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Propyl-phenyl-ether derivative and melanogenesis inhibitor, skin-lightening agent, antimicrobial agent, and cosmetic containing said propyl-phenyl-ether derivative

A technology of propyl phenyl ether and its derivatives, which can be applied in the direction of chemicals for biological control, biocides, skin care preparations, etc., and can solve the problems of not showing antibacterial effects, etc.

Inactive Publication Date: 2015-07-01
SEIWA KASEI CO JP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compound is only effective against acne bacteria and does not show broad antibacterial effects

Method used

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  • Propyl-phenyl-ether derivative and melanogenesis inhibitor, skin-lightening agent, antimicrobial agent, and cosmetic containing said propyl-phenyl-ether derivative
  • Propyl-phenyl-ether derivative and melanogenesis inhibitor, skin-lightening agent, antimicrobial agent, and cosmetic containing said propyl-phenyl-ether derivative
  • Propyl-phenyl-ether derivative and melanogenesis inhibitor, skin-lightening agent, antimicrobial agent, and cosmetic containing said propyl-phenyl-ether derivative

Examples

Experimental program
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Effect test

Embodiment

[0147] Hereinafter, specific embodiments of the present invention will be described using examples, but the scope of the present invention is not limited by the following examples.

Synthetic example 11－

[0148] Synthesis Example 11 - Synthesis of (4'-tert-butylphenoxy)propyl

[0149] Add sodium hydroxide (0.26g) and tetrabutylammonium bromide (0.43g) to 4-tert-butylphenol (1.00g), stir at room temperature, add bromopropyl (1.64g), and then After stirring for 5 hours, ethyl acetate and water were added, and the target substance was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and 1.37 g of the obtained residue was subjected to silica gel column chromatography. The mixture was eluted with hexane / ethyl acetate=20 / 1, and concentrated under reduced pressure to obtain a product. The obtained product was confirmed to have a different Rf value from each raw material and a spot of UV absorption by HPTLC analysis, and the raw material was identified as 1-(4'-tert-butylphenoxy)propyl group represented by the structural formula shown below.

[0150]

Synthetic example 21－

[0151] Synthesis Example 21 - Synthesis of (4'-tert-butylphenoxy)ethyl

[0152] Add sodium hydroxide (0.26g) and tetrabutylammonium bromide 0.43g to 4-tert-butylphenol (1.00g), stir at room temperature, add bromoethane (2.20g), and stir at 40°C After 5 hours, ethyl acetate and water were added, and the target substance was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and 0.97 g of the obtained residue was subjected to silica gel column chromatography. The mixture was eluted with hexane / ethyl acetate=20 / 1, and concentrated under reduced pressure to obtain a product. The obtained product was confirmed to be a compound having UV absorption by HPTLC analysis, and was identified as a 1-(4'-tert-butylphenoxy)ethyl group represented by the structural formula shown below from the raw material.

[0153]

[0154] Synthesis Example 31, Synthesis of 2-Di-Hydroxy-3-Phenoxypropyl

[0155] Add water (5.00g) and ...

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PUM

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Abstract

Provided is a compound that exhibits an excellent melanogenesis-inhibiting effect (skin-lightening effect), exhibits an excellent antimicrobial effect, excels in terms of temporal stability and the like, and is suitable for use as an ingredient of a cosmetic. Said compound is a propyl-phenyl-ether derivative compound comprising a propyl group that has a substituent such as a hydroxyl group and is bound to the hydroxyl group of a phenol group that has a substituent such as a tert-butyl group. A melanogenesis inhibitor, skin-lightening agent, and antimicrobial agent containing the aforementioned compound as an active ingredient are also provided, as is a cosmetic characterized by containing said compound.

Description

technical field [0001] The present invention relates to propylphenyl ether derivatives suitable for use as raw materials for cosmetics and the like. The present invention also relates to a melanin production inhibitor, a whitening agent, and an antibacterial agent containing the above-mentioned propyl phenyl ether derivative as an active ingredient, and a cosmetic characterized by blending the above-mentioned propyl phenyl ether derivative. Background technique [0002] In recent years, when using cosmetics, various effects such as anti-whitening effect such as melanin production inhibitory effect, antibacterial effect, anti-acne, anti-dandruff, and anti-wrinkle are expected to be used more and more. Therefore, it is expected that the raw materials of cosmetics exhibit the above-mentioned effects. Among them, the whitening effect, particularly the melanin production inhibitory effect is highly expected. [0003] When the skin is exposed to ultraviolet rays, active oxygen i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23A01N31/14A01P3/00A61K8/34A61K8/37A61K8/40A61K8/41A61K8/44A61K8/46A61K31/085A61K31/10A61K31/136A61K31/192A61K31/198A61K31/277A61P17/00A61P31/04A61P43/00A61Q19/00A61Q19/02C07C65/21C07C205/37C07C217/30C07C217/84C07C229/26C07C255/54C07C279/14C07C323/12
CPCA61K8/34A01N31/14C07C43/23A61Q17/005A61Q19/02C07C65/21A01N37/12C07C69/30A61K8/37A61K8/345A61P17/00A61P17/16A61P31/04A61P43/00A61K8/375A61K8/39C07C43/295C07C69/28
Inventor 吉冈正人平德久中村清香
Owner SEIWA KASEI CO JP
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