5-methylol-furfural-5-furfural-methanol, preparation method thereof and medical application thereof

A technology of hydroxymethylfurfural and methanol, which is applied in the application field of preparing anti-aging drugs, can solve problems such as not seen, and achieve remarkable curative effect

Inactive Publication Date: 2009-09-30
JILIN UNIV
View PDF0 Cites 16 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, there are no reports about 5-hydroxymethylfurfural acetal-5-furfural methanol compound and its preparation method and its medicinal use. This compound is a new compound and is prepared for the first time. The new medicinal use of this compound is discovered for the first time.

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
  • 5-methylol-furfural-5-furfural-methanol, preparation method thereof and medical application thereof
  • 5-methylol-furfural-5-furfural-methanol, preparation method thereof and medical application thereof
  • 5-methylol-furfural-5-furfural-methanol, preparation method thereof and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] a. Synthesis

[0072] Dissolve 5-HMF in dimethyl sulfoxide, adjust the pH to 3.0 with p-toluenesulfonic acid, raise the reaction temperature to 115°C under stirring conditions, heat and reflux for 3 hours, after cooling, adjust the pH with 0.1M NaOH lye was 7.0, filtered, and the filtrate was concentrated to dryness to obtain the crude product of 5-hydroxymethylfurfural acetal-5-furfural methanol;

[0073] b.Purification

[0074] The crude 5-hydroxymethylfurfural acetal-5-furfural methanol was subjected to silica gel column chromatography and repeated recrystallization from methanol and acetone to obtain pure 5-hydroxymethylfurfural acetal-5-furfural methanol with a yield of 60%.

Embodiment 2

[0076] a.Synthesis method

[0077] Dissolve 5-HMF in dimethyl sulfoxide, adjust the pH to 3.5 with p-toluenesulfonic acid, raise the reaction temperature to 125°C under stirring and heat to reflux for 3 hours, after cooling, use 0.1M NaOH lye to adjust the pH to 7.0, filter, and concentrate the filtrate to dryness to obtain the crude product of 5-hydroxymethylfurfural acetal-5-furfural methanol;

[0078] b.Purification

[0079] Crude 5-hydroxymethylfurfural acetal-5-furfural methanol was subjected to silica gel column chromatography and repeated recrystallization from methanol and acetone to obtain pure 5-hydroxymethylfurfural acetal-5-furfural methanol with a yield of 65%.

Embodiment 3

[0081] a. Synthesis

[0082] Dissolve 5-HMF in dimethyl sulfoxide, add concentrated sulfuric acid dropwise to adjust the pH to 4.0, raise the reaction temperature to 120°C under stirring and heat to reflux for 3 hours, after cooling, adjust the pH to 7.0 with 0.1M NaOH lye , filtered, and the filtrate was concentrated to dryness to obtain the crude product of 5-hydroxymethylfurfural acetal-5-furfural methanol;

[0083] b.Purification

[0084] Crude 5-hydroxymethylfurfural acetal-5-furfural methanol was subjected to silica gel column chromatography and repeated recrystallization from methanol and acetone to obtain pure 5-hydroxymethylfurfural acetal-5-furfural methanol with a yield of 70%.

[0085] The acid used to adjust acidity in the present invention can be concentrated sulfuric acid.

[0086] In the present invention, lye adopts Na 2 CO 3 , KOH solution.

[0087] The embodiment 1 of preparation medicament:

[0088] 5-Hydroxymethylfurfural acetal-5-furfural methanol 5...

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 relates to 5-methylol-furfural-5-furfural-methanol, a preparation method thereof and medical application thereof, and belongs to a new compound, a preparation method thereof and medical application thereof. 5-methylol-furfural as a raw material is synthesized into the new compound through intermolecular polymerization reaction under the acid condition, the chemical name of the new compound is the 5-methylol-furfural-5-furfural-methanol, and the yield reaches more than 60 percent. The 5-methylol-furfural-5-furfural-methanol has wide medical application in preparing anti-ageing medicaments.

Description

technical field [0001] The invention relates to 5-hydroxymethylfurfural acetal-5-furfural methanol, a preparation method thereof and an application in preparation of anti-aging medicines. Background technique [0002] 5-Hydroxymethylfurfural acetal-5-furfural methanol is a chemically synthesized compound with anti-aging effects. [0003] [0004] The structural feature of 5-hydroxymethylfurfural acetal-5-furfural methanol is that two molecules of 5-hydroxymethylfurfural (5-hydroxymethyl-2-furfural, referred to as 5-HMF) are polymerized into 5-hydroxymethylfural containing two furan rings. Methylfurfural derivatives. 5-HMF is a pyrolysis product of sugar, which is widely present in the production and storage of various sugar-containing drugs and foods. According to literature reports, 5-HMF is a non-competitive inhibitor of oxidized levodopa, and introduces different substituents The drug effect of the group also changes accordingly; 5-HMF can inhibit the oxidation of gl...

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): C07D307/46A61K31/341A61P39/06
Inventor 卢丹李平亚刘金平李海军
Owner JILIN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap