731817-58-6

Basic information

• Product Name: 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-6,7-diyl diacetate
• Synonyms: 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-6,7-diyl diacetate
• CAS NO: 731817-58-6
• Molecular Weight: 354.316
• Mol File: 731817-58-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-6,7-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-6,7-diyl diacetate(731817-58-6)
• EPA Substance Registry System: 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-6,7-diyl diacetate(731817-58-6)

Safety Data

• Hazardous Substances Data: 731817-58-6(Hazardous Substances Data)

Upstream product

• 21967-41-9 baicalin 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 480-11-5 oroxylin A 

Relevant articles and documents

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.

2-substituted benzopyran-4-one compounds and application thereof

The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.

COMPOUNDS AND METHODS TO INCREASE ANTI-P-GLYCOPROTEIN ACTIVITY OF BAICALEIN BY ALKYLATION ON THE A RING

The present invention is directed to analogs of baicalein according to formula (I): where R5 is H, (CI-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl group, an acyl group, a C1-C20 alkyl or ether group, a phosphate, diphosphate, triphosphate or phosphodiester group; R6 and R7 are each independently H, (C1-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl or together form a -OCR1R20- group wherein each of R1 and R2 is independently H, a C1-C3 alkyl group or an optionally substituted phenyl or benzyl group; and R8 is H, OH, an O-acyl group, a C1,-C4 alkyl or alkoxy group, F, Cl, Br or I, or a pharmaceutically acceptable salt thereof, which exhibit anti-P-glycoprotein activity and methods of enhancing the bioavailability of active compounds, especially orally administered compounds, by inhibition of P-glycoprotein 170 (P-gp 170) and/or CYP450 enzyme, especially CYP450 3A4 enzyme. Pharmaceutical compositions based upon these novel derivatives according to the present invention are also described herein.