CAS 607-80-7|5-[(1S,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole|Fagarol|Sesamin(Fagarol)|asarinin|Sezamin|Sesamin|NSC 36403|d-Sesamin|(1S,3aR,4S,6aR)-...

General Information

Structure

Molecular Formula

C₂₀H₁₈O₆

Molecular Mass

354.35332

Exact Mass

354.1103383

Charge

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

Canonic Smiles

C1Oc2c(O1)cc(cc2)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2

Isomeric Smiles

c12c(ccc(c1)[C@H]1OC[C@H]3[C@@H]1CO[C@@H]3c1cc3c(cc1)OCO3)OCO2

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.4466996

LogD (pH = 7.4)

2.4466996

Log P

2.4466996

Molar Refractivity

89.7458

Polarizability

35.8571

Polar Surface Area

55.38

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

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

Synonyms

FagarolSesamin(Fagarol)SezaminSesaminNSC 36403d-Sesamin(1S,3aR,4S,6aR)-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(1S,3aR,4S,6aR)-Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-Furo[3,4-c]furan5,5'-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-1,3-benzodioxole(+)-SesaminTetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furanSesaminSesamin

IUPAC Traditional name

asarinin

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem SID

PubChem CID

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Storage Temperature

-20°C

2-8°C

MSDS Link

Download link

German water hazard class

Product Information

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

59867

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

TRC

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity