-ethylhexyl ^* 1 5.0

(3) Octamethylcyclotetrasiloxane 10.0

(4) Decamethylcyclopentasiloxane 10.0

(5)Dimethicone 5.0

(6) Particulate Titanium Oxide 10.0

(7) Particulate Zinc Oxide 5.0

(8) Polyalkylene modified organosiloxane 5.0

(9) Nylon powder 2.0

(10) Polyethylene end 1.0

(11) Glycerin 5.0

(12)Ethanol 5.0

(13) Preservatives Appropriate amount

(14) Spices Appropriate amount

(15) Cistus ladaniferus L. extract ^* 2 0.2

(16) Dipotassium glycyrrhizinate ^* 3 0.1

(17) Morus alba extract ^* 4 0.1

(18) Rose flower extract ^* 5 0.01

(19) Green tea extract ^* 6 0.01

(20) Bee flower extract ^* 7 0.01

(21) Gentian extract ^* 8 0.01

(22) Distilled water surplus

^* 1 Manufactured by BASF Corporation

^* 2 Manufactured in Example 1

^* 3 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 7 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 8 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 17: Water-in-oil sunscreen]

Components (1) to (9) were heated and mixed at 70°C. Components (10)-(13) and (15)-(20) heated and mixed at 50°C were added thereto, and then component (14) was added to obtain a water-in-oil type sunscreen.

(Element) (%)

(1) Polyalkylene modified organosiloxane 2.0

(2) Octyl palmitate 15.0

(3) Decamethylcyclopentasiloxane 20.0

(4) Glyceryl Tribehenate 1.0

(5) Particulate Zinc Oxide 12.0

(6) Particulate Titanium Oxide 3.0

(7) p-methoxycinnamic acid-2-ethylhexyl ^* 1 7.0

(8) 4-tert-butyl-4'-methoxydibenzoylmethane ^* 2 1.0

(9) Perilla oil ^* 3 0.05

(10)Dipropylene glycol 5.0

(11)Ethanol 5.0

(12)Polyethylene end 3.0

(13) Preservatives Appropriate amount

(14) Spices Appropriate amount

(15) Cistus ladaniferus L. extract ^* 4 0.2

(16) White birch extract ^* 5 0.2

(17) Mugwort Extract ^* 6 0.2

(18) Mannitol ^* 7 0.05

(19)Lime peel extract ^* 8 0.2

(20) Distilled water surplus

^* 1 Manufactured by BASF Corporation

^* 2 Manufactured by Jibden Corporation

^* 3 Manufactured in Example 1

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 Manufactured by Wako Pure Chemical Industries, Ltd.

^* 7 Manufactured by Wako Pure Chemical Industries, Ltd.

^* 8 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 18: Water-in-oil cream]

Heat and mix ingredients (1) to (8) at 70°C, add ingredients (9) to (16) and (18) to (25) that have been heated and mixed at 50°C, and then Ingredient (17) was added to obtain a water-in-oil cream.

(Element) (%)

(1) Hydrogenated soybean lecithin 0.05

(2) Polyoxyalkylene modified organosiloxane 2.0

(3) Cholesterol hydroxystearate 2.0

(4) Cholesterol 0.2

(5)Trakane 2.0

(6) Decamethylcyclopentasiloxane 7.0

(7) Ethylene glycol diisooctanoate 15.0

(8) 2-Hydroxy-4-methoxybenzophenone-5-sulfonic acid ^* 1 1.0

(9) Magnesium L-Ascorbyl Phosphate 3.0

(10) Sodium citrate 0.5

(11) Disodium edetate 0.05

(12) Ethanol 2.0

(13) 1,3-Butanediol 5.0

(14)Crystalline cellulose 2.0

(15) spherical nylon powder 1.0

(16) Preservatives Appropriate amount

(17) Spices Appropriate amount

(18) Cistus ladaniferus L. extract ^* 2 0.3

(19) Molasses extract ^* 3 0.1

(20) Hops extract ^* 4 0.1

(21) Arnica Extract ^* 5 0.1

(22) Barley extract ^* 6 0.1

(23) Almond extract ^* 7 0.1

(24) Calamus extract ^* 8 0.1

(25) Distilled water Surplus

^* 1 Manufactured by Baditsushi Co., Ltd.

^* 2 Manufactured in Example 1

^* 3 Manufactured by Sun Chemical Corporation

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 Manufactured by Sansho Pharmaceutical Co., Ltd.

^* 7 Made by Esperi Corporation

^* 8 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 19: Cream]

Heat and mix the following ingredients (1) to (10) at 70°C, add and mix the ingredients (11) to (13), (24) and (27) after heating and mixing at 70°C The mixture was added with ingredients (14)-(23), (25) and (26), and cooled to room temperature to obtain a cream.

(Element) (%)

(1) Stearyl cetyl alcohol mixture 3.0

(2) Glycerin fatty acid esters 2.0

(3) Polyoxyethylene monooleate (20) Sorbitan 1.0

(4) Sorbitan monostearate 1.0

(5) Sodium N-stearyl-N-methylaminoethanesulfonate 0.5

(6) Vaseline 5.0

(7)Dimethicone 3.0

(8) Glyceryl tri-2-ethylhexanoate 20.0

(9) dl-α-tocopherol ^* 1 1.0

(10)Titanium oxide 1.0

(11) Dipropylene glycol 10.0

(12)L-Magnesium Ascorbyl Phosphate 3.0

(13)Sodium citrate 0.5

(14) Dipotassium glycyrrhizinate ^* 2 0.1

(15) Lactic acid (50% aqueous solution) 0.1

(16) Carrot extract ^* 3 0.1

(17) Asarum extract ^* 4 0.3

(18) Hawthorn Seed Extract ^* 5 0.02

(19) Honeysuckle Extract ^* 6 0.02

(20) Cattail pollen extract ^* 7 0.02

(21) Soybean extract ^* 8 0.02

(22) Angelica extract ^* 9 0.02

(23) Disodium edetate 0.03

(24) Preservatives Appropriate amount

(25) Spices Appropriate amount

(26) Cistus ladaniferus L. extract ^* 10 0.5

(27) Distilled water Surplus

^* 1 Made by エ—ザイ company

^* 2 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 3 Manufactured by Ichimaru Farcos Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 6 Manufactured by Nagaoka Spice Co., Ltd.

^* 7 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 8 Manufactured by Hyang Young Industrial Co., Ltd.

^* 9 Manufactured by Nippon Powder Pharmaceutical Co., Ltd.

^* 10 manufactured in Example 1

[Example 20: beauty cream]

Heat and mix the following components (1)-(5) and (23) at 70°C, and add the mixed components (6)-(22) to the mixture after cooling to room temperature to obtain a beauty cream.

(Element) (%)

(1) Polyvinyl alcohol 15.0

(2) Glycerin 10.0

(3) Polyoxyethylene(10) methylglucose 3.0

(4) Glyceryl tricaprylate 5.0

(5) Sodium polyoxyethylene alkyl ether phosphate 1.0

(6) Ethanol 20.0

(7) Clay 2.0

(8) Titanium oxide 2.0

(9) Seaweed Extract ^* 1 0.1

(10) Dipotassium glycyrrhizinate ^* 2 0.1

(11) Wheat Germ Extract ^* 3 0.1

(12) Papaya Extract ^* 4 0.1

(13) Rice bran extract ^* 5 0.01

(14) Forsythia forsythia extract ^* 6 0.01

(15) Raspberry extract ^* 7 0.01

(16) Calamus extract ^* 8 0.01

(17) Rehmannia glutinosa extract ^* 9 0.01

(18) Lactic acid (50% aqueous solution) 0.5

(19) Sodium lactate (50% aqueous solution) 0.5

(20) Preservatives Appropriate amount

(21) Spices Appropriate amount

(22) Cistus ladaniferus L. extract ^* 10 0.02

(23) Distilled water balance

^* 1 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 2 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 3 Chenghe Huasei Co., Ltd.

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 5 Manufactured by Hyang Young Industrial Co., Ltd.

^* 6 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 7 Manufactured by Esperis Corporation

^* 8 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 9 Manufactured by Hyang Young Industrial Co., Ltd.

^* 10 manufactured in Example 1

[Example 21: Liquid Foundation]

The following ingredients (1)-(7) were heated and mixed, and ingredients (13)-(18) were added to this mixture, and the temperature was maintained at 70°C. Components (8) to (12) were mixed and kept at 70° C., and the previous mixture was added and uniformly emulsified. After cooling, components (19) to (25) were added to obtain a liquid foundation.

(Element) (%)

(1) Dipentaerythritol fatty acid ester 2.0

(2) Liquid paraffin 5.0

(3) Stearic acid 2.0

(4) Cetyl Alcohol 1.0

(5) Self-emulsifying glycerol monostearate 1.0

(6) p-Methoxycinnamic acid-2-ethylhexyl 8.0

(7) Appropriate amount of preservatives

(8) Glycerin 5.0

(9) Triethanolamine 1.0

(10)Carboxymethylcellulose 0.5

(11) Bentonite 0.2

(12) Distilled water balance

(13)Titanium oxide 6.0

(14) Particulate Titanium Oxide 2.0

(15) Particulate Zinc Oxide 4.0

(16)Mica 2.0

(17) Talc 4.0

(18) Coloring pigment Appropriate amount

(19) Cistus ladaniferus L. extract ^* 1 0.01

(20) Scutellaria baicalensis extract ^* 2 0.1

(21) Peony Extract ^* 3 0.1

(22) Daisy Extract ^* 4 0.1

(23) Elderberry extract ^* 5 0.1

(24) Sapinberry Extract ^* 6 0.1

(25) Spices Appropriate amount

^* 1 Manufactured in Example 1

^* 2 Manufactured by Ichimaru Farcos Co., Ltd.

^* 3 Manufactured by Ichimaru Farcos Co., Ltd.

^* 4 Manufactured by Ichimaru Farcos Co., Ltd.

^* 5 Made by Sepetsu Co., Ltd.

^* 6 Manufactured by Hyang Young Industrial Co., Ltd.

The various cosmetics obtained from Examples 8-21 all have long-lasting stability, and are good for preventing and improving skin dullness, brown spots and freckles caused by sun exposure, and wrinkles and skin sagging caused by aging when used on the skin. It is a variety of skin-beautifying cosmetics with a sense of transparency.

[Example 22] Inhibition of melanin production and cell viability test using cell culture

Cells were cultured using B16 melanoma from mouse mice. On two 6-well plates, take an appropriate amount of MEM medium containing 10% FBS, seed B16 melanoma cells, and place them statically in 5 vol% carbon dioxide at 37°C. The next day, add and mix the sample preparation solution, make the Cistusladaniferus L. extract obtained in example 1 and the labdan acids and methyl ester and ethyl ester thereof obtained in example 2, and the final concentration is 0 (contrast), 5, 10 μg/ mL, whitening agent white lily extract (manufactured by Maruzen Pharmaceutical Co., Ltd.) 0, 100 μg/mL. On the fifth day of culture, the medium was replaced, and the sample preparation solution was added again. On the next day, the culture medium was removed, one plate was washed with phosphate buffer (pH 7), and the cells were recovered. The degree of whitening of the B16 melanoma cultured cells was evaluated according to the following criteria.

In addition, as a comparative example, the same test was performed on the coix seed extract (100 μg/mL), which is known to have an action of inhibiting melanin production.

The coix seed extract is obtained by adding 100 mL of 70 vol% aqueous ethanol to 10 g of coix seed (Japanese Bureau), extracting at room temperature for 3 days, and then filtering. At this time, the dry solid fraction of the coix seed extract was 0.8%.

(judgement standard)

++: Compared with the control, it is extremely white.

+: Compared with the control, it is clearly white.

±: Compared with the control, it is slightly white.

-: Compared with the control, it is also black.

For the remaining plate, fix the cells with formalin and add 1% gentian violet solution for staining. The cell viability corresponding to each reagent concentration was measured with a monolayer culture cell densitometer (manufactured by Olympus). The above results are shown in Table 1-2.

Table 1-2 (Results)

Sample final concentration (μg/mL) Added concentration of licorice extract (μg/mL) degree of whiteness Cell viability (%) Cistus ladaniferus L. extract^*1 10 100 ++ 102 Acid Mixture^*2 5 100 ++ 108 Methyl ester mixture^*2 5 100 ++ 97 Ethyl ester mixture^*2 5 100 ++ 93 Compound 1^*2 5 100 ++ 95 Compound 4^*2 5 100 ++ 96 Compound 7^*2 5 100 ++ 98 Coix Seed Extract^*3 100 100 ++ 97 Cistus ladaniferus L. extract^*1 20 0 + 100 Acid Mixture^*2 10 0 + 92 Methyl ester mixture^*2 10 0 + 90 Ethyl ester mixture^*2 10 0 + 90 Compound 1^*2 10 0 + 94 Compound 4^*2 10 0 + 93 Compound 7^*2 10 0 + 98 Coix Seed Extract^*3 200 0 ± 100 Licorice Extract^*4 0 200 ± 98

^* 1 Manufactured in Example 1

^* 2 Manufactured in Example 2

^* 3 manufactured in Example 22

^* 4 Manufactured by Maruzen Pharmaceutical Co., Ltd.

As is known from the results in Table 1-2, Cistus ladaniferus L extract, labdan acids, and their methyl and ethyl esters have the function of inhibiting melanin production even alone, and are toxic to B16 melanoma cultured cells. weak. Furthermore, by using the whitening agent licorice extract in combination, a whitening enhancement effect was obtained compared with the case of a single treatment. Therefore, Cistus ladaniferus L. extract, labdanic acid and its methyl and ethyl esters are combined with white lily extract and applied to the skin to play an extremely good role in inhibiting melanin production. It can be expected to effectively inhibit skin damage caused by sun exposure. Whitening and skin beautifying effects such as darkening, brown spots, and freckles.

[Example 23] Production method of black currant (Crofossus Gli) fruit extract

10g black ear currant (Ribes nigrum L.) fruit is pulverized, add 50vol% hydrous ethanol 100mL, after carrying out 3 days extraction at room temperature, obtain black ear currant (Crophes nigrum L.) fruit extract through filtration (dry solid content is 2.4%).

[Example 24] The production method of Inula inula (Inula chinensis) fruit extract

Add 50vol% hydrous ethanol 100mL to the raceme of 10g Inula britannica L., at room temperature, after carrying out 3 days of extraction, after filtering, obtain Inula britannica fruit extract (dry solid content is 0.5%).

[Example 25] Production method of cranberry fruit extract

Crush 10g of cranberry (Vaccinium macrocorpon Aiton or Vaccinium oxycoccus) fruit, add 100mL of 50vol% water-containing 1,3-butanediol, extract at room temperature for 3 days, and filter to obtain cranberry fruit extract (1.5% dry solids).

[Example 26] Manufacturing method of Spatholobus extract

The stem of 10g Pamakamatou (Hamakayumatow) (Mucuna birdwoodiana Tutcher) is pulverized, and 100mL of 50vol% hydrous ethanol is added, at room temperature, after carrying out 3 days of extraction, after filtering, the extract of Millipeda japonica (dry solid content) is obtained. 1.5%).

[Example 27] Manufacturing method of birch sap

Birch sap (dry solid content: 0.8%) was obtained by punching a white birch (Betula platyphylla Sukatchuvvar. Japonica Hara) tree before flowering, and taking the outflowing liquid.

[Example 28] The production method of the cornflower extract

In the fruit of 10g Alnus firma Sieb.et Zucc., add 50vol% aqueous ethanol 100mL, at room temperature, after extracting for three days, obtain the Alnus firma extract (the dry solid content is 1.0 %).

[Example 29] Production method of cactus extract

Dry the stem nodes of Opuntia Streptacantha, add 100 mL of distilled water to 10 g of the powder, and extract at 70° C. for 8 hours. After cooling, filter, concentrate, dry and solidify the filtrate, add 100 g of 30 vol% aqueous 1,3-butanediol to dissolve, and obtain cactus extract (dry solid content: 1.0%).

[Example 30] Manufacturing method of Luo Han Guo extract

In the dry fruit of 10g Momordica grosbenorii (Momordica grosbenorii Swingle), add 50vol% hydrous ethanol 100mL, at room temperature, after carrying out 3 days extraction, after filtering, obtain the Luo Han Guo extract (dry solid content is 1.3 %).

[Example 31: cream]

Various creams with the ingredients shown in Table 2-2 were prepared.

First, components (1) to (6) were mixed, heated, and kept at 70° C., and then component (16) heated and kept at 70° C. was added. Furthermore, after mixing components (7)-(15), it cooled and obtained a cream.

The whitening and skin-beautifying effects of each of the obtained creams were investigated by the following test methods.

(experiment method)

For each test cream, 15 women aged 27 to 54 were evaluated by a special group. Twice every morning and night, after washing the face, smear an appropriate amount of test cream on the face, try it for 12 weeks, and press the button below The standard of whitening and skin beautification was evaluated. Evaluation results are expressed in terms of the number of people in each evaluation panel.

(evaluation standard)

<Evaluation> <Content>

Effective The dullness of the skin visibly disappeared.

Slightly effective Dullness of the skin is less noticeable.

Void No change from before use.

(ingredients and results)

As shown in the results of Table 2-2, compared with the comparative product, the cream of the present invention, which is used in combination with the Cistus ladaniferus L. extract and the various components of the above-mentioned (B2) component (components (8)-(13)), is used for Skin, can more effectively prevent and improve the dullness of the skin, and achieve the effect of skin beautification.

[Example 32 Cell activation test using cell culture]

Neonatal fibroblasts NB1RGB were used. Take an appropriate amount of culture medium on a 24-well plate, sow fibroblasts NB1RGB, and place it statically in carbon dioxide with a concentration of 5 vol% at 37°C. The next day, add the mixed reagent preparation solution so that the final concentrations of the Cistus ladaniferus L. extract obtained in Example 1, the labdan acids and their methyl and ethyl esters obtained in Example 2 are 0 (control), 5, and 10 μg /mL; cell activator cactus extract is 0, 100 μg/mL. On the fourth day of culture, the medium was replaced, and the reagent preparation solution was added again. On the next day, the culture medium was removed, the cells were washed with phosphate buffer solution, and collected. The number of fibroblast NB1RGB cells propagated in each reagent preparation solution was used as a control, and the cell proliferation rate after comparison was evaluated.

In addition, as a comparative example, the same test was performed on a soybean extract (100 μg/mL), which is known to have a cell-activating effect. The soybean extract was obtained by adding 100 mL of 70 vol% aqueous ethanol to 10 g of soybean seeds, extracting at room temperature for 3 days, and then filtering. At this time, the dry solid content of the soybean extract was 0.5%.

(evaluation standard)

Various reagent adjustment solutions were added, and the number of proliferated cells was compared with that of the control, and the cell proliferation rate was used as an index to evaluate the cell activation effect. The number of cells was also counted with a hemocytometer.

Table 3-2 (Results)

Addition concentration of sample (μg/mL) Cactus extract added concentration (μg/mL) Cell activation rate (%) Cistus ladaniferus L. extract^*1 10 100 230 Acid Mixture^*2 5 100 290 Methyl ester mixture^*2 5 100 280 Ethyl ester mixture^*2 5 100 305 Compound 1^*2 5 100 300 Compound 4^*2 5 100 310 Compound 7^*2 5 100 315 Soybean Extract^*3 100 100 170 Cistus ladaniferus L. extract^*1 20 0 120 Acid Mixture^*2 10 0 130 Methyl ester mixture^*2 10 0 125 Ethyl ester mixture^*2 10 0 135 Compound 1^*2 10 0 128 Compound 4^*2 10 0 130 Compound 7^*2 10 0 135 Soybean Extract^*3 200 0 108 Cactus Extract^*4 0 200 110

^* 1 Manufactured in Example 1

^* 2 Manufactured in Example 2

^* 3 manufactured in Example 32

^* 4 manufactured in Example 29

As shown by the results in Table 3-2, it was confirmed that the plant extract has cell activation ability on neonatal fibroblast NB1RGB. When combined with cell activator cactus extract, it has stronger cell activation ability. Therefore, since the cell activator of the present invention uses Cistus ladaniferus L. extract and labdanic acid and its methyl and ethyl esters in combination with cactus extract for skin, it has played an extremely good anti-aging effect, and its anti-aging effect is expected. It can effectively improve skin wrinkles and skin sagging caused by aging, exposure to ultraviolet rays, etc.

[Example 33: Cream]

Various creams with the ingredients shown in Table 4-2 were prepared respectively.

First, components (1) to (6) were mixed, and a part of component (16) heated and maintained at 70° C. was added to the mixture kept at 70° C. after heating. Components (7) to (15) were mixed there, and then cooled to obtain a cream.

The wrinkle-improving effect of each of the obtained creams was investigated by the following test method.

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 26

^* 3 manufactured in Example 27

^* 4 manufactured in Example 28

^* 5 manufactured in Example 29

^* Manufactured by 6 Sigma

^* 7 Manufactured by Toyo Refined Sugar Co., Ltd.

(experiment method)

For each cream of the test material, 20 women aged 35 to 59 formed a special group, twice a day, in the morning and in the evening, and applied an appropriate amount of cream on the face after washing for 12 weeks. The wrinkle-improving effect after application was evaluated according to the following criteria.

(evaluation standard)

<Evaluation> <Content>

Effective Skin wrinkles visibly disappeared.

Slightly effective Skin wrinkles become less noticeable.

Void No change from before use.

As shown in the results in Table 4, it was found that the cream of the present invention, in which the extract of Cistus ladaniferus L. was used in combination with various components of component (B), can improve skin "wrinkles" and the like when applied to the skin , into elastic and beautiful skin.

[Example 34: Cream]

The following ingredients (1)-(10) were heated and mixed to 70°C. To this mixture, add and mix components (11)-(13), (22) and (25) after heating and mixing at 70°C, and then add and mix components (14)-(21), (23 ) and (24), and then cooled to room temperature to obtain a cream.

(Element) (%)

(1) Stearyl cetyl alcohol mixture 3.0

(2) Glycerin Fatty Acid Ester 2.0

(3) Polyoxyethylene monooleate (20) Sorbitan 1.0

(4) Sorbitan monostearate 1.0

(5) Sodium N-stearyl-N-methylaminoethanesulfonate 0.5

(6) Vaseline 5.0

(7)Dimethicone 3.0

(8) Glyceryl tri-2-ethylhexanoate 20.0

(9) dl-α-tocopherol 1.0

(10)Titanium oxide 1.0

(11) Dipropylene glycol 10.0

(12)L-Magnesium Ascorbyl Phosphate 3.0

(13)Sodium citrate 0.5

(14)Dipotassium glycyrrhizinate 0.1

(15) Lactic acid (50% aqueous solution) 0.1

(16) Spatholobus extract ^* 1 0.1

(17) Glucose Rutinoside Extract ^* 2 0.3

(18) Cactus Extract ^* 3 0.02

(19) Luo Han Guo Extract ^* 4 0.02

(20) Birch Sap ^* 5 5.0

(21) Disodium edetate 0.03

(22) Preservatives Appropriate amount

(23) Spices Appropriate amount

(24) Cistus ladaniferus L. extract ^* 6 0.5

(25) Distilled water Surplus

^* 1 Manufactured in Example 26

^* 2 Manufactured by Toyo Refined Sugar Co., Ltd.

^* 3 manufactured in Example 29

^* 4 manufactured in Example 30

^* 5 manufactured in Example 27

^* 6 Manufactured in Example 1

[Example 35: Water-in-oil cream]

The following ingredients (1)-(8) were heated and mixed to 70°C. Components (9) to (16), (18) to (21) which were heated and mixed at 50°C were added to this mixture, and then component (17) was added to obtain a water-in-oil cream.

(Element) (%)

(1) Hydrogenated soybean lecithin 0.05

(2) Polyoxyalkylene modified organosiloxane 2.0

(3) Cholesterol hydroxystearate 2.0

(4) Cholesterol 0.2

(5)Trakane 2.0

(6) Decamethylcyclopentasiloxane 7.0

(7) Ethylene glycol diisooctanoate 15.0

(8) 4-tert-butyl-4'-methoxydibenzoylmethane 1.0

(9) L-Magnesium Ascorbyl Phosphate 3.0

(10) Sodium citrate 0.5

(11) Disodium edetate 0.05

(12) Ethanol 2.0

(13) 1,3-Butanediol 5.0

(14) Crystalline cellulose 2.0

(15) spherical nylon powder 1.0

(16) Preservatives Appropriate amount

(17) Spices Appropriate amount

(18) Cistus ladaniferus L. extract ^* 1 0.3

(19) Cornflower extract ^* 2 0.1

(20) Luo Han Guo Extract ^* 3 0.1

(21) Distilled water Surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 28

^* 3 manufactured in Example 30

The various creams obtained in Examples 34 and 35 all have long-lasting stability and are good for preventing and improving skin dullness, brown spots and freckles caused by sun exposure, and wrinkles and skin sagging caused by aging. , is a variety of skin-beautifying cosmetics with a sense of transparency.

[Example 36: facial cleanser]

Heat and mix the following ingredients (1)-(10), keep it at 70° C., cool it to room temperature, add and mix (11)-(14) to obtain a facial cleanser.

(Element) (%)

(1) N-coconut oil fatty acid acyl-L-glutamic acid triethanolamine 20.0

(2) Betaine lauryl dimethylamine acetate 10.0

(3) Coconut oil fatty acid diethanolamide 3.0

(4) Coconut Oil Fatty Acid Potassium 5.0

(5) Stearic acid 2.0

(6) Glycerin 20.0

(7) Macrogol 400 5.0

(8) Erythritol 2.0

(9) Propylene Glycol 10.0

(10) Preservatives Appropriate amount

(11) Spices Appropriate amount

(12) Cistus ladaniferus L. extract ^* 1 1.0

(13) Coix Seed Extract ^* 2 1.0

(14) Distilled water surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 22

The obtained face cleanser was excellent in stability over time, and was used on the skin, and it was a cleanser for brightening the skin with a sense of transparency.

[Example 37: Gel cosmetics]

The following ingredients (1)-(5) and (16) were heated and mixed, and cooled to room temperature. To this mixture, (6) to (10) which were heated and mixed at 70° C. were added and mixed, and further, (11) to (15) were added and mixed to obtain a gel cosmetic.

(Element) (%)

(1) Methylcellulose 2.0

(2) Xanthan Gum 1.0

(3) Sodium alginate 0.2

(4) Alkyl modified carboxylated ethylene polymer 0.2

(5) Sodium hyaluronate 1% aqueous solution 2.0

(6) Glycerin 10.0

(7) Macrogol 20000 1.0

(8) Methyl Glucose 2.0

(9) Hydrogenated egg yolk phospholipids 0.2

(10) Phytosterols 0.1

(11) Sodium hydroxide 0.1

(12) Preservatives Appropriate amount

(13) Spices Appropriate amount

(14) Cistus ladanifcrus L. extract ^* 1 0.001

(15) Black currant extract ^* 2 0.3

(16) Distilled water Surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 23

[Example 38: Oil gel cosmetics]

The following ingredients (1) to (9) were heated and mixed at 70°C, and cooled to room temperature. To this mixture, (10) and (16) were added and mixed, and further, (11) to (15) were added and mixed to obtain an oil gel cosmetic.

(Element) (%)

(1) Polyethylene oxide (20) Polyoxypropylene (4) Cetyl ether 1.0

(2) Polyoxyethylene (20) glyceryl triisostearate 0.2

(3) Alkyl modified carboxylated ethylene polymer 0.2

(4) Glycerin 10.0

(5) Dipropylene glycol 2.0

(6) 1,3-Butanediol 5.0

(7)Polyoxyethylene(10)methylglucose 0.2

(8) Glyceryl tri-2-ethylhexanoate 75.0

(9)Trakane 2.0

(10) Triethanolamine 0.1

(11) Preservatives Appropriate amount

(12) Spices Appropriate amount

(13) Cistus ladaniferus L. extract ^* 1 0.005

(14) Astaxanthin ^* 2 0.05

(15) Rutin glucoside ^* 3 0.05

(16) Distilled water Surplus

^* 1 Manufactured in Example 1

^* Made by 2 Sigma Corporation

^* 3 Manufactured by Toyo Refined Sugar Co., Ltd.

[Example 39: Lotion]

Mix and dissolve the following components (1)～(9) and (12), (16) and add to components (10), (11), (13)～(15) and (17)～(21) ) to obtain lotion.

(Element) (%)

(1) Macadamia oil 0.01

(2) Borage grass oil 0.01

(3) Cetyl octanoate 0.01

(4) Glyceryl tri-2-ethylhexanoate 0.01

(5) Acetic acid-dl-α-tocopherol 0.02

(6) Sorbitan sesquioleate 0.1

(7) Polyoxyethylene monooleate (20) Sorbitan 0.1

(8) Polyethylene oxide (8) Alkyl ether phosphoric acid 0.2

(9)Ethanol 10.0

(10) Sorbitol (70% aqueous solution) 5.0

(11) Glycerin 1.0

(12) Sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate 0.2

(13) Lactic acid (50% aqueous solution) 0.1

(14) Sodium lactate (50% aqueous solution) 0.3

(15) Preservatives Appropriate amount

(16) Spices Appropriate amount

(17) Cistus ladaniferus L. extract ^* 1 0.01

(18)Dipotassium glycyrrhizinate 0.1

(19) Cornflower extract ^* 2 0.05

(20) Licorice Extract ^* 3 0.05

(21) Distilled water Surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 28

^* 3 Manufactured by Maruzen Pharmaceutical Co., Ltd.

[Example 40: lotion]

Mix and dissolve the ingredients (1) to (9) and add to (10) to (16) to obtain lotion.

(Element) (%)

(1) γ-Sucrose linoleate 0.05

(2) Polyoxyethylene monoisostearate (50) hardened castor oil 1.0

(3) L-Ascorbic Acid Isopalmitate 0.1

(4) Polyoxyethylene (10) alkyl ether phosphoric acid 0.1

(5) Octyl methoxycinnamic acid 0.05

(6) Glycerin 3.0

(7) L-serine 0.1

(8) 1,3-Butanediol 5.0

(9)Ethanol 8.0

(10) Sodium citrate 0.02

(11) Citric acid 0.05

(12) Preservatives Appropriate amount

(13) Spices Appropriate amount

(14) Cistus ladaniferus L. extract ^* 1 0.05

(15) Inula extract ^* 2 0.2

(16) Distilled water surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 24

[Example 41: cloudy lotion]

The mixture obtained by mixing and dissolving the following components (1) to (10) was added to the mixed and dissolved components (11) to (19) to obtain a cloudy lotion.

(Element) (%)

(1) Polyoxyethylene (60) hardened castor oil 0.7

(2) Sodium polyoxyethylene alkyl ether phosphate 0.2

(3) Cholesterol 0.01

(4) Hydrogenated egg yolk phospholipids 0.02

(5)Dimethicone 0.05

(6) Acetic acid-dl-α-tocopherol 0.5

(7) 2-ethylhexyl p-methoxycinnamic acid 0.2

(8) Glycyrrhetinic acid stearyl 0.1

(9) Ethanol 15.5

(10) Polyethylene glycol 6000 0.2

(11) Citric acid 0.01

(12) Disodium monohydrogen phosphate 0.2

(13) Astaxanthin ^* 1 0.0001

(14) Preservatives Appropriate amount

(15) Spices Appropriate amount

(16) Cistus ladaniferus L. extract ^* 2 0.002

(17) Rutin glucoside ^* 3 0.001

(18) Black currant fruit extract ^* 4 0.1

(19) Distilled water Surplus

^* Made by 1 Sigma Corporation

^* 2 Manufactured in Example 1

^* 3 Manufactured by Toyo Refined Sugar Co., Ltd.

^* 4 manufactured in Example 23

[Example 42: Emulsion]

Heat and mix the following ingredients (1)-(8) to 70°C. To this mixture, was added and mixed, and the mixed (9) to (11) and (17) were heated at 70° C. and cooled. To this, (12) and (13) to (16) were added and mixed to obtain an emulsion.

(Element) (%)

(1) Hydrogenated soybean lecithin 3.0

(2) Cholesterol 0.2

(3) Polyethylene oxide (5) Cetyl ether 0.2

(4) Polyethylene oxide (10) hardened castor oil 1.0

(5) Stearyl cetyl alcohol mixture 2.0

(6) Olive Tridecane 5.0

(7) Dipropylene glycol 7.0

(8) 1,3-Butanediol 5.0

(9) Trimethylglycine 2.0

(10)Hydroxypropylmethylcellulose 0.1

(11) Carboxyvinyl polymer 0.2

(12) Potassium hydroxide 0.1

(13) Preservatives Appropriate amount

(14) Spices Appropriate amount

(15) Cistus ladaniferus L. extract ^* 1 0.1

(16) Cactus Extract ^* 2 0.5

(17) Distilled water Surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 29

[Example 43: Sunscreen Lotion]

Components (1) to (11) were heated and mixed at 70°C to disperse into a slurry. Components (12)-(14) and (16)-(20) dissolved and mixed at 50°C were mixed here, and component (15) was added to obtain a sunscreen lotion.

(Element) (%)

(1) Neopentyl glycol dicaprate 10.0

(2) p-Methoxycinnamic acid-2-ethylhexyl 5.0

(3) Octamethylcyclotetrasiloxane 10.0

(4) Decamethylcyclopentasiloxane 10.0

(5)Dimethicone 5.0

(6) Particulate Titanium Oxide 10.0

(7) Particulate Zinc Oxide 5.0

(8) Polyalkylene modified organosiloxane 5.0

(9) Glycyrrhetinic acid stearyl 0.3

(10) Nylon powder 2.0

(11)Polyethylene end 1.0

(12) Glycerin 5.0

(13)Ethanol 5.0

(14) Preservatives Appropriate amount

(15) Spices Appropriate amount

(16) Cistus ladaniferus L. extract ^* 1 0.2

(17)Dipotassium glycyrrhizinate 0.1

(18) Spatholobus extract ^* 2 0.1

(19) Cranberry Extract ^* 3 0.1

(20) Distilled water Surplus

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 26

^* 3 manufactured in Example 25

[Example 44: Water-in-oil sunscreen]

Under the condition of 70°C, the following ingredients (1) to (8) were heated and mixed. Components (9)-(13) and (15)-(18) which were heated and mixed at 50°C were added and mixed therein, and then component (14) was added to obtain a water-in-oil type sunscreen.

(Element) (%)

(1) Polyalkylene modified organosiloxane 2.0

(2) Octyl palmitate 15.0

(3) Decamethylcyclopentasiloxane 20.0

(4) Glyceryl Tribehenate 1.0

(5) Particulate Zinc Oxide 12.0

(6) Particulate Titanium Oxide 3.0

(7) p-Methoxycinnamic acid-2-ethylhexyl 7.0

(8) 4-tert-butyl-4'-methoxydibenzoylmethane 1.0

(9) Astaxanthin ^* 1 0.05

(10)Dipropylene glycol 5.0

(11)Ethanol 5.0

(12)Polyethylene end 3.0

(13) Preservatives Appropriate amount

(14) Spices Appropriate amount

(15) Cistus ladaniferus L. extract ^* 2 0.2

(16) Birch Sap ^* 3 0.2

(17) Cornflower extract ^* 4 0.2

(18). Distilled water balance

^* Made by 1 Sigma Corporation

^* 2 Manufactured in Example 1

^* 3 manufactured in Example 27

^* 4 manufactured in Example 28

[Example 45: Beauty Essence]

A mixture was prepared by heating and mixing components (7) to (12) and (19) at 50°C, and cooling to room temperature. To this mixture, a solution obtained by mixing and dissolving the following ingredients (1) to (6) at 50°C and ingredients (13) to (18) were added to obtain a viscous beauty serum.

(Element) (%)

(1) Polyoxyethylene isostearate (50) hardened castor oil 0.2

(2) Hydrogenated soybean lecithin 0.5

(3) Glycerin 7.0

(4) dl-α-tocopherol 0.3

(5) Cholesterol 0.1

(6) Ethanol 6.0

(7) Sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate 0.2

(8)L-Magnesium Ascorbyl Phosphate 0.5

(9) Citric acid 0.01

(10)Sodium citrate 0.1

(11) Xanthan gum 0.1

(12)Methylcellulose 0.1

(13) Cistus ladaniferus L. extract ^* 1 0.1

(14) Licorice Extract ^* 2 0.1

(15) Coix Seed Extract ^* 3 0.1

(16) Cranberry fruit extract ^* 4 0.1

(17) Preservatives Appropriate amount

(18) Spices Appropriate amount

(19) Distilled water Surplus

^* 1 Manufactured in Example 1

^* 2 Manufactured by Maruzen Pharmaceutical Co., Ltd.

^* 3 manufactured in Example 22

^* 4 manufactured in Example 25

[Example 46: Beauty cream]

Heat and mix the following components (1)-(5) and (19) at 70°C, and add the mixed components (6)-(18) to the mixture after cooling to room temperature to obtain a cosmetic cream.

(Element) (%)

(1) Polyvinyl alcohol 15.0

(2) Glycerin 10.0

(3) Polyoxyethylene (10) methylglucose 3.0

(4) Glyceryl tricaprylate 5.0

(5) Sodium polyoxyethylene alkyl ether phosphate 1.0

(6) Ethanol 20.0

(7) Clay 2.0

(8) Titanium oxide 2.0

(9) Seaweed Extract 0.1

(10)Dipotassium glycyrrhizinate 0.1

(11) Cactus Extract ^* 1 0.1

(12) Birch Sap ^* 2 1.0

(13) Inula extract ^* 3 0.1

(14) Lactic acid (50% aqueous solution) 0.5

(15) Sodium lactate (50% aqueous solution) 0.5

(16) Preservatives Appropriate amount

(17) Spices Appropriate amount

(18) Cistus ladaniferus L. extract ^* 4 0.02

(19) Distilled water surplus

^* 1 manufactured in Example 29

^* 2 manufactured in Example 27

^* 3 manufactured in Example 24

^* 4 Manufactured in Example 1

[Example 47: Liquid Foundation]

The following components (1)-(7) were heated and mixed, and components (13)-(18) were heated and mixed in this mixture, and maintained at 70°C. To the mixture of components (8) to (12) kept at 70°C, the above mixture was added to uniformly emulsify. After cooling, components (19) to (22) were added to obtain a liquid foundation.

(Element) (%)

(1) Dipentaerythritol fatty acid ester 2.0

(2) Liquid paraffin 5.0

(3) Stearic acid 2.0

(4) Cetyl Alcohol 1.0

(5) Self-emulsifying glycerol monostearate 1.0

(6) p-methoxycinnamic acid-2-ethylhexyl 8.0

(7) Appropriate amount of preservatives

(8) Glycerin 5.0

(9) Triethanolamine 1.0

(10)Carboxymethylcellulose 0.2

(11) Bentonite 0.5

(12) Distilled water balance

(13)Titanium oxide 6.0

(14) Particulate Titanium Oxide 2.0

(15) Particulate Zinc Oxide 4.0

(16)Mica 2.0

(17) Talc 4.0

(18) Coloring pigment Appropriate amount

(19) Cistus ladaniferus L. extract ^* 1 0.01

(20) Coix Seed Extract ^* 2 0.5

(21) Cornflower extract ^* 3 1.0

(22) Spices Appropriate amount

^* 1 Manufactured in Example 1

^* 2 manufactured in Example 22

^* 3 manufactured in Example 28

The various cosmetics obtained in Examples 37 to 47 all have long-lasting stability, and are effective in preventing and improving skin dullness, brown spots and freckles caused by sun exposure, and wrinkles and skin sagging caused by aging. Skin-beautifying cosmetics with a sense of transparency.

Industrial availability

As described above, the present invention can provide a skin external preparation excellent in skin beautification effects, especially whitening and/or anti-aging effects. This good effect is that the compound represented by the above-mentioned general formula (1) is used in combination with a specific component to achieve an enhanced effect. When the compound represented by the above-mentioned general formula (1) is used alone and the specific component is used alone, it cannot be achieved. Remarkable and excellent skin beautification, whitening and/or anti-aging effects are achieved.

Claims (3)

1. skin whitening external agent contains in (A) one or more following general formula (1), general formula (1) R ¹Expression-CH ₂OH or COOR ⁶, R ⁶Expression hydrogen, carbon number be 1～3 low alkyl group or can with the salifiable cation of COO shape, R ²～R ⁵Independent respectively expression hydrogen atom or methyl ... A ... expression=C (CH ₃)-,-C (CH ₃)=,-C (=CH ₂)-,-CH (CH ₃)-or-C (OH) (CH ₃The chemical compound of)-expression, (B) be selected from the active ingredient that the moisture 1,3 butylene glycol extract of 50vol% of 50vol% aquiferous ethanol extract, Flos Inulae 50vol% aquiferous ethanol extract, the cranberry fruit of one or more the 70vol% aquiferous ethanol extract by oil-soluble Radix Glycyrrhizae extract, Semen Coicis, black currant fruit constitutes

General formula (1)

2. one kind prevents skin aging external agent, contains in (A) one or more following general formula (1), general formula (1) R ¹Expression-CH ₂OH or COOR ⁶, R ⁶Expression hydrogen, carbon number be 1～3 low alkyl group or can with the salifiable cation of COO shape, R ₂～R ₅Independent respectively expression hydrogen atom or methyl ... A ... expression=C (CH3)-,-C (CH3)=,-C (=CH ₂)-,-CH (CH ₃)-or-C (OH) (CH ₃The chemical compound of)-expression and (B1) active ingredient that constitutes of one or both the Purified Water extract that is selected from Radix et Caulis Opuntiae Dillenii, astaxanthin

General formula (1)

3. claim 1 or 2 described external agent, the represented chemical compound of described general formula (1) be the following compounds 1,4 extracted in one or more the plant among the plant group who constitutes by the Cistus ladaniferus L. that is selected from Cistaceae, Cistus creticus L., CistusMonopehensis L., Cistus salvifolius and 7 and this chemical compound through the chemical compound of esterification, or the following compounds 3,6 and 9 of ethyl esterization

Chemical compound 1 chemical compound 4

Chemical compound 2 chemical compounds 5

Chemical compound 3 chemical compounds 6

Chemical compound 7

Chemical compound 8

Chemical compound 9