(3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

• ChemBase ID: 155875
• Molecular Formular: C18H18O4
• Molecular Mass: 298.33312
• Monoisotopic Mass: 298.12050906
• SMILES: c1cc(cc(c1)O)C[C@@H]1COC(=O)[C@H]1Cc1cccc(c1)O
• Canonical SMILES: Oc1cccc(c1)C[C@@H]1C(=O)OC[C@H]1Cc1cccc(c1)O
• InChI: InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m1/s1
• InChIKey: HVDGDHBAMCBBLR-PBHICJAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
• IUPAC Traditional name: enterolactone
• Synonyms: trans-α,β-Bis(3-hydroxybenzyl)butyrolactone; Enterolactone

Database IDs

• CAS Number: 78473-71-9
• MDL Number: MFCD01861506
• Beilstein Number: 4699604
• PubChem SID: 162250013; 24868670
• PubChem CID: 114739

CALCULATED PROPERTIES

• Acid pKa: 9.163039
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.6070313
• LogD (pH = 7.4): 3.5997064
• Log P: 3.607125
• Molar Refractivity: 82.708 cm^3
• Polarizability: 32.213398 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (HPLC)
• Empirical Formula (Hill Notation): C18H18O4

DETAILS

Sigma Aldrich - 45199

Biochem/physiol Actions
Enterolactone is the major human metabolite of dietary sesamin (lignan from sesame seeds).1 A phytoestrogen, it shows an inverse correlation with risk of breast cancer in one study.2