(3S,4S)-3,4-bis({[4-(benzyloxy)-3-methoxyphenyl]methyl})oxolan-2-one

• ChemBase ID: 172558
• Molecular Formular: C34H34O6
• Molecular Mass: 538.63016
• Monoisotopic Mass: 538.23553881
• SMILES: [C@@H]1([C@@H](COC1=O)Cc1ccc(c(c1)OC)OCc1ccccc1)Cc1ccc(c(c1)OC)OCc1ccccc1
• Canonical SMILES: COc1cc(ccc1OCc1ccccc1)C[C@@H]1COC(=O)[C@H]1Cc1ccc(c(c1)OC)OCc1ccccc1
• InChI: InChI=1S/C34H34O6/c1-36-32-19-26(13-15-30(32)38-21-24-9-5-3-6-10-24)17-28-23-40-34(35)29(28)18-27-14-16-31(33(20-27)37-2)39-22-25-11-7-4-8-12-25/h3-16,19-20,28-29H,17-18,21-23H2,1-2H3/t28-,29+/m1/s1
• InChIKey: GJONVZSUXWNNKA-WDYNHAJCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-3,4-bis({[4-(benzyloxy)-3-methoxyphenyl]methyl})oxolan-2-one
• IUPAC Traditional name: (3S,4S)-3,4-bis({[4-(benzyloxy)-3-methoxyphenyl]methyl})oxolan-2-one
• Synonyms: (3R,4R)-rel-Dihydro-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-2(3H)-furanone; trans-(±)-Dihydro-3,4-bis[[3-methoxy-4-(phenylmethoxy)phenyl]methyl]-2(3H)-furanone; rac Matairesinol Dibenzyl Diether

Database IDs

• CAS Number: 116261-30-4
• PubChem SID: 164228468
• PubChem CID: 13963125

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 7.032517
• LogD (pH = 7.4): 7.032517
• Log P: 7.032517
• Molar Refractivity: 153.8242 cm^3
• Polarizability: 60.263325 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - M197855

Protected rac Matairesinol (M197850). A 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 redu

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)