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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
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  • 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

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  • 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
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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...

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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

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Application Information

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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
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