CN102697666A - Cyclodextrin salicylic acid inclusion complex aqueous solution, as well as preparation method and application thereof - Google Patents
Cyclodextrin salicylic acid inclusion complex aqueous solution, as well as preparation method and application thereof Download PDFInfo
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- CN102697666A CN102697666A CN2012101728816A CN201210172881A CN102697666A CN 102697666 A CN102697666 A CN 102697666A CN 2012101728816 A CN2012101728816 A CN 2012101728816A CN 201210172881 A CN201210172881 A CN 201210172881A CN 102697666 A CN102697666 A CN 102697666A
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Abstract
本发明属于医疗保健技术领域，具体为一种环糊精水杨酸包合物水溶液及其制备方法和应用。本发明将环糊精水溶液与水杨酸水溶液按一定的摩尔比混合，在0～100℃下静置1小时以上，即得到环糊精水杨酸包合物水溶液。由此制备的环糊精水杨酸包合物水溶液可用于制备接触皮肤的化妆品或药物，如抗痘膏、爽肤水、洗面奶、洗发水等。本发明的环糊精水杨酸包合物水溶液，可调节水杨酸在皮肤表面释放速度、控制水杨酸在皮肤表面的局部浓度，保证水杨酸在皮肤表面的有效浓度，降低水杨酸的刺激性和毒副作用，减少过浓的水杨酸对皮肤的刺激。本发明原料来源简易、生产工艺简便，可产生良好的经济效益。
The invention belongs to the technical field of medical care, and specifically relates to an aqueous solution of a cyclodextrin salicylic acid inclusion compound, a preparation method and application thereof. The invention mixes the cyclodextrin aqueous solution and the salicylic acid aqueous solution according to a certain molar ratio, and stands at 0-100 DEG C for more than 1 hour to obtain the cyclodextrin salicylic acid clathrate aqueous solution. The cyclodextrin salicylic acid inclusion compound aqueous solution prepared in this way can be used to prepare cosmetics or medicines that contact the skin, such as anti-acne ointment, toner, facial cleanser, shampoo and the like. The aqueous solution of cyclodextrin salicylic acid inclusion compound of the present invention can adjust the release rate of salicylic acid on the skin surface, control the local concentration of salicylic acid on the skin surface, ensure the effective concentration of salicylic acid on the skin surface, and reduce the salicylic acid concentration on the skin surface. The irritating and toxic side effects of acid can reduce the skin irritation caused by too concentrated salicylic acid. The invention has simple sources of raw materials, simple and convenient production process, and can produce good economic benefits.
Description
Technical field
The invention belongs to the health care technology field, be specifically related to a kind of cyclodextrin salicylic acid clathrate aqueous solution.
Background technology
Cyclodextrin be one type by 6～12 glucoses through α-1, the 4 glycosidic bond cyclic oligomer sugar compounds that is formed by connecting, normal temperature and pressure is the white crystalline powder of water solublity, irreducibility down, structure is both ends open, up-narrow and down-wide flowerpot shape.Cyclodextrin commonly used is that (α-CD, β-CD, γ-CD) three kinds and these three kinds of cyclodextrin groups cyclodextrin derivative through modifying, the glucose unit number that it contains is respectively 6,7,8 for α, β, γ.Through the structure of these three kinds of cyclodextrin is modified, can obtain some hydrophilic cyclodextrin derivative commonly used (with the hydroxyl hydrogen of cyclodextrin methylate, glycosylation, hydroxyalkylation), the hydrophobic cyclodextrin derivant (with the hydroxyl hydrogen of cyclodextrin ethylize, acylated) with amphipathic cyclodextrin derivative (with the outside introducing of cyclodextrin molecular hydrophobic side chains).The cyclodextrin inner chamber can inclusion a certain size medicine form clathrate, cyclodextrin is as main body, medicine is as object, medicine is can all or part of entering cyclodextrin hole inner, forms clathrate.Through forming cyclodextrin clathrate, can improve medicine solubility property, regulate drug releasing rate, improve medicine stability, improve the pharmaceutical preparation performance, reduce zest and the toxic and side effects of medicine etc.Cyclodextrin clathrate has good safety, excellent biological compatibility and good production storage characteristics etc.The formation of clathrate depends primarily on structure and the character and the enclose of the two ratio of Subjective and Objective.The Subjective and Objective molecular size will mate, and the molecular weight of guest molecule is preferably in 100～400.No matter different types of cyclodextrin adopts oral or non-oral route as the cyclodextrin clathrate that carrier forms, and guest molecule is got in the body with the mode of rapid release, slow release, controlled release or promotion molecule absorption.
Salicylic acid is claimed oxybenzoic acid again, molecular formula C
7H
6O
3, molecular weight 138, white crystalline powder, 1g salicylic acid can be dissolved in 25 ℃ of water of 460ml, 15ml boiling water, 2.7ml respectively
Ethanol, 3ml
Acetone, 3ml
Ether, 42ml
Chloroform, 135ml benzene, 52ml Oleum Terebinthinae, about 60ml
GlycerolAnd 80ml
Petroleum etherIn.Salicylic acid is medicine, spice, dyestuff, rubber chemicals etc.
Fine chemicalsImportant source material.At medical industry, salicylic acid itself is used for local hyperkeratosis and skin fungus and infects as Cidex-7.Salicylic acid can dissolve the formation shape material between cutin, horny layer is produced come off, and gathers blocked up horny layer so can remove, and enhances metabolism.The major function of keratodermatitis is to protect each confluent monolayer cells of skin, and the epidermis cell metabolism meeting of layer upon layer is passed naturally outward, after outermost horn cell is aging stiff gradually, under normal circumstances can consider to be worth doing naturally.The old cutin that does not normally come off can make skin seem to make skin metabolism speed slack-off in coarse dark Shen, even forms acne and block pore.Salicylic acid can be removed unnecessary horny layer, promotes the epidermis cell fast updating simultaneously; If when epidermis cell all is fresh full of vitality again young tender cell, just can let skin recover smooth careful naturally.Salicylic acid is fat-soluble, can infiltrate the deep layer of pore along the greasy sebaceous gland of secretion, help dissolving the horny layer of old accumulation in the pore, improves the situation that pore blocks, therefore the formation of acne capable of blocking and dwindle the pore that is stretched.Salicylic acid acts on the follicular wall cell, can help to remove the hair follicle that is blocked and clogs, and revises abnormal cell detachment; Can prevent that to slight comedo pore from blocking; The most effective to blackhead, it can reduce the undesired obscission of follicular wall, prevents the generation of new focus.Salicylic function is that the cleaning aging cutin makes skin seem comparatively careful, also relatively is not easy long acne.Salicylic acid removes cutin, promotes skin metabolism, can pore refining, remove blackhead, effectively desalinate microgroove and wrinkle, and reappear skin gloss.
It is very wide that salicylic acid uses, and eczema, chronic eczema, comedo, dandruff all possibly used salicylic acid, and concentration can be used for exfoliation at the salicylic acid of 3-6%, and being higher than 6% has destructiveness to tissue.40% concentration is suitable for treating clavus, thick cocoon, viral verruca with next.Because the acid of high concentration bigcatkin willow has certain nocuity; Rose in 1999 between the salicylic acid concentration limit 0.2-1.5% that cosmetics are contained of hygiene department; Contain the bigcatkin willow acidify and make up of the safety of article palpus filling poster, and the child below 3 years old also must not use with definite life-time service.
The present invention proposes a kind of cyclodextrin parcel salicylic acid that utilizes; Regulate salicylic acid at skin surface rate of release, control salicylic acid local concentration at skin surface; Guarantee the valid density of salicylic acid at skin surface; Reduce salicylic zest and toxic and side effects, reduce of the stimulation of the salicylic acid of overrich skin.
Summary of the invention
The object of the present invention is to provide a kind of cyclodextrin salicylic acid clathrate aqueous solution.
The method for preparing of cyclodextrin salicylic acid clathrate aqueous solution provided by the invention is that cyclodextrin aqueous solution is mixed with aqueous solution of salicylic acid, and in the mixed solution, cyclodextrin and salicylic molar concentration are respectively 100/1～1/100; Leaving standstill more than 1 hour under 0～100 ℃, obtaining the aqueous solution after cyclodextrin wraps up salicylic acid, i.e. cyclodextrin salicylic acid clathrate aqueous solution.
Among the present invention, said cyclodextrin is the cyclic oligomer sugar compounds that is formed by connecting through α-1,4 glycosidic bond by 6～8 glucoses, or the cyclodextrin derivative of the hydroxyl of such cyclic oligomer sugar compounds through obtaining after modifying.
Among the present invention, cyclodextrin aqueous solution concentration is 10
-4Mol
.L
-1~ saturated solution concentration, the concentration of aqueous solution of salicylic acid are 10
-4Mol
.L
-1~ saturated solution concentration.
Among the present invention, in the cyclodextrin salicylic acid clathrate aqueous solution, the mol ratio of cyclodextrin and salicylic acid enclose is 1:1.
The cyclodextrin salicylic acid clathrate aqueous solution of the present invention's preparation can be used for preparing in the cosmetics or medicine of contacting skin.Specifically, can add in the substrate of skin care item or medicine, as be added in anti-pox cream, cosmetic water, cleansing milk, the shampoo.Ring salicylic acid and cyclodextrin formation clathrate utilizes the slow releasing function of cyclodextrin can better control salicylic release and the salicylic acid concentration at skin surface.Cyclodextrin and salicylic acid clathrate have combined the characteristic and the salicylic advantage of cyclodextrin simultaneously, and skin is had safer protective effect, strengthen salicylic acid in time that skin surface stops; Better improve skin to salicylic absorption, improve its utilization ratio.Cyclodextrin and salicylic acid clathrate aqueous solution have characteristics such as physico-chemical property is stable, nontoxic, water solublity is strong, can process cosmetics dosage form and pharmaceutical dosage forms such as emulsion, cream frost, water preparation.Raw material sources of the present invention are simple and easy, production technology is easy, can produce good economic benefit.
Description of drawings
Fig. 1 is salicylic structural formula.
Fig. 2 is salicylic nuclear magnetic spectrogram.
The salicylic acid that Fig. 3 obtains for embodiment 1 and the nuclear-magnetism figure of alpha-cyclodextrin inclusion complex.
The salicylic acid that Fig. 4 obtains for embodiment 2 and the nuclear-magnetism figure of beta-cyclo dextrin included compound.
The salicylic acid that Fig. 5 obtains for embodiment 3 and the nuclear-magnetism figure of gamma-cyclodextrin inclusion complex.
The salicylic acid that Fig. 6 obtains for embodiment 4 and the nuclear-magnetism figure of hp-beta-cyclo dextrin included compound.
The specific embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is further described.
Embodiment 1: with 10
-3The alpha-cyclodextrin aqueous solution and 10 of molL
-2The aqueous solution of salicylic acid of molL is mixed according to mol ratio 1:1, under 25 ℃, leaves standstill 1 hour, can obtain α cyclodextrin-salicylic acid inclusion complex aqueous solution, available nuclear-magnetism experiment show the generation of inclusion complex, binding ratio is 1:1.Shown in Fig. 2, H on salicylic acid hydroxyl and the carboxyl and D
2The O exchange velocity is too fast, detects less than nuclear magnetic signal, and the nuclear-magnetism displacement of Hd is 7.910; The nuclear-magnetism displacement of Ha is 7.546, and the nuclear-magnetism displacement of Hb and Hc is 7.005, when salicylic acid with after alpha-cyclodextrin mixes; Variation has taken place in the nuclear-magnetism displacement of H, and the nuclear-magnetism of Hd is displaced to 7.960 shown in Fig. 3, and the nuclear-magnetism of Ha is displaced to 7.556; The nuclear-magnetism of Hb and Hc is displaced to 7.031, and obvious variation has taken place in the nuclear-magnetism displacement.
Embodiment 2: with 10
-4The beta cyclodextrin aqueous solution and 10 of molL
-2The aqueous solution of salicylic acid of molL is mixed according to mol ratio 1:100, under 50 ℃, leaves standstill 12 hours, can obtain beta cyclodextrin-salicylic acid inclusion complex aqueous solution, the nuclear-magnetism experiment show generation of beta cyclodextrin-salicylic acid inclusion complex, binding ratio is 1:1.When salicylic acid with after beta-schardinger dextrin-mixes, the nuclear-magnetism displacement of Hd is 7.878 shown in Fig. 4, the nuclear-magnetism displacement of Ha is 7.545, the nuclear-magnetism displacement of Hb and Hc is 6.984, obvious variation has taken place in the nuclear-magnetism displacement.
Embodiment 3: with 10
-2The γ cyclodextrin aqueous solution and 10 of molL
-4The aqueous solution of salicylic acid of molL is mixed according to mol ratio 100:1, under 0 ℃, leaves standstill 24 hours, can obtain γ cyclodextrin-salicylic acid inclusion complex aqueous solution, the nuclear-magnetism experiment show generation of γ cyclodextrin-salicylic acid inclusion complex, binding ratio is 1:1.
When salicylic acid with after gamma-cyclodextrin mixes, the nuclear-magnetism displacement of Hd as shown in Figure 5 is 7.685, the nuclear-magnetism displacement of Ha is 7.450, the nuclear-magnetism displacement of Hb and Hc is 6.868, obvious variation has taken place in the nuclear-magnetism displacement.Salicylic acid and gamma-cyclodextrin combine back nuclear-magnetism displacement maximum, explain that gamma-cyclodextrin is best to salicylic parcel effect, and optimum is used for the host molecule of salicylic acid inclusion complex.
Embodiment 4: with 10
-1The hp-beta-schardinger dextrin-aqueous solution and 10 of molL
-1The aqueous solution of salicylic acid of molL is mixed according to mol ratio 10:1; Under 0 ℃, left standstill 2 hours; Can obtain hp-beta-schardinger dextrin--salicylic acid inclusion complex aqueous solution, the nuclear-magnetism experiment show generation of hp-beta-schardinger dextrin--salicylic acid inclusion complex, binding ratio is 1:1.
When salicylic acid with after the hp-beta-schardinger dextrin-mixes, the nuclear-magnetism displacement of Hd as shown in Figure 6 is 7.920, the nuclear-magnetism displacement of Ha does, 7.585, the nuclear-magnetism displacement of Hb and Hc is 7.034, obvious variation has taken place in the nuclear-magnetism displacement.
Claims (6)
1. the method for preparing of a cyclodextrin salicylic acid clathrate aqueous solution, it is characterized in that concrete steps are: be that cyclodextrin aqueous solution is mixed with aqueous solution of salicylic acid, in the mixed solution, cyclodextrin and salicylic molar concentration are respectively 100/1～1/100; Leaving standstill more than 1 hour under 0～100 ℃, obtaining the aqueous solution after cyclodextrin wraps up salicylic acid, i.e. cyclodextrin salicylic acid clathrate aqueous solution.
2. the method for preparing of cyclodextrin salicylic acid clathrate aqueous solution according to claim 1; It is characterized in that said cyclodextrin is through α-1 by 6～8 glucoses; The cyclic oligomer sugar compounds that 4 glycosidic bonds are formed by connecting, the cyclodextrin derivative that obtains after perhaps modifying by the hydroxyl process of such cyclic oligomer sugar compounds.
3. the method for preparing of cyclodextrin salicylic acid clathrate aqueous solution according to claim 1 and 2 is characterized in that cyclodextrin aqueous solution concentration is 10
-4Mol
.L
-1~ saturated solution concentration, the concentration of aqueous solution of salicylic acid are 10
-4Mol
.L
-1~ saturated solution concentration.
4. the method for preparing of cyclodextrin salicylic acid clathrate aqueous solution according to claim 1 and 2 is characterized in that the mol ratio of cyclodextrin and salicylic acid enclose is 1:1 in the cyclodextrin salicylic acid clathrate aqueous solution.
5. the cyclodextrin salicylic acid clathrate aqueous solution for preparing by the said method of one of claim 1-4.
6. cyclodextrin salicylic acid clathrate aqueous solution according to claim 5 is in the cosmetics of preparation contacting skin or the application in the medicine.
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Cited By (13)
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|---|---|---|---|---|
| CN104814895A (en) * | 2015-05-08 | 2015-08-05 | 湖南红星盛康油脂股份有限公司 | Formula of natural hair shampoo and preparation method thereof |
| CN105403549A (en) * | 2015-12-24 | 2016-03-16 | 江南大学 | Determination method of relative hydrophobicity of starch |
| CN106491386A (en) * | 2016-11-02 | 2017-03-15 | 广州美尔生物科技有限公司 | A kind of cyclodextrin Herba bromi japonici acyl group ortho-aminobenzoic acid clathrate aqueous solution and preparation method and application |
| CN106726690A (en) * | 2016-12-27 | 2017-05-31 | 广东迪美新材料科技有限公司 | A kind of water-soluble salicylic acid microballoon and preparation method thereof |
| CN107595655A (en) * | 2017-10-10 | 2018-01-19 | 上海格兰化妆品有限公司 | A kind of salicylic drug-loading system and its preparation method and application |
| CN108210346A (en) * | 2018-01-10 | 2018-06-29 | 上海应用技术大学 | It is a kind of to load salicylic compound wall materials microcapsules and preparation method thereof |
| CN108295080A (en) * | 2018-03-15 | 2018-07-20 | 山东滨州智源生物科技有限公司 | A kind of preparation method of salicylic acid HYDROXYPROPYL BETA-CYCLODEXTRIN inclusion compound |
| CN113318032A (en) * | 2021-06-21 | 2021-08-31 | 杭州诺诚洗涤科技有限公司 | Anti-aging moisturizing cosmetic and preparation method thereof |
| CN113520893A (en) * | 2021-08-03 | 2021-10-22 | 加来(济南)生活科技有限公司 | Exfoliating composition and exfoliating gel |
| CN114028265A (en) * | 2021-12-16 | 2022-02-11 | 爱西美(珠海)生物技术有限公司 | Supermolecule embedded salicylic acid and preparation method thereof |
| CN114366692A (en) * | 2022-01-26 | 2022-04-19 | 山东福瑞达生物股份有限公司 | Oil-control acne-removing composition and application thereof |
| CN115025009A (en) * | 2022-06-15 | 2022-09-09 | 羽楠(广州)化妆品有限公司 | Multifunctional Mannich root ice river mud space sand-shaped clean mud film and preparation method thereof |
| WO2024027193A1 (en) * | 2022-08-03 | 2024-02-08 | 苏州隽德生物科技有限公司 | Skin-care product composition and pharmaceutical composition comprising sulfonated calixarene, and use of sulfonated calixarene |
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| CN104814895A (en) * | 2015-05-08 | 2015-08-05 | 湖南红星盛康油脂股份有限公司 | Formula of natural hair shampoo and preparation method thereof |
| CN105403549B (en) * | 2015-12-24 | 2017-11-28 | 江南大学 | A kind of method for determining starch relative hydrophobicity |
| CN105403549A (en) * | 2015-12-24 | 2016-03-16 | 江南大学 | Determination method of relative hydrophobicity of starch |
| CN106491386B (en) * | 2016-11-02 | 2019-12-03 | 广州美尔生物科技有限公司 | A kind of cyclodextrin oat acyl group ortho-aminobenzoic acid inclusion compound aqueous solution and the preparation method and application thereof |
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| CN106726690A (en) * | 2016-12-27 | 2017-05-31 | 广东迪美新材料科技有限公司 | A kind of water-soluble salicylic acid microballoon and preparation method thereof |
| CN107595655A (en) * | 2017-10-10 | 2018-01-19 | 上海格兰化妆品有限公司 | A kind of salicylic drug-loading system and its preparation method and application |
| CN108210346A (en) * | 2018-01-10 | 2018-06-29 | 上海应用技术大学 | It is a kind of to load salicylic compound wall materials microcapsules and preparation method thereof |
| CN108210346B (en) * | 2018-01-10 | 2020-06-23 | 上海应用技术大学 | Composite wall material microcapsule loaded with salicylic acid and preparation method thereof |
| CN108295080A (en) * | 2018-03-15 | 2018-07-20 | 山东滨州智源生物科技有限公司 | A kind of preparation method of salicylic acid HYDROXYPROPYL BETA-CYCLODEXTRIN inclusion compound |
| CN113318032A (en) * | 2021-06-21 | 2021-08-31 | 杭州诺诚洗涤科技有限公司 | Anti-aging moisturizing cosmetic and preparation method thereof |
| CN113318032B (en) * | 2021-06-21 | 2022-04-15 | 珠海世纪康美生物科技有限公司 | Anti-aging moisturizing cosmetic and preparation method thereof |
| CN113520893A (en) * | 2021-08-03 | 2021-10-22 | 加来(济南)生活科技有限公司 | Exfoliating composition and exfoliating gel |
| CN114028265A (en) * | 2021-12-16 | 2022-02-11 | 爱西美(珠海)生物技术有限公司 | Supermolecule embedded salicylic acid and preparation method thereof |
| CN114366692A (en) * | 2022-01-26 | 2022-04-19 | 山东福瑞达生物股份有限公司 | Oil-control acne-removing composition and application thereof |
| CN114366692B (en) * | 2022-01-26 | 2023-08-25 | 山东福瑞达生物股份有限公司 | Oil-control acne-removing composition and application thereof |
| CN115025009A (en) * | 2022-06-15 | 2022-09-09 | 羽楠(广州)化妆品有限公司 | Multifunctional Mannich root ice river mud space sand-shaped clean mud film and preparation method thereof |
| WO2024027193A1 (en) * | 2022-08-03 | 2024-02-08 | 苏州隽德生物科技有限公司 | Skin-care product composition and pharmaceutical composition comprising sulfonated calixarene, and use of sulfonated calixarene |
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