Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthetic method of astaxanthin

A technology of astaxanthin and a new method, applied in the field of preparation of carotenoid products, can solve the problems of large molecular weight of triphenylphosphine, troublesome post-processing and high production cost, and achieve high product quality, convenient post-processing and high production cost. low effect

Inactive Publication Date: 2007-10-03
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
View PDF0 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above route uses triphenylphosphine, and the last step of the reaction to obtain astaxanthin is triphenylphosphine oxide, which is highly toxic and cannot be left in food and feed. It needs to be strictly removed, and the post-treatment is very troublesome; Phenylphosphine has a large molecular weight and a large dosage, which makes the production cost higher

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of astaxanthin
  • Synthetic method of astaxanthin
  • Synthetic method of astaxanthin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of bis(N, N-methyl, methoxy) 3-hexenediamide

[0037] Mix 15g of trans-3-hexene-1,6-dioic acid and 50mL of dichloromethane, add dropwise 30g of oxalyl chloride under ice bath, control the temperature below 20°C, add DMF1ml dropwise after the dropwise addition, and put the above mixture at room temperature The reaction was carried out at low temperature for half an hour, and then at about 40°C for two hours. The solvent was distilled off under reduced pressure to obtain a tan oil. Dilute with 30 mL of chloroform. Another 50 mL of chloroform, 50 mL of pyridine, and 25 g of N, O-dimethylhydroxylamine hydrochloride were mixed, and the chloroform solution of the acid chloride prepared above was added dropwise under ice cooling. Control the temperature below 20°C for 24 hours. After the reaction is complete, add 100 mL of water, separate the layers, wash the layers with 100 mL of water, dry the organic layer with anhydrous magnesium sulfate, filter, evaporate the...

Embodiment 2

[0039] Synthesis of 4-octene-2,7-dione

[0040] Cool the Grignard reagent prepared by 18 g of iodomethane, 3.5 g of magnesium, and 100 mL of anhydrous tetrahydrofuran to below -10°C, and add 11.5 g of bis(N,N-methyl, methoxy) 3-hexenediamide compound to dissolve A solution in 50 mL of anhydrous tetrahydrofuran. Add 100mL of saturated ammonium chloride aqueous solution and 100mL of ethyl acetate to separate layers, then wash the layers with 100mL saturated sodium chloride aqueous solution, and wash the organic layer with anhydrous magnesium sulfate Dry, filter, and evaporate the solvent under normal pressure to obtain 4.7 g of 4-octene-2,7-dione with a yield of 66%.

Embodiment 3

[0042] Synthesis of Diethyl 2,7-Dimethyl-1,4,7-octatriene-1,8-diphosphonate

[0043]Weigh 2.9g of 60% sodium hydride, wash with n-hexane, add 50mL of anhydrous toluene, add dropwise a solution of 26g of diethyl methylene bisphosphonate dissolved in 20mL of anhydrous toluene under nitrogen protection, and control the temperature at 25°C After the dropwise addition, react for another half an hour, then add 4.2 g of 4-octene-2,7-dione in 20 mL of anhydrous toluene dropwise at a controlled temperature below 25°C, and react for another hour after the dropwise addition, and the reaction is complete Add 100mL of water to wash and separate the layers, dry the organic layer with anhydrous magnesium sulfate, filter, and evaporate the solvent under reduced pressure to obtain 2,7-dimethyl-1,4,7-octatriene-1,8-bisphosphonic acid diethyl Esters 12g.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

This invention relates to a synthetic method of astaxanthin compound. In existing method, toxicity of byproduct triphenylphosphine oxide is bigger, the aftertreatment is highly trouble. In this invention :(1) dissolve 2, 7 - dimethyl - 2, 4, 6 - octo- -triene -triene - 1 , 8 - double phosphonate ester in anhydrous solvent, add alkali alkali under nitrogen shield , whipping; (2) by distribution droplets method drop 3 - methyl - 5 - ( 2, 6, 6 - trimethyl - 3 - oxo - 4 - hydroxy cyclohexene - 1 - group) - 2, 4 - pentylene aldehyde to solution obtained by (1), after drop finish, decant to water, then by decompression and steam to divide anhydrous solvent from obtained hybrid, subsequently use organic solvent for extraction, aband on dehydration layer. The organic layer use anhydrous desiccant to dry, filtration, evaporate organic solvent, add spirits solvent, recirculate under nitrogen shield, gain astaxanthin.

Description

technical field [0001] The invention relates to the preparation of carotenoid products, in particular to a method for synthesizing astaxanthin compounds. Background technique [0002] Astaxanthin is the compound with the most difficult synthesis and high value among the eight carotenoid products that have been industrially produced. It is widely used in the production of health care products, medicines, cosmetics, food and feed, etc. In food, it can not only be used for coloring, but also can effectively keep fresh and prevent discoloration, taste and deterioration. It can also be used for coloring of beverages, foods, seasonings, etc. Astaxanthin has a bright color and can be unintentionally combined with actin. Its application in aquatic feed can improve the skin and muscle color of farmed fish, and increase the disease resistance of fish and shrimp. [0003] Most of the production of astaxanthin is obtained by chemical synthesis, and the industria...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C403/24C07F9/40
Inventor 皮士卿潘亚金李斌劳学军
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com