2,3-bis[(3-hydroxyphenyl)methyl](1,2,4-13C3)butane-1,4-diol

• ChemBase ID: 168020
• Molecular Formular: C18H22O4
• Molecular Mass: 305.34284451
• Monoisotopic Mass: 305.1618737
• SMILES: c1c(cc(cc1)C[13CH](C(Cc1cccc(c1)O)[13CH2]O)[13CH2]O)O
• Canonical SMILES: O[13CH2][13CH](C(Cc1cccc(c1)O)[13CH2]O)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/i11+1,12+1,15+1
• InChIKey: DWONJCNDULPHLV-IPDAJEFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-bis[(3-hydroxyphenyl)methyl](1,2,4-^1^3C₃)butane-1,4-diol
• IUPAC Traditional name: 2,3-bis[(3-hydroxyphenyl)methyl](1,2,4-^1^3C₃)butane-1,4-diol
• Synonyms: (2R,3R)-rel-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol-13C3; (R*,R*)-(±)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol-13C3; rac Enterodiol-13C3

Database IDs

• CAS Number: 918502-74-6
• PubChem SID: 162262152
• PubChem CID: 71316342

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; Methanol
• Apperance: White Solid
• Melting Point: 176-179°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E558942

A labelled 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 o

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)