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High-performance fat-soluble antioxidant fat-soluble tea-polyphenol and preparation method thereof

A fat-soluble tea polyphenol and a technology for tea polyphenols, which are applied in the field of high-performance antioxidant fat-soluble tea polyphenols and their preparation, can solve the problems of affecting esterification reaction, suboptimal antioxidant performance, reduced antioxidant performance, etc. problem, to achieve the effect of long induction time, excellent anti-lipid peroxidation performance, and simple method

Inactive Publication Date: 2008-09-03
SHANGHAI JIAODA ONLLY CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Phosphorus trichloride, which is less active than phosphorus pentachloride, can generally be used for the acylation of fatty acids, but it is highly volatile, highly toxic, and strongly irritating, and its unreacted residues may affect the next esterification reaction (will undergo halogen addition reaction with double bond)
[0016] In the prior art, after tea polyphenols are oxyacylated with acid chlorides, the reaction is terminated by washing with water, and the organic phase is directly concentrated to obtain fat-soluble tea polyphenol products. The products have not been purified, and contain a large amount of unreacted fatty acid chlorides, which are washed into fatty acids , so the actual content of fat-soluble tea polyphenols in its products is very low, and its antioxidant performance per unit mass is of course correspondingly reduced, and the product process conditions (including acylating agent preparation and oxyacylation reaction) have not been targeted screening, its Antioxidant properties are also not optimal

Method used

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  • High-performance fat-soluble antioxidant fat-soluble tea-polyphenol and preparation method thereof
  • High-performance fat-soluble antioxidant fat-soluble tea-polyphenol and preparation method thereof
  • High-performance fat-soluble antioxidant fat-soluble tea-polyphenol and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1 fatty acid chloride preparation

[0098]Weigh 104 grams (0.4mol) of palmitic acid, put it in a 250ml three-necked bottle (with stirring, feeding port, condenser)*, and then add 36ml (0.49mol) of thionyl chloride. Repeatedly raise and lower the temperature between 20°C and 50°C, while stirring the reaction until no bubbles are generated, add 0.62ml (0.08mol) N,N-dimethylformamide after cooling, and then repeatedly rise and fall between 20°C and 50°C Temperature, stir the reaction until no bubbles are generated, and there is no solid after cooling, and the temperature is raised and lowered repeatedly about 5 to 8 times. The reaction solution was scanned by UV (400nm-200nm), and there was no thionyl chloride peak at around 280nm**.

[0099] Weigh 10 grams (0.0245 mol) of raw material tea polyphenols (total polyphenol content 70%), add appropriate amount of 400 ethyl acetate and stir, add 7.2 grams (0.086 mol) of sodium bicarbonate, (add in 4 times) gradually ...

Embodiment 2

[0103] Embodiment 2 preparation of fat-soluble tea polyphenols

[0104] The acylating agent is prepared as above.

[0105] Weigh 10 grams (0.0245mol) of raw material tea polyphenols (total polyphenol content 95%), add an appropriate amount of 400 g ethyl acetate and stir, add 9.26 grams (0.11mol) of sodium acetate, (add in 4 times) gradually add the palmitoyl chloride prepared above 18.95ml (0.061mol), while insulated and stirred at 32°C for 9 hours, then added 200ml of dilute hydrochloric acid for shaking, left to stand, and separated into layers. Separate, wash the organic layer twice with water, concentrate the organic layer in vacuo, recover ethyl acetate to dryness, add 90% ethanol solution, put it in a separatory funnel, and extract twice 80ml×2 times with petroleum ether, separate the ethanol layer, vacuum Concentrate, recover ethanol, and dry to obtain a solid product, which is light brown to light yellow powder.

[0106] Raw materials: palmitoyl chloride: sodium bic...

Embodiment 3

[0107] Embodiment 3 preparation of fat-soluble tea polyphenols

[0108] The acylating agent is prepared as above.

[0109] Weigh 10 grams (0.0245mol) of raw material tea polyphenols (total polyphenol content 40%), add appropriate amount of 400 ethyl acetate and stir, add 8.23 ​​grams (0.098mol) of sodium bicarbonate, (add in 4 times) gradually add the above-mentioned prepared palm Acyl chloride 15.16ml (0.049mol), while insulated and stirred at 45°C for 8 hours, then added 200ml of dilute hydrochloric acid to shake, let stand, and separate layers. Separate, wash the organic layer twice with water, concentrate the organic layer in vacuo, recover ethyl acetate to dryness, add 90% ethanol solution, put it in a separatory funnel, and extract twice 80ml×2 times with petroleum ether, separate the ethanol layer, vacuum Concentrate, recover ethanol, and dry the solid to obtain the product, which is light brown to light yellow powder.

[0110] Raw materials: palmitoyl chloride: sodiu...

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Abstract

The invention relates to a high performance fat soluble anti-oxidant fat soluble tea polyphenol and a preparation method thereof. The content of the fat soluble tea polyphenol is 45-65, the content of the total esterified esters is 45-65, and the fat soluble tea polyphenol is obtained by reacting thionyl chloride and C12-C18 fatty acid to prepare fatty acyl chloride and then acylation the fatty acyl chloride with tea polyphenol. When the concentration of fat soluble tea polyphenol is 500ppm, inhibition ratio of AAPH can reach 98. 7; when the concentration is 50ppm, the inhibition ratio of DPPH is 90. 5; and when the temperature is 120 degree C and the concentration is 200ppm, the induction time is 280. 8min. The fat soluble tea polyphenol may not only be apply to the lipid products, but also be simple to prepare, and the preparation method is a method suitable for industrial production.

Description

technical field [0001] The invention relates to a fat-soluble high-performance antioxidant fat-soluble tea polyphenol and a preparation method thereof. More precisely, the present invention relates to a fat-soluble antioxidant that can be dissolved in oil and organic solvents but insoluble in water; it can resist oxygen free radicals and lipid peroxidation. The preparation method of the invention adopts oxyacylation and purification conditions, so that the product of the invention has higher anti-lipid peroxidation performance which is obviously better than similar products in the prior art. Background technique [0002] At present, the commonly used fat-soluble antioxidants mainly include: BHA (butyl hydroxyanisole), BHT (dibutyl hydroxytoluene), PG (propyl gallate), TBHQ (tert-butyl hydroquinone), vitamin E, V C Palmitate, rosemary extract, etc. Among them, BHA, BHT, PG, and TBHQ are all chemically synthesized antioxidants, and TBHQ has the best antioxidant effect, and ...

Claims

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Application Information

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IPC IPC(8): C07D311/62C07H17/00C11B5/00C09K15/08
Inventor 邵卫樑杭晓敏张蔚胡天喜丁伟奇卢聪聪
Owner SHANGHAI JIAODA ONLLY CO LTD
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