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Artificial synthesis method of capsaicin homologue

A technology for artificial synthesis, capsaicin, is applied in the field of artificial synthesis of capsaicin homologues, and can solve problems such as being difficult to apply to an industrial production process, being unfriendly to the environment, and having complicated steps.

Active Publication Date: 2013-06-12
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] Embodiment 1. the artificial synthesis of capsaicin

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

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

Embodiment 2

[0057] The synthesis of embodiment 2. dihydrocapsaicin

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

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

Embodiment 3

[0068] Embodiment 3. the synthesis of nordihydrocapsaicin

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

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

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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 homologues. Background technique [0002] It has been 133 years since capsaicin was prepared from peppers by solvent extraction in 1876. The chemical structural formula of capsaicin was identified in 1919, and the structure of dihydrocapsaicin was not identified until 1955. By 1968, the structures of five capsaicin homologues (including homocapsaicin Homocapsaicin, homodihydrocapsaicin Homodihydrocapsaicin and nordihydrocapsaicin nordihydrocapsaicin) were simultaneously published. The main member of capsaicin has been shown to be a mutagenic active substance. In 1995, U.S. Patent No. 5,397,385 (James I., Anti-fouling Coating Composition Containing Capsaicin) showed that capsaicin is an effective antifouling agent for marine vessels. [0003] Capsaicin extracted from chili peppers is a very complex mixture. The com...

Claims

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Application Information

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