CN117481988A - Composition for inhibiting ergothioneine photodegradation, and preparation method and application thereof - Google Patents
Composition for inhibiting ergothioneine photodegradation, and preparation method and application thereof Download PDFInfo
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- CN117481988A CN117481988A CN202311568857.9A CN202311568857A CN117481988A CN 117481988 A CN117481988 A CN 117481988A CN 202311568857 A CN202311568857 A CN 202311568857A CN 117481988 A CN117481988 A CN 117481988A
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- ergothioneine
- composition
- photodegradation
- ester
- copolymer
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- SSISHJJTAXXQAX-ZETCQYMHSA-N L-ergothioneine Chemical compound C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC(=S)N1 SSISHJJTAXXQAX-ZETCQYMHSA-N 0.000 title claims abstract description 133
- 229940093497 ergothioneine Drugs 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 238000001782 photodegradation Methods 0.000 title claims abstract description 34
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000002537 cosmetic Substances 0.000 claims abstract description 46
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229940089468 hydroxyethylpiperazine ethane sulfonic acid Drugs 0.000 claims abstract description 38
- 229920001577 copolymer Polymers 0.000 claims abstract description 35
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000002148 esters Chemical class 0.000 claims abstract description 34
- -1 diethyl hexyl 2, 6-naphthalene dicarboxylate Chemical compound 0.000 claims abstract description 26
- UFVWHIGSVGIZRQ-UHFFFAOYSA-N bis(2-ethylhexyl) naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OCC(CC)CCCC)C=CC2=CC(C(=O)OCC(CC)CCCC)=CC=C21 UFVWHIGSVGIZRQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229940031765 diethylhexyl 2,6-naphthalate Drugs 0.000 claims abstract description 15
- 229940114077 acrylic acid Drugs 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims description 12
- 230000001804 emulsifying effect Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
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- 239000002562 thickening agent Substances 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 230000002335 preservative effect Effects 0.000 claims description 4
- 230000002421 anti-septic effect Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 2
- BQMNFPBUAQPINY-UHFFFAOYSA-N azane;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound [NH4+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C BQMNFPBUAQPINY-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 229940105990 diglycerin Drugs 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 229940113120 dipropylene glycol Drugs 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 0.000 claims description 2
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 8
- 230000004224 protection Effects 0.000 abstract description 8
- 238000000354 decomposition reaction Methods 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 29
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- 230000002087 whitening effect Effects 0.000 description 9
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- 229920006243 acrylic copolymer Polymers 0.000 description 5
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- 230000037394 skin elasticity Effects 0.000 description 5
- 230000005855 radiation Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001815 facial effect Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
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- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- SYJHWANRKNXQFU-UHFFFAOYSA-N 3,4-diethyl-1-hexylnaphthalene-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C(CCCCCC)=C(C(O)=O)C(CC)=C(CC)C2=C1 SYJHWANRKNXQFU-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 206010004950 Birth mark Diseases 0.000 description 1
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- 241000196324 Embryophyta Species 0.000 description 1
- 101000713272 Homo sapiens Solute carrier family 22 member 4 Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000023813 Isia Species 0.000 description 1
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- 241001465754 Metazoa Species 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
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- 241000519995 Stachys sylvatica Species 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
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- 210000000887 face Anatomy 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
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- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
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- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/592—Mixtures of compounds complementing their respective functions
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Cosmetics (AREA)
Abstract
The invention belongs to the technical field of cosmetics, and particularly relates to a composition for inhibiting photodegradation of ergothioneine, and a preparation method and application thereof. The composition for inhibiting the photodegradation of ergothioneine comprises the following components: ergothioneine, hydroxyethylpiperazine ethane sulfonic acid, acrylic acid (ester) copolymer, diethyl hexyl 2, 6-naphthalene dicarboxylate; the mass ratio of the four components is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate= (1-5): (1-10): (1:10): (1-10). According to the invention, the combination of the weak acid hydroxyethyl piperazine ethane sulfonic acid, the acrylic acid (ester) copolymer and the 2, 6-diethyl hexyl naphthalate with the ergothioneine realizes the protection of the ergothioneine under the cooperation of a specific mass ratio, effectively inhibits the visible light decomposition of the ergothioneine, and improves the stability of the ergothioneine in the application of cosmetics.
Description
Technical Field
The invention belongs to the technical field of cosmetics, and particularly relates to a composition for inhibiting photodegradation of ergothioneine, and a preparation method and application thereof.
Background
Ergothioneine is a rare natural chiral amino acid, and has extremely strong functions of scavenging free radicals, whitening, resisting aging and detoxifying. Ergothioneine was isolated from ergot in 1909 and is therefore named. It has now been found that they can be synthesized in most fungi, some fungi, streptococci, mycobacteria and other microorganisms and absorbed and accumulated by plants and animals.
In the human body, ergothioneine enters the nucleus and mitochondria through a special OCTN1 transport protein, and has the physiological functions of scavenging free radicals, repairing cells, maintaining DNA steady state, stimulating the activity of the cells and inhibiting apoptosis. Ergothioneine is naturally safe and has no acne-causing property, and in the European Union, the United states, japan and other areas, a plurality of products are marketed as ergothioneine for the main common food and oral cosmetic products.
However, during the experiment and application process, the ergothioneine has the defects of easy decomposition of visible light and poor stability, and the degradation of the ergothioneine can lead to the reduction or disappearance of the efficacy of the product and also bring unpleasant smell, so that a method for protecting the ergothioneine is necessary to be found, so that the ergothioneine has better stability in cosmetic application.
Disclosure of Invention
The invention aims to overcome the defects and shortcomings of the prior art and provide a composition for inhibiting the photodegradation of ergothioneine, a preparation method and application thereof, wherein the pH value of the composition is adjusted, and a photo-protecting agent is added to protect the ergothioneine, so that the stability of the composition in food and cosmetic application is improved.
In order to achieve the above object, the present invention adopts the technical scheme that:
in a first aspect, the present invention provides a composition for inhibiting photodegradation of ergothioneine, comprising the following components: ergothioneine, hydroxyethylpiperazine ethanesulfonic acid, acrylic acid (ester) copolymers and diethyl hexyl 2, 6-naphthalate; the mass ratio of the ergothioneine to the hydroxyethyl piperazine ethane sulfonic acid to the acrylic acid (ester) copolymer to the 2, 6-diethyl hexyl naphthalate is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate= (1-5): (1-10): (1:10): (1-10).
Ergothioneine is a photosensitive compound, and can be used for improving pigmentation of skin in cosmetic application, thereby improving skin color, masking speckle, whitening skin, increasing skin sensitivity to ultraviolet rays, improving phototherapy and other optical treatment effects, and relieving and repairing skin damaged by exposure to ultraviolet rays, and relieving discomfort and erythema caused by insolation. However, too high a content of ergothioneine may cause the skin to be too sensitive, leading to skin discomfort, erythema, allergic reactions and other skin problems, just because ergothioneine can increase the sensitivity and response of the skin.
In addition, ergothioneine was found to degrade under both alkaline and light conditions to produce trimethylamine. Through tests, the ergothioneine is most sensitive under the illumination condition, the generated trimethylamine has heavier smell and the ergothioneine has more degradation amount, so the invention realizes the protection of the ergothioneine in the composition by purposefully adding weak acid to adjust the pH value and adding the photo-protecting agent, and improves the stability of the ergothioneine in cosmetic application.
Acrylic copolymers are one of the components widely used as photo-protectants in cosmetic and personal care products, and have good photo-stability, which can help the product resist damage by ultraviolet radiation, and also help to uniformly distribute the components in the product, ensure better spreadability, and have good adhesion; diethyl-2, 6-naphthalate is a chemical sunscreen ingredient capable of absorbing the energy of ultraviolet a (UVA) and ultraviolet B (UVB) radiation, converting it into thermal energy, thereby reducing the damage to the skin by ultraviolet radiation, and is relatively good in photostability and therefore generally useful as an effective photo-protecting agent in cosmetic and sunscreen products. The inventor discovers that the acrylic acid (ester) copolymer and the 2, 6-diethyl naphthalene dicarboxylic acid hexyl ester have different light absorption spectrum ranges, and when the acrylic acid (ester) copolymer and the 2, 6-diethyl naphthalene dicarboxylic acid hexyl ester are compounded and used, the acrylic acid (ester) copolymer and the 2, 6-diethyl naphthalene dicarboxylic acid diethyl hexyl ester are matched with each other, so that the acrylic acid (ester) copolymer and the 2, 6-diethyl naphthalene dicarboxylic acid diethyl ester can provide wider-spectrum light protection and cover more ultraviolet radiation with different wavelengths, thereby synergistically enhancing the light protection effect, and also have synergistic stability, so that the stability of the composition is enhanced. Therefore, the invention adopts acrylic acid (ester) copolymer and 2, 6-diethyl hexyl naphthalate as photo-protective agents to effectively inhibit photodegradation of ergothioneine.
The ergothioneine is easy to degrade under alkaline conditions, so the invention tries to adjust the pH value by adding weak acid, and controls the pH value within the range of 5.0-6.0, and the stability of the ergothioneine is obviously improved; the hydroxyethyl piperazine ethane sulfonic acid is used as a hydrogen ion buffer, is very effective in maintaining a stable pH value and can stabilize the pH value for a long time, so that the degradation problem of the ergothioneine can be more durable and effectively inhibited by adding the hydroxyethyl piperazine ethane sulfonic acid to control the pH value of the composition containing the ergothioneine.
Preferably, the mass ratio of the ergothioneine, the hydroxyethyl piperazine ethane sulfonic acid, the acrylic copolymer and the 2, 6-diethyl hexyl naphthalene dicarboxylate is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate= (3-5): (3-10): (2:10): (2-10).
The inventors have found through a plurality of experiments that when the mass ratio of ergothioneine, hydroxyethyl piperazine ethane sulfonic acid, acrylic copolymer and 2, 6-diethyl hexyl naphthalene dicarboxylate in the composition is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate= (3-5): (3-10): (2:10): (2-10) the ergothioneine can better exert the photosensitive effect without excessively negatively affecting the skin, and the hydroxyethyl piperazine ethane sulfonic acid, the acrylic acid (ester) copolymer and the 2, 6-diethyl hexyl naphthalene dicarboxylate can better exert the synergistic effect within the preferred mass ratio range to inhibit the degradation of the ergothioneine, thereby obviously enhancing the stability of the ergothioneine in cosmetic application.
Preferably, the mass ratio of the ergothioneine, the hydroxyethyl piperazine ethane sulfonic acid, the acrylic copolymer and the 2, 6-diethyl hexyl naphthalene dicarboxylate is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate = 3:3:2:2.
it is found through experimental investigation that when the mass ratio of the ergothioneine, the hydroxyethyl piperazine ethane sulfonic acid, the acrylic copolymer and the 2, 6-diethyl hexyl naphthalene dicarboxylate in the composition is the ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate = 3:3:2:2, the prepared composition can inhibit photodegradation of the ergothioneine to the greatest extent and fully maintain the stability of the ergothioneine in the composition.
In a second aspect, the present invention provides a method for preparing the composition for inhibiting ergothioneine photodegradation, comprising the steps of:
(1) Weighing ergothioneine, acrylic acid (ester) copolymer and 2, 6-diethyl hexyl naphthalate, mixing, dissolving and dispersing uniformly;
(2) Adding hydroxyethyl piperazine ethane sulfonic acid to regulate the pH value, and controlling the pH value within the range of 5.0-6.0 to obtain the composition for inhibiting the photodegradation of ergothioneine.
The preparation method of the composition for inhibiting the photodegradation of ergothioneine is simple to operate, the pH value of the composition is adjusted by adding weak acid hydroxyethyl piperazine ethane sulfonic acid, and the protection of ergothioneine in the composition is realized by adding acrylic acid (ester) copolymer and 2, 6-diethyl hexyl naphthalene dicarboxylate photo-protecting agent, so that the stability of the composition in cosmetic application is improved.
In a third aspect, the present invention provides a cosmetic comprising ergothioneine, comprising a composition for inhibiting photodegradation of ergothioneine as described above.
Preferably, the content of the composition for inhibiting the photodegradation of ergothioneine in the cosmetic containing ergothioneine is 0.3-3.5% by mass.
The composition for inhibiting the photodegradation of the ergothioneine with specific mass percentage can realize better whitening effect, and provide obvious effects of resisting wrinkles and improving skin elasticity.
Preferably, the composition for inhibiting the photodegradation of ergothioneine contains 1-3.5% by mass of the cosmetic containing ergothioneine.
The composition for inhibiting the photodegradation of the ergothioneine with the specific mass percentage has the best effects of whitening, resisting wrinkles and improving skin elasticity.
Preferably, the ergothioneine-containing cosmetic also comprises the following components in percentage by mass: 2% of humectant, 0.2% of thickener, 0.5% of preservative and the balance of water.
According to the invention, the specific component proportion is selected, so that the prepared ergothioneine-containing cosmetic has better effects of whitening skin, resisting wrinkles and improving skin elasticity.
Preferably, the ergothioneine-containing cosmetic comprises at least one of the following (1) - (3):
(1) The humectant comprises at least one of glycerin, butanediol, 1, 2-hexanediol, dipropylene glycol and diglycerin;
(2) The thickener comprises at least one of ammonium acryloyldimethyl taurate/VP copolymer, polyacrylate crosslinked polymer-6 and sodium polyacrylate;
(3) The preservative comprises at least one of p-hydroxyacetophenone, phenoxyethanol and chlorophenylglycol.
In a fourth aspect, the present invention provides a method for preparing the ergothioneine-containing cosmetic, comprising the steps of:
(1) Sequentially adding humectant, antiseptic, thickener and water into an emulsifying pot, heating to 80-85deg.C, emulsifying, homogenizing for 3min at 2500rpm; defoaming in vacuum, stirring and cooling to 45 ℃ and stirring at 15rpm;
(2) Placing the composition for inhibiting the photodegradation of ergothioneine in the emulsifying pot in the step (1), homogenizing for 2min at 2500rpm, stirring and mixing at 45deg.C under a stirring speed of 15rpm;
(3) Cooling to 30deg.C to obtain the cosmetic containing ergothioneine.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, the weak acid hydroxyethyl piperazine ethane sulfonic acid, the acrylic acid (ester) copolymer and the 2, 6-diethyl hexyl naphthalate are combined with the ergothioneine, and the four components are cooperated under a specific mass ratio to realize the protection of the ergothioneine, so that the visible light decomposition of the ergothioneine is effectively inhibited, and the stability of the ergothioneine in cosmetic application is improved.
Detailed Description
For a better description of the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to the following specific examples. It will be appreciated by persons skilled in the art that the specific embodiments described herein are for purposes of illustration only and are not intended to be limiting.
Table 1: formulation table (mass%) of ergothioneine-containing cosmetics of examples 1-4
Table 2: formulation table (mass%) of ergothioneine-containing cosmetics of comparative examples 1 to 8
The preparation method of the ergothioneine-containing cosmetics of examples 1 to 4 and comparative examples 1 to 8 comprises the following steps:
(1) Weighing ergothioneine, acrylic acid (ester) copolymer and 2, 6-naphthalene dicarboxylic acid diethyl hexyl ester, mixing, dissolving and dispersing uniformly, adding hydroxyethyl piperazine ethane sulfonic acid to adjust pH value, and controlling pH value within 5.0-6.0 to obtain the composition for inhibiting photodegradation of ergothioneine.
(2) Sequentially adding humectant, antiseptic, thickener and water into an emulsifying pot, heating to 80-85deg.C, emulsifying, homogenizing for 3min at 2500rpm; defoaming in vacuum, stirring and cooling to 45 ℃ and stirring at 15rpm;
(3) Placing the composition for inhibiting the photodegradation of ergothioneine obtained in the step (1) into an emulsifying pot in the step (2), homogenizing for 2min at 2500rpm, stirring, and mixing at 45 ℃ under heat preservation, wherein the stirring speed is 15rpm;
(4) Cooling to 30deg.C to obtain cosmetic containing ergothioneine.
Effect example 1
The effect example uses the cosmetics containing ergothioneine prepared in the above examples 1-4 and comparative examples 1-8 as samples, the content of ergothioneine in the cosmetics is measured, and degradation of the ergothioneine during use of the cosmetics is simulated by illumination conditions (1000 Lux), so as to test the inhibition effect of the present invention on photodegradation of ergothioneine, and the specific method is as follows:
(1) The samples were placed in clear plastic bottles and left to stand in an illumination incubator at 25℃with an incubator photoperiod of 24:0 (light/dark). Samples were taken at regular daily intervals, and tested for 5 days for changes in ergothioneine content for example 3 and comparative examples 1-8.
(2) The content of ergothioneine is determined by high performance liquid chromatography, and HPLC conditions are as follows: chromatographic column: hypersil ODS C18 column (250 mm. Times.4.6 mm, particle size 5 μm); column temperature: 30 ℃; mobile phase: acetonitrile-water (3:97); flow rate: 1.0mL/min; detection wavelength: 254nm; sample injection amount: 20. Mu.L.
The results of the ergothioneine content test are shown in Table 3.
TABLE 3 Table 3
| Time | Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 1 | Comparative example 2 |
| 1d | 0.1 | 0.5 | 0.3 | 0.4 | 0.29 | 0.292 |
| 2d | 0.0995 | 0.5 | 0.3 | 0.4 | 0.285 | 0.287 |
| 3d | 0.099 | 0.4995 | 0.2998 | 0.4995 | 0.281 | 0.286 |
| 4d | 0.0975 | 0.498 | 0.2996 | 0.498 | 0.275 | 0.28 |
| 5d | 0.0965 | 0.4975 | 0.2995 | 0.497 | 0.26 | 0.271 |
| Time | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 |
| 1d | 0.3 | 0.3 | 0.296 | 0.295 | 0.295 | 0.3 |
| 2d | 0.297 | 0.29 | 0.289 | 0.2875 | 0.286 | 0.296 |
| 3d | 0.2855 | 0.285 | 0.285 | 0.278 | 0.281 | 0.292 |
| 4d | 0.282 | 0.281 | 0.2785 | 0.274 | 0.277 | 0.289 |
| 5d | 0.275 | 0.275 | 0.271 | 0.26 | 0.265 | 0.286 |
As can be seen from Table 3, the invention can effectively protect ergothioneine by adding weak acid hydroxyethyl piperazine ethane sulfonic acid, acrylic acid (ester) copolymer and diethyl hexyl 2, 6-naphthalene dicarboxylic acid with the content of the preferable range, obviously improve the problem of content reduction of ergothioneine due to photodegradation, and enhance the stability of the ergothioneine in the composition; as can be seen from comparison of comparative examples 1-4 with examples, when the composition is not added with the hydroxyethylpiperazine ethane sulfonic acid, the acrylic acid (ester) copolymer and the diethyl hexyl 2, 6-naphthalene dicarboxylate, or when only any two of the three components are added, the content of the ergothioneine in the cosmetic is obviously lower than that of the examples, which shows that the three components of the hydroxyethylpiperazine ethane sulfonic acid, the acrylic acid (ester) copolymer and the diethyl hexyl 2, 6-naphthalene dicarboxylate are mutually influenced, the photodegradation effect of inhibiting the ergothioneine is synergistically enhanced, the stability of the ergothioneine in the cosmetic is obviously improved, while the pH value is controlled by replacing the hydroxyethylpiperazine ethane sulfonic acid with citric acid and carbonic acid respectively in comparative examples 5-6, the effect of which is obviously deteriorated, and when the content of the hydroxyethylpiperazine ethane sulfonic acid and the diethyl hexyl 2, 6-naphthalene dicarboxylate added in comparative examples 7-8 is out of the preferred range of the invention, the content of the ergothioneine in the cosmetic is also lower than that of the examples, the invention sufficiently shows that the synergistic effect of the invention of inhibiting the ergothioneine in the specific photodegradation of the cosmetic by adding the hydroxyethylpiperazine ethane sulfonic acid, the acrylic acid (ester) and the diethyl naphthalate.
Effect example 2
The skin conditioning and whitening effects of the cosmetics containing ergothioneine prepared in examples 1 to 4 and comparative examples 1 to 8 were evaluated by the following methods.
1. Instrument and sample
Instrument: visia-CR (Canfield); image-Pro skin analysis by synthesis software (MediaCybernetics).
Sample: the samples of examples 1-4 and the samples of comparative examples 1-8 were 12 in total.
2. Selection of a subject
Qualified volunteers were enrolled and signed with informed consent to ensure that 120 were finally completed, 10 volunteers were tried per sample.
Inclusion criteria: healthy female volunteers, chinese, 35-45 years old, with daily habits of using skin care products; the faces of volunteers all have fine lines/wrinkles around eyes, and are insensitive to common cosmetics; subject compliance is high.
Exclusion criteria: antihistamines used in the last week or immunosuppressants used in the last month; any anti-inflammatory drug was administered to the subject in the last two months; insulin dependent diabetes mellitus patients; a patient suffering from a respiratory disease undergoing treatment; people with allergic constitution, allergic dermatitis, etc., and people with skin history; a person who is receiving dermatological treatment or takes light acids, whitening drugs and anti-aging drugs within one month; the test area has skin characterizers with large areas of birthmarks, scratches, white spots, moles, keloids, and the like affecting the test.
3. Testing environmental conditions: the temperature of the test environment is 20-22 ℃, the humidity is 40-60%, and real-time dynamic monitoring is carried out.
4. The using method of the product comprises the following steps: samples of examples and comparative examples were taken by 10 groups of people, respectively. The dosage and frequency of the skin care product are 0.5 g/time and 2 times/day (1 time each in the morning and evening). During the test, the subjects avoid excessive uv exposure.
5. Test procedure
(1) ISIA CR taking facial shots
A. Wrinkle score: cleaning with a cleaning reference article before use and at 4 weeks after sample use, and performing VISIA CR facial photographing after sitting still for 20min in a constant temperature and humidity room. The evaluation was performed based on the effect of the values of the VISIA tester, and the values were selected for the wrinkle scores of the left-hand graph (left eye circumference) and the right-hand graph (right eye circumference).
B. Skin color analysis: cleaning with a cleaning reference article before use and at 4 weeks after sample use, and performing VISIA CR facial photographing after sitting still for 20min in a constant temperature and humidity room. And selecting test areas corresponding to the left half face and the right half face for skin color analysis, and calculating ITA degrees.
(2) Skin elasticity test
Opening the Cutometer Q software, clicking the tool bar Measurement or directly clicking the upper right corner Measurement button, taking down the probe cover after the start of the pump is finished, clicking OK, vertically and lightly contacting the probe with the skin subjected to cleaning or sample smearing treatment within the reciprocal time of 5s, preferably retracting the springs at the top end of the probe, starting the test, removing the probe until the test cycle time is finished, and covering the probe cover.
6. And (3) calculating and analyzing results: the data output are the average of 10 persons per group and the test results are shown in tables 4-6.
TABLE 4 wrinkle score Change
TABLE 5 skin elasticity test results
| Sample source | Before use | After 4 weeks of use | Improvement rate/% |
| Example 1 | 66.3 | 79.52 | 19.94 |
| Example 2 | 66 | 83.2 | 26.06 |
| Example 3 | 65.5 | 84.2 | 28.55 |
| Example 4 | 64.7 | 78.92 | 21.98 |
| Comparative example 1 | 64.5 | 72.3 | 12.09 |
| Comparative example 2 | 65 | 71.5 | 10 |
| Comparative example 3 | 65.8 | 75.7 | 15.05 |
| Comparative example 4 | 65.3 | 76.3 | 16.85 |
| Comparative example 5 | 65 | 70.3 | 8.15 |
| Comparative example 6 | 65.3 | 70.5 | 7.96 |
| Comparative example 7 | 64.5 | 69.9 | 8.37 |
| Comparative example 8 | 64.7 | 70 | 8.19 |
TABLE 6 skin ITA test results
As can be seen from tables 4-6, the technical scheme of the invention can effectively inhibit the degradation of ergothioneine, so that the ergothioneine in the product can fully exert the effects of anti-aging, whitening, antioxidation and the like, thereby ensuring the stability of the effect of the product; while the efficacy test data of comparative examples 1 to 8 are significantly lower than those of examples, it is shown that in comparative examples 1 to 4, when any of the components of hydroxyethylpiperazine ethane sulfonic acid, acrylic acid (ester) copolymer and diethyl hexyl 2, 6-naphthalate according to the present invention is absent, the content of ergothioneine in the prepared cosmetics is reduced due to degradation, resulting in reduced efficacy of anti-aging, whitening, etc., and in comparative examples 7 to 8, the content of hydroxyethylpiperazine ethane sulfonic acid and diethyl hexyl 2, 6-naphthalate is beyond the preferred range of the present invention, and also, ergothioneine cannot be effectively and sufficiently protected, resulting in reduced content, thereby adversely affecting the efficacy of the prepared cosmetics.
In conclusion, the pH value of the formula is regulated by adding the weak acid hydroxyethyl piperazine ethane sulfonic acid, and simultaneously, the acrylic acid (ester) copolymer and the 2, 6-diethyl hexyl naphthalate are added to carry out light protection on the ergothioneine, so that the three components synergistically inhibit the photodegradation of the ergothioneine under a specific mass ratio, the full protection of the ergothioneine is realized, the stability of the ergothioneine in cosmetic application is effectively improved, and the efficacy stability of the ergothioneine-containing product is ensured.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted equally without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
1. A composition for inhibiting photodegradation of ergothioneine, comprising the following components: ergothioneine, hydroxyethylpiperazine ethanesulfonic acid, acrylic acid (ester) copolymers and diethyl hexyl 2, 6-naphthalate;
the mass ratio of the ergothioneine to the hydroxyethyl piperazine ethane sulfonic acid to the acrylic acid (ester) copolymer to the 2, 6-diethyl hexyl naphthalate is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate= (1-5): (1-10): (1:10): (1-10).
2. The composition for inhibiting photodegradation of ergothioneine according to claim 1, wherein the mass ratio of ergothioneine, hydroxyethylpiperazine ethane sulfonic acid, acrylic acid (ester) copolymer, and diethyl hexyl 2, 6-naphthalate is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate= (3-5): (3-10): (2:10): (2-10).
3. The composition for inhibiting photodegradation of ergothioneine according to claim 1, wherein the mass ratio of ergothioneine, hydroxyethylpiperazine ethane sulfonic acid, acrylic acid (ester) copolymer, and diethyl hexyl 2, 6-naphthalate is ergothioneine: hydroxyethyl piperazine ethane sulfonic acid: acrylic acid (ester) copolymer: diethyl hexyl 2, 6-naphthalate = 3:3:2:2.
4. a process for the preparation of a composition for inhibiting photodegradation of ergothioneine according to any of claims 1-3, comprising the steps of:
(1) Weighing ergothioneine, acrylic acid (ester) copolymer and 2, 6-diethyl hexyl naphthalate, mixing, dissolving and dispersing uniformly;
(2) Adding hydroxyethyl piperazine ethane sulfonic acid to regulate the pH value, and controlling the pH value within the range of 5.0-6.0 to obtain the composition for inhibiting the photodegradation of ergothioneine.
5. A cosmetic comprising ergothioneine, characterized by comprising a composition for inhibiting photodegradation of ergothioneine according to any of claims 1 to 3.
6. The ergothioneine-containing cosmetic according to claim 5, wherein the ergothioneine photodegradation-inhibiting composition has a mass percentage of 0.3 to 3.5% in the ergothioneine-containing cosmetic.
7. The ergothioneine-containing cosmetic according to claim 6, wherein the ergothioneine photodegradation-inhibiting composition has a mass percentage of 1 to 3.5% in the ergothioneine-containing cosmetic.
8. The ergothioneine-containing cosmetic according to claim 5, further comprising the following components in mass percent: 2% of humectant, 0.2% of thickener, 0.5% of preservative and the balance of water.
9. The ergothioneine-containing cosmetic according to claim 8, comprising at least one of the following (1) - (3):
(1) The humectant comprises at least one of glycerin, butanediol, 1, 2-hexanediol, dipropylene glycol and diglycerin;
(2) The thickener comprises at least one of ammonium acryloyldimethyl taurate/VP copolymer, polyacrylate crosslinked polymer-6 and sodium polyacrylate;
(3) The preservative comprises at least one of p-hydroxyacetophenone, phenoxyethanol and chlorophenylglycol.
10. Process for the preparation of a cosmetic product containing ergothioneine according to any of claims 5 to 9, characterized by comprising the following steps:
(1) Sequentially adding humectant, antiseptic, thickener and water into an emulsifying pot, heating to 80-85deg.C, emulsifying, homogenizing for 3min at 2500rpm; defoaming in vacuum, stirring and cooling to 45 ℃ and stirring at 15rpm;
(2) Placing the composition for inhibiting the photodegradation of ergothioneine in the emulsifying pot in the step (1), homogenizing for 2min at 2500rpm, stirring and mixing at 45deg.C under a stirring speed of 15rpm;
(3) Cooling to 30deg.C to obtain the cosmetic containing ergothioneine.
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| KR20090056910A (en) * | 2007-11-30 | 2009-06-03 | 엘브이엠에이취 러쉐르쉐 | Cosmetic composition comprising ascorbic acid 2-glucoside and ergothioneine |
| EP2717833A2 (en) * | 2011-06-08 | 2014-04-16 | DSM IP Assets B.V. | Cosmetic compositions |
| CN114522109A (en) * | 2022-03-14 | 2022-05-24 | 广州科妙生物科技有限公司 | Whitening and skin-refreshing ampoule essence microemulsion and preparation method thereof |
| CN115363980A (en) * | 2022-10-08 | 2022-11-22 | 广州市百好博有限公司 | Composition containing ergothioneine and persimmon extract and application thereof |
| CN115444775A (en) * | 2022-10-27 | 2022-12-09 | 广州精创舞台设备科技有限公司 | Stable composition suitable for cosmetics and skin care product thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20090056910A (en) * | 2007-11-30 | 2009-06-03 | 엘브이엠에이취 러쉐르쉐 | Cosmetic composition comprising ascorbic acid 2-glucoside and ergothioneine |
| EP2717833A2 (en) * | 2011-06-08 | 2014-04-16 | DSM IP Assets B.V. | Cosmetic compositions |
| CN114522109A (en) * | 2022-03-14 | 2022-05-24 | 广州科妙生物科技有限公司 | Whitening and skin-refreshing ampoule essence microemulsion and preparation method thereof |
| CN115363980A (en) * | 2022-10-08 | 2022-11-22 | 广州市百好博有限公司 | Composition containing ergothioneine and persimmon extract and application thereof |
| CN115444775A (en) * | 2022-10-27 | 2022-12-09 | 广州精创舞台设备科技有限公司 | Stable composition suitable for cosmetics and skin care product thereof |
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