(+-)-Dihydrodaidzein (HCID 176907)

Overview

Dihydrodaidzein is a hydroxyisoflavanone that is isoflavanone carrying two hydroxy substituents located at positions 4' and 7. It has a role as a metabolite.

Names & identifiers

Preferred name: (+-)-Dihydrodaidzein
IUPAC: 7-hydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
English name: Dihydrodaidzein
Molecular formula: C15H12O4
Molecular weight: 256.25

Names & synonyms

dihydrodaidzein17238-05-07,4'-Dihydroxyisoflavanone(+-)-DihydrodaidzeinDTXSID70912308CHEBI:75842RefChem:546552DTXCID601341330Dihydro Daidzein7-hydroxy-3-(4-hydroxyphenyl)chroman-4-one(+/-)-DihydrodaidzeinDihydrodaidzein (keto)

Show more names

Dihydrodaidzein>(±)-DihydrodaidzeinDIHYDRODAIDZEIN hplcDihydrodaidzein standardDihydrodaidzein, 10 mM in DMSO7-Hydroxy-3-(4-hydroxyphenyl)-4-chromanoneinhibit,Endogenous Metabolite,Dihydrodaidzein,Inhibitor

MFCD002104947-hydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneIsoflavanone, 4',7-dihydroxy-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-Benzopyran-4-oneFT-06669484',7-dihydroxy-IsoflavanoneSCHEMBL131543orb1218639

Database identifiers

CAS: 17238-05-0
PubChem CID: 176907
DTXSID: DTXSID70912308
ChEBI: CHEBI:75842
EC Number: 112-251-4
Nikkaji: J668.309F

Properties

Computed structural properties

XLogP: 2.4
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 19
Formal charge: 0
Complexity: 335

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point250 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 250 · 250-251°C
Boiling point: 529.5 · 529.5±50.0 °C(Predicted)
Density: 1.386 · 1.386±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer, Under Inert Atmosphere
solubility: 0.1 mg/ml · ≤0.1mg/ml in ethanol;30mg/ml in DMSO;10mg/ml in dimethyl formamide
pka: 7.71 · 7.71±0.40(Predicted)
form: powder to crystal
color: Light orange to Yellow to Green
biological source: synthetic
λmax: 313 nm · 313nm(EtOH aq.)(lit.)
InChI: 1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2
InChIKey: JHYXBPPMXZIHKG-UHFFFAOYSA-N
SMILES: O1CC(C(=O)c3c1cc(cc3)O)c2ccc(cc2)O
CAS DataBase Reference: 17238 · 17238-05-0
UNSPSC Code: 12352200 · 12352200
NACRES: 25 · NA.25
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
WGK Germany: 3 · WGK 3
HS Code: 2932990090 · 2932990090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: WGK 3
hs_code: 2932990090
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2
Precautionary statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313

Chemistry & industry

Pharmacology

Metabolism/MetabolitesDihydrodazein has known human metabolites that include Tetrahydrodaidzein and (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[[3-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxane-2-carboxylic acid.

Cellular LocationsMembrane

Applications · 2 items

UsesA metabolite of Daidzein.

UsesDaidzein is an isoflavonoid phytoestrogenic compound found in soybeans, pea pods, clover, kudzu, and other legumes. Dihydrodaidzein is an active, estrogenic metabolite of daidzein. It has vasodilatory action on rat isolated aortic rings at 1 μg/ml. It stimulates the estrogen receptor-dependent growth of breast cancer MCF-7 cells at micromolar concentrations. Dihydrodaidzein is produced by the metabolism of daidzein in colonic bacteria and may be further metabolized to various bioactive compounds, including equol .