Novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates) as well as preparation method and new application thereof

A technology of methyl gentisate and oxybenzoic acid, which is applied in the field of skin whitening, can solve problems such as unsuitable whitening agents, and achieve the effects of simple process route, obvious social and economic benefits, and high yield

Inactive Publication Date: 2012-07-04
四川华肤生物科技有限责任公司 +2
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Hydroquinone, that is, hydroquinone (HQ) is a traditional whitening and freckle-removing ingredient, but due to safety issues, the CTFA 2000 edition of the review summary of cosmetic ingredients clear...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates) as well as preparation method and new application thereof
  • Novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates) as well as preparation method and new application thereof
  • Novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates) as well as preparation method and new application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Novel gentisic acid derivatives 2-hydroxy-5-alk(H)oxybenzoates, the structural formula of which is:

[0021]

[0022] In the structural formula, R 1 Any one of hydrogen, methyl, ethyl, benzyl and p-nitrobenzyl, R 2 is hydrogen or methyl.

[0023] The novel gentisic acid derivative 2-hydroxy-5-alk(H)oxybenzoate is used in the field of skin whitening.

[0024] A method for preparing novel gentisic acid derivatives 2-hydroxy-5-alk(H)oxybenzoates, including methyl gentisate, halogenated hydrocarbons, potassium carbonate, sodium hydroxide and α-hydroxy acid esters;

[0025] The molar ratio of methyl gentisate to halogenated hydrocarbons and potassium carbonate is 1:1.2:1.5, the molar ratio to sodium hydroxide is 1:2~5, and the molar ratio to α-hydroxy acid ester is 1 :2;

[0026] First, add methyl gentisate and anhydrous acetone in sequence in the container (the ratio of methyl gentisate to anhydrous acetone is 1:0.2~1), add halogenated hydrocarbon under st...

Embodiment 2

[0049] Embodiment 2: This embodiment prepares ethoxycarbonylmethyl 2-hydroxy-5-methoxybenzoate (6a for short), and its structural formula is as follows:

[0050]

[0051] The processing steps of the present embodiment are as follows:

[0052] Preparation of ethoxycarbonylmethyl 2-hydroxy-5-methoxybenzoate (abbreviated as 6a)

[0053] Take 50 mg (0.30 mmol) of pure methyl gentisate, dissolve it in 10 mL of acetone, and then add 62 mg (0.45 mmol) of K 2 CO 3 , 0.51g (0.36mmol) CH 3I, the reaction was stirred under reflux, followed by TLC until the reaction was complete, filtered, the filtrate was concentrated under reduced pressure, and the crude product was separated and purified by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain 2-hydroxy-5-methoxybenzene Methyl formate. Take 50mg (0.27mmol) of methyl 2-hydroxy-5-methoxybenzoate, dissolve it in 10ml of 95% methanol solution, and slowly add NaOH solid under stirring at room temperature, then raise ...

Embodiment 3

[0054] Embodiment 3: This embodiment prepares ethoxycarbonylmethyl 2-hydroxy-5-ethoxybenzoate (6b for short), and its structural formula is as follows:

[0055]

[0056] The processing steps of the present embodiment are as follows:

[0057] Preparation of ethoxycarbonylmethyl 2-hydroxy-5-ethoxybenzoate (6b for short):

[0058] Take 50 mg (0.30 mmol) of pure methyl gentisate, dissolve it in 10 mL of acetone, and then add 62 mg (0.45 mmol) of K 2 CO 3 , 0.39g (0.36mmol) BrCH 2 CH 3 , reflux and stir the reaction, TLC traced until the reaction was complete, filtered, the filtrate was concentrated under reduced pressure, and the crude product was separated and purified by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain 2-hydroxy-5-ethoxybenzoic acid methyl ester. Take 50mg (0.26mmol) of methyl 2-hydroxy-5-ethoxybenzoate, dissolve it in 10ml of 95% methanol solution, and slowly add NaOH solid under stirring at room temperature, then raise the tempera...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates), which have a structural formula shown in the specification, wherein R1 is any one of hydrogen, methyl, ethyl, benzyl and p-nitrobenzyl; and R2 is hydrogen or methyl. The invention also discloses a new application of the novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates) in the beauty and whitening field. The novel gentisic acid derivatives (2-hydroxy-5-alkyl (H) oxo benzoates) have the advantages of low toxicity, high stability, better pharmacological activity and excellent beauty and whitening effect.

Description

technical field [0001] The invention relates to the field of skin whitening, in particular to a novel gentisic acid derivative 2-hydroxy-5-alk(H)oxybenzoate, a preparation method and a new application thereof. Background technique [0002] Cosmetic companies at home and abroad are exploring and developing raw materials with whitening and freckle-removing effects. Whitening and freckle-removing cosmetics have always been the best-selling products in the Asian market. According to statistics, about 70% of women believe that one of the biggest obstacles to beauty is the formation of facial freckles, chloasma, and age spots. They are common skin diseases of pigmentation, which affect appearance and cause serious psychological pressure to patients. The current whitening and freckle-removing raw materials have many deficiencies in terms of safety and efficacy, such as the toxicity of hydroquinone and the easy decomposition of vitamin C. [0003] Gentisic acid is 2,5-dihydroxybenz...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C69/92C07C67/08A61K31/235A61P17/00
Inventor 李利宋长伟张南尹述凡熊丽丹李颖
Owner 四川华肤生物科技有限责任公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap