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

• ChemBase ID: 73014
• Molecular Formular: C20H18O6
• Molecular Mass: 354.35332
• Monoisotopic Mass: 354.1103383
• SMILES: c12c(ccc(c1)[C@H]1OC[C@H]3[C@@H]1CO[C@@H]3c1cc3c(cc1)OCO3)OCO2
• Canonical SMILES: C1Oc2c(O1)cc(cc2)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2
• InChI: InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
• InChIKey: PEYUIKBAABKQKQ-AFHBHXEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(1S,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole
• IUPAC Traditional name: asarinin
• Synonyms: Fagarol; Sezamin; Sesamin(Fagarol); Sesamin; (1S,3aR,4S,6aR)-5,5'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole; (+)-Sesamin; NSC 36403; Sesamin; d-Sesamin; 5,5'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole; [1S-(1α,3aα,4α,6aα)]-5,5'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole; Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan; (1S,3aR,4S,6aR)-Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-Furo[3,4-c]furan; Sesamin

Database IDs

• CAS Number: 607-80-7
• MDL Number: MFCD00216134
• PubChem SID: 24899834; 162037934
• PubChem CID: 72307

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.4466996
• LogD (pH = 7.4): 2.4466996
• Log P: 2.4466996
• Molar Refractivity: 89.7458 cm^3
• Polarizability: 35.8571 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: crystalline; Powder; White Solid
• Melting Point: 121-123°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95%; ≥98.0% (HPLC)
• Grade: analytical standard
• Salt Data: Free Base
• Shelf Life: (limited shelf life, expiry date on the label)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C20H18O6

DETAILS

Selleck Chemicals - S2392

Research Area: Metabolic Disease
Biological Activity:
Sesamin(Fagarol) is a lignan isolated from the bark of Fagara plants and from sesame oil. It has been used as a dietary fat-reduction supplement. Sesamin truly increases fat metabolism. [1]

Sigma Aldrich - S9314

Biochem/physiol Actions
Non-competitive Δ5-desaturase inhibitor.

Sigma Aldrich - 59867

Biochem/physiol Actions
Non-competitive Δ5-desaturase inhibitor.

Toronto Research Chemicals - S280500

A lignan isolated from the bark of Fagara plants and from sesame oil. Studies show that it has has multiple functions such as cholesterol-lowering and anti-hypertensive activities. It induces the expression of the gene for aldehyde dehydrogenase, an alcoh

REFERENCES

• http://en.wikipedia.org/wiki/Sesamin
• Matsumura, Y. et al.: Biolog. Pharmac. Bull., 21, 469 (1998)
• Tsuruoka, N. et al.: Biosci. Biotechnol. Biochem., 69, 179 (1998)
• Ide, T. et al.: Biochim. Biophys. Acta Mol. Cell Biol. Lipids, 1534, 1 (1998)