(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

• ChemBase ID: 70501
• Molecular Formular: C15H14O3
• Molecular Mass: 242.26986
• Monoisotopic Mass: 242.09429431
• SMILES: C1[C@@H](Cc2ccc(cc2O1)O)c1ccc(cc1)O
• Canonical SMILES: Oc1ccc(cc1)[C@H]1COc2c(C1)ccc(c2)O
• InChI: InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1
• InChIKey: ADFCQWZHKCXPAJ-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
• IUPAC Traditional name: (-)-equol
• Synonyms: (S)-3-(4-Hydroxy-phenyl)-chroman-7-ol; (S)-3,4-Dihydro-3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol; 3-(4-Hydroxy-phenyl)-chroman-7-ol; (-)-Equol; (S)-(-)-4',7-Isoflavandiol; (S)-Equol; (S)-3-(4-Hydroxyphenyl)chroman-7-ol; 4',7-Isoflavandiol; Equol

Database IDs

• CAS Number: 531-95-3
• MDL Number: MFCD00200962
• PubChem SID: 162036216
• PubChem CID: 91469
• CHEMBL: 198877
• Chemspider ID: 82594
• KEGG ID: C14131
• Wikipedia Title: Equol

CALCULATED PROPERTIES

• Acid pKa: 9.632071
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.191646
• LogD (pH = 7.4): 3.1891518
• Log P: 3.1916778
• Molar Refractivity: 68.9602 cm^3
• Polarizability: 26.442783 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 189-192°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: Estrogen; progestogen Receptor

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - E593001

(S)-Equol and R-Equol are metabolites of the soy isoflavones Daidzein (D103500) and Genistein. Both have significant biological actions.

REFERENCES

• Heinonen, S., et al.: Anal. Biochem., 274, 211 (1999)
• Setchell, K., et al.: J. Nutr., 132, 3577 (1999)
• Thigpen, J., et al.: Comp. Med., 53, 607 (1999)
• Yee, S., et al.: Food Chem. Toxicol., 46, 2713 (1999)