Preparation method of pure micronized diosmin

Abstract

The invention relates to a preparation method of pure micronized diosmin, which comprises the following steps: 1) hesperidin phenolic hydroxyl group protection; 2) halogenating reaction; 3) protecting group removal and double bond generation; and 4) drying to obtain the micropowder. The six secondary hydroxyl groups on the hesperidin glycosyl group have low activity, the two hydroxyl groups on 6- and 7'- sites of the flavone parent nucleus are subjected to hydroxyl group protection, the flavone parent nucleus is halogenated to generate halogenated diosmin, and the protecting group removal is performed to obtain the diosmin.

Description

technical field [0001] The invention relates to a preparation method of pure micronized diosmin. Background technique [0002] Diosmin (Diosmin), chemical formula: C 28 h 32 o 15 , molecular weight: 608.6, chemical name: 7[[6-oxo-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranose-]oxy]-5-hydroxyl-2 -(3-Hydroxy-4-methoxyphenyl)-4hydro-chromen-4-one. CAS No.520-27-4, flavonoids, English alias: 7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-Dglucopyranosyl]oxy]-5-hydroxy-2-( 3-hy droxy-4-methoxyphcnyl)-4H-1-benzopyran-4-one. Also known as coriander glycoside, diosmin, citrus glucoside, light yellow crystalline powder, almost insoluble in water, soluble in dimethyl sulfoxide, almost insoluble in ethanol, soluble in dilute alkaline solution. The structural formula is as follows: [0003] [0004] Diosmin (Diosmin) also known as coriander glycosides, diosmin, citrus glycosides, molecular formula C 28 h 32 o 15 , Molecular weight 601, present in the root of Rutaceae Zanthoxylum ni...

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Problems solved by technology

Horowitz Robert M.GeatiLi Rruno used bromine to dehydrogenate hesperidin in "Flavonoid Compound of Cilous.Isolation and Structure of erioditcyol Glycoside" (JAM chem.Soc, 1960, 82(11): 2803) in two steps. The process is cumbersome, the conditions are complicated, and the toxic reagent bromine water is used, the cost is high, the yield is only 56.2%, and the content is 92.0%. The dehydrogenation of hesperidin by NBS / benzoyl peroxide is complex and requires special reagents , cost is higher, yield is low, is not suitable for industrialized production; Hydrogen, using pyridine as a solvent, the process is relatively simple, the yield is 94%, but the content is unknown; Yang Ailing in "Extraction Technology of Hesperidin and Its Series Products" (Fine Chemical Industry, 2002, 19 (5): 259-261 ) reported method yield only reaches 56%, and will use acetic anhydride, pyridine, bromine gas, dichloromethane etc., reagent is more, difficult to operate; "(Journal of Fourth Military Medical University, 2008, 29 (21): 1947) reported that although the synthesis process of hesperidin does not use pyridine, strong alkaline substances such as sodium hydroxide and potassium carbonate are used, which seriously corrodes the equipment and reduces the yield. The rate is only 70%, and the content is unknown; Shan Yang, Li Gaoyang, Wang Qiuan, etc. used iodine / pyridine dehydrogenation, the yield is high, but the content is unknown; Luo Meng used two ways of bromine and iodine to dehydrogenate in "The Synthesis and Research of Diosmin" (Chemical Intermediates, 2004, 6: 29-30). Hydrogen, iodine dehydrogenation yield 69%, content 99%, bromodehydrogenation yield only 58%, content 89%

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