CN112300228A - A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method - Google Patents
A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method Download PDFInfo
- Publication number
- CN112300228A CN112300228A CN202011196901.4A CN202011196901A CN112300228A CN 112300228 A CN112300228 A CN 112300228A CN 202011196901 A CN202011196901 A CN 202011196901A CN 112300228 A CN112300228 A CN 112300228A
- Authority
- CN
- China
- Prior art keywords
- phloretin
- aminotriacetylglucoside
- sodium
- modified
- hydroxyphenylpropionate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Abstract
The invention provides a preparation method of a phloretin derivative containing a phloroglucinol group, which is a phloretin modified by amino triacetyl glucoside, wherein hydroxyl in p-hydroxy-phenyl propionic acid in raw materials for synthesizing the phloretin is subjected to modified grafting in advance, and then is subjected to synthetic reaction with phloroglucinol, namely phloroglucinol, so that the corresponding phloretin derivative containing the phloroglucinol group and the corresponding phloretin modified by the amino triacetyl glucoside are obtained. The derivative not only retains the inoxidizability and the anti-inflammation of the phloretin, but also has good water solubility and skin absorption efficiency, so that the obtained phloretin derivative can be widely applied to various forms of cosmetic products and has excellent inoxidizability and anti-inflammation effects.
Description
Technical Field
The invention relates to the field of cosmetics, in particular to a cosmetic containing phloretin derivatives containing phloroglucinol groups and a preparation method thereof.
Background
The cosmetic is a product which is applied to the surface part of a human body in a smearing or other similar mode so as to achieve the effects of cleaning, maintaining, beautifying and the like on the surface part. At present, the cosmetics on the market are various in variety, and among them, cosmetics for relieving skin inflammation, resisting oxidation and resisting aging are most favored by women.
Phloretin, namely 2,4, 6-trihydroxy-3- (4-hydroxyphenyl) propiophenone, is a flavonoid natural compound which is mainly distributed in the peel and root bark of juicy fruits such as apples and pears and various vegetable juices. The effects of phloretin in whitening skin, removing acne, resisting oxidation and resisting inflammation are attributed to the 2,4, 6-trihydroxy group in phloretin molecules, namely phloroglucinol group or phloroglucinol group.
However, when the phloretin is added into a formula as a functional component and directly coated on the surface of human skin, solid powder is easily formed and adhered to the skin, stimulation to the skin is likely to be generated, and medicines cannot effectively permeate the surface of the skin and reach a blood circulation system, so that the skin anti-inflammatory effect of the phloretin is greatly limited. Moreover, the water solubility of the phloretin is poor, the absorption utilization rate of the phloretin by the human skin is relatively low, and even if the preparation or the composition containing the phloretin is prepared into the temperature-sensitive gel, the action time of the phloretin on the surface of the human skin can be prolonged, but the absorption efficiency of the human skin on the phloretin cannot be fundamentally improved.
Phloretin can be modified to improve its anti-inflammatory, antioxidant and skin absorption efficiency. However, the active groups which are easily modified and grafted in the phloretin molecule are mainly phenolic hydroxyl groups, so that the phloretin is directly modified, and the phenolic hydroxyl groups, particularly phloroglucinol groups, in the phloretin molecule are easily damaged, so that the oxidation resistance and the anti-inflammation performance of the modified phloretin derivative are reduced, and the application of the modified phloretin derivative in cosmetics is not facilitated.
Therefore, the technical report that the preparation or the composition containing the phloretin is prepared into the temperature-sensitive gel, so that the temperature-sensitive gel keeps a semi-solid state continuously in the using process, the acting time of the phloretin on the surface of human skin is prolonged, the absorption degree of the human skin on the phloretin is improved, and the temperature-sensitive gel has a good anti-inflammatory effect. However, the application diversity of phloretin is limited by the gel preparation.
Meanwhile, the method does not fundamentally solve the problems of poor water solubility and low skin absorption efficiency of phloretin.
Therefore, the invention aims to modify phloretin on the basis of keeping phloretin triphenol groups in phloretin molecules through modifying research on the phloretin, so that the water solubility of the phloretin derivative can be improved while the anti-inflammatory and anti-oxygen properties of the phloretin derivative are ensured, the absorption efficiency of human skin on the phloretin derivative can be improved, the application diversity of cosmetics containing the phloretin derivative is enriched, and the effects of relieving skin inflammation, resisting oxidation and resisting aging of the cosmetics containing the phloretin derivative are improved.
Disclosure of Invention
In order to solve the problems of the existing phloretin-containing cosmetics, the invention provides a phloretin derivative containing phloroglucinol groups, a preparation method thereof and cosmetics containing the phloretin derivative.
A preparation method of a phloretin derivative containing a phloroglucinol group is disclosed, wherein the phloretin derivative containing the phloroglucinol group is modified by amino triacetyl glucoside, and the preparation method comprises the following steps:
(1) preparation of bromoamino triacetyl glucose
Adding glucosamine into acetic anhydride with 3-5 times of molar weight, dropwise adding triethylamine with 5-6 times of molar weight under the condition of ice-water bath, reacting for 2 hours, adding enough water to precipitate a product, filtering, washing a filter cake with water, and drying in vacuum to obtain aminotetraacetylglucose; dissolving dried aminotetraacetylglucose in dichloromethane, dropwise adding hydrobromic acid with 2.5-4 times of molar weight of aminotetraacetylglucose at normal temperature, wherein the hydrobromic acid is provided by hydrobromic acid acetic acid solution with mass concentration of 30%, reacting for 1.5-3 hours, pouring into ice water, extracting a water phase by dichloromethane, combining organic phases, rapidly washing the organic phase by saturated sodium bicarbonate solution and saturated saline solution respectively until the pH value is 7, drying anhydrous magnesium sulfate, filtering, distilling the filtrate at normal temperature under reduced pressure to recover dichloromethane, and obtaining bromoaminotriacetylglucose product.
(2) Preparation of sodium p-hydroxyphenylpropionate aminotriacetylglucoside
Mixing and adding aqueous solutions of sodium p-hydroxyphenylpropionate, sodium hydroxide and potassium iodide into a reaction container, stirring at room temperature for reaction, wherein the concentration of the sodium p-hydroxyphenylpropionate is 0.2-0.5mol/L, the concentration of the sodium hydroxide is 20-50g/L, and the concentration of the potassium iodide is 1-3g/L, then dropwise adding bromoaminotriacetylglucose dissolved in acetone into the reaction container, stirring at room temperature for reaction for 6-8 hours, separating out a solid, namely sodium p-hydroxyphenylpropionate aminotriacetylglucoside, and sequentially washing with sodium hydroxide and deionized water after suction filtration to obtain the solid sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
(3) Preparation of phloretin modified by amino triacetyl glucoside
Dissolving sodium p-hydroxyphenylpropionate aminotriacetylglucoside, acetic acid and phloroglucinol in an ethyl acetate solvent, reacting for 4-8 hours under the catalytic action of boron trifluoride diethyl etherate to obtain the aminotriacetylglucoside modified phloretin shown in the formula (I), and distilling and separating to obtain the aminotriacetylglucoside modified phloretin product.
Wherein, the molar ratio of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside to the acetic acid to the phloroglucinol is 1 (1.5-2) to 1.5-2. Wherein, in the step (2), the ratio of the molar amount of the bromoaminotriacetylglucose to the molar amount of the sodium p-hydroxyphenylpropionate which is dripped is (1.2-1.5):1, thereby improving the yield of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
Wherein in the step (3), the amount of boron trifluoride diethyl etherate as a catalyst is 1-5g based on 1 mol of sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
The phloretin modified by the amino triacetyl glucoside synthesized by the invention reserves the phloroglucinol group therein, and ensures the inoxidizability and the anti-inflammation of the phloretin modified by the amino triacetyl glucoside. Meanwhile, an aminotriacetylglucoside group is grafted and introduced on a phenolic hydroxyl group of the 4-hydroxyphenyl group, so that the water solubility and the skin absorption efficiency of the phloretin derivative are improved, the obtained phloretin derivative can be widely applied to various forms of cosmetic products, and has excellent oxidation resistance and anti-inflammatory effects.
A cosmetic containing an aminotriacetylglucoside-modified phloretin, which is characterized in that: the content of the aminotriacetylglucoside modified phloretin is 1-3 wt.%.
Further, the cosmetic is one of nourishing cream, facial mask, cream, skin moistening cream, essence, cream and plaster. Further, the cosmetic is a nourishing cream, and the nourishing cream comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 1-2% of hydrogenated lanolin, 0.5-2% of polyoxyethylene sorbitan monostearate, 6-8% of beeswax, 1-2% of cetyl alcohol, 2-4% of caprylic/capric triglyceride, 6-10% of glycerol, 3-4% of liquid paraffin, 0.1-0.5% of triethanolamine, 0.1-0.2% of essence and the balance of deionized water.
Further, the cosmetic is a facial mask, and the facial mask comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 0.2-1% of carbomer, 0.3-0.5% of triethanolamine, 2-3% of ascorbic acid polypeptide, 43-5% of palmitoyl pentapeptide, 8-12% of glycerol, 2-4% of hydroxypropyl methyl cellulose, 3-5% of propylene glycol, 2-4% of hydrolyzed gelatin, 1-2% of sorbitan sesquioleate, 1-2% of hydrogenated lanolin, 2-4% of caprylic/capric triglyceride and the balance of deionized water.
Detailed Description
The present invention will be described below with reference to specific examples, but these are not intended to be all the invention. Firstly, preparing the phloretin derivative containing the phloroglucinol group according to the following preparation method, wherein the phloretin derivative containing the phloroglucinol group is phloretin modified by amino triacetyl glucoside:
(1) preparation of bromotetraacetylglucose
Adding glucosamine into acetic anhydride with 3-5 times of molar weight, dropwise adding triethylamine with 5-6 times of molar weight under the condition of ice-water bath, reacting for 2 hours, adding enough water to precipitate a product, filtering, washing a filter cake with water, and drying in vacuum to obtain aminotetraacetylglucose; dissolving dried aminotetraacetylglucose in dichloromethane, dropwise adding hydrobromic acid with 2.5-4 times of molar weight of aminotetraacetylglucose at normal temperature, wherein the hydrobromic acid is provided by hydrobromic acid acetic acid solution with mass concentration of 30%, reacting for 1.5-3 hours, pouring into ice water, extracting a water phase by dichloromethane, combining organic phases, rapidly washing the organic phase by saturated sodium bicarbonate solution and saturated saline solution respectively until the pH value is 7, drying anhydrous magnesium sulfate, filtering, distilling the filtrate at normal temperature under reduced pressure to recover dichloromethane, and obtaining bromoaminotriacetylglucose product.
(2) Preparation of sodium p-hydroxyphenylpropionate aminotriacetylglucoside
Mixing and adding aqueous solutions of sodium p-hydroxyphenylpropionate, sodium hydroxide and potassium iodide into a reaction container, stirring at room temperature for reaction, wherein the concentration of the sodium p-hydroxyphenylpropionate is 0.2-0.5mol/L, the concentration of the sodium hydroxide is 20-50g/L, and the concentration of the potassium iodide is 1-3g/L, then dropwise adding bromoaminotriacetylglucose dissolved in acetone into the reaction container, stirring at room temperature for reaction for 6-8 hours, separating out a solid, namely sodium p-hydroxyphenylpropionate aminotriacetylglucoside, and sequentially washing with sodium hydroxide and deionized water after suction filtration to obtain the solid sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
(3) Preparation of phloretin modified by amino triacetyl glucoside
Dissolving sodium p-hydroxyphenylpropionate aminotriacetylglucoside, acetic acid and phloroglucinol in an ethyl acetate solvent, reacting for 4-8 hours under the catalytic action of boron trifluoride diethyl etherate to obtain the aminotriacetylglucoside modified phloretin shown in the formula (I), and distilling and separating to obtain the aminotriacetylglucoside modified phloretin product.
Wherein the molar ratio of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside to the acetic acid to the phloroglucinol is 1:1.5: 1.5; in the step (2), the ratio of the molar weight of the dropwise added bromoaminotriacetylglucose to the molar weight of the sodium p-hydroxyphenylpropionate is 1.3: 1; in the step (3), the amount of boron trifluoride diethyl etherate as a catalyst is 3g based on 1 mol of sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
Then, according to the following component requirements, the prepared aminotriacetylglucoside modified phloretin is added into a nutrition cream and a facial mask product to prepare the corresponding nutrition cream and facial mask product.
The nutrient cream comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 1-2% of hydrogenated lanolin, 0.5-2% of polyoxyethylene sorbitan monostearate, 6-8% of beeswax, 1-2% of cetyl alcohol, 2-4% of caprylic/capric triglyceride, 6-10% of glycerol, 3-4% of liquid paraffin, 0.1-0.5% of triethanolamine, 0.1-0.2% of essence and the balance of deionized water.
The mask comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 0.2-1% of carbomer, 0.3-0.5% of triethanolamine, 2-3% of ascorbic acid polypeptide, 43-5% of palmitoyl pentapeptide, 8-12% of glycerol, 2-4% of hydroxypropyl methyl cellulose, 3-5% of propylene glycol, 2-4% of hydrolyzed gelatin, 1-2% of sorbitan sesquioleate, 1-2% of hydrogenated lanolin, 2-4% of caprylic/capric triglyceride and the balance of deionized water.
Specifically, specific compositions of the respective examples and performance test results thereof are given in tables 1 and 2. The performance tests include, among others, an antioxidant test, an anti-inflammatory test, and a user experience evaluation.
The antioxidant test comprises DPPH free radical inhibition rate, OH free radical inhibition rate and O2-The inhibition rate of free radicals is three aspects. The anti-inflammation test adopts a mouse ear swelling experiment to carry out test, corresponding nutrient cream and facial mask liquid are directly smeared on the red swelling part of the mouse ear, the nutrient cream and the facial mask liquid are smeared according to the smearing dosage of 100mg/Kg of body weight based on the mass of the aminotriacetylglucoside modified phloretin, and then the swelling inhibition rate is calculated.
The user experience evaluation criteria are:
and 3, dividing: comfortable, and has good anti-inflammatory and antioxidant effects.
And 2, dividing: more comfortable, and has general anti-inflammatory and antioxidant effects.
1 minute: more comfortable, and has no obvious anti-inflammatory and antioxidant effects.
0 minute: discomfort and unobvious anti-inflammatory and antioxidant effects.
TABLE 1
TABLE 2
As can be seen from table 1 and table 2 above, the aminotriacetylglucoside modified phloretin of the present invention has excellent anti-inflammatory and antioxidant effects when applied to cosmetics. And the actual user experience is comfortable, the effect is obvious, and the corresponding product has high absorption rate on the skin surface and has no sensitive stimulation.
Claims (8)
1. A preparation method of a phloretin derivative containing a phloroglucinol group is disclosed, wherein the phloretin derivative containing the phloroglucinol group is modified by amino triacetyl glucoside, and the preparation method comprises the following steps:
(1) preparation of bromotetraacetylglucose
Adding glucosamine into acetic anhydride with 3-5 times of molar weight, dropwise adding triethylamine with 5-6 times of molar weight under the condition of ice-water bath, reacting for 2 hours, adding enough water to precipitate a product, filtering, washing a filter cake with water, and drying in vacuum to obtain aminotetraacetylglucose; dissolving dried aminotetraacetylglucose in dichloromethane, dropwise adding hydrobromic acid with 2.5-4 times of molar weight of aminotetraacetylglucose at normal temperature, wherein the hydrobromic acid is provided by hydrobromic acid acetic acid solution with mass concentration of 30%, reacting for 1.5-3 hours, pouring into ice water, extracting a water phase by dichloromethane, combining organic phases, rapidly washing the organic phase by saturated sodium bicarbonate solution and saturated saline solution respectively until the pH value is 7, drying anhydrous magnesium sulfate, filtering, distilling the filtrate at normal temperature under reduced pressure to recover dichloromethane, and obtaining bromoaminotriacetylglucose product.
(2) Preparation of sodium p-hydroxyphenylpropionate aminotriacetylglucoside
Mixing and adding aqueous solutions of sodium p-hydroxyphenylpropionate, sodium hydroxide and potassium iodide into a reaction container, stirring at room temperature for reaction, wherein the concentration of the sodium p-hydroxyphenylpropionate is 0.2-0.5mol/L, the concentration of the sodium hydroxide is 20-50g/L, and the concentration of the potassium iodide is 1-3g/L, then dropwise adding bromoaminotriacetylglucose dissolved in acetone into the reaction container, stirring at room temperature for reaction for 6-8 hours, separating out a solid, namely sodium p-hydroxyphenylpropionate aminotriacetylglucoside, and sequentially washing with sodium hydroxide and deionized water after suction filtration to obtain the solid sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
(3) Preparation of phloretin modified by amino triacetyl glucoside
Dissolving sodium p-hydroxyphenylpropionate aminotriacetylglucoside, acetic acid and phloroglucinol in an ethyl acetate solvent, reacting for 4-8 hours under the catalytic action of boron trifluoride diethyl etherate to obtain the aminotriacetylglucoside modified phloretin shown in the formula (I), and distilling and separating to obtain the aminotriacetylglucoside modified phloretin product.
Wherein, the molar ratio of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside to the acetic acid to the phloroglucinol is 1 (1.5-2) to 1.5-2.
2. The method for producing a phloretin derivative having a phloroglucinol group according to claim 1, comprising: in the step (2), the ratio of the molar amount of the bromoaminotriacetylglucose to the molar amount of the sodium p-hydroxyphenylpropionate added dropwise is (1.2-1.5):1, so that the yield of the sodium p-hydroxyphenylpropionate aminotriacetylglucoside can be improved.
3. The method for producing a phloretin derivative having a phloroglucinol group according to claim 1, comprising: in the step (3), the amount of boron trifluoride diethyl etherate as a catalyst is 1-5g based on 1 mol of sodium p-hydroxyphenylpropionate aminotriacetylglucoside.
4. An aminotriacetylglucoside-modified phloretin, which is produced by the production method according to any one of claims 1 to 3.
5. A cosmetic comprising the aminotriacetylglucoside-modified phloretin according to claim 4, wherein: the content of the aminotriacetylglucoside modified phloretin is 1-3 wt.%.
6. The cosmetic of claim 5, wherein the cosmetic is one of a nourishing cream, a facial mask, a cream, a skin lotion, an essence, a cream, and a patch.
7. The cosmetic according to claim 6, wherein the cosmetic is a nourishing cream, and the nourishing cream comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 1-2% of hydrogenated lanolin, 0.5-2% of polyoxyethylene sorbitan monostearate, 6-8% of beeswax, 1-2% of cetyl alcohol, 2-4% of caprylic/capric triglyceride, 6-10% of glycerol, 3-4% of liquid paraffin, 0.1-0.5% of triethanolamine, 0.1-0.2% of essence and the balance of deionized water.
8. The cosmetic according to claim 6, wherein the cosmetic is a mask, and the mask comprises the following components in percentage by weight:
1-3% of aminotriacetylglucoside modified phloretin, 0.2-1% of carbomer, 0.3-0.5% of triethanolamine, 2-3% of ascorbic acid polypeptide, 43-5% of palmitoyl pentapeptide, 8-12% of glycerol, 2-4% of hydroxypropyl methyl cellulose, 3-5% of propylene glycol, 2-4% of hydrolyzed gelatin, 1-2% of sorbitan sesquioleate, 1-2% of hydrogenated lanolin, 2-4% of caprylic/capric triglyceride and the balance of deionized water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011196901.4A CN112300228A (en) | 2020-10-31 | 2020-10-31 | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011196901.4A CN112300228A (en) | 2020-10-31 | 2020-10-31 | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112300228A true CN112300228A (en) | 2021-02-02 |
Family
ID=74333188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011196901.4A Pending CN112300228A (en) | 2020-10-31 | 2020-10-31 | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112300228A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006002422A2 (en) * | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | Compounds for immunopotentiation |
| CN102286050A (en) * | 2011-06-24 | 2011-12-21 | 天津大学 | Glucose-containing platinum complex for treating tumors and preparation method thereof |
| CN105362229A (en) * | 2015-11-19 | 2016-03-02 | 五邑大学 | Water-soluble phloretin solid dispersion and preparation method thereof |
-
2020
- 2020-10-31 CN CN202011196901.4A patent/CN112300228A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006002422A2 (en) * | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | Compounds for immunopotentiation |
| CN102286050A (en) * | 2011-06-24 | 2011-12-21 | 天津大学 | Glucose-containing platinum complex for treating tumors and preparation method thereof |
| CN105362229A (en) * | 2015-11-19 | 2016-03-02 | 五邑大学 | Water-soluble phloretin solid dispersion and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| SHOU-YUAN WU,ET AL.: "A new dihydrochalcone glycoside from the stems of Homalium stenophyllum", 《NATURAL PRODUCT RESEARCH》 * |
| 赵育,等: "几种喜树碱-糖缀合物的合成及其抗肿瘤活性研究", 《中国海洋大学学报》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103230408B (en) | Method for preparing phloretin | |
| JP2024505861A (en) | Oligogalacturonic acid polysaccharide, complex and its preparation method and use thereof | |
| CN112656709A (en) | Skin care compositions and uses thereof | |
| CN117045564B (en) | Skin care product containing peony extract and preparation method thereof | |
| EP2833863A1 (en) | Novel oligosaccharide compounds and the cosmetic use thereof | |
| CN112300228A (en) | A cosmetic containing phloretin derivative containing phloroglucinol group and its preparation method | |
| CN112125940A (en) | Cosmetic containing tetraacetyl glucoside modified phloretin and preparation method thereof | |
| CN112972332B (en) | Rose whitening essence and preparation method thereof | |
| CN112494347B (en) | Skin care water emulsion and preparation method thereof | |
| CN112724155B (en) | Method for preparing white glabridin by subcritical technology | |
| CN108143674A (en) | A kind of lotion containing peony seed oil and preparation method thereof | |
| CN109700690B (en) | Poria cocos moisturizing emulsion and preparation method thereof | |
| KR20010000390A (en) | Skin Improvement Composition Including Anti-Aging and Anti-Acne with Kimchi Extract | |
| CN109745241B (en) | Poria cocos mask liquid and preparation method thereof | |
| FR2973381A1 (en) | New oligosaccharide compounds useful e.g. for maintaining the integrity of the constituent molecules in the extracellular matrix and for reducing the glycation and/or hyperkeratinization process | |
| KR20030055950A (en) | Cosmetic composition containing punica granatum l. extract for anti-aging effect | |
| CN112603842A (en) | Active rose extract and application thereof | |
| CN109692142B (en) | Poria cocos facial cleanser and preparation method thereof | |
| CN117224454B (en) | Anti-aging/anti-saccharification essence and preparation method thereof | |
| CN114272165B (en) | Skin-whitening and tightening plant essence skin-care emulsion and preparation method thereof | |
| KR20050097698A (en) | A method for producing oleanolic acid and ursolic acid from persimmon peel | |
| CN114939093B (en) | Whitening and moisturizing composition containing amino acid and application of composition in cosmetics | |
| JP2002370960A (en) | Skin care preparation and method for using the same | |
| JP3429297B1 (en) | External preparation for skin | |
| KR101838025B1 (en) | Method of the natural arbutin contained in natural products |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |