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Novel antioxidant and preparation method thereof

An antioxidant, a new type of technology, applied in the direction of food ingredients as antioxidants, carbon-based compound preparation, chemical instruments and methods, etc., can solve the limitation of natural antioxidant antioxidant effect, natural antioxidant antioxidant effect and structure are not very deep and other problems, to meet the requirements, high boiling point, strong antioxidant activity effect

Inactive Publication Date: 2017-04-19
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the research on the relationship between the antioxidant effect and structure of natural antioxidants is not very deep, which makes the further enhancement of the antioxidant effect of natural antioxidants very limited.

Method used

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  • Novel antioxidant and preparation method thereof
  • Novel antioxidant and preparation method thereof
  • Novel antioxidant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: concrete steps are as follows:

[0031] a. in N 2 protection, 7.8 ml compound 2-methoxy-4-methylphenol was added to 19 ml 85% H 3 PO 4 , stirred for 5 minutes, controlled the temperature at 75°C, added 6.5ml of tert-butanol, dried over anhydrous sodium sulfate, and rotary evaporated to obtain a bright yellow oily liquid. The crude product was subjected to column chromatography, followed by petroleum ether, petroleum ether: ethyl acetate = 20 :0.5 to separate a colorless oily liquid with a yield of 70%, product: 2-methoxy-6-tert-butyl-4-methylphenol.

[0032] 1 HNMR(500M, CDCl3)δ1.49 (s, 9H), 2.37 (s, 3H), 3.93 (s, 3H), 5.91(s,1H), 6.67 (s, 1H), 6.78(d, J=0.35 Hz.2H).

[0033] b.N 2 Protection, 0°C, ice-water bath, dissolve 3ml of the compound 2-methoxy-6-tert-butyl-4-methylphenol in 20ml of tert-butanol, stir well, add 2ml of liquid bromine dropwise (with a 5ml glass syringe, plastic needle slowly Add dropwise for 10 minutes, keep the solution light...

Embodiment 2

[0039] Example 2: The specific steps are: dissolve 1 gram of (E)-3-(3-(tert-butyl)-4,5-dihydroxyphenyl)acrylic acid obtained in Example 1 in 70ml of ethanol, add 2ml of concentrated Sulfuric acid solution, heated to reflux at 90°C for 1h, cooled at room temperature. Rotary evaporation at 40°C, remove most of the methanol, add water, extract with ethyl acetate, the organic phase is sequentially washed with NaHCO 3 , washed with saturated brine, Na 2 SO 4 Drying, spin-drying, ethanol crystallization, (E)-3-(3-(tert-butyl)-4,5-dihydroxyphenyl) ethyl acrylate was obtained with a yield of 95%.

Embodiment 3

[0040] Embodiment 3: The specific steps are: 1 gram of (E)-3-(3-(tert-butyl)-4,5-dihydroxyphenyl)acrylic acid obtained in Example 1 is dissolved in hot 50ml lauryl alcohol, Add 2ml of concentrated sulfuric acid, heat to reflux at 90°C for 1h, and cool at room temperature. Rotary evaporation at 100°C, remove most of the lauryl alcohol, add water, extract with ethyl acetate, the organic phase is successively washed with NaHCO 3 , washed with saturated brine, Na 2 SO 4 Drying, spin-drying, and crystallization of benzene gave (E)-3-(3-(tert-butyl)-4,5-dihydroxyphenyl)ethyl acrylate with a yield of 95%.

[0041] (E)-3-(3-(tert-butyl)-4,5-dihydroxyphenyl)acrylic acid obtained by the present invention and C 1 -C 22 Alcohols can undergo esterification reaction to form the corresponding (E)-3-(3-(tert-butyl)-4,5-dihydroxyphenyl)acrylate, the reaction conditions are similar, and will not be described in detail here.

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Abstract

The invention relates to a novel antioxidant and a preparation method thereof. The structural formula of the antioxidant is shown in img file = 'dest _ path _ image 001. TIF 'wi = '152 'he = '86 ', wherein R is an alkyl group CnH2n +1, and n is 0 to 22. According to the technical scheme of the invention, an obtained product is strong in antioxidant activity at normal temperatures and high temperatures, better in lipid solubility and relatively good in water solubility. The product can be used as an antioxidant for fatty foods and can enhance the absorbability of drugs in a human body. The product is easy in salification and has a higher boiling point. At a high temperature, the product is not easy to volatilize, so that the requirements of fatty foods on high-temperature antioxidants can be met. The product comprises carboxyl groups and phenolic hydroxyl groups, so that the coupling between molecules is easily formed in a high-temperature environment to generate compounds larger in molecular weight and higher in boiling point. The product is difficult to volatilize at a high temperature, so that the antioxidant activity of the product can be better realized in a high-temperature frying environment.

Description

technical field [0001] The invention relates to a novel antioxidant and a preparation method thereof. Background technique [0002] With the development of science and technology in recent years, the relationship between oxidative deterioration of oils and their products and various human diseases in the process of production, transportation, storage and use has attracted more and more attention. People are paying more and more attention to their health. Antioxidants The use of antioxidants is more important, and antioxidants have become an indispensable substance in the oil industry. At present, there are many types of antioxidants that people have studied. Most of the research focuses on the extracts of natural substances such as Chinese herbal medicines and spices; the application of antioxidants in the fields of biology and medicine; and the use of antioxidant health products in preventing diseases and delaying aging. [0003] However, the research on the relationship b...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/08C09K15/08A61K47/14A23L29/00
CPCA23V2002/00A61K47/14C07C41/30C07C45/43C07C45/64C07C51/353C07C67/08C07C69/732C09K15/08C07C59/52C07C47/565C07C47/575C07C43/23A23V2200/02
Inventor 翁新楚史高生
Owner SHANGHAI UNIV
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