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3,4,5-trimethoxycinnamate derivative, its preparation method and skin whitening composition containing the derivative

A technology of trimethoxycarnitine and trimethoxybenzenesulfonyl, applied in the field of new 3,4,5-trimethoxycinnamate derivatives, can solve the problem of lack of consumers, increase melanin, and increase the generation of skin free radicals Increase and other problems to achieve the effect of excellent skin whitening effect

Active Publication Date: 2022-02-01
AMOREPACIFIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, in the living body, the generation of free radicals in the skin will be increased through the polymerization and oxidation process using Tyrosine or DOPA as the substrate and enzymes such as Tyrosinase as the catalyst. Increased, or, when there is an inflammatory response or exposure to UV light, also increased melanin production
[0005] In particular, ultraviolet rays increase the production of melanin, and locally increased melanin develops into freckles, etc., which may cause undesired results in terms of aesthetics, and in serious cases, cause skin cancer, etc., which may be life-threatening
[0006] For these reasons, although many melanin production inhibitors have been developed, such as ointments, creams, and lotions containing arbutin, glutathione, vitamin A, vitamin C, etc., there are actually no whitening products that satisfy consumers. Effective whitening products
In addition, although whitening agents containing hydroquinone have a whitening effect to some extent, their use is limited due to severe skin irritation

Method used

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  • 3,4,5-trimethoxycinnamate derivative, its preparation method and skin whitening composition containing the derivative
  • 3,4,5-trimethoxycinnamate derivative, its preparation method and skin whitening composition containing the derivative
  • 3,4,5-trimethoxycinnamate derivative, its preparation method and skin whitening composition containing the derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: Preparation of (+)-3,4,5-trimethoxymenthyl cinnamate ((+)-menthyl 3,4,5-trimethoxycinnamate)

[0091] [chemical formula 2]

[0092]

[0093] Dissolve 10 g of 3,4,5-trimethoxycinnamic acid (0.042 mol) in 100 mL of pyridine (pyridine), cool in an ice-water bath at 10°C, and then add 8.9 g (0.050 mol) of benzenesulfonate dropwise to it Acid chloride benzenesulfonyl chloride (benzenesulfonyl chloride) for 30 minutes. After slowly raising the reaction temperature to normal temperature and stirring for 2 hours, 6.5 g (0.042 mol) of 1R,2S,5R-(+)-menthol was dissolved in 30 mL of pyridine and added dropwise to the reaction solution for 3 minutes. After further stirring for 2 hours, the solvent was distilled off, and the residue was dissolved in 300 ml of ethyl acetate, after which the ethyl acetate solution was washed with 5% hydrochloric acid and distilled water, and magnesium sulfate and activated carbon were added thereto, followed by drying and decolorization...

Embodiment 2

[0096] Example 2: Preparation of (-)-3,4,5-trimethoxymenthyl cinnamate ((-)-menthyl 3,4,5-trimethoxycinnamate)

[0097][chemical formula 3]

[0098]

[0099] The target compound (11.5 g, 73%) was obtained as a white solid in the same manner as in Example 1 except that (-)-menthol was used instead of (+)-menthol.

[0100] LC (ethyl acetate:alkane=1:1) Rf=0.65

[0101] 1 H NMR (DMSO-d6, δ): 7.62 (d, 1H, J = 15.9Hz), 7.07 (s, 2H), 6.08 (d, 1H, J = 15.9Hz), 4.75 (m, 1H), 3.81 ( 3,6H),3.68(s,3H),1.88(m,2H),1.63(m,2H),1.43(m,2H),1.03(m,2H),0.91(m,6H),0.75(d ,3H,J=7.2Hz).

Embodiment 3

[0102] Example 3: Preparation of (+_)-3,4,5-trimethoxymenthyl cinnamate ((+_)-menthyl 3,4,5-trimethoxycinnamate)

[0103] [chemical formula 4]

[0104]

[0105] The target compound (11.0 g, 70%) was obtained as a white solid in the same manner as in Example 1 except that (±)-menthol was used instead of (+)-menthol.

[0106] TLC (ethyl acetate:alkane=1:1) Rf=0.65

[0107] 1 H NMR (DMSO-d6, δ): 7.62 (d, 1H, J = 15.9Hz), 7.07 (s, 2H), 6.08 (d, 1H, J = 15.9Hz), 4.75 (m, 1H), 3.81 ( 3,6H),3.68(s,3H),1.88(m,2H),1.63(m,2H),1.43(m,2H),1.03(m,2H),0.91(m,6H),0.75(d ,3H,J=7.2Hz).

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Abstract

The present invention relates to a novel 3,4,5-trimethoxycinnamate derivative, a preparation method thereof, and a composition containing the same for skin whitening. The compound acts on tyrosinase, an enzyme that produces melanin, and exhibits a skin whitening effect by inhibiting melanin production. Compared with kojic acid known as an existing skin whitening agent, it exhibits a more excellent skin whitening effect than kojicin known as a skin whitening agent, and can be applied to various skin whitening cosmetics or skin External preparations, etc.

Description

technical field [0001] The present invention relates to a novel 3,4,5-trimethoxycinnamate derivative, a preparation method thereof, and a skin whitening composition containing the derivative. Background technique [0002] Human skin color is determined by the combination of red blood cells, carotene and melanin in the blood, but the difference in skin color between races, or hyperpigmentation such as moles and freckles is caused by melanin. [0003] Melanin, which exists in the epidermis as the outer shell of the skin, has the function of blocking ultraviolet rays to protect the skin organs below the dermis, and at the same time has the function of capturing free radicals generated in the skin organism, thereby protecting the proteins and genes in the skin. effective role. However, melanin produced by internal and external stress stimuli is a stable substance that does not disappear even if the stress disappears until it is discharged through keratinization of the skin. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/618A61K8/36A61Q19/02
CPCA61K8/36A61Q19/02C07C69/618
Inventor 卢浩植金容震朴录贤李存桓李昌锡
Owner AMOREPACIFIC CORP
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