Method for semi-synthesizing 3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone

A 5-OH, dihydroflavonoid technology, used in the fields of food, cosmetics, chemistry and medicine

Inactive Publication Date: 2016-04-13
闻永举
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to utilize cheap 5-OH, 7-O-generation dihydroflavone compounds, especially 5-OH-dihydroflavone-7 -O-glycoside compounds, large-scale preparation of 5-OH, 7-O-generation-3-deoxyanthocyanin and 5-OH, 7-OH-3-deoxyanthocyanin, solution of anthocyanin Class, gradually becoming popular in the international market, the problem of high price and short supply

Method used

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  • Method for semi-synthesizing 3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone
  • Method for semi-synthesizing 3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone
  • Method for semi-synthesizing 3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Take 20g of naringin with 98% naringin in 50ml of DMSO and heat to dissolve. Take another 3g of KBH4 and add in portions until naringin is completely reduced to naringin-type flavan-4-ol (about overnight, try to prevent absorption of moisture in the air, UV monitoring , scanning under alkaline conditions, there is no absorption peak at 360nm). Slowly add 5ml of concentrated sulfuric acid and stir evenly (the solution turns light red, generating naringin-type flavan-4-cations, taking a small amount of water and diluting, the color can fade, and generating naringin-type flavan-4-ol ), slowly added 120ml of anhydrous n-butanol, precipitated to the bottom, stood still for 30min, poured out the n-butanol solution, added 20ml of anhydrous n-butanol to the precipitate, stirred quickly to dissolve, poured out the n-butanol, and 40ml of anhydrous pyridine was added, 8.7g of iodine was added, stirred until dissolved, and the reaction was continued in a water bath at 55°C for 96h ...

Embodiment 2

[0085] Take 5g of the Apigeninidin-7-O-neohesperidoside sample in Example 1, add 100ml of 10% hydrochloric acid and 20% ethanol solution to hydrolyze at 60°C for 10h, add 100ml of water, wash with 120g of macroporous adsorption resin D101, 500ml of water to remove impurities, and wash with 1500ml of 75% ethanol After decompression, the ethanol was recovered under vacuum to obtain Apigeninidin, 1.7g of orange powder. [M] + 255; a small amount dissolved in water is orange, and paper chromatography shows yellow spots; on the UV spectrum, there are maximum absorption at 480nm and 279nm; the color and UV spectrum are consistent with the literature (P.SuganyaDevi1, M.Saravanakumar, S.Mohanda. Identification of 3-deoxyanthocyanins from redsorghum (Sorghumbicolor) bran and its biological properties. African Journal of Pure and Applied Chemistry, 2011, 5(7):181-193).

[0086] Example 3: Preparation of Diosmetinidin-7-O-rutinoside from Hesperidin

Embodiment 3

[0087]Take 20g of hesperidin with a content of 95% (pre-dried at 90°C for 3-4 hours), heat and dissolve 50ml of DMSO, and take another 3g of KBH4, and add in portions until the naringin is completely reduced to hesperidin-type flavan 4-ol (about overnight , UV monitoring, scanning under alkaline conditions, no absorption peak at 360nm). Slowly add 5ml of concentrated sulfuric acid (first 2ml is very slow, the solution turns light red), stir evenly (the solution turns light red), add slowly add 120ml of anhydrous n-amyl alcohol, precipitate and sink to the bottom, stand still for 30min, pour out the normal Pentanol solution, add 20ml of anhydrous n-pentanol to the precipitate, quickly stir and knead to dissolve, pour out the n-pentanol solution, and treat it twice in the same way, add 40ml of anhydrous pyridine, add 8.3g of iodine, stir until dissolved, add anhydrous 5g of calcium sulfate in water, stirred evenly, and reacted continuously in a water bath at 55°C for 96h under a...

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Abstract

The invention relates to a method for semi-synthesizing 5-OH-7-O-substituted-3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone, and relates to the fields of chemistry and pharmacy, food and cosmetics. According to the invention, 5-OH-7-O-substituted flavanone is reduced into 5-OH-7-O-substituted flavan-4-ol with reducing agents such as potassium borohydride; direct acid dehydration is carried out, such that a 5-OH-7-O-substituted flavan-4-carbonium ionic compound is produced; water is removed, and iodine-pyridine solvent dehydrogenation is carried out, such that 5-OH-7-O-substituted-3-deoxyanthocyanidin is produced. The 5-OH-7-O-substituted-3-deoxyanthocyanidin is subjected to macroporous absorption resin enrichment, and harmful impurities such as pyridine are removed; and ethanol elution and reduced-pressure recovery are carried out, such that the final product is obtained. According to the invention, multiple reaction steps are integrated into a one-step reaction; operation is simple; and yield is relatively high. The method is suitable for industrial productions. With the method, flavanone glycosides such as hesperidin and naringin can be prepared into 3-deoxyanthocyanidin with good water solubility and oxidation resistance.

Description

technical field [0001] The method for semi-synthesizing 3-deoxyanthocyanidin from 5-OH, 7-O-generation dihydroflavone belongs to the fields of chemistry, medicine, food and cosmetics. Background technique [0002] Free radical damage and free radical prevention: The cell membrane has a loose chemical structure, is extremely elastic and flexible, and its electrons are easily lost. Therefore, once the cell membrane is attacked by free radicals, its electrons are taken away, and its function will be lost, causing various inflammations, further deterioration, and various diseases, such as cardiovascular system diseases and tumors. Some endogenous enzymes, such as superoxide dismutase (SOD), catalase, glutathione peroxidase, and compounds such as vitamin C, vitamin E, and carotene, have the ability to scavenge free radicals . In addition to the above-mentioned substances, in order to reduce the harm of free radicals, it is also necessary to find and discover exogenous free radi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00
Inventor 闻永举申秀丽
Owner 闻永举
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