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

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

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

• 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 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 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 
• 93-97-0 benzoic acid anhydride 

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 

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.

Synthetic method of oroxylin

The invention relates to a synthetic method of oroxylin. The method disclosed by the invention comprises the following steps: carrying out acetylation reaction on 5, 6, 7-trihydroxy flavone and aceticanhydride in pyridine at room temperature; reacting an obtained acetylate with benzyl bromide or benzyl chloride in the presence of an inorganic base, and carrying out hydrolysis reaction on a product in alkaline water; and reacting with methyl iodide in the presence of an inorganic base, and finally debenzylating in the presence of concentrated sulfuric acid to obtain the target product oroxylin. The method for synthesizing oroxylin provided by the invention has the advantages of simple and feasible operation, high product purity, high reaction yield and the like, and is easier for industrial production compared with the existing method.

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 synthesis of Oroxylin A

Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalin is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A glucuronide methyl ester which on de-glycosylation results in the formation of Oroxylin A.

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.

Synthesis of oroxylin A starting from naturally abundant baicalin

– A new approach to oroxylin A, a monomethylated trihydroxyflavone, is described. The starting material was baicalin, a representative naturally abundant flavonoid glucuronide. First, conditions for the cleavage of the glycosidic bond were established, using a mixture of water and conc. sulfuric acid (5:2) at 121 °C for 40 min. The hydrolysis was performed in a high-pressure steam sterilizer so that the temperature and reaction time were precisely controlled. Subsequent acetylation of the crude material furnished baicalein 6,7-diacetate on a preparative scale and in a reproducible manner. Next, the C-7 position was protected site-selectively with a methoxymethyl (MOM) group, taking advantage of an unexpected sequential migration of the two acetyl groups among the C-5, C-6, and C-7 positions under basic conditions. The removal of the two remaining acetyl groups followed by site-selective methylation of the C-6 position furnished 5-hydroxy-6-methoxy-7-methoxymethoxyflavone (oroxylin A C-7 MOM ether). Finally, by the deprotection of the MOM ether, oroxylin A was obtained in 6 total steps and 62% overall yield from baicalin.

Method for synthesizing oroxylin A in which baicalin is used as an initiator for conveniently and efficiently synthesizing oroxylin by a chemical synthesis method

Provided is a method for synthesizing oroxylin A, which utilizes baicalin as an initiator for conveniently and efficiently synthesizing oroxylin by a chemical synthesis method. The method for synthesizing oroxylin A comprises a methylation step for using baicalin as an initiator, and subjecting the initiator to a methylation reaction in an alkaline first reaction solution, so that a 6-hydroxyl group of the initiator is methylated to obtain an intermediate product, wherein the first reaction solution is composed of an inorganic base and a methylating agent; and a protecting group removal step for removing a carbohydrate group of the intermediate product in an acidic second reaction solution to form a hydroxyl group, thereby completing the synthesis of the oroxylin A.

Synthetic method for oroxylin A

The invention provides a synthetic method for oroxylin A. According to the invention, baicalin is used as a starting material, and oroxylin A can be synthesized by using a simple and effective chemical synthesis method.

Enzymatic production of oroxylin A and hispidulin using a liverwort flavone 6-O-methyltransferase

Oroxylin A and hispidulin, compounds which are abundant in both Scutellaria and liverwort species, are important lead compounds for the treatment of ischemic cerebrovascular disease. Their enzymatic synthesis requires an O-methyltransferase able to interact with the related flavonoid's 6-OH group, but such an enzyme has yet to be identified in plants. Here, the gene encoding an O-methyltransferase (designated PaF6OMT) was isolated from the liverwort species Plagiochasma?appendiculatum. A test of alternative substrates revealed that its strongest preferences were baicalein and scutellarein, which were converted into, respectively, oroxylin A and hispidulin. Allowed a sufficient reaction time, the conversion rate of these two substrates was, respectively, 90% and 100%. PaF6OMT offers an enzymatic route to the synthesis of oroxylin A and hispidulin.