(3S)-3,4-bis[(3-hydroxyphenyl)methyl](2,3,5-13C3)oxolan-2-one

• ChemBase ID: 168022
• Molecular Formular: C18H18O4
• Molecular Mass: 301.31108451
• Monoisotopic Mass: 301.13057357
• SMILES: c1c(cc(cc1)CC1[13C@@H]([13C](=O)O[13CH2]1)Cc1cccc(c1)O)O
• Canonical SMILES: Oc1cccc(c1)C[13C@@H]1[13C](=O)O[13CH2]C1Cc1cccc(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-/m0/s1/i11+1,17+1,18+1
• InChIKey: HVDGDHBAMCBBLR-AQPGKPQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3,4-bis[(3-hydroxyphenyl)methyl](2,3,5-^1^3C₃)oxolan-2-one
• IUPAC Traditional name: (3S)-3,4-bis[(3-hydroxyphenyl)methyl](2,3,5-^1^3C₃)oxolan-2-one
• Synonyms: (3R,4R)-rel-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone-13C3; trans-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-Furanone-13C3; HPMF-13C3; trans-2,3-Bis(3-hydroxybenzyl)-γ-butyrolactone-13C3; rac Enterolactone -13C3

Database IDs

• CAS Number: 918502-72-4
• PubChem SID: 162262154
• PubChem CID: 71316343

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

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 70-73°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E558952

A labelled 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 cancer.

REFERENCES

• Ayella, A. et al.: Nut. Res., 30, 762 (2010)
• Pianjing, P. et al.: J. Agric. Food Chem., 59, 212 (2010)
• Buck, K. et al.: Am. J. Clinic. Nut., 92, 141 (2010)