480-11-5

Basic information

• Product Name: Oroxylin
• Synonyms: Oroxylin;OLOXYLINA;5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one;5,7-Dihydroxy-6-methoxyflavone;Oroxylia A;6-Methoxybaicalein;Baicalein 6-methyl ether;oxoxylin A
• CAS NO: 480-11-5
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.2635
• Product Categories: Miscellaneous Natural Products
• Mol File: 480-11-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 195-197℃
• Boiling Point: 346.76°C (rough estimate)
• Flash Point: 207.4°C
• Appearance: /
• Density: 1.420
• Vapor Pressure: 2.6E-12mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: 2-8°C
• PKA: 6.48±0.40(Predicted)
• CAS DataBase Reference: Oroxylin(CAS DataBase Reference)
• NIST Chemistry Reference: Oroxylin(480-11-5)
• EPA Substance Registry System: Oroxylin(480-11-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 480-11-5(Hazardous Substances Data)

Usage

Description

Oroxylin, also known as Oroxylin A, is a dihydroxyand monomethoxy-flavone with hydroxy groups positioned at C-5 and C-7 and a methoxy group at C-6. It is a naturally occurring flavonoid found in various plants and has been recognized for its potential health benefits and therapeutic properties.

Uses

Used in Pharmaceutical Industry:
Oroxylin is used as a therapeutic agent for its potential anti-inflammatory, antioxidant, and anti-cancer properties. It has been shown to modulate various signaling pathways involved in inflammation and cancer progression, making it a promising candidate for the development of novel pharmaceuticals.
Used in Nutraceutical Industry:
Oroxylin is also used as an ingredient in the nutraceutical industry due to its potential health benefits. It can be found in dietary supplements and functional foods, where it may contribute to the overall health and well-being of consumers by providing antioxidant and anti-inflammatory support.
Used in Cosmetic Industry:
In the cosmetic industry, Oroxylin may be used as an active ingredient in skincare products due to its antioxidant and anti-inflammatory properties. It could potentially help protect the skin from environmental stressors and promote a healthy skin appearance.

InChI:InChI=1/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3

Upstream product

• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 36948-76-2 oroxyloside 
• 67047-06-7 7-(benzyloxy)-4-oxo-2-phenyl-4H-1-benzopyran-5,6-diyl diacetate 
• 67047-05-6 4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate 
• 4670-34-2 7-benzyloxy-6-methoxy-5-hydroxyflavone 
• 82475-02-3 5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester 
• 82475-03-4 Baicalin methyl ester 
• 731817-58-6 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-6,7-diyl diacetate 
• 77-78-1 dimethyl sulfate 
• 21967-41-9 baicalin 
• 485-80-3 S-adenosyl-L-methionine 
• 102-92-1 Cinnamoyl chloride 
• 100-52-7 benzaldehyde 
• 70185-52-3 6′-hydroxy-2′,3′,4′-trimethoxychalcone 

Downstream Products

• 123549-15-5 oroxylin A 7-acetyl ester 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 740-33-0 mosloflavone 
• 981-92-0 5,7-diacetyl-6-methoxyflavone 
• 36948-76-2 oroxylin A 7-O-glucuronide 
• 1263323-03-0 C₁₈H₁₅BrO₅ 
• 1263323-08-5 C₂₃H₂₆N₂O₅ 
• 1263323-07-4 C₂₂H₂₃NO₆ 
• 1263323-06-3 C₂₃H₂₅NO₅ 
• 1263323-05-2 C₂₂H₂₃NO₅ 
• 1263323-04-1 C₂₂H₂₅NO₅ 
• 1263323-19-8 C₂₄H₂₇NO₆ 
• 1263323-18-7 C₂₅H₂₉NO₅ 
• 1263323-17-6 C₂₄H₂₇NO₅ 

Relevant articles and documents

5,6,7-TRISUBSTITUTED FLAVONES FROM GOMPHRENA MARTIANA

Two 5,6,7-trisubstituted flavones have been isolated from Gomphrena martiana and indentified as 5,6-dimethoxy-7-hydroxyflavone and 5,6-dihydroxy-6-methoxyflavone.Key Word Index -Gomphrena martiana; Amaranthaceae; flavonoids; 5,6-dimethoxy-7-hydroxyflavone; 5,7-dihydroxy-6-methoxyflavone.

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.

Process for Preparing Oroxylin A

A process for preparing oroxylin A includes: subjecting baicalin to a methylation reaction using a methylating reagent in the presence of a base to methylate the 6-hydroxyl group of baicalin, so as to form a methylated compound; and subjecting the methylated compound to a deglucuronidation reaction in the presence of an acid, so as to form oroxylin A.