2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

• ChemBase ID: 155890
• Molecular Formular: C18H22O4
• Molecular Mass: 302.36488
• Monoisotopic Mass: 302.15180918
• SMILES: c1cc(cc(c1)O)CC(CO)C(Cc1cccc(c1)O)CO
• Canonical SMILES: OCC(C(Cc1cccc(c1)O)CO)Cc1cccc(c1)O
• InChI: InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2
• InChIKey: DWONJCNDULPHLV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
• IUPAC Traditional name: 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
• Synonyms: 3,3′-[2,3-Bis(hydroxymethyl)butane-1,4-diyl]diphenol; Enterodiol

Database IDs

• CAS Number: 80226-00-2
• MDL Number: MFCD00201089
• Beilstein Number: 8997364
• PubChem SID: 24868669; 162250028
• PubChem CID: 123725

CALCULATED PROPERTIES

• Acid pKa: 9.793418
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 2.6481817
• LogD (pH = 7.4): 2.64646
• Log P: 2.6482036
• Molar Refractivity: 86.3606 cm^3
• Polarizability: 33.263485 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 7
• 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: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C18H22O4

DETAILS

Sigma Aldrich - 45198

Biochem/physiol Actions
Referred to as a "mammalian lignan," enterodiol is produced by metabolism of plant lignans by intestinal flora.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 45198.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.