552-66-9

Basic information

• Product Name: Daidzin
• Synonyms: 4h-1-benzopyran-4-one,7-(beta-d-glucopyranosyloxy)-3-(4-hydroxyphenyl)-5-hydro;7-(beta-d-glucopyranosyloxy)-3-(4-hydroxyphenyl)-5-hydroxy-4h-1-benzopyran-4;7-(beta-d-glucopyranosyloxy)-3-(4-hydroxyphenyl)-5-hydroxy-4h-1-benzopyran-4-on;7,4-dihydroxyisoflavone7-glucoside;daidzoside;GLUCOSYL-7-DAIDZEIN;DAIDZEIN-7-GLUCOSIDE;DAIDZEIN-7-O-BETA-D-GLUCOPYRANOSIDE
• CAS NO: 552-66-9
• Molecular Formula: C₂₁H₂₀O₉
• Molecular Weight: 416.38
• Product Categories: pharmacetical;The group of Daidzin;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Glucuronides;Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;inhibitor;Inhibitors
• Mol File: 552-66-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 234-236°C
• Boiling Point: 727.558 °C at 760 mmHg
• Flash Point: 259.792 °C
• Appearance: White powder
• Density: 1.573 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.695
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated)
• PKA: 9.65±0.30(Predicted)
• BRN: 59741
• CAS DataBase Reference: Daidzin(CAS DataBase Reference)
• NIST Chemistry Reference: Daidzin(552-66-9)
• EPA Substance Registry System: Daidzin(552-66-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DJ3094000
• F: 10
• Hazardous Substances Data: 552-66-9(Hazardous Substances Data)

Usage

Description

Daidzin, a plant isoflavone glycoside, is a potent inhibitor of human mitochondrial aldehyde dehydrogenase (ALDH-I). It is derived from Daidzein and is also considered a metabolite of isoflavone derivatives. Daidzin is presented as a white powder and has garnered attention for its potential applications in various industries.

Uses

Used in Pharmaceutical Applications:
Daidzin is used as an inhibitor in the pharmaceutical industry, specifically for its role in inhibiting human mitochondrial aldehyde dehydrogenase (ALDH-I). This inhibition property makes it a promising candidate for the development of drugs targeting various health conditions related to ALDH-I dysregulation.
Used in Research and Development:
As a derivative of Daidzein and a metabolite of isoflavone derivatives, Daidzin is utilized in research and development for studying the effects of isoflavones on human health and their potential applications in medicine. Its inhibitory properties allow researchers to explore its impact on various biological processes and pathways.
Used in Nutraceutical Applications:
Daidzin, due to its isoflavone nature, may also find use in the nutraceutical industry as a supplement or ingredient in products aimed at promoting health and well-being. Its potential benefits in modulating ALDH-I activity could contribute to the development of nutraceutical products targeting specific health concerns.

Biochem/physiol Actions

Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.

InChI:InChI=1/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21?/m1/s1

Synthetic route

7,4’-dihydroxyisoflavone 7-glucoside (552-66-9) → daidzein (486-66-8)

Conditions	Yield
In hydrogenchloride

Upstream product

• 486-66-8 daidzein 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 133-89-1 UDP-glucose 
• 50-99-7 D-glucose 
• 1105697-68-4 4'-O-hexanoyldaidzein-7-yl 2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranoside 
• 17720-60-4 2,4,4'-trihydroxy deoxybenzoin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 171973-40-3 2-hydroxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl 4'-hydroxybenzyl ketone 
• 602329-45-3 7,4'-di-O-hexanoyl-daidzein 
• 602329-51-1 4'-O-hexanoyl-daidzein 
• 124590-31-4 6''-O-malonyldaidzin 
• 5328-37-0 L-arabinose 
• 602329-60-2 4'-O-hexanoyldaidzein 7-O-2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranoside 

Downstream Products

• 88048-23-1 3-(4-acetoxy-phenyl)-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-chromen-4-one 
• 308366-15-6 daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside 
• 486-66-8 daidzein 
• 1093135-87-5 C₄₇H₆₃NO₂₉ 
• 1079288-28-0 daidzein 7-O-β-maltotetraoside 
• 3682-01-7 daidzein diacetate 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 

Relevant articles and documents

Biosynthesis of novel daidzein derivatives using Bacillus amyloliquefaciens whole cells

Biotransformation of daidzein was performed by using Bacillus amyloliquefaciens KCTC 13588, Lactococcus lactis subsp. lactis KCTC 3769, Leuconostoc citreum KCTC 13186, Kluyveromyces lactis var. lactis KCTC 17704, Pediococcus pentosaceus KCTC 3116, and Lac

Molecular and Structural Characterization of a Promiscuous C-Glycosyltransferase from Trollius chinensis

Herein, the catalytic promiscuity of TcCGT1, a new C-glycosyltransferase (CGT) from the medicinal plant Trollius chinensis is explored. TcCGT1 could efficiently and regio-specifically catalyze the 8-C-glycosylation of 36 flavones and other flavonoids and could also catalyze the O-glycosylation of diverse phenolics. The crystal structure of TcCGT1 in complex with uridine diphosphate was determined at 1.85 ? resolution. Molecular docking revealed a new model for the catalytic mechanism of TcCGT1, which is initiated by the spontaneous deprotonation of the substrate. The spacious binding pocket explains the substrate promiscuity, and the binding pose of the substrate determines C- or O-glycosylation activity. Site-directed mutagenesis at two residues (I94E and G284K) switched C- to O-glycosylation. TcCGT1 is the first plant CGT with a crystal structure and the first flavone 8-C-glycosyltransferase described. This provides a basis for designing efficient glycosylation biocatalysts.

Assessing the regioselectivity of oleD-catalyzed glycosylation with a diverse set of acceptors

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavonesnY (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2- methoxyestradiol)- were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.