2284-31-3

Basic information

• Product Name: PRATENSEIN
• Synonyms: 4'-METHOXY-3',5,7-TRIHYDROXYISOFLAVONE;PRATENSEIN;PRALENREIN;OROBOL 4'-METHYL ETHER;5,7,3'-Trihydroxy-4'-methoxyisoflavone;5,7-Dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one;PATCHOULI ALCOHOL (RG)
• CAS NO: 2284-31-3
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26
• Product Categories: Iso-Flavones
• Mol File: 2284-31-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 272-273°
• Boiling Point: 576.7°Cat760mmHg
• Flash Point: 220.3°C
• Appearance: /
• Density: 1.512g/cm³
• Vapor Pressure: 6.73E-14mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: PRATENSEIN(CAS DataBase Reference)
• NIST Chemistry Reference: PRATENSEIN(2284-31-3)
• EPA Substance Registry System: PRATENSEIN(2284-31-3)

Safety Data

• Hazardous Substances Data: 2284-31-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3' positions, and by a methoxy group at the 4' position.

InChI:InChI=1/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

Upstream product

• 480-23-9 orobol 
• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 36191-03-4 calycosin-7-O-β-D-glucopyranoside 
• 63240-66-4 3',4',6'-tri-O-benzyl-2'-hydroxy-4-methoxychalcone 
• 70413-06-8 2,3',4,6-tetrahydroxy-4'-methoxy-desoxybenzoin 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 122087-35-8 5,7,3'-trihydroxy-4'-methoxyisoflavanone 

Relevant articles and documents

THE FIRST IDENTIFICATION OF ISOFLAVONES FROM A BRYOPHYTE

Bryum capillare is shown to accumulate the isoflavones orobol and pratensein as the 7-O-glucosides and predominantly, as the 7-(6''-malonylglucosides).This is the first finding of isoflavonoids in bryophytes.The phylogenetic relevance of this observation is briefly discussed.Key Word Index - Bryum capillare; Bryales; Musci; moss; isoflavones; orobol; pratensein; 7-O-glucosides; 6''-malonyl glucosides; NMR spectra.

Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover)

Biochanin A and formononetin are the predominant isoflavones in red clover. In a previous study (J. Agric. Food Chem. 2002, 50, 4783-4790), it was demonstrated that human liver microsomes converted biochanin A and formononetin to genistein and daidzein. This paper now shows CYP1B1-catalyzed O-demethylation of biochanin A and formononetin to produce genistein and daidzein, respectively, which inhibit CYP1B1. Recombinant human CYP1A1 or CYP1B1 was incubated with biochanin A or formononetin. CYP1A1 catalyzed isoflavone 4′-O-demethylation and hydroxylations with similar efficiency, whereas CYP1B1 favored 4′-O-demethylation over hydroxylations. Three of the biochanin A metabolites (5,7,3′-trihydroxy-4′-methoxyisoflavone, 5,7,8-trihydroxy-4′-methoxyisoflavone, and 5,6,7-trihydroxy-4′- methoxyisoflavone) were characterized by 1H NMR spectroscopy and mass spectrometry. Daidzein (Ki = 3.7 μM) exhibited competitive inhibition of CYP1B1 7-ethoxyresorufin O-deethylase activity, and genistein (Ki = 1.9 μM) exhibited mixed inhibition. Biochanin A and/or formononetin may exert anticarcinogenic effects directly by acting as competitive substrates for CYP1B1 or indirectly through their metabolites daidzein and genistein, which inhibit CYP1B1.