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Citral derivative as well as preparation method and application thereof

A technology of citral and compounds, applied in the field of citral derivatives and its preparation, can solve problems such as albinism or skin cancer, irregular skin pigmentation, and browning enzymes

Active Publication Date: 2022-07-29
JIANGXI ACAD OF FORESTRY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, excessive melanin production may lead to albinism or skin cancer, and irregular distribution may lead to irregular skin pigmentation such as melasma, freckles, and age spots
Additionally, a serious problem caused by tyrosinase is the browning enzymatic reaction, which causes rapid color and quality degradation of fruits and vegetables

Method used

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  • Citral derivative as well as preparation method and application thereof
  • Citral derivative as well as preparation method and application thereof
  • Citral derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A kind of preparation method of citral derivative, its synthetic route is as follows:

[0017]

[0018] Specifically include the following steps:

[0019] In a 50 mL round-bottom flask, 0.681 g anthranilamide (5.0 mmol), 0.913 g citral (6.0 mmol) and 10 mL DMSO were added, and the reaction was carried out at 100° C. overnight. TLC was monitored until the reaction was complete (about 20 hours). After the reaction was completed, the reaction solution was cooled to room temperature, and 10 mL of H was added. 2 O, extracted with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and separated by column chromatography (eluent: petroleum ether: ethyl acetate=5:1) to obtain 0.174 g of compound 1.

[0020] test it, and the test results are as follows Figure 1-2 shown. 1 H NMR (400MHz, CDCl 3 )δ11.56(s,1H),8.33–8.24(m,1H),7.79–7.68(m,2H),7.49–7.39(m,1H),6.14(s,1H),5.19(s,1H) ,2.38–2.22(m,7H),1.71(s,3...

Embodiment 2

[0022] Diphenolase activity analysis experiment:

[0023] The specific operation is: dissolve the sample in double-distilled water to prepare sample solutions of different concentrations (citral compounds have poor water solubility, so they are dissolved in DMSO). In this experiment, the substrate was 0.5 mmol / L L-DOPA, and all manipulations were performed at 30 °C. In a 3 mL system, 0.3 mL of substrate solution, 0.05 mol / L phosphate buffer (pH 6.8) 0.75 mL, 1.8 mL of double distilled water, and 0.1 mL of sample solution with different concentrations were added to the cuvette in sequence, and finally 0.05 mL was added. The mushroom tyrosinase aqueous solution was shaken up immediately, and the curve of its absorbance value changing with time was measured using a UV-Vis spectrophotometer (wavelength was 475 nm). The slope of the obtained straight line is the enzyme activity, and the extinction coefficient is 3700L / (mol*cm) -1 Calculation. In the control group, the samples we...

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Abstract

The invention discloses a citral derivative as well as a preparation method and application thereof. The citral derivative has a structure as shown in a formula (I), the citral derivative is synthesized by taking citral as a substrate, the tyrosinase resisting activity IC50 of the citral derivative is 103 + / -2 mu M, and the citral derivative can meet the requirement for preparing an anti-tyrosinase composition.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a citral derivative and its preparation method and application. Background technique [0002] Tyrosinase is a multifunctional enzyme widely isolated from microorganisms, plants, and animals. As a dinuclear copper-containing enzyme, it can catalyze the conversion of o-diphenols or monophenols into appropriate quinones to produce melanin. Therefore, it plays an important role in the biosynthesis of melanin. Melanin is an important pigment found in animal hair, eyes and skin. However, excessive melanin production may lead to albinism or skin cancer, and irregular distribution may lead to irregular skin pigmentation such as chloasma, freckles, and age spots. Additionally, a serious problem caused by tyrosinase is the browning enzyme reaction, which causes rapid color and quality degradation of fruits and vegetables. [0003] Citral is extracted from the essential oils...

Claims

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Application Information

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IPC IPC(8): C07D239/90A61K31/517A61P17/18A61K8/49A61Q19/02A23B7/154
CPCC07D239/90A61P17/18A61K8/4953A61Q19/02A23B7/154Y02A50/30
Inventor 黄亚茹杨杰芳龚春杨海宽廖圣良曾凡新迟韵阳李升星华小菊周诚
Owner JIANGXI ACAD OF FORESTRY
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