JP2021080197A - Antiallergic agent - Google Patents

Abstract

【Task】
Anti-allergic agents expected to have anti-allergic effects, anti-allergic agents containing fragrance compounds as active ingredients, degranulation inhibitors, β-hexosaminidase release inhibitors, flavor / aroma compositions containing them, and various products containing them. The purpose is to provide.
SOLUTION: One or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone and cis-jasmon are contained as an active ingredient.
[Selection diagram] Fig. 1

Description

The present invention is an antiallergic agent, a degranulation inhibitor, and β-, which contain one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as active ingredients. Regarding hexosaminidase release inhibitor. Furthermore, the present invention relates to flavor / aroma compositions and various products containing these.

In recent years, the increase in allergic diseases has become so remarkable that it becomes a social problem. In particular, allergic reactions such as pollinosis, bronchial asthma, allergic rhinitis, and allergic conjunctivitis are called type I allergies (immediate type allergies) and are said to be caused by excessive immune reactions.
In the treatment of allergic diseases, drugs such as antihistamines and steroids have been prescribed as symptomatic treatments, but these drugs have side effects such as drowsiness and dry mouth gastrointestinal disorders, and long-term administration has become a problem. .. Therefore, it has been desired to develop a safe, secure and easy-to-manufacture effective material that can reduce, suppress or prevent allergic symptoms and can be incorporated into daily eating habits.

Under such circumstances, substances having an anti-allergic action contained in plant components and food components originating from natural products that are familiar and have no side effects are being searched for. For example, an anti-allergic food (Patent Document 1) containing a water-soluble extract, a tea extract, and a perilla leaf extract extracted from the seeds of a perilla family plant that relieves all allergic symptoms, and partial decomposition of hemicellulose obtained from corn hulls. Contains anti-allergic agent (Patent Document 2) that suppresses the occurrence of atopic dermatitis, which contains a substance as an active ingredient, Seikoboku, Kinugasatake, Musigoke, Kosho, Tamarind, Shozuku, Yamadoritake, Kiiroiguchi, Suikazura, and Philanthus embrica. Anti-allergic agents effective for treating various allergic diseases and alleviating their symptoms (Patent Document 3), anti-allergic compositions consisting of isoflavones (Patent Document 4), Mikan family Mikan genus, Citrus genus, Agassosma and Izuhahako An antiallergic agent (Patent Document 5) has been reported, which comprises a processed product and / or an extract of a plant of a genus or the like as an active ingredient, and improves immunological deterioration due to aging and stress and improves allergic diseases. Further, as a single fragrance product, a single product having an anti-allergic effect in essential oils (Non-Patent Documents 1 and 2) has been reported.

However, the above-mentioned antiallergic agents often have problems that it is difficult to maintain a certain effect because the preparation method for securing a sufficient amount is often complicated or requires a long time. In that sense, it cannot be said that it has a satisfactory anti-allergic effect, and basically it was necessary to take it orally as before.
There are few reports on single fragrances, and there are no reports that have been comprehensively verified.

Although histamine is widely known as an index of allergy, β-hexosaminidase is also released at the same time as histamine in degranulation from mast cells. Since it is easier to measure the β-hexosaminidase release inhibitory effect than histamine, β-hexosaminidase activity is generally used as an index for evaluating the antiallergic effect.

By the way, fragrances are used in various foods and drinks and various products closely related to daily life such as cosmetics, and in addition to the function of enhancing the flavor of foods and drinks, various physiology such as relaxation and promotion of concentration The effect has also been confirmed. However, there are many unclear points about the physiological effect, and new uses that are useful in daily life are expected. If the fragrance can reduce, suppress or prevent allergic symptoms, it can be a simpler and more economical anti-allergic agent. However, as mentioned above, there are not enough reports on the anti-allergic effect, the degranulation inhibitory effect, and the β-hexosaminidase release inhibitory effect of a single fragrance.

Japanese Unexamined Patent Publication No. 11-56297 JP-A-2002-338488 Japanese Unexamined Patent Publication No. 2004-262905 Japanese Unexamined Patent Publication No. 2006-348003 Japanese Unexamined Patent Publication No. 2011-213647

Jitsutakara, 6 others "Anti-allergic effect of geranium essential oil and its main component, citronellol" Japan Society for Bioscience and Biotechnology 2016 Annual Meeting 2E099 Kobayashi and 5 others "Anti-allergic effect of fennel essential oil and its main component, trans-anethole" Japan Society for Bioscience and Biotechnology 2017 Annual Meeting 2B10a07

The present invention has been made in view of such circumstances, and is expected to have an effect of preventing, suppressing, and reducing allergic reactions, and is a fragrance substance that is safe, has a low inoculation load, and is easy to obtain and manufacture as a raw material. It is an object of the present invention to provide an antiallergic agent containing an active ingredient, a degranulation inhibitor, a β-hexosaminidase release inhibitor, a flavor / aroma composition containing the same, and various products.

As a result of diligent studies to solve the above problems, the present inventors surprisingly selected one or two species from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon. We have found that the above substances have an anti-allergic effect, an inhibitory effect on degranulation, and an inhibitory effect on β-hexosaminidase release, and further studies have finally completed the present invention. The study was conducted in an assay system for cell experiments, respecting the recent ideas of animal welfare and animal cruelty prevention.

The present invention relates to the following [1] to [8].
[1] An antiallergic agent containing one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient.
[2] The antiallergic agent according to [1], which is based on a degranulation inhibitory action.
[3] A flavor / aroma composition having an anti-allergic effect, which comprises the anti-allergic agent according to [1] or [2].
[4] Anti-allergic foods and drinks, anti-allergic foods and drinks, which contain the anti-allergic agent according to [1] or [2], or the flavor / aroma composition having the anti-allergic effect according to [3]. Cosmetics for allergies, oral compositions for anti-allergies, pharmaceuticals for anti-allergies or daily miscellaneous products for anti-allergies.
[5] A degranulation inhibitor containing one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient.
[6] A flavor / aroma composition having a degranulation inhibitory effect, which comprises the degranulation inhibitor according to [5].
[7] A food or drink for suppressing degranulation, degranulation, which comprises the degranulation inhibitor according to [5] or the flavor / aroma composition having the degranulation inhibitory effect according to [6]. Cosmetics for suppression, oral compositions for suppressing degranulation, pharmaceuticals for suppressing degranulation, or daily miscellaneous goods for suppressing degranulation.
[8] A β-hexosaminidase release inhibitor containing one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient.

One or more perfume substances or perfume compositions selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon of the present invention are antiallergic agents, degranulation inhibitors, and β. -Useful as an inhibitor of hexosaminidase release. Further, since the specific fragrance substance of the present invention is a general-purpose ingredient as a fragrance, it is easily available, has high utility in various products, and is expected to have an extremely high range of application.

It is a graph which shows the result of having calculated the β-hexosaminidase activity of Comparative Example 1 and Examples 1 to 4 when TMP-BSA was used as a stimulant. It is a graph which shows the result of having calculated the β-hexosaminidase activity of Comparative Example 2 and Example 5-8 when A23187 was used as a stimulant.

Hereinafter, the present invention will be described in detail.

<Anti-allergic agent, degranulation inhibitor, β-hexosaminidase release inhibitor>
An antiallergic agent containing, for example, one or more selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient is, for example, a so-called anti-I. It may be a type allergic agent. Further, it may be based on the degranulation inhibitory action of mast cells or basophils.

The mechanism of type I allergic reaction is as follows.
(1) When an antigen (allergen) such as pollen or mite invades the living body, it is taken up by an antigen-presenting cell (macrophage or the like) and presents the antigen to a helper T cell (Th2 cell). T cells issue commands to differentiate B cells into immunoglobulin E (Immunoglobulin E) antibody-producing cells.
(2) IgE antibody-specific IgE antibody is produced from IgE antibody-producing cells.
(3) The IgE antibody binds to the high-affinity IgE receptor (FcεRI) expressed on mast cells or basophils.
(4) When IgE on the receptor is cross-linked by the antigen that has invaded again, the receptor aggregates and secretes chemical mediators such as histamine, β-hexosaminidase, leukotriene, and prostaglandin (chemical mediator). It is degranulated) and allergic symptoms develop.

Specific examples of the above allergic symptoms include bronchial asthma, rhinitis, hay fever, food allergies, atopic dermatitis, urticaria, and anaphylactic shock, but the effects of the antiallergic agent of the present invention are limited to these. Not done.

The degranulation inhibitor and β-hexosaminidase release inhibitor of the present invention are any of application to foods such as health foods, preventive agents, ameliorating agents, palliative agents and therapeutic agents for allergic effects. Of course, it may be more than one.

<Specific fragrance ingredients>
Salicylaldehyde, benzylsalicylate, mintlactone, and cis-jasmon, which are fragrance substances exhibiting antiallergic action, degranulation inhibitory action, and β-hexosaminidase release inhibitory action in the present invention, were obtained by any method. It may be a thing. That is, it may be a commercially available product, may be synthesized by a known method, may be extracted from a natural product, or may be produced by a fermentation method or the like. The fragrance substance referred to here is synonymous with a compound used as a fragrance.

<Aroma / flavor composition>
The antiallergic agent, degranulation inhibitor, or β-hexosaminidase release inhibitor of the present invention is added / blended to a flavor or fragrance to form an aroma composition or a flavor composition (hereinafter referred to as an aroma / flavor composition). It is also within the scope of the present invention.
Since the specific fragrance component used in the present invention is widely used as a fragrance, the antiallergic agent, degranulation inhibitor, and β-hexosaminidase release inhibitor of the present invention are easily compatible with many flavors or fragrances. Moreover, even if they are blended with the blended fragrance, the balance of the scent of the blended fragrance as a whole is not disturbed.

The following description takes up the antiallergic agent, but the degranulation inhibitor and the β-hexosaminidase release inhibitor defined in the present invention are the same as the antiallergic agent.
Specific examples of fragrances that can coexist with the antiallergic agent of the present invention are shown below.
Flavors include synthetic fragrances such as esters, alcohols, aldehydes, ketones, acetals, phenols, ethers, lactones, furans, hydrocarbons, nitrogen-containing compounds, sulfur-containing compounds, and acids. And so on.
Natural fragrances may be used if necessary.
Examples of the above esters include acetoacetic acid esters (methyl, ethyl, etc.), anisic acid esters (methyl, ethyl, etc.), benzoic acid esters (allyl, isoamyl, ethyl, geranyl, linaryl, phenylethyl, hexyl, cis-3). -Hexenyl, benzyl, methyl, etc.), anthranyl ester (cinnamyl, cis-3-hexenyl, methyl, ethyl, linaryl, isobutyl, etc.), octanoate ester (allyl, isoamyl, ethyl, octyl, hexyl, butyl, methyl, linaryl, etc.) Etc.), Octenoic acid ester (methyl, ethyl, etc.), Octincarboxylic acid ester (methyl, ethyl, etc.), Caproic acid ester (allyl, amyl, isoamyl, methyl, ethyl, isobutyl, propyl, hexyl, cis-3-hexenyl, etc.) Trans-2-hexenyl, linaryl, geranyl, cyclohexyl, etc.), hexenoic acid ester (methyl, ethyl, etc.), valerate ester (amyl, isopropyl, isobutyl, ethyl, cis-3-hexenyl, trans-2-hexenyl, cinnamyl, Phenylethyl, methyl, etc.), silicic acid ester (allyl, ethyl, methyl, isopropyl, propyl, 3-phenylpropyl, benzyl, cyclohexyl, methyl, etc.), acetate ester (anicil, amyl, α-amylcinnamyl, isoamyl, isobutyl, etc.) Isopropyl, isopregil, isobornyl, isoeugenyl, eugenyl, 2-ethylbutyl, ethyl, 3-octyl, calvir, dihydrocarbyl, p-gredyl, o-cresyl, geranyl, α- or β-santalyl, cyclohexyl, cycloneryl, dihydrocuminyl, Dimethylbenzylcarvinyl, cinnamyl, styralyl, decyl, dodecyl, esterinyl, guainyl, neryl, nonyl, phenylethyl, phenylpropyl, butyl, furfuryl, propyl, hexyl, cis-3-hexenyl, trans-2-hexenyl, cis-3 -Nonenyl, cis-6-nonenyl, cis-3, cis-6-nonazienyl, 3-methyl-2-butenyl, menthyl, heptyl, benzyl, bornyl, myrsenyl, dihydromyrsenyl, myltenyl, methyl, 2- Methylbutyl, menthyl, linaryl, rosinyl, etc.), stearic acid ester (ethyl, propyl, butyl, etc.), lactic acid ester (isoamyl, ethyl, tyl, etc.), nonanoic acid ester (ethyl, phenylethyl, methyl, etc.), hydroxyhexanoic acid Examples thereof include esters (ethyl, methyl, etc.), phenylacetic acid esters (isoamyl, isobutyl, ethyl, geranyl, citronellyl, cis-3-hexenyl, methyl, etc.) and the like.

As the alcohols, for example, aliphatic alcohols (isoamyl alcohol, isopregol, 2-ethylhexanol, 1-octanol, 3-octanol, 1-decanol, 1-dodecanol, etc.), terpene alcohols, aromatic alcohols and the like are preferably exemplified. can do.
Examples of the aldehydes include aliphatic aldehydes, aromatic aldehydes, and terpene aldehydes.
Examples of the ketones include menton, pregon, piperitone, α-, β-, γ- or δ-damascenone, α-, β- or γ-damacenone, nuitocatone, 2-sec-butyldiclohexanone, and malt. Cyclic ketones such as α-, β- or γ-yonone, α-, β- or γ-methylyonone, α-, β- or γ-isomethylyonone, aromatic ketones such as acetophenone, anicylideneacetone, and raspberry ketone. , Diacetyl, chain ketones such as 2-hebutanone, and the like can be exemplified.
Examples of the acetals include acetaldehyde diethyl acetal, acetaldehyde, diamil acetal, 2-phenylpropanal dimethyl acetal and the like.

Examples of the phenols include eugenol, isoeugenol, 2-methoxy-4-vinylphenol, thymol, guaiacol and the like.
Examples of ethers include anethole, 1,4-cineole, 1,8-cineole, dibenzyl ether, linalool oxide, limonene oxide, nerol oxide, rose oxide, vanillyl butyl ether and the like.
Examples of the lactones include γ- or δ-decalactone, γ-heptalactone, γ-nononalactone and the like.

Examples of the furans include furan, 2-methylfuran, 3-methylfuran, 2-ethylfuran, 2,5-diethyltetrahydrofuran, 3-hydroxy-2-methyltetrahydrofuran, furfuryl acetate and the like.
Examples of hydrocarbons include terpinene, terpinene, farnesene, limonene, ocimene, myrcene, α- or β-pinene and the like.

Examples of the acids include octanoic acid, nonanoic acid, decanoic acid, 2-decenoic acid, geranic acid, dodecanoic acid, myristic acid, stearic acid, lactic acid, phenylacetic acid, pyruvic acid, cyclohexanecarboxylic acid and the like. it can.

Examples of the fragrance include hydrocarbons, alcohols, phenols, aldehydes and / or acetals, ketones and / or ketals, ethers, synthetic musk, acids, lactones, esters, halogen-containing compounds and the like. Can be mentioned. Natural fragrances may be used if necessary.

The above-mentioned hydrocarbons are not particularly limited as long as they are volatile organic compounds composed of carbon and hydrogen, and are aliphatic hydrocarbons, ring hydrocarbons, terpene hydrocarbons, and aromatic hydrocarbons. Kind and the like are exemplified. Preferably 1,3,5-undecatorien, p-cymen, α-pinene, α-phellandrene, β-cariophyllene, β-pinene, Δ-calene, aloosine, ocimene, dihydromyrcene, dipentene, sclarene, sedrene. , Terpinene, terpinene, phellandrene, visaborene, myrcene, limonene, adamantane, camphene and the like.

The alcohols are not particularly limited as long as they are volatile organic compounds having a hydroxyl group, and examples thereof include aliphatic alcohols, ring-type alcohols, terpene alcohols, aromatic alcohols, and the like, preferably 10. -Undecenol, 1-octen-3-ol, 2,6-nonadienol, 2-tert-butylcyclohexanol, 2-ethylhexanol, 2-heptanol, 3,5,5-trimethylhexanol, 3-octanol, 3-phenylpropi Lu alcohol, L-menthol, n-decyl alcohol, p, α-dimethylbenzyl alcohol, p-tert-butylcyclohexanol, p-methyldimethylbenzylcarbinol, α, 3,3-trimethyl-2-norbornanmethanol , Α-n-amyl cinnamic alcohol, α-fenkyll alcohol, β-phenylethyl alcohol, anis alcohol, amber core, ambrinol, isononyl alcohol, isophytol, isopregol, isobornol, ethyllinalol, octanol, carbeol , Geraniol, Santarol, cis-3-hexen-1-ol, cis-6-nonenor, citronellol, dihydro-α-futterpineol, dihydrocitronellol, dihydromilsenol, dihydrolinalol, dimethylphenylethylcarbinol, Dimethylbenzyl carbinol, synamic alcohol, styralyl alcohol, sedrol, tapineol, tapinen-4-ol, timbrelol, tetrahydrogeraniol, tetrahydromilsenol, tetrahydromugor, tetrahydrolinalol, nerol, nerolidol, nonanol , Nonyl alcohol, Nopol, Hydrotropyl alcohol, Bakudanol, Farnesol, Phytoyl, Phenylethylmethylethylcarbinol, Phenoxyethyl alcohol, Flufuryl alcohol, Vetiberol, Perilla alcohol, benzyl alcohol, Mayor, Milsenol, Miltenol, Laban Examples include jurol and linalol.

The phenols are not particularly limited as long as they are phenolic compounds and derivatives thereof and are organic compounds having a scent. For example, monovalent, divalent, trivalent phenolic compounds, polyphenols, or these. Examples thereof include ether derivatives of the compounds of the above, preferably p-cresol, estragor, eugenol, hinokithiol, 2,6-dimethoxyphenol, 4-ethylguayacol, 4-methylguayacol, β-naphthol isobutyl ether, isosaflor, guayacol. , Saflor, dihydroeugenol, timol, shogaol and the like.

The aldehydes or acetals are not particularly limited as long as they are volatile organic compounds having an aldehyde group or an acetal group in the molecule, and are not particularly limited as long as they are aliphatic aldehydes or acetals, terpene aldehydes or acetals, aromatic aldehydes or acetals. Etc., preferably 10-undecenyl, 2,4-dimethyl-4,4a, 5,9b-tetrahydroindeno [1,2d] -1,3-dioxin, 2,4-decadienal, 2,6- Nadienal, 2-butyl 4,4,6-trimethyl-1,3-dioxane, 2-hexyl-5-methyl-1,3-dioxolane, 2-methylaldehyde, 2-methylundecal dimethylacetal, 3-ethyl -2,4-dioxaspiro [5.5] undeca-8-ene, 3-ethyl-8 (9), 11-dimethyl-2,4-dioxaspiro [5.5] undeca-8-ene, 3-propylbicyclo [2.2.1] -Hepta-5-en-2-carboxyaldehyde, 4-isopropyl-5,5-dimethyl-l, 3-dioxane, 4-heptenal, 5-methyl-5-propyl-2- ( 1-Methylbutyl) -1,3-dioxane, o-methoxycinnamic aldehyde, o-methoxybenzaldehyde, p-tolylaldehyde, α-n-hexylcinnamic aldehyde, α-amylcinnamic aldehyde, acetaldehyde, acetaldehyde ethyllinalyl acetal , Acetaldehyde diethyl acetal, anisaldehyde, aldehyde C-10, aldehyde C-11, aldehyde C-12, aldehyde C-6, aldehyde C-6DEA, aldehyde C-6DMA, aldehyde C-6PG acetal, aldehyde C-8, aldehyde C-8DEA, Aldehyde C-8DMA, Aldehyde C-9, Aldehyde C-9DEA, Aldehyde C-9DMA, Isocyclocitral, Ethylvanillin, Cantoxal, Cucumberaldehyde, Cuminaldehyde, Geranial, Cyclamenaldehyde, Sis-6-nonenal , Citral, Citroneral, Citroneryloxyacetaldehyde, Sinensal, Dupical, Trans-2-hexenal, Trans-2-hexenal Diethylacedar, Triplar, Neral, Hydrotropaldehyde, Vanillin, Hydroxycitroneral, Phenylacetaldehyde, Phenylacetaldehyde P. G. Examples thereof include acetal, phenylacetaldehyde, dimethylacetal, furfural, florarozone, heliotropin, helional, perillaaldehyde, bergamar, belt acetal, berundaldehyde, benzaldehyde, homomylacaldehyde, mylacaldehyde, meronal, lylar, and lilial.

The above-mentioned ketones or ketals are not particularly limited as long as they are volatile organic compounds having a ketone group or a ketal group in the molecule, and are not particularly limited as long as they are aliphatic ketones or ketals, terpene-based ketones or ketals, aromatic ketones or ketals. Etc. are exemplified, and preferably 2-sec-butylcyclohexanone, 2-acetyl-3,3-dimethylnorbornane, 2-acetyl-5-methylfuran, 2-acetylfuran, 2-butyl1,4-dioxaspiro [4, 4] Nonan, 2-hexylcyclopentanone, 3-hydroxy-4,5-dimethyl-2- (5H) -furanone, 5-ethyl-3-hydroxy-4-methyl-2 (5H) -furanone, 6- Methyl-3,5-heptadien-2-one, d-pregon, l-carboxylic, o-tert-butylcyclohexanone, p-tert-butylcyclohexanone, p-methylacetophenone, p-methoxyacetophenone, α-dynascon, α- Fencon, β-Methylnaphthylketone, Acetylsedrene, Acetphenone, Anisylacetone, Allylα-Ionone, Ionone, IsoE Super, Isojasmon, Isodamascon, Isolongihoranone, Iron, Ethylisoamylketone, Ethylmaltor, Cashmerelan, Power Lawn, Kamfer, Corebon, Hecycloten, Dihydrocarboxylic, Dihydrojasmon, Dibenzyl Ketone, Cedrenone, Sotron, Damascon, Damasenon, Trimofix, Nutcaton, Flaneol, Plicaton, Florex, Beltfix, Belbenon, Benzophenone, Maltoyl, Examples thereof include methyl ionone, methyl cyclopentenolone, methyl heptenone, menton, and raspberry ketone.

The ethers are not particularly limited as long as they are volatile organic compounds having an ether group in the molecule, and examples thereof include aliphatic ethers, terpene ethers, and aromatic ethers, and 1,4-cineole is preferable. , 1,8-cineole, p-cresylmethyl ether, β-cariophyllene oxide, β-naphthylisobutyl ether, β-naphthylethyl ether, β-naphthylmethyl ether, anethol, ambroxane, isoamylphenylethyl ether, iso Bornyl methyl ether, glycalva, cyclan bar, diphenyl oxide, sedlum bar, sedrill methyl ether, theaspiran, nerol oxide, phenylethyl methyl ether, madrox, linalol oxide, limetol, lubofix, luboflor, rose oxide, rose furan, etc. Is exemplified.

The synthetic musk is not particularly limited as long as it is an organic compound having a musk scent or a musk-like scent, and is 10-oxahexadecanolide, 11-oxahexadecanolide, 12-oxahexadecanolide. , Ambrettolide, Umbrettolide, Exaltride, Exalton, Galaxolide, Cyclohexadecanolide, Cyclopentadecanolide, Cyclopentadecanolide, Sibeton, Serbolide, Celestride, Tonalide, Fantride, Pentalido, Formylethyltetramethyltetraline, Muscon, Examples include bersalides.

The above-mentioned acids are not particularly limited as long as they are organic compounds having a carboxyl group in the molecule, and are phenylacetic acid, 2-ethylbutyric acid, 2-ethylhexanoisoquaid, 2-decenoic acid. , 2-Methylbutyric Acid, 2-MethylHeptanoic Acid, Undecanoic Acid, Undecylenic Acid, Myristic Acid, Lactic Acid, Linolic Acid, Linolenic Acid, Maleic Acid, Malonic Acid Etc. are exemplified.

The lactones are not particularly limited as long as they are volatile organic compounds having a lactone group in the molecule, and examples thereof include aliphatic lactones, terpene-based lactones, and aromatic lactones, preferably 6-methylcoumarin. γ-n-butyrolactone, γ-undecalactone, γ-hexalactone, γ-heptalactone, δ-2-decenolactone, coumarin, dihydrojasmon lactone, jasmine lactone, jasmolactone, octahydrocoumarin, dihydrocoumarin, 3- Examples include propylphthalide and the like.

The esters are not particularly limited as long as they are volatile organic compounds having an ester group in the molecule, and examples thereof include aliphatic esters, terpene esters, aromatic esters, and preferably 1-ethynyl siglohexyl. Acetate, 1-octen-3-yl acetate, 2-ethylhexyl acetate, 2-phenoxyethyl isoamyl acetate, l-mentyl acetate, l-mentyl propionate, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl Acetate, acetylisooygenol, acetyleugenol, anisyl acetate, amyl salicylate, amylvalerate, allylcyclohexyloxyacetate, allyl cinnamate, allylphenoxyacetate, allylbutyrate, isoamyl angelate, isoamyl isovalerate, isoamyl isobuchi Rate, isoamyl undecilenate, isoamyl octanoate, isoamyl salicylate, isoamyl cinnamate, isoamyl decanoate, isoamyl decanoate, isoamyl butyrate, isoamyl propionate, isoamyl hexanoate, isoamyl heptine carbonate, isobutyl cinna Mate, isobutyl valerate, isobutyl phenyl acetate, iso butyl butyrate, iso butyl propionate, iso butyl hexanoate, iso butyl benzoate, isopregyl acetate, isopropyl acetate, isobornyl propionate, ethyl 2-tert-butyl cyclohexyl carbonate , Ethyl o-methoxybenzoate, ethyl p-anisate, ethyl acetate, ethyl acetoacetate, ethyl isovalerate, ethyl isobutyrate, ethyl octine carbonate, ethyl cinnamate, ethyl valerate, ethyl phenyl acetate, ethyl butyrate, ethyl Propionate, ethyl heptanoate, ethyl heptine carbonate, ethyl pelargonate, ethyl benzoate, ethylene dodecandioate, ethylene brush rate, eugenyl phenyl acetate, octyl acetate, octyl isovalerate, octyl isobutyrate, octyl Octanoate, octylbutyrate, octylhebutanoate, octylhomet, osimenyl acetate, cariophyllene acetate, cariophyllenhomet, calvir acetate, guaia Cucacetate, cuminyl acetate, geranyl acetate, geranyl isovalerate, geranyl isobutyrate, geranyl titrate, geranyl phenyl acetate, geranyl butyrate, santalyl acetate, diethyl adipate, diethyl succinate, diethyl sevacate, diethyl tartrate. , Benzylphthalate, cyclohexylacetate, cyclohexylisovalerate, cyclohexylethylacetate, cyclohexylrotonate, cis-3-hexenylpropionate, cis-3-hexenylbenzoate, cis-3-hexenylhomete, cis-3-3- Hexenyllactate, citril acetate, citronellyl acetate, citronellylphenyl acetate, citronellyl butyrate, dihydrocarbyl acetate, dihydrocuminyl acetate, dihydrotaipinyl acetate, dihydromyrsenyl acetate, dimethylsuccinate, dimethylphenylethyl Carvinyl acetate, turpinylhomet, decahydro-β-naphthylhomet, decyl acetate, tetrahydrofurfurylbutyrate, tetrahydrogeranyl acetate, triacetin, triethylcitrate, tricyclodecyl acetate, neryl acetate, neryl isobuty Rate, nerylbutyrate, nerylpropionate, butylacetate, butylhexanoate, butyllevulinate, furfurylacetate, heliotropyl acetate, benzyl2-methylbutyrate, benzylacetate, benzylisovalerate, benzylisobuty Rate, benzyl caprilate, benzyl salicylate, benzyl cycinamate, benzyl titrate, benzyl dodecanoate, benzyl valerate, benzyl phenyl acetate, benzyl butyrate, benzyl propionate, benzyl hexanoate, benzyl benzoate, benzyl ho Mate, Pentyl Salicylate, Methyl Salicylate, Methyl Cyclooctyl Carbonate, Methyl Cyclogeranate, Methyl Cyclopentylidene Acetate, Methyl Dihydro Jasmonate, Methyl Jasmonate, Methyl Sinnamate, Methyl Decanoate, Methyl Decin Carbonate, Linalyl Sinna Mate, Linalyl Butyrate, Linalyl Propionate, Linalyl Hexanoate, Linalyl Benzoate, Linalyl Homete, Loginyl phenylace Examples thereof include tate, loginyl butyrate, loginyl propionate, and loginyl homeate.

The halogen-containing compound is not particularly limited as long as it is an organic compound containing halogen in the molecule, and examples thereof include paradichlorobenzene and bromostyrene.

Furthermore, in addition to the above flavors and fragrances, the fragrances described in "Synthetic Fragrance Chemistry and Product Knowledge Augmented New Edition" (published on December 20, 2016, edited by the Synthetic Fragrance Editorial Committee, The Chemical Daily) can be used. ..

These flavors and fragrances may be used alone or in admixture of two or more. Commercially available products can also be used for these. Further, as a single product, a synthetic product may be used, or a natural product such as a plant may be introduced. Essential oils, resinoids, balsams, absolutes, concrete, tinctures and the like can also be prepared by known methods.

The natural fragrances that may be used in combination with flavors or fragrances are not particularly limited, and are not limited to almond oil, anise oil, avies fa oil, amyris oil, angelica oil, ambassador tincture, amber sage, amblet seed oil, etc. Iran Iran Oil, Insense Oil, Winter Green Oil, Elemi Oil, Oak Moss Absolute, Oak Moss Essence, Oak Moss Oil, Opoponax Oil, Oris Absolute, Orange Oil, Orange Flower Absolute, Cascarilla Oil, Castorium Resinoid, Cassia China Oil, Cassie Absolute, Cassher Oil, Kananga Java Oil, Camomile Oil Blue, Camo Mill Oil, Columns Oil, Cardamon Oil, Galvanum Oil, Caraway Oil, Guayak Wood Oil, Guayak Oil, Cumin Oil, Clove Bourbon Oil, Clove Oil, Costas Oil, Copaiba Balsam, Copaiva Oil, Coriander Oil, Cypress Oil, Sandalwood Oil, Cistrab Danum Oil, Cedarwood Oil, Citronella Oil, Civet Absolute, Jasmine Absolute, Juniper Berry Oil, Shownow Oil, John Kill Absolute, Ginger Oil, Ginger Glass Oil, Cinnamon Ceylon oil, Sweet fennel oil, Styrax oil, Spike lavender oil, Spare mint oil, Sage oil, Sage clary oil, Geranium oil, Geranium glass oil, Geradium bourbon oil, Cellory oil, Thyme oil, Taragon oil, Tangerine Oil, Tuberose Absolute, Trubal Sam, Trubal Sam Oil, Tonka Beans Oil, Natsumeg Oil, Narcissus Absolute, Neroli Bigarad Oil, Verbena Oil, Violet Leave Absolute, Pine Oil, Basil Oil, Parcel Seed Oil, Patchouli Oil, Vanilla Oil, Vanilla Reginoid, Hisop Oil, Bitter Almond Oil, Bitter Fennell Oil, Hinoki Oil, Hiba Oil, Pimento Berry Oil, Hyacinth Absolute, Petit Glen Oil, Butu Oil, Bay Oil, Petit Grain Glass Oil, Petit Grain Paraguay Oil, Petit Grain Bergamot Oil , Petit Grain Mandarin, Petit Grain Lemon Oil, Vetiva Oil Java, Vetiva Bourbon, Penny Royal Oil, Pepper Oil, Peppermint Oil, Peruvian Sam, Peruvian Sam Oil, Bergamot Oil, Benzoin Oil, Benzoin Reginoid, Boad Rose Oil, Hosho Oil , Horwood Oil, Majorum Oil, Mandarin Oil, Mimosa Absolute, Mill Oil, Muskton Kintinki, Mace Oil, Melissa Oil, Eucalyptus Oil, Lime Oil, Labandine Oil, Labdanum Oil, Lavender Oil, Lou Oil, Lemon Oil, Lemongrass Oil, Examples thereof include rose domei, rose bulgarian oil, rosemary oil, roman camomile oil, laurel oil, and lobage oil. These natural materials can also be used in various forms such as essential oils, resinoids, balsams, absolutes, concrete and tinctures.

The amount of the fragrance substance having an anti-allergic effect added / blended to the fragrance / flavor composition referred to in the present invention varies greatly depending on the coexisting fragrance or the purpose of use of the fragrance / flavor composition, and therefore should be uniformly specified. However, it is usually preferably about 0.001 to 20% by weight based on the aroma / flavor composition.

<Product>
The product targeted by the present invention is not particularly limited, and the benefit of adding an antiallergic agent containing one or more selected from the group consisting of the specific fragrance substances targeted by the present invention as an active ingredient can be obtained. It can cover a wide range of objects, including liquids, solids, semi-solids and fluids.
Typical examples of products containing the antiallergic agent of the present invention as an active ingredient include foods and drinks, oral compositions, pharmaceuticals, cosmetics, daily necessities and the like.
Furthermore, typical examples of products containing a flavor / aroma composition containing the antiallergic agent of the present invention as an active ingredient include foods and drinks, oral compositions, pharmaceuticals, cosmetics, daily necessities, and the like. Can be done. Here, pharmaceutical products include pharmaceutical products.

Specifically, as foods and drinks, for example, beverages such as fruit juice beverages, fruit liquors, carbonated beverages, soft beverages, drinks, dairy beverages; frozen desserts such as ice creams, sherbets, and ice candy. Classes; desserts such as jelly and pudding; chocolate, chewing gum, tablets; Japanese sweets such as sheep syrup; jams; candy class; herb tea such as jasmine tea and the like.

Examples of the oral composition include toothpaste, toothpaste, liquid toothpaste, mouthwash, mouthwash, mouth spray and the like.

Cosmetics or daily / miscellaneous goods include, for example, fragrance products, basic cosmetics, finishing cosmetics, hair cosmetics, tanning cosmetics, medicated cosmetics, hair care products, soaps, body cleaners, bath cleaners, detergents, soft finishes, and cleaners. Examples include agents, kitchen detergents, bleaching agents, aerosol agents, deodorants, air fresheners, repellents, and other miscellaneous goods.

More specifically
・ As fragrance products, perfume, eau de parfum, eau de toilette, cologne, etc.;
・ Basic cosmetics include face wash cream, vanishing cream, cleansing cream, cold cream, massage cream, milky lotion, lotion, beauty essence, facial mask, makeup remover, etc.
・ As finish cosmetics, foundation, powder powder, solid powder, talcum powder, lipstick, lip balm, blusher, eyeliner, mascara, eye shaving, eyebrow, eye pack, nail enamel, enamel limba, etc.;
・ As hair cosmetics, pomade, brilantin, set lotion, hair stick, hair solid, hair oil, hair treatment, hair cream, hair tonic, hair liquid, hair spray, bandolim, hair nourishing agent, hair dye, etc.;
・ As tanning cosmetics, suntan products, sunscreen products, etc.;
・ As medicated cosmetics, antiperspirants, after-shaving lotions and gels, permanent wave agents, medicated soaps, medicated shampoos, medicated skin cosmetics, etc.;
・ As hair care products, shampoo, conditioner, conditioner, treatment, hair pack, etc.;
Can be mentioned.
・ As soap, cosmetic soap, bath soap, perfume soap, transparent soap, synthetic soap, etc.;
・ Body cleansers include body soap, body shampoo, and hand soap;
・ Bath salts (bath salts, bath tablets, bath liquids, etc.), foam baths (bubble baths, etc.), bath oils (bath perfumes, bath capsules, etc.), milk baths, bath jerry, bath cubes, etc.;
・ As detergents, heavy detergents for clothing, light detergents for clothing, liquid detergents, laundry soaps, compact detergents, powder soaps, etc.;
・ As a flexible finish, softener, furnicia care, etc.;
・ Cleaners, house cleaners, toilet cleaners, bathroom cleaners, glass cleaners, mold removers, drain pipe cleaners, etc.
・ As kitchen detergents, kitchen soaps, synthetic kitchen soaps, dishwashing detergents, etc.;
-As bleaching agents, oxidizing bleaching agents (chlorine bleaching agents, oxygen bleaching agents, etc.), reducing bleaching agents (sulfur bleaching agents, etc.), optical bleaching agents, etc.;
・ As an aerosol agent, spray type, powder spray, etc.;
・ As deodorants and air fresheners, solid type, gel type, liquid type, etc.;
・ As miscellaneous goods, take paper, toilet paper, etc.;
Can be mentioned.

When the flavor / aroma composition containing the anti-allergic agent of the present invention or the anti-allergic agent of the present invention as an active ingredient is used in various products as described above, the type of product and the final form of the product (for example, liquid form, etc.) Depending on the product form such as solid, powdered, gelled, mist, aerosol, etc.), the flavor / aroma composition containing the antiallergic agent or the antiallergic agent of the present invention as an active ingredient can be directly applied to the product. It may be added or added; for example, it may be added or added in a liquid state by dissolving it in polyhydric alcohols such as alcohols, propylene glycol and glycerin; and natural gums such as Arabic gum and tragant gum. Can be solubilized or emulsified and dispersed with other types of surfactants (eg, nonionic surfactants such as glycerin fatty acid ester and sucrose fatty acid ester, anionic surfactants, cationic surfactants, amphoteric surfactants, etc.) It may be added or imparted in solution or dispersed form; it may be added or imparted in the form of a powder film formed with natural gums such as arabic gum and excipients such as gelatin and dextrin. It may be treated with an encapsulant to form microcapsules and added or added.

Further, the flavor / aroma composition containing the antiallergic agent of the present invention as an active ingredient may be used by being included in an inclusion agent such as cyclodextrin to stabilize the flavor / aroma composition and to make it sustained release.

The amount of the flavor / aroma composition added or imparted to the product, which contains the antiallergic agent of the present invention or the antiallergic agent of the present invention as an active ingredient, is the type and form of the product, the antiallergic effect and action required for the product, and the flavor / flavor. It can be adjusted according to the content of the antiallergic agent in the aroma composition and the like.

When the product is a food or drink, an oral composition, a pharmaceutical product, etc., the amount of the flavor / aroma composition containing an antiallergic agent as an active ingredient is generally about 0.05 to 30 with respect to the mass of the product. It is preferably about% by mass, particularly about 0.1 to 20% by mass.
At that time, in these products, based on the mass of the product, the addition amount or the addition amount of the flavor / aroma composition containing the antiallergic agent as an active ingredient is 0.01 to 20% by mass, and the antiallergic agent It is preferable that the addition amount or the addition amount is 0.001 to 25% by mass, particularly 0.01 to 20% by mass, from the viewpoint of satisfactorily exerting the above-mentioned excellent effects of the antiallergic agent of the present invention.

In addition, the products are fragrance products, basic cosmetics, finishing cosmetics, hair cosmetics, tanning cosmetics, medicated cosmetics, hair care products, soaps, body cleaners, bath detergents, detergents, soft finishes, cleaners, kitchen detergents, bleaching agents. In the case of aerosols, deodorants / fragrances, miscellaneous goods, etc., the amount of flavor / aroma composition added or given containing the antiallergic agent of the present invention as an active ingredient is the effect expected by each product. -Although it can be adjusted arbitrarily according to the action, in general, the amount of the flavor / fragrance composition containing the antiallergic agent as an active ingredient is about 0.001 to 25% by mass, particularly 0. It is preferably about 0.01 to 20% by mass.

At that time, based on the mass of the product, the addition amount or the addition amount of the flavor / aroma composition containing the antiallergic agent as an active ingredient is 0.001 to 25% by mass, particularly 0.01 to 20% by mass. The addition amount or the addition amount of the antiallergic agent is 0.01 to 25% by mass, particularly 0.1 to 20% by mass, so that the above-mentioned excellent effect of the antiallergic agent of the present invention is satisfactorily exhibited. It is preferable from the viewpoint of causing.

The foods and drinks, oral compositions, pharmaceuticals, cosmetics or daily / miscellaneous goods targeted by the present invention are foods and drinks, oral compositions, pharmaceuticals, cosmetics or daily necessities as long as they can exert the desired effects. -It may contain various compounding agents and additives that are commonly used in general merchandise products. For example, antioxidants, preservatives, antibacterial agents, pH regulators, sweeteners, acidulants, bulking agents, pigments, emulsifiers, functional substances, existing flavor improvers, milk components, nitrogen-containing compounds such as amino acids and peptides. , Various fragrance materials, various fragrances, surfactants, abrasives, binders, wetting agents, other solvents and the like. Two or more of these compounding agents / additives may be used in combination in any combination.

More specifically, antioxidants include butylhydroxytoluene, butylhydroxyanisole, citric acid, glutathione, selenium, lycopene, vitamin A, vitamin E, vitamin C, etc., as well as pyrolopyrrole derivatives and extracts from various plants. Examples thereof include free radical scavengers obtained from substances, superoxide dismutase, enzymes having antioxidant properties such as glutathione peroxidase, and the like.

Preservatives and antibacterial agents include benzoic acid, sodium benzoate, isopropyl paraoxybenzoate, isobutyl paraoxybenzoate, ethyl paraoxybenzoate, methyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, sodium hyposulfate, hyposulfate. Sodium, potassium pyrosulfate, sorbic acid, potassium sorbate, sodium dehydroacetate, luapricin, udo extract, egonoki extract, kawarayomogi extract, oolong tea extract, shirako protein extract, enzymatically decomposed honeybee extract, tea catechins, Examples thereof include apple polyphenol, pectin decomposition product, chitosan, lysozyme, ε-polylysine and the like.
pH adjusters include adipic acid, citric acid, trisodium citrate, gluconodeltalactone, gluconic acid, potassium gluconate, sodium gluconate, DL-tartaric acid, L-tartaric acid, DL-potassium hydrogen tartrate, L-tartaric acid. Potassium hydrogen, DL-sodium tartarate, L-sodium tartarate, potassium carbonate (anhydrous), sodium hydrogen carbonate, sodium carbonate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, disodium dihydrogen pyrophosphate, fumaric acid, monofumaric acid Examples thereof include sodium, DL-tartaric acid, DL-sodium malate, phosphoric acid, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, sodium dihydrogen phosphate and the like.

Examples of sweeteners include sugar, fructose, lactose, glucose, palatinose, malt sugar, trehalose, sorbitol, erythritol, martitol, reduced palatinose, xylitol, lactitol candy, oligosaccharide, aspartame, sucralose, acesulfame potassium, saccharin, sodium saccharin. Examples thereof include stevia, stevia extract, stebioside, neotheme, ariteme, somatin, neohesperidin dihydrochalcone, paramethoxycinnamic aldehyde, perilartin, licorice and the like.

Examples of the acidulant include acetic acid, lactic acid, citric acid and the like.

Examples of the bulking agent include saccharides, polysaccharides, modified starch, casein, gelatin, carboxymethyl cellulose, lecithin and the like.

Examples of pigments include natural pigments and organic synthetic pigments. Specifically, hibiscus pigments, hakuruberry pigments, plum pigments, glue pigments, duberry pigments, grape juice pigments, blackberry pigments, blueberry pigments, mulberry pigments, and morero. Cherry pigment, red carant pigment, loganberry pigment, paprika powder, malt extract, rutin, flavonoid, red cabbage pigment, red bean pigment, adzuki bean pigment, turmeric pigment, olive tea, cowberry pigment, chlorella powder, saffron pigment, perilla pigment , Strawberry pigment, chicory pigment, pecannut pigment, safflower pigment, safflower pigment, purple potato pigment, lac pigment, spirulina pigment, onion pigment, tamarind pigment, capsicum pigment, gardenia jasminoides pigment, caramel pigment, shikon pigment, citan pigment, okiami pigment, Examples include orange pigment, carotene carotene, blue No. 1, yellow No. 4, green No. 3 and the like.

Examples of the emulsifier include fatty acid monoglyceride, fatty acid diglyceride, fatty acid triglyceride, propylene glycol fatty acid ester, sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin, enzyme-treated lecithin, starch, processed starch, dextrin, sorbitan fatty acid ester, and Kiraya extract. , Arabian gum, tragant gum, guar gum, karaya gum, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein and the like.

The functional substance means a substance having a nutritional function and a bioregulatory function, for example, docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), DHA and / or EPA-containing fish oil, linoleic acid, γ-linolenic acid, α. -Animal and vegetable oils and fats such as linolenic acid, lecithin and diacylglycerol and their derivatives, animal and plant extracts such as rosemary, sage, perilla oil, chitin, chitosan, royal jelly and propolis, vitamin A, vitamin D, vitamin E, vitamin F, Vitamin K, coenzyme Q10, vitamins such as α-lipoic acid, coenzymes and derivatives thereof, polyphenols such as γ-oryzanol, catechin, anthocyanin, isoflavone, rutin, chlorogenic acid, teaflavin, dietary fiber such as indigestible dextrin, Sugars such as palatinose, xylitol and oligosaccharides, salts such as calcium malate citrate (CCM), milk protein-derived substances such as caseinphosphopeptide, lactoferrin and milky peptides, lactic acid bacteria, hem iron, sodium fluoride, foot Fluoride such as potassium oxide, stannous fluoride, strontium fluoride, sodium monofluorophosphate, potassium salt of orthophosphoric acid, water-soluble phosphoric acid compound such as sodium salt, tranexamic acid, epsilon aminocaproic acid, dl-acetate Tocophenol, α-bisabolol, dihydrocholesterol, chlorohexidine salts, azulene, glycyrrhetin, glycyrrhetinic acid, glycyrrhizinic acid and its salts, chelating phosphoric acid compounds such as copper chlorophyllin sodium, chlorophyll, glycerophosphate, copper compounds such as copper gluconate, Aluminum lactate, strontium chloride, potassium nitrate, hydroxamic acid and its derivatives, sodium tripolyphosphate, methoxyethylene, epidihydrocholesterin, allantinchlorohydroxyaluminum, ascorbic acid, lysozyme chloride, isopropylmethylphenol, benzethonium chloride, cetylpyridinium chloride, trichlorocarba Examples thereof include phosphoric acid, zinc citrate, and abacus extract.

Examples of milk components include raw milk, milk, whole milk powder, skim milk powder, fresh cream, milk proteins such as casein and whey, those derived from milk such as goats and sheep, and their decomposition products.

Known flavor-improving materials include, for example, sucralose, cyclodextrin, theanine, hesperidin glycosides, sugar cane extract and the like.
As the various fragrance materials, for example, the above-mentioned natural fragrances, natural essential oils and the like and various synthetic fragrances can be used.
The various fragrances are not particularly limited, but the above-mentioned fragrances can be used.

<Evaluation method>
In the present invention, the antiallergic action based on the degranulation inhibitory action is evaluated by measuring the enzymatic activity of β-hexosaminidase released from cells by degranulation.

β-hexosaminidase is one of the chemical mediators released by leukocytes and is known to be released almost simultaneously with histamine, which is a causative agent of allergies. Rat basophil leukemia cells (RBL-2H3) are known to have the same function as human basophils and mast cells, and have an inhibitory effect on β-hexosaminidase release from RBL-2H3. It is considered to be an index of allergy-suppressing effect, particularly type I allergy-suppressing effect. Therefore, the antiallergic effect can be evaluated by measuring the inhibition of β-hexosaminidase release from RBL-2H3. Moreover, the evaluation of the β-hexosaminidase release inhibitory effect has a higher correlation with the evaluation of in vivo than other evaluation methods.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

<RBL-2H3 cell degranulation suppression test>
The anti-allergic effect was evaluated by evaluating the degranulation inhibitory effect.
RBL-2H3 was seeded on a 96-well plate at ^{a concentration of 2.0 × 10 4} cells / mL, and the sample numbers shown in Table 1 were obtained. 1 to 5 were added respectively, and the cells were cultured at 37 ° C. for 48 hours, then the anti-TNP-IgE antibody was added, and the cells were further cultured at 37 ° C. for 2 hours. Cells were washed with Tyrode's buffer and replaced with a degranulation solution containing a stimulant that promotes degranulation. The stimulants at this time include (1) TNP-BSA (bovine serum albumin (BSA) bound to a plurality of TNPs (trinitropeneyl)) (Comparative Examples 1 and Examples 1 to 4) or (2) A23187 ( Calcium ionophore) (Comparative Example 2 and Examples 5-8) was used. After reacting at 37 ° C. for 30 minutes, the supernatant is collected, the substrate (4-nitrophenyl-N-acetyl-β-D-glucosanide) is added, and the mixture is incubated at 37 ° C. for 30 minutes to 1 hour to glycine. The solution was added to stop the reaction.

<Calculation of β-hexosaminidase activity>
Sample No. For each of the samples 1 to 5, the absorbance of p-nitrophenol produced by the reaction of β-hexosaminidase present in the granules with the substrate was measured using a microplate reader (measurement wavelength: 405 nm). Taking β-hexosaminidase activity obtained by completely lysing the same number of cells with a surfactant (Triton) as 100%, the absorbances of Comparative Examples 1 and 2 and Examples 1 to 8 were determined by the following formula. Converted to hexosaminidase activity.

β-hexosaminidase activity (%) = (absorbance of p-nitrophenol in degranulation solution using antigen or A23187) / (absorbance of p-nitrophenol when RBL-2H3 is dissolved in Triton) × 100

FIG. 1 shows the results of calculating the β-hexosaminidase activity of Comparative Examples 1 and Examples 1 to 4 when TNP-BSA was used as a stimulant. Table 2 shows the numerical values of β-hexosaminidase activity.

FIG. 2 shows the results of calculating the β-hexosaminidase activity of Comparative Examples 2 and Examples 5 to 8 when A23187 was used as the stimulant. Table 3 shows the values of β-hexosaminidase activity.

Claims (8)

An antiallergic agent containing one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient. The antiallergic agent according to claim 1, which is based on a degranulation inhibitory action. A flavor / aroma composition having an anti-allergic effect, which comprises the anti-allergic agent according to claim 1 or 2. Anti-allergic foods and drinks, anti-allergic cosmetics, which contain the anti-allergic agent according to claim 1 or 2, or the flavor / aroma composition having the anti-allergic effect according to claim 3. Anti-allergic oral composition, anti-allergic drug or anti-allergic daily miscellaneous goods. A degranulation inhibitor containing one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient. A flavor / aroma composition having a degranulation inhibitory effect, which comprises the degranulation inhibitor according to claim 5. A food or drink for suppressing degranulation, a fragrance for suppressing degranulation, which comprises the degranulation inhibitor according to claim 5 or the flavor / aroma composition having the degranulation suppressing effect according to claim 6. Cosmetics, oral compositions for suppressing degranulation, pharmaceuticals for suppressing degranulation, or daily miscellaneous goods for suppressing degranulation. A β-hexosaminidase release inhibitor containing one or more compounds selected from the group consisting of salicylaldehyde, benzyl salicylate, mint lactone, and cis-jasmon as an active ingredient.

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