Process for synthesizing luteolin

A technology of luteolin and reaction temperature, applied in the production of bulk chemicals, organic chemistry, etc., can solve problems such as difficulty in realizing large-scale production, affecting product quality, inappropriateness, etc., achieving convenient operation, guaranteed product quality, and reaction conditions. mild effect

Inactive Publication Date: 2007-01-31
NANJING RALLY BIOCHEM
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been reported in China that 2,4,6-trihydroxyacetophenone is obtained by using phloroglucinol as the starting material according to the conventional Hoesch rule, and the corresponding compound is synthesized by condensation of the dihydroxyl group at the 4 and 6 positions with methyl group and isovanillin. Alone, it takes 6 days, the yield is low, and then through cyclization oxidation, hydroiodic acid demethylation, the total yield of luteolin is only 3-5%, and there is a by-product orange ketone (also known as aurong), Affect product quality (Lu Yuhua etc., Acta Pharmaceutica Sinica, 15 (8), 1980); Then there are reports to first synthesize chalcones by protecting the phenolic hydroxyl groups of corresponding aldehydes and ketones with chloromethyl methyl ether, and then prepare polyhydroxy flavones, yield Increased to 22% (Gexia et al., Chinese Journal of Pharmaceutical Industry, 34(4) 2003)
However, it is inappropriate to use the carcinogenic compound chloromethyl ether as a protective agent
[0005] In addition, there is still a method of 1,3 substituted propanedione for the total synthesis of luteolin (D.Nagarathnam et al, J.Org.Chem, 56(16), 4884-4887, 1991), and the intermediate needs silane to protect the hydroxyl group. Using LIHMDS polyanion lithium, the reaction conditions are nitrogen gas and -78 ° C, it is difficult to achieve large-scale production

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
  • Process for synthesizing luteolin
  • Process for synthesizing luteolin
  • Process for synthesizing luteolin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment one, the preparation of luteolin

[0020] Add 30Kg of 3',4'-dimethoxy-5,7-dihydroxyflavone and 120Kg of pure anhydrous pyridine into the enamel reaction kettle, stir to dissolve, heat up the temperature slowly to about 100°C, divide Add aluminum trichloride in batches, a large amount of heat is released, the temperature is controlled not to exceed 180°C, and the addition of aluminum trichloride is completed in about 1 hour. After the addition, react at 160°C-180°C for 3-5 hours, track whether the demethylation is complete by high performance liquid phase, and determine the reaction time.

[0021] Pump 1000Kg of water into the hydrolysis kettle, pre-cool to 10°C, put the above-mentioned reactant into the hydrolysis kettle while it is hot, stir, remove the gas, cool, and separate the crude product in the centrifuge. Wash with 50Kg cold water, wash with DMF / H 2 O and 95% ethanol were recrystallized twice to obtain 22.1Kg of luteolin, with a yield of 81%, and a...

Embodiment 2

[0022] Embodiment two, 3', the preparation of 4'-dimethoxy-5,7-dihydroxyflavone

[0023] Add 20Kg of phloroglucinol and 60Kg of ethyl 3,4-dimethoxybenzoylacetate into the enamel reaction kettle, stir, dissolve, heat, and raise the temperature to 140°C-160°C, under vacuum (1330Pa) pressure reduction Reflux for 2 hours, put 80Kg of diphenyl ether in a little cold, and then reflux reaction at 140°C-160°C for 4-5 hours under vacuum (6600Pa) under reduced pressure, cool, and when cooled to 30°C, filter with suction, soak in 40Kg95% ethanol for 30 Minutes, beating, centrifuge filter to obtain 21Kg of yellow crude product of 3',4'-dimethoxy-5,7-dihydroxyflavone. The mother liquor was cooled, and after standing still, a small amount of crude product was obtained by filtration, with a yield of 42.2%, and HPLC≥92%. The crude product was used in the demethylation reaction without further purification.

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 new method of synthesis common mignonette element. The initial material is phloroglucin, protective group is not needed, 3',4'-dimethoxy-5,7-ferrichrysin can be got after it directly condensated and cyclizated with 3,4-dimethoxy benzoyl acetic acid ethyl ester, then common mignonette element is got after catalysis demethylate by alchlor / pyridine, the whole yield is 34.2%.

Description

field of invention [0001] The present invention relates to the fields of organic medicinal chemistry and functional food chemistry, in particular, the present invention relates to a new total synthesis manufacturing process of luteolin for antitussive and expectorant drugs and functional food. Background technique [0002] The chemical name of luteolin is: 3', 4', 5, 7-tetrahydroxyflavone; English name: Luteolin. Molecular formula: C 15 h 10 o 6 ; Molecular Weight: 286.24; CAS: [491-70-3]. [0003] Luteolin, also known as qinglan aglycone, is a common active ingredient isolated from the effective Chinese herbal medicine Jinye Qinglan in Xinjiang for treating bronchitis and Prunella vulgaris from Anhui. Its natural products have been used in clinical treatment of cough, expectorant, anti-inflammatory and have good curative effect. However, due to the low extraction rate of natural products, it is difficult to purify and clinically apply. There are many reports about sem...

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 Patents(China)
IPC IPC(8): C07D311/30
CPCY02P20/55
Inventor 陈新梅以成
Owner NANJING RALLY BIOCHEM
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