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

• ChemBase ID: 90404
• Molecular Formular: C15H14O3
• Molecular Mass: 242.26986
• Monoisotopic Mass: 242.09429431
• SMILES: O1c2cc(ccc2CC(C1)c1ccc(cc1)O)O
• Canonical SMILES: Oc1ccc(cc1)C1COc2c(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
• InChIKey: ADFCQWZHKCXPAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
• IUPAC Traditional name: equol
• Synonyms: (+/-)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-chromen-7-ol; (+/-)-Equol; (+/-)-7-Hydroxy-3-(4-hydroxyphenyl)chroman; 3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol; 4′,7-Dihydroxyisoflavane; (±)-Equol; 3-(4-Hydroxyphenyl)chroman-7-ol

Database IDs

• CAS Number: 94105-90-5
• MDL Number: MFCD00016662
• Beilstein Number: 87752
• PubChem SID: 162077214; 24868878
• PubChem CID: 382975

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

Safety Information

• Storage Warning: Irritant/Hygroscopic/Store under Argon
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

Product Information

• Purity: ≥99.0% (TLC); 95+%; 98%
• Empirical Formula (Hill Notation): C15H14O3

DETAILS

Apollo Scientific Ltd - OR60026

Racemic mixture

Sigma Aldrich - 45405

Biochem/physiol Actions
Metabolite of daidzein. Weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor.1