5928-26-7

Basic information

• Product Name: Biochanin A-beta-D-glucoside
• Synonyms: SISSOSTRIN;SISSOTRIN;BIOCHANIN A-7-GLUCOSIDE;BIOCHANIN A 7-O-BETA-D-GLUCOPYRANOSIDE;BIOCHANIN A-7-O-GLUCOSIDE;SISSOTRIN BIOCHEMIKA;biochanin a 7-o-β-d-glucopyranoside;5-Hydroxy-3-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS NO: 5928-26-7
• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.4
• Product Categories: Iso-Flavones
• Mol File: 5928-26-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 754.9 °C at 760 mmHg
• Flash Point: 265.4 °C
• Appearance: /
• Density: 1.545 g/cm³
• Vapor Pressure: 6.05E-24mmHg at 25°C
• Refractive Index: 1.674
• PKA: 6.10±0.20(Predicted)
• BRN: 1302648
• CAS DataBase Reference: Biochanin A-beta-D-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: Biochanin A-beta-D-glucoside(5928-26-7)
• EPA Substance Registry System: Biochanin A-beta-D-glucoside(5928-26-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 5928-26-7(Hazardous Substances Data)

Usage

Definition

ChEBI: A glycosyloxyisoflavone that is biochanin A attached to a beta-D-glucopyranosyl residue at position 7 via glycosidic linkage.

InChI:InChI=1/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3

Upstream product

• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant articles and documents

Microbial glycosylation of daidzein, genistein and biochanin a: Two new glucosides of biochanin A

Biotransformation of daidzein, genistein and Biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and Biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl Biochanin A and 5-O-glucosyl Biochanin A (isosissotrin). Biotransformation products were obtained with 22%-40% isolated yield.