CN116903686A - Whitening compound, preparation method and whitening cosmetic - Google Patents

Whitening compound, preparation method and whitening cosmetic Download PDF

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Publication number
CN116903686A
CN116903686A CN202310892935.4A CN202310892935A CN116903686A CN 116903686 A CN116903686 A CN 116903686A CN 202310892935 A CN202310892935 A CN 202310892935A CN 116903686 A CN116903686 A CN 116903686A
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CN
China
Prior art keywords
parts
whitening
compound
arbutin
hydroquinone
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.)
Withdrawn
Application number
CN202310892935.4A
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Chinese (zh)
Inventor
王宏伟
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Guangzhou Hongqi Biotechnology Co ltd
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Guangzhou Hongqi Biotechnology Co ltd
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Priority to CN202310892935.4A priority Critical patent/CN116903686A/en
Publication of CN116903686A publication Critical patent/CN116903686A/en
Withdrawn legal-status Critical Current

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    • 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
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The invention provides a whitening compound, a preparation method and a whitening cosmetic, and belongs to the technical field of cosmetics. The composite material is prepared from the following raw materials in parts by weight: 5-7 parts of whitening compound, 1-2 parts of carbomer, 4-5 parts of glycerin, 2-4 parts of 1, 2-butanediol, 1-2 parts of nicotinamide, 0.01-0.03 part of EDTA disodium, 0.2-0.4 part of xanthan gum, 0.5-1 part of vitamin C, 1-2 parts of tea polyphenol, 1-2 parts of silk fibroin and 50-60 parts of water. The whitening cosmetic prepared by the invention has good whitening effect, is easy to absorb, is safe and has no side effect, and can form a protective barrier on the surface of skin, thereby having good whitening and moisturizing effects.

Description

Whitening compound, preparation method and whitening cosmetic
Technical Field
The invention relates to the technical field of cosmetics, in particular to a whitening compound, a preparation method and a whitening cosmetic.
Background
The pursuit of a beautiful appearance is the nature of everyone, and the condition and appearance of the skin are important components thereof, and healthy and fair skin is pursued by people. For this reason, the demand for whitening cosmetics has been the leading end of various cosmetic demands.
Skin tissue is the first protective barrier of a person and can be broadly divided into epidermis, dermis and subcutaneous tissue. The color of the skin is mainly determined by the amount, size and distribution of melanin contained in skin cells.
The problem with skin lightening is mainly dependent on the ability of melanocytes to synthesize melanin. Between human epidermis basal lamina cells, there are distributed melanocytes, which contain tyrosinase, which is a polyphenol enzyme belonging to the class of oxidoreductases, which are then subjected to a series of metabolic processes to finally produce melanin. The more melanin is produced, the darker the skin; on the contrary, the more fair the skin is. Tyrosinase has unique double catalytic functions, is a key enzyme for melanin synthesis in organisms, and has close relation with human aging. Its abnormal overexpression can lead to pigmentation disorders in humans. Tyrosinase inhibitors can be used for treating pigmentation dermatoses such as freckle, chloasma and senile plaque. Therefore, the arbutin, vitamin C derivatives, kojic acid and derivatives thereof, green tea extracts, licorice extracts and other traditional Chinese medicine extracts in the whitening cosmetics popular in the market at present are all tyrosinase inhibitors, and mainly inhibit melanin synthesis by inhibiting the activity of tyrosinase, thereby playing a role in whitening.
In the patent CN201010214873.4, a whitening composition is disclosed, which contains mulberry bark extract, chamomile extract, rhodiola rosea extract, grape seed extract, licorice extract, mulberry extract, arbutin, kojic dipalmitate, nicotinamide, tetrahydrocurcumin, humectant and preservative, and the effective whitening component in the invention can inhibit the activity of tyrosinase, block melanin transport, inhibit melanin formation, and can be used in whitening cosmetics, and is safe and effective.
The invention discloses a plant extract composition with a whitening function and application thereof in a whitening cosmetic in the patent CN201310210916.5, and the plant extract composition is prepared by compounding a white mulberry root-bark extract, a licorice extract, a peony extract, a kapok extract, an angelica extract and a cortex moutan extract. The plant composition can be used in a whitening formula, and has the functions of inhibiting tyrosinase activity, scavenging free radicals and whitening skin.
In a whitening cosmetic and a preparation method thereof, patent CN201210511695.0 discloses a whitening cosmetic, which is prepared from the following raw materials in percentage by weight: 50 to 70 weight percent of cucumber seed oil, 15 to 25 weight percent of johnsongrass oil and 15 to 25 weight percent of calendula oil, and the preparation method comprises the following steps: 50 to 70 weight percent of cucumber seed oil, 15 to 25 weight percent of johnsongrass oil and 15 to 25 weight percent of calendula oil are mixed at the temperature of 20 to 25 ℃ and stirred uniformly to obtain the product; the whitening cosmetic is prepared from natural vegetable oil, is green and safe, and has no irritation to skin.
Disclosure of Invention
The invention aims to provide a whitening compound, a preparation method and a whitening cosmetic, which have good whitening effect, are easy to absorb, are safe and have no side effect, and can form a protective barrier on the surface of skin, so that good whitening and moisturizing effects are achieved.
The technical scheme of the invention is realized as follows:
the invention provides a whitening compound, which has a structure shown in a formula I:
the invention further provides a preparation method of the whitening compound, which comprises the following steps:
s1, reacting arbutin with thionyl chloride to prepare an intermediate I, wherein the structure is as follows:
s2, reacting the intermediate I with hydroquinone to obtain a product.
As a further improvement of the invention, the mol ratio of arbutin to thionyl chloride in the step S1 is 1:1-1.05.
As a further development of the invention, the molar ratio of intermediate I to hydroquinone in step S2 is 2-2.1:1.
As a further improvement of the present invention, a base is also added in step S2.
As a further improvement of the present invention, the base is at least one selected from NaOH, KOH, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
As a further improvement of the invention, the method specifically comprises the following steps:
s1, dissolving 1 molar equivalent of arbutin and 1-1.05 molar equivalent of thionyl chloride in dichloromethane, and reacting for 20-30min at room temperature to obtain an intermediate I;
s2, dissolving 2-2.1 mol equivalent of intermediate I and 1mol equivalent of hydroquinone in dichloromethane, adding 3-5 mol equivalent of alkali, heating and refluxing for 2-3h, and separating by column chromatography to obtain the product.
The invention further provides a whitening cosmetic containing the whitening compound.
As a further improvement of the invention, the invention is prepared from the following raw materials in parts by weight: 5-7 parts of whitening compound, 1-2 parts of carbomer, 4-5 parts of glycerin, 2-4 parts of 1, 2-butanediol, 1-2 parts of nicotinamide, 0.01-0.03 part of EDTA disodium, 0.2-0.4 part of xanthan gum, 0.5-1 part of vitamin C, 1-2 parts of tea polyphenol, 1-2 parts of silk fibroin and 50-60 parts of water.
The invention has the following beneficial effects: the whitening compound contains the structure of arbutin and hydroquinone, has good whitening effect, can hydrolyze to generate hydroquinone and glucose, and can deactivate enzyme and prevent skin melanin from generating by coagulating amino acid in tyrosinase.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions of the prior art, the drawings which are used in the description of the embodiments or the prior art will be briefly described, it being obvious that the drawings in the description below are only some embodiments of the invention, and that other drawings can be obtained according to these drawings without inventive faculty for a person skilled in the art.
Fig. 1 is a synthetic route pattern of the whitening compound.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Preparation example 1
As shown in fig. 1, the preparation method of the whitening compound specifically comprises the following steps:
s1, dissolving 0.1mol of arbutin and 0.1mol of thionyl chloride in 200mL of dichloromethane, and reacting for 20min at room temperature to obtain an intermediate I;
s2, dissolving 0.2mol of intermediate I and 0.1mol of hydroquinone in 200mL of dichloromethane, adding 0.3mol of NaOH, heating and refluxing for 2h, and separating by column chromatography to obtain the product with the total yield of 84.2%.
Preparation example 2
As shown in fig. 1, the preparation method of the whitening compound specifically comprises the following steps:
s1, dissolving 0.1mol of arbutin and 0.105mol of thionyl chloride in 200mL of dichloromethane, and reacting for 30min at room temperature to obtain an intermediate I;
s2, dissolving 0.21mol of intermediate I and 0.1mol of hydroquinone in 200mL of dichloromethane, adding 0.5mol of KOH, heating and refluxing for reaction for 3h, and separating by column chromatography to obtain the product with the total yield of 85.4%.
Preparation example 3
As shown in fig. 1, the preparation method of the whitening compound specifically comprises the following steps:
s1, dissolving 0.1mol of arbutin and 0.102mol of thionyl chloride in 200mL of dichloromethane, and reacting at room temperature for 25min to obtain an intermediate I;
s2, dissolving 0.205mol of intermediate I and 0.1mol of hydroquinone in 200mL of dichloromethane, adding 0.4mol of alkali, heating and refluxing for 2.5h, and separating by column chromatography to obtain the product with the total yield of 87.2%.
Example 1
A whitening cosmetic is prepared from the following raw materials in parts by weight: 5 parts of whitening compound, 1 part of carbomer, 4 parts of glycerin, 2 parts of 1, 2-butanediol, 1 part of nicotinamide, 0.01 part of EDTA disodium, 0.2 part of xanthan gum, 0.5 part of vitamin C, 1 part of tea polyphenol, 1 part of silk fibroin and 50 parts of water.
Example 2
A whitening cosmetic is prepared from the following raw materials in parts by weight: 7 parts of whitening compound, 2 parts of carbomer, 5 parts of glycerin, 4 parts of 1, 2-butanediol, 2 parts of nicotinamide, 0.03 part of EDTA disodium, 0.4 part of xanthan gum, 1 part of vitamin C, 2 parts of tea polyphenol, 2 parts of silk fibroin and 60 parts of water.
Example 3
A whitening cosmetic is prepared from the following raw materials in parts by weight: 6 parts of whitening compound, 1.5 parts of carbomer, 4.5 parts of glycerin, 3 parts of 1, 2-butanediol, 1.5 parts of nicotinamide, 0.02 part of EDTA disodium, 0.3 part of xanthan gum, 0.7 part of vitamin C, 1.5 parts of tea polyphenol, 1.5 parts of silk fibroin and 55 parts of water.
Comparative example 1
The difference compared to example 3 is that the whitening compound is replaced by an equivalent amount of hydroquinone.
Comparative example 2
The difference compared to example 3 is that the whitening compound is replaced by an equal amount of arbutin.
Test example 1 antioxidant efficacy test
Experimental group: the whitening cosmetics prepared in examples 1 to 3;
comparison group: the whitening cosmetics prepared in comparative examples 1 to 2;
positive comparative example: reference VC.
0.02604g DPPH (96% by weight) is accurately weighed, dissolved and fixed to 100mL by ethanol with the volume concentration of 95%, and the DPPH concentration is 0.25 g.L -1 And storing for standby. At the time of experiment, 12ml0.25 g.L -1 The DPPH solution of (2) was fixed to 100mL with 95% ethanol, and the DPPH concentration was 0.03 g.L -1 . Baseline was scanned using 95% ethanol as reference solution. 0.03 g.L was measured -1 The DPPH solution of (C) has a maximum absorption wavelength of 518nm at 400-600 nm.
Determination of absorbance of the blank control: 5mL of a DPPH solution of 0.03 g.L-1 was taken in a 10mL EP tube, and 0.1mL of a 95% strength by volume ethanol solution was added thereto and mixed. The absorbance at 518nm was measured and designated A 0 。
Measuring the absorbance of the liquid to be measured: 5mL of 0.03 g.L -1 To the EP tube, 0.1mL of the solution to be measured was added, and the mixture was mixed well. The absorbance at 518nm was measured and designated A i 。
Data processing, namely calculating the clearance E, E=1-A of the obtained data according to the following formula i /A 0 ×100％
The results of the radical scavenging rate obtained by the measurement are shown in Table 1:
TABLE 1
Group of Clearance (%)
Positive control 91.2
Example 1 94.5
Example 2 95.1
Example 3 95.5
Comparative example 1 83.5
Comparative example 2 85.2
As can be seen from the above table, the whitening cosmetics prepared in examples 1 to 3 of the present invention have good antioxidant effect.
Test example 2 whitening effect test
Volunteers 100 ages (24-55 years), randomly divided into 5 groups, 20 persons each, and tested the whitening cosmetics prepared in examples 1-3 and comparative examples 1-2, respectively. The using method comprises the following steps: 2-4mL of whitening cosmetics are applied at approximately the same time every night for 28 days, and then the results are collected and the test data are summarized in Table 2.
TABLE 2 whitening effect table
Group of Has obvious effect In general Invalidation of Obvious efficiency (%) Effective rate (%)
Example 1 17 2 1 85 95
Example 2 16 4 0 80 95
Example 3 18 2 0 90 100
Comparative example 1 6 4 10 30 50
Comparative example 2 9 3 8 45 60
As can be seen from the above table, the whitening cosmetics prepared in examples 1 to 3 of the present invention have good whitening effect.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.

Claims (9)

1. A whitening compound characterized by having a structure as shown in formula I:
2. a method for preparing the whitening compound as set forth in claim 1, comprising the steps of:
s1, reacting arbutin with thionyl chloride to prepare an intermediate I, wherein the structure is as follows:
s2, reacting the intermediate I with hydroquinone to obtain a product.
3. The method according to claim 2, wherein the molar ratio of arbutin to thionyl chloride in step S1 is 1:1-1.05.
4. The process according to claim 2, wherein the molar ratio of intermediate I to hydroquinone in step S2 is 2-2.1:1.
5. The method according to claim 2, wherein a base is further added in step S2.
6. The method according to claim 5, wherein the base is at least one selected from the group consisting of NaOH, KOH, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate.
7. The preparation method according to claim 2, characterized by comprising the following steps:
s1, dissolving 1 molar equivalent of arbutin and 1-1.05 molar equivalent of thionyl chloride in dichloromethane, and reacting for 20-30min at room temperature to obtain an intermediate I;
s2, dissolving 2-2.1 mol equivalent of intermediate I and 1mol equivalent of hydroquinone in dichloromethane, adding 3-5 mol equivalent of alkali, heating and refluxing for 2-3h, and separating by column chromatography to obtain the product.
8. A whitening cosmetic comprising the whitening compound according to claim 1.
9. The whitening cosmetic according to claim 8, which is prepared from the following raw materials in parts by weight: 5-7 parts of whitening compound, 1-2 parts of carbomer, 4-5 parts of glycerin, 2-4 parts of 1, 2-butanediol, 1-2 parts of nicotinamide, 0.01-0.03 part of EDTA disodium, 0.2-0.4 part of xanthan gum, 0.5-1 part of vitamin C, 1-2 parts of tea polyphenol, 1-2 parts of silk fibroin and 50-60 parts of water.
CN202310892935.4A 2023-07-19 2023-07-19 Whitening compound, preparation method and whitening cosmetic Withdrawn CN116903686A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202310892935.4A CN116903686A (en) 2023-07-19 2023-07-19 Whitening compound, preparation method and whitening cosmetic

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202310892935.4A CN116903686A (en) 2023-07-19 2023-07-19 Whitening compound, preparation method and whitening cosmetic

Publications (1)

Publication Number Publication Date
CN116903686A true CN116903686A (en) 2023-10-20

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Country Status (1)

Country Link
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Application publication date: 20231020