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Esculin hydrate thioctic ester compound with antioxidant activity, and preparation method thereof

An anti-oxidant activity, the technology of echinocortin, is applied in the direction of food ingredients containing organic compounds, food ingredients as antioxidants, organic chemistry, etc., to achieve the effect of preventing oxidative discoloration, easy availability of raw materials, and high utilization of raw materials

Inactive Publication Date: 2018-11-13
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, alopecia also has anti-oxidation, anti-inflammatory, antibacterial, anti-coagulant, analgesic and other activities, and its ability to scavenge oxygen free radicals is relatively close to that of Vc. It has not been found that alopecia is used in the development of antioxidants and other aspects. According to the research report of the present invention, the natural antioxidant fenceretine is used as the reaction raw material, and its structure is modified to generate a frenchetine lipoate compound with novel structure and better oxidation resistance.

Method used

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  • Esculin hydrate thioctic ester compound with antioxidant activity, and preparation method thereof
  • Esculin hydrate thioctic ester compound with antioxidant activity, and preparation method thereof
  • Esculin hydrate thioctic ester compound with antioxidant activity, and preparation method thereof

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Experimental program
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Effect test

preparation Embodiment 1

[0024] Put 100mg (0.29mmol) afraetin and 66.6mg (0.32mmol) lipoic acid in a 100mL reactor, add 60mL acetonitrile to fully dissolve, add 61.9mg (0.3mmol) DCC and 3.5mg chlorinated chlorinated Sulfone was protected by nitrogen gas. After ultrasonic reaction at 35°C for 4 hours, the obtained reaction liquid was cooled to room temperature, concentrated under reduced pressure, and left to separate layers. The lower oil phase was separated by column chromatography, and the eluent was anhydrous sodium sulfate After drying, filtering, and concentrating under reduced pressure, 137.9 mg of the target product acridine lipoate was obtained, with a yield of 88.79%.

[0025] 1 H-NMR (400MHz, DMSO-d6) δ (ppm): 7.74 (1H, d), 6.87 (1H, s), 6.73 (1H, s), 5.90 (1H, d), 5.81 (1H, d), 5.31(1H, s), 4.01-4.30(3H, m), 3.89(1H, t), 3.52(3H, s), 3.39-3.50(2H, m), 2.63-2.49(3H, m), 2.30( 2H, t), 2.00-1.71 (4H, m), 1.53 (2H, q), 1.28 (2H, m); 13 C-NMR (400MHz, DMSO-d 6 )δ (ppm): 173.4, 160.6, 148.6, ...

preparation Embodiment 2

[0028] Put 100mg (0.29mmol) afracetin and 60.6mg (0.29mmol) lipoic acid in a 100mL reactor, add 60mL acetonitrile to fully dissolve, add 61.9mg (0.3mmol) DCC and 6.7mgTEBAC to the reactor, and feed Nitrogen protection, ultrasonic reaction at 45°C for 4h, cooling the obtained reaction liquid to room temperature, concentrating under reduced pressure, standing for layering, taking the lower layer of oil phase column chromatography, and drying and filtering the eluent with anhydrous sodium sulfate, reducing Concentrated under reduced pressure to obtain 121.3 mg of the target product afraxin lipoate, with a yield of 78.14%.

preparation Embodiment 3

[0031] Put 100mg (0.29mmol) alopecia and 78.7mg (0.38mmol) lipoic acid in a 100mL reactor, add 60mLTHF to fully dissolve, add 61.9mg (0.3mmol) DCC and 3.5mg thionyl chloride to the reactor , pass through nitrogen protection, after ultrasonic reaction at 55°C for 3 hours, cool the obtained reaction solution to room temperature, concentrate under reduced pressure, stand and separate layers, take the lower oil phase and separate it by column chromatography, and dry the eluent with anhydrous sodium sulfate Filtration and concentration under reduced pressure gave 129.3 mg of the target product, afracetin lipoate, with a yield of 83.26%.

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Abstract

The invention discloses an esculin hydrate thioctic ester compound with antioxidant activity, and a preparation method thereof. According to the preparation method, esculin hydrate and thioctic acid are taken as raw materials, in an organic solvent, esterification reaction is adopted so as to synthesize an esculin hydrate thioctic ester compound with a novel structure. The esculin hydrate thiocticester compound can be taken as a food anti-oxidant, is capable of preventing influences of oxidation deterioration of food especially grease or food rich in grease on food local flavor and editable quality, and at the same time, the esculin hydrate thioctic ester compound can be added into cosmetic to inhibit skin aging and cosmetic self oxidation deactivation as an anti-oxidant. The raw materials are easily available; the steps are simple; and the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention relates to the technical field of synthesis of food and cosmetic additives, in particular to an alopecia lipoate compound with antioxidant activity and a preparation method thereof. Background technique [0002] Due to the technological progress of the food additive industry, the research, development, production and application of food antioxidants have been greatly developed. Antioxidant is an important food additive. It is mainly used to prevent or delay the automatic oxidation of oil, and it can also prevent the nutritional damage, browning, and fading of food due to oxidation during storage. At the same time, in recent years, studies have found that human skin will age due to oxidation and ultraviolet radiation, so more and more antioxidants are also used in the cosmetics industry. At present, countries are doing a lot of research work for the development of new antioxidants, and the research on the artificial synthesis and semi-syn...

Claims

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Application Information

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IPC IPC(8): C07D409/14A23L33/10A61K8/49A61P39/06A61Q19/02A61Q19/08
CPCA23V2002/00A61K8/4986A61Q19/02A61Q19/08A23L33/10A61P39/06C07D409/14A23V2200/02A23V2200/048A23V2250/30
Inventor 梁承远贾敏一阮淞淞李洁田蕾鞠星可李菡赵倩倩王学川
Owner SHAANXI UNIV OF SCI & TECH
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