82475-02-3

Basic information

• Product Name: 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester
• Synonyms: 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester
• CAS NO: 82475-02-3
• Molecular Weight: 474.421
• Mol File: 82475-02-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester(82475-02-3)
• EPA Substance Registry System: 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester(82475-02-3)

Safety Data

• Hazardous Substances Data: 82475-02-3(Hazardous Substances Data)

Upstream product

• 82475-03-4 Baicalin methyl ester 
• 77-78-1 dimethyl sulfate 
• 21967-41-9 baicalin 

Downstream Products

• 480-11-5 oroxylin A 
• 36948-76-2 oroxyloside 

Relevant articles and documents

An unambiguous and practical synthesis of Oroxylin A: a commonly misidentified flavone

Oroxylin A, a major flavonoid in the extracts of Oroxylum indicum as well as Scutellaria baicalensis possesses useful medicinal properties. Many of the published routes claiming the synthesis of Oroxylin A (1) have in fact led to a regioisomer Negletein that was misinterpreted as Oroxylin A. In the present work, we describe a novel, straight-forward and scalable semi-synthetic approach for rapid access to the title compound, the structure of which is unambiguously secured by NMR and X-ray crystallographic analysis of a derivative. This work also encompasses the synthesis of a glycosylated derivative of Oroxylin A viz OAGME (2), which has marked pharmacological importance.

Crystal structures of the flavonoid Oroxylin A and the regioisomers Negletein and Wogonin

The flavonoid Oroxylin A (6-methoxychrysin or 5,7-dihydroxy-6-methoxy-2- phenyl-4H-chromen-4-one, C16H12O5) and its regioisomers are of increasing interest for a variety of bioactive functions and their pharmaceutical formulation is of importance. Previous difficulties in the separation and misidentification of Oroxylin A from its regioisomers Wogonin (8-methoxychrysin or 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one) and Negletein (5,6- dihydroxy-7-methoxyflavone or 5,6-dihydroxy-7-methoxy-2-phenyl-4H-chromen- 4-one) render its full structural and powder X-ray characterization highly desirable. The low-temperature (100 K) crystal structures of Oroxylin A, Negletein and Wogonin sesquihydrate are reported for the first time. Wogonin crystallizes in two related but distinct hydrated forms. These have very similar powder diffractograms, indicating that such issues need to be addressed for its pharmaceutical formulation.

Metabolites of baicalein in human urine

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