4-[(3aR,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol

• ChemBase ID: 177757
• Molecular Formular: C19H18O6
• Molecular Mass: 342.34262
• Monoisotopic Mass: 342.1103383
• SMILES: [C@@H]12[C@@H](C(OC1)c1cc(c(cc1)O)O)COC2c1cc2c(cc1)OCO2
• Canonical SMILES: Oc1cc(ccc1O)C1OC[C@H]2[C@@H]1COC2c1ccc2c(c1)OCO2
• InChI: InChI=1S/C19H18O6/c20-14-3-1-10(5-15(14)21)18-12-7-23-19(13(12)8-22-18)11-2-4-16-17(6-11)25-9-24-16/h1-6,12-13,18-21H,7-9H2/t12-,13-,18?,19?/m0/s1
• InChIKey: CGEORJKFOZSMEZ-IJKBLAIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3aR,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol
• IUPAC Traditional name: 4-[(3aR,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol
• Synonyms: 4-[(3aR,6aR)-4-(1,3-Benzodioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,2-benzenediol; epi-Sesamin Monocatechol

Database IDs

• CAS Number: 1105568-81-7
• PubChem SID: 164233667
• PubChem CID: 53325346

CALCULATED PROPERTIES

• Acid pKa: 9.213736
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.216252
• LogD (pH = 7.4): 2.2097614
• Log P: 2.2163355
• Molar Refractivity: 87.9407 cm^3
• Polarizability: 34.605434 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S280515

A Sesamin (S280500) metabolite which acts as antioxidant in the liver.

REFERENCES

• Hamanda, N., et al.: Bioorg. Med. Chem., 19, 1959 (2011)