3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 1876
• Molecular Formular: C21H20O9
• Molecular Mass: 416.3781
• Monoisotopic Mass: 416.11073222
• SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)Oc1ccc2c(c1)occ(c2=O)c1ccc(O)cc1
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/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
• InChIKey: KYQZWONCHDNPDP-QNDFHXLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: daidzin; 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one; daidzein 7-O-β-D-glucoside
• Synonyms: Daidzein-7-O-β-D-glucopyranoside; Daidzin; Daidzoside; Daidzein 7-glucoside; Daidzein-7-glucoside; Daidzein 7-O-glucoside; 4',7-Dihydroxyisoflavone; 7-O-B-D-GLUCOPYRANOSIDE; 7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one; Daidzin

Database IDs

• CAS Number: 552-66-9
• EC Number: 207-635-4
• MDL Number: MFCD00017466
• Beilstein Number: 59741
• PubChem SID: 160965331; 24858323; 46505206
• PubChem CID: 107971

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.962957
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.46222103
• LogD (pH = 7.4): 0.45072386
• Log P: 0.46236962
• Molar Refractivity: 101.8464 cm^3
• Polarizability: 40.17439 Å^3
• Polar Surface Area: 145.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.71
• LOG S: -2.8
• Solubility (Water): 6.61e-01 g/l

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• RTECS: DJ3094000; DJ3100040
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 24-26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: mouse ... Aldh1a2(19378), Maoa(17161)rat ... Aldh1a2(116676)
• Mechanism of Action: Antidipsotropic

Product Information

• Purity: ≥95.0% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard
• Biological Source: Isol. from soya bean meal, roots of Pueraria lobata and shoots of Piptanthus nepalensis. Also from Baptisia spp., Glycine max, Medicago sativa, Thermopsis spp. and others in Leguminosae
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Cancer preventive and an alcohol dependency treatment
• Empirical Formula (Hill Notation): C21H20O9

DETAILS

DrugBank - DB02115

Drug information: experimental

Sigma Aldrich - 30408

Biochem/physiol Actions
Daidzin is an isoflavone reported to have anti-oxidant, anti-carcinogenic, and anti-artherosclerotic activities. Daidzin is the major active component of the traditional Chinese medicine (TCM) derived from radix puerariae (Kudzu) that is commonly used to treat alcohol abuse. Daidzin is a potent and selective inhibitor of mitochondrial aldehyde dehydrogenase 2 (ALDH-2).
Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 30408.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 42926

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.1

REFERENCES

• Inone, T. et al., Chem. Pharm. Bull., 1974, 22, 1422
• Ayabe, S. et al., J.C.S. Perkin 1, 1982, 2725