Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Economic, practical, and environment friendly method for preparing norathyriol

A mangiferin aglycone and reaction technology, applied in the direction of organic chemistry and the like, can solve the problems of difficult product separation, great environmental hazards, and high reagent toxicity, and achieve the effects of short process route, cheap raw materials, and few synthesis steps.

Inactive Publication Date: 2012-02-15
KPC PHARM INC
View PDF7 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] In view of this, the purpose of the present invention is to study and solve the defects and deficiencies such as long reaction route, low yield, difficult product separation, high reagent toxicity and large environmental hazards in the existing method, and provide a short synthetic route , a method for preparing mangiferin with high reaction yield and environmental friendliness

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
  • Economic, practical, and environment friendly method for preparing norathyriol
  • Economic, practical, and environment friendly method for preparing norathyriol
  • Economic, practical, and environment friendly method for preparing norathyriol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of mangiferin aglycone by the method of the present invention

[0039] Weigh 26.1g (0.10mol) of 2-bromo-4,5-dimethoxybenzoic acid and put it into a 250mL reaction flask, add 20mL of 1,2-dichloroethane, 16.7g (0.14mol) of thionyl chloride , heated to reflux for 1 hour, added 20.4g of zinc chloride (0.15mol) and 18.5g (0.12mol) of 3,5-dimethoxyphenol, stirred, continued to heat at 75 ° C for 2.5 hours, steamed out 1 under reduced pressure, 2-dichloroethane solvent, add 80.0g of sodium hydroxide aqueous solution (about 0.20mol sodium hydroxide) with a concentration of 10%, continue to heat and reflux for 2 hours, cool down, a large amount of white solids are precipitated, filter, and the filtrate is washed with water to The water washing solution was neutral, drained and dried to obtain 28.4 g of white 1,3,6,7-tetramethoxyxanone with a yield of 90%. IR v max (KBr)cm -1 : 3442, 2961, 2939, 2836, 1627, 1507, 1457, 1425, 1271, 1211, 1158, 1122; 1 HN...

Embodiment 2

[0041] Example 2: Preparation of mangiferin aglycone by the method of the present invention

[0042] Weigh 104.4g (0.40mol) of 2-bromo-4,5-dimethoxybenzoic acid and put it into a 500mL reaction flask, add 100mL of 1,2-dichloroethane, 59.5g (0.50mol) of thionyl chloride , heated to reflux for 1 hour, added 54.4g (0.40mol) of zinc chloride and 65.0g (0.42mol) of 3,5-dimethoxyphenol, stirred, continued to heat at 60 ° C for 3 hours, steamed out 1 under reduced pressure, 2-dichloroethane solvent, add 120.0g of sodium hydroxide aqueous solution (about 0.60mol sodium hydroxide) with a concentration of 20%, continue to heat under reflux for 3 hours, cool down, a large amount of white solids are precipitated, filter, and the filtrate is washed with water to The water washing solution was neutral, drained and dried to obtain 113.0 g of white 1,3,6,7-tetramethoxyxanone with a yield of 89%. IR v max (KBr)cm -1 : 3442, 2961, 2939, 2836, 1627, 1507, 1457, 1425, 1271, 1211, 1158, 1122; ...

Embodiment 3

[0044] Example 3: Preparation of mangiferin aglycone by the method of the present invention

[0045] Weigh 52.2g (0.20mol) of 2-bromo-4,5-dimethoxybenzoic acid and put it into a 250mL reaction flask, add 40mL of 1,2-dichloroethane, 35.7g (0.30mol) of thionyl chloride , heated to reflux for 1 hour, added 32.6g (0.24mol) of zinc chloride and 30.8g (0.20mol) of 3,5-dimethoxyphenol, stirred, continued to heat at 40°C for 4 hours, steamed out 1 under reduced pressure, 2-dichloroethane solvent, add 80.0g of sodium hydroxide aqueous solution (about 0.60mol sodium hydroxide) with a concentration of 30%, continue to heat under reflux for 2.5 hours, cool down, and precipitate out a large amount of white solids, filter, and the filtrate is washed with water to The water washing solution was neutral, drained and dried to obtain 56.9 g of white 1,3,6,7-tetramethoxyxanone with a yield of 90%. IR v max (KBr)cm -1 : 3442, 2961, 2939, 2836, 1627, 1507, 1457, 1425, 1271, 1211, 1158, 1122; 1...

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 the field of medicinal chemistry, and discloses a two-step method for preparing norathyriol. The method comprises steps that: 2-bromine-4,5-dimethoxybenzoic acid is added to 1,2-dichloroethane; thionyl chloride is added to the mixture, and the mixture is heated and refluxed for 1 hour; zinc chloride and 3,5-dimethyoxy phenyl hydroxide are added to the mixture, the mixtureis stirred, and are heated for 2 to 4 hours under a temperature of 40 to 80 DEG C; the 1,2-dichloroethane solvent is removed through reduced-pressure distillation; 10% to 30% of a sodium hydroxide solution by mass is added to the mixture, and the mixture is heated and refluxed for 2 to 3 hours, such that 1,3,6,7-xanthone tetramethoxide is produced; 1,3,6,7- xanthone tetramethoxide is added to an ethylene glycol solvent, and hydrochloric acid is added to the mixture; the mixture is heated and refluxed for 3 to 5 hours, such that norathyriol is obtained. Compared to prior arts, the preparation method provided by the invention has advantages of short synthetic route, less step, simple operation, and high yield. The raw materials adopted in the method are cheap and easy to obtain. The processes are safe, and bring low toxicity. The method is environment friendly, and is suitable for industrialized productions. The method provides high economical and practical values.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an economical, practical and environment-friendly method for preparing mangiferin aglycone. Background technique [0002] Mango aglycone, English name norathyriol, naturally exists in various plants such as Hypericum sampsonii Hance and Garcinia aponicum Thunb.Ex Murray. Recent studies have found that mangiferin aglycone is the active metabolite of mangiferin (Wang, Hui; Ye, Guan; Ma, Chun-Hui; Tang, Yi-Hong; Fan, Ming-Song; Li, Zhi-Xiong; Huang, Cheng -Gang.Identification and determination of four metabolites of mangiferin in rat urine.Journal of Pharmaceutical and Biomedical Analysis(2007), 45(5), 793-798; Sanugul, Kanjana; Akao, Teruaki; Li, Yan; Kakiuchi, Nobuko; Nakamura, Norio; Hattori, Masao. Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosyl bond. Biological & Pharmaceutical Bulle...

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): C07D311/86
Inventor 周荣光
Owner KPC PHARM INC
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
Eureka Blog
Learn More
PatSnap group products