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

• ChemBase ID: 168019
• Molecular Formular: C18H22O4
• Molecular Mass: 302.36488
• Monoisotopic Mass: 302.15180918
• SMILES: c1c(cc(cc1)C[C@@H]([C@H](Cc1cccc(c1)O)CO)CO)O
• Canonical SMILES: OC[C@H]([C@H](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/t15-,16-/m1/s1
• InChIKey: DWONJCNDULPHLV-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
• IUPAC Traditional name: (2S,3S)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
• Synonyms: (2R,3R)-rel-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol; (R*,R*)-(±)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol; rac Enterodiol

Database IDs

• CAS Number: 77756-22-0
• PubChem SID: 162262151
• PubChem CID: 12106235

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

Physical Property

• Solubility: Acetone; Ethyl Acetate; Methanol
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - E558940

A compound closely related to Enterolactone (E558950). A metabolite of sesame lignans (sesamin, sesamolin). Inhibits colonic cancer cell growth by inducing cell cycle arrest and apoptosis. Possible relationship between exposure and reduced risk of breast

REFERENCES

• Hirano, T. et al.: Res. Com. Chem. Path. Pharmac., 64, 227 (1989)
• Ayella, A. et al.: Nut. Res., 30, 762 (1989)
• Pianjing, P. et al.: J. Agric. Food Chem., 59, 212 (1989)
• Buck, K. et al.: Am. J. Clinic. Nut., 92, 141 (1989)