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Artificial synthesis method of capsaicin homologue

A technology of artificial synthesis and capsaicin, which is applied in the field of artificial synthesis of capsaicin homologues, can solve the problems of unfriendly environment, difficult to apply to industrial production process, cumbersome steps, etc.

Active Publication Date: 2010-06-02
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are undoubtedly of great reference value for the preparation of a small amount of samples in the laboratory, but they cannot be completely copied for the industrial production scale.
These methods have cumbersome steps, some have low yields, and some are not friendly to the environment, so it is difficult to apply to industrial production processes

Method used

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  • Artificial synthesis method of capsaicin homologue
  • Artificial synthesis method of capsaicin homologue
  • Artificial synthesis method of capsaicin homologue

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1. Artificial synthesis of capsaicin

[0041] (1) 4-Methyl-3-hydroxy-1-pentene

[0042] A reflux condenser, dropping funnel and stirrer were installed on a two-liter round bottom flask, and then 24.3 grams of magnesium bar (1.0 mol) and 1 liter of dry ether were added. Under the protection of nitrogen, 100 ml of 2-bromopropane (131 g, 1.06 mol) was added dropwise, and the dropping rate was controlled to maintain reflux. After the addition is completed, heat to reflux for 20 minutes, and add 70 ml of dry acrolein in 100 ml of ether under cooling with an ice water bath, and control the dropping rate to maintain the reaction temperature below 15°C. After the addition, the reaction was continued for one hour at room temperature. Slowly add 500 ml of 2N HCl under ice-water bath cooling, the ether solution is separated, the aqueous phase is extracted with ether to obtain the ether extract, the ether solution and the ether extract are combined and dried with sodium sulfat...

Embodiment 2

[0057] Example 2. Synthesis of dihydrocapsaicin

[0058] (1) 6-Methyl-3-hydroxy-1-heptene

[0059] A reflux condenser, dropping funnel and stirrer were installed on a two-liter round bottom flask, and then 24.3 grams of magnesium bar (1.0 mol) and 1 liter of dry ether were added. 126 ml of 1-bromo-3-methylbutane (159 g 1.05 mol) was added dropwise under the protection of nitrogen. Control the drip rate to maintain the reflux. After the addition is completed, heat to reflux for 20 minutes, and add 70 ml of dry acrolein in 100 ml of ether under cooling with an ice water bath, and control the dropping rate to maintain the reaction temperature below 15°C. After the addition, the reaction was continued for one hour at room temperature. Slowly add 500 ml of 2N HCl under ice-water bath cooling, the ether solution is separated, the aqueous phase is extracted with ether to obtain the ether extract, the ether solution and the ether extract are combined and dried with sodium sulfate and fi...

Embodiment 3

[0068] Example 3. Synthesis of nordihydrocapsaicin

[0069] (1) 5-Methyl-3-hydroxy-1-hexene

[0070] A reflux condenser, dropping funnel and stirrer were installed on a two-liter round bottom flask, and then 24.3 grams of magnesium bar (1.0 mol) and 1.0 liter of dry ether were added. Under nitrogen protection, 115 ml of isobutyl bromide (140 g, 1.02 mol) was added dropwise. Control the drip rate to maintain the reflux. After the addition is completed, heat to reflux for 20 minutes, and add 70 ml of dry acrolein in 100 ml of ether under cooling with an ice water bath, and control the dropping rate to maintain the reaction temperature below 15°C. After the addition, the reaction was continued for one hour at room temperature. Slowly add 500 ml of 2N HCl under ice-water bath cooling, the ether solution is separated, the aqueous phase is extracted with ether to obtain the ether extract, the ether solution and the ether extract are combined and dried with sodium sulfate and filtered,...

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Abstract

The invention belongs to the field of artificial synthesis of natural products and relates to an artificial synthesis method of a capsaicin homologue. The artificial synthesis method of the capsaicin homologue is to lead 4-hydroxy-3-methoxy-benzylamine hydrochloride to be reacted with the corresponding long-chain acid (E)-8-methyl-6-nonenoic acid and 8-methyl nonanoic acid or 7-methyl octanoic acid for preparing the capsaicin homologue. The long-chain acid synthesis method is characterized in that the method can avoid the use of triphenyl phosphine and other toxic substances which are commonly used in the existing patents and toxic substance-triphenyl phosphineoxide in byproducts, thereby being relatively environment-friendly. For different capsaicin homologues, the required starting raw materials are different. In particular, dihydrocapsaicin is applicable to large-scale industrial production.

Description

Technical field [0001] The invention belongs to the field of artificial synthesis of natural products, and relates to an artificial synthesis method of capsaicin homologs. Background technique [0002] It has been 133 years since capsaicin was produced from peppers by solvent extraction in 1876. The chemical structure of capsaicin was identified in 1919, and the structure of dihydrocapsaicin was only identified in 1955. By 1968, the structures of five capsaicin homologues (including homocapsaicin, homodihydrocapsaicin, and nordihydrocapsaicin) were published simultaneously. The main members of capsaicin have been shown to be mutagenic active substances. In 1995, there was a US patent: 5,397,385, (James I., Anti-fouling Coating Composition Containing Capsaicin), which showed that capsaicin is an effective antifouling agent for marine ships. [0003] The capsaicin extracted from pepper is a very complex mixture. The composition and relative proportion of capsaicin produced in diff...

Claims

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Application Information

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IPC IPC(8): C07C233/20C07C233/18C07C231/02C07C57/03C07C53/126C07C51/09
Inventor 周圣泽
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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