Flavone derivative, preparation method and application thereof, and whitening product containing flavone derivative

A technology of derivatives and flavonoids, applied in the field of daily chemical products, can solve the problems of low whitening effect of natural flavonoids and difficulty in meeting market demands.

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A technology of derivatives and flavonoids, applied in the field of daily chemical products, can solve the problems of low whitening effect of natural flavonoids and difficulty in meeting market demands.

CN110305098AActive Publication Date: 2019-10-08SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA

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Examples

Experimental program

Comparison scheme

Effect test

Embodiment 1

[0071] The preparation of compound C1 (5-styryl catechin) and compound D1 (7-styryl catechin), the specific synthesis steps are as follows:

[0072] In a 100mL round bottom flask, the raw material catechin (580mg, 2mmol, 1eq) or epicatechin (580mg, 2mmol, 1eq), and phenylacetaldehyde (600μL, 2.5eq) were added to diethylene glycol (40mL ), add 5.3% hydrochloric acid (14mL) dropwise, heat and react at 120°C for 2 hours, after the reaction is complete, remove the solvent in vacuo, add ethyl acetate (50mL) to dissolve, wash with water (20mL×3), and separate the organic phase , the organic phase was concentrated to dryness in vacuo, and separated by column chromatography (selecting 200-300 mesh silica gel, the eluent is a mixed solution of dichloromethane and methanol, volume ratio 20:1), to obtain the colorless oily target product, According to the results of column chromatography, C1 (5-styryl catechin) was firstly obtained with a yield of 75%, and then D1 (7-styryl catechin) was...

Embodiment 2

[0078] For the preparation of compound C2, the specific synthetic steps differ from those in Example 1 in that catechin was replaced by 3',4'-dimethoxycatechin, and the yield was 52%.

[0079] Structure Characterization:

[0080] 1 H NMR (400MHz, CDCl 3 ), δ=7.72(m,2H),7.44(m,2H),7.30-7.21(m,2H),6.97-6.96(m,2H),6.87-6.77(m,2H),5.98(s,1H ),6.52(d,1H),5.82(s,1H),5.02(s,1H),4.89-4.88(m,2H),3.83(s,3H),3.75(s,3H),2.86-2.81( m,2H).

[0081] HRMS(ESI-ion trap)m / z:[M+H]+calculated value C 25 h 24 o 6 420.1573, found 420.1572.

Embodiment 3

[0083] The preparation of compound C3, the specific synthesis steps are as follows:

[0084] (1) In a 100mL round-bottomed flask, the raw materials afucatechin (540mg, 2mmol, 1eq) and thionyl chloride (600μL, 2.5eq) were added to 1,4-dioxane (20mL), 1 mL of dimethylformamide was added dropwise and reacted at room temperature for 12 hours. After the reaction was completed, the solvent was removed in vacuo to obtain 4'-chloroafucatechin;

[0085] (2) In a 100mL round bottom flask, add raw materials 4'-chloroafucatechin (600mg, 1eq) and phenylacetaldehyde (600μL, 2.5eq) into diethylene glycol (40mL), dropwise 5.3% hydrochloric acid (14mL), heat reaction at 140°C for 2 hours, after the reaction, remove the solvent in vacuo, add ethyl acetate (50mL) to dissolve, wash with water (20mL×3), separate the organic phase, and concentrate the organic phase in vacuo To dryness, use column chromatography to separate (choose 200-300 mesh silica gel, the eluent is a mixture of dichloromethane...

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Abstract

The invention provides a flavone derivative, a preparation method and application thereof, and a whitening product containing the flavone derivative. The flavone derivative is a compound provided witha structure shown as a formula I or a formula II. The flavone derivative is prepared through the method that flavonoid compounds and phenylacetaldehyde compounds are taken as raw materials, and underthe acid environment, reaction is conducted in an organic solvent. Styryl is adopted to modify the flavonoid compounds, the obtained flavone derivative can significantly inhibit melanin production and resist oxidation, the effect of the flavone derivative is superior than the effect of the unmodified flavonoid compounds and alpha-arbutin commonly used in the market, and the flavone derivative canbe used for preparing products such as whitening skin care products, cosmetics, drugs, health care products or foods.

Description

technical field [0001] The invention belongs to the technical field of daily chemical products, and in particular relates to a flavonoid derivative, its preparation method, application and whitening product containing the same. Background technique [0002] With the development of society and the acceleration of the pace of modern life, various problems occur on human skin due to ultraviolet rays, sunlight, and the human body itself. Most of them are skin cell damage, resulting in skin spots, pigmentation, and dryness. Healthy fair skin is what most people pursue, so cosmetics with whitening function are more and more popular. The study of compounds with whitening, anti-oxidation and pigmentation reduction effects has become one of the focuses of basic research on skin care. [0003] At present, whitening cosmetics mainly add arbutin, vitamin C and its derivatives and other ingredients with whitening and anti-oxidation effects, but gradually exposed poor absorption, instabi...

Claims

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Application Information

Patent Timeline

08 Oct 2019

Publication

CN110305098A

IPC: C07D311/62; C07D335/06; C07D215/20; A61K8/49; A61Q19/02; A61Q19/08; A61Q19/00; A61K31/352; A61K31/382; A61K31/47; A61P17/16; A61P17/18; A23L33/10

CPC: A23V2002/00; A61K8/4926; A61K8/498; A61K8/4986; A61Q19/00; A61Q19/02; A61Q19/08; A23L33/10

Inventors: 汪君; 王子豪