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

Chemical synthetic process of gingerols

A technology of gingerol and process method, applied in the field of innovative drug preparation and process, to achieve the effects of less discharge, high yield and mild process conditions

Inactive Publication Date: 2013-06-19
朱志成
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved in the present invention is to provide a simple and efficient gingerol synthesis method to solve the defects in the existing separation or chemical synthesis technology

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
  • Chemical synthetic process of gingerols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1,6-gingerol:

[0026] Add 40 grams of gingerone and 2 liters of dry tetrahydrofuran to a 5-liter four-necked bottle. Add an electric stirrer, a low temperature thermometer and a dropping funnel to the flask, and replace it with dry nitrogen several times. Soak the flask in a dry ice-acetone bath, and when the temperature of the solution in the flask drops to -60°C, slowly add a mixture of n-hexanal (40 ml) and 500 ml tetrahydrofuran through a dropping funnel. The dropwise addition process takes 1 hour. After the dropwise addition was completed, the reaction temperature was slowly raised to -40°C and stirred for 5 hours. 100 ml of methanol was added to the reaction solution. The reaction mixture was concentrated in an ice bath at 0°C. The obtained oil was separated by silica gel column chromatography. The mobile phase is ethyl acetate / petroleum ether=2%~5%. The product was concentrated to a viscous oil. Yield: 52 g, 87%. 1 H-NMR (CDC...

Embodiment 2

[0027] The synthesis of embodiment 2,8-gingerol:

[0028] 8-gingerol was synthesized by a method similar to 6-gingerol. Yield: 72%; 1 H-NMR (CDCl 3 , 500 MHz)δ 0.87 (s, 3H), 1.26 (m, 12H), 2.50 (m, 2H), 2.78 (m, 4H), 2.99 (brs, 1H), 3.88 (s, 3H), 4.02 (m , 1H), 5.59 (s, 1H), 6.65 (m, 2H), 6.82 (d, 1H, J = 8.0 Hz).

Embodiment 3

[0029] The synthesis of embodiment 3,10-gingerol:

[0030] 10-gingerol was synthesized similarly to 6-gingerol. Yield: 75%; 1H-NMR (CDCl 3 , 500 MHz) δ 0.87 (s, 3H), 1.26 (m, 16H), 2.51 (m, 2H), 2.78 (m, 4H), 3.12 (brs, 1H), 3.88 (s, 3H), 4.02 (m , 1H), 5.55 (s, 1H), 6.65 (m, 2H), 6.82 (d, 1H, J = 8.0 Hz).

[0031]

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

The invention provides a simple, convenient and efficient process for synthesizing 6-gingerol, 8-gingerol and 10-gingerol. Deprotonation and straight-chain fatty aldehyde condensation of zingiberone are performed in an inert solvent, so that the crude product of gingerol are obtained. The crude product is subjected to posttreatment at a low temperature and purified through silica gel column chromatography so that 6-gingerol, 8-gingerol or 10-gingerol having the purity exceeding 95% can be obtained. Besides, the yield exceeds 70%.

Description

technical field [0001] The invention relates to a synthesis process of a pharmaceutical candidate compound and a food additive, which is a new synthesis process of a natural product with anti-cancer, anti-inflammation, anti-oxidation and antihypertensive effects, and belongs to the technical field of innovative drug preparation and process. Background technique [0002] Ginger is a kind of rhizome spice seasoning widely planted in the world. In China and even the whole of Asia, it is also a traditional medicinal and edible plant. , The effect of drying dampness and eliminating phlegm. Modern medical research shows: Ginger has anticoagulant, anti-oxidation, anti-tumor, boosting blood pressure, strengthening the heart, lowering blood fat, anti-atherosclerosis, protecting gastric mucosa, protecting liver and gallbladder, anti-inflammatory, antitussive, anti-dizzy and anti-emetic, Central nervous system inhibition and other effects. [0003] Gingerol is the main spicy substan...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/72C07C49/255
Inventor 朱志成
Owner 朱志成
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