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

• ChemBase ID: 172556
• Molecular Formular: C20H22O6
• Molecular Mass: 361.36304451
• Monoisotopic Mass: 361.15170294
• SMILES: [13C@@H]1([C@@H]([13CH2]O[13C]1=O)Cc1ccc(c(c1)OC)O)Cc1ccc(c(c1)OC)O
• Canonical SMILES: COc1cc(ccc1O)C[13C@@H]1[13C](=O)O[13CH2][C@H]1Cc1ccc(c(c1)OC)O
• InChI: InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m1/s1/i11+1,15+1,20+1
• InChIKey: MATGKVZWFZHCLI-HWLGJPFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl](2,3,5-^1^3C₃)oxolan-2-one
• IUPAC Traditional name: (3S,4S)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl](2,3,5-^1^3C₃)oxolan-2-one
• Synonyms: (3R,4R)-rel-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone-13C3; trans-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone-13C3; rac Matairesinol-13C3

Database IDs

• PubChem SID: 164228466
• PubChem CID: 71749910

CALCULATED PROPERTIES

• Acid pKa: 9.644701
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.2917516
• LogD (pH = 7.4): 3.28933
• Log P: 3.2917826
• Molar Refractivity: 95.6344 cm^3
• Polarizability: 37.27576 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M197852

A labelled plant lignan found in oil seeds, whole grains, vegetables and fruits that may offer health benefits when used in daily diet. It is a precursor to enterolignans that have potential anticancer properties and may reduce the risk of cardiovascular

REFERENCES

• Niemeyer, H.B. et al.: J. Agric. Food Chem., 51, 6317 (2003)
• Sakakibara, N. et al.: Org. Biomol. Chem., 1, 2474 (2003)
• Milder, I.E. et al.: Br. J. Nutr., 93, 393 (2003)