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607-80-7 molecular structure
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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 and InChIs

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

Cite this record

CBID:73014 http://www.chembase.cn/molecule-73014.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
607-80-7
MDL Number
MFCD00216134
PubChem SID
24899834
162037934
PubChem CID
72307

CALCULATED PROPERTIES

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 cm3
Polarizability 35.8571 Å3 Polar Surface Area 55.38 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Apperance
crystalline expand Show data source
Powder expand Show data source
White Solid expand Show data source
Melting Point
121-123°C expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
≥95% expand Show data source
≥98.0% (HPLC) expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C20H18O6 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2392 external link
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 external link
Biochem/physiol Actions
Non-competitive Δ5-desaturase inhibitor.
Sigma Aldrich - 59867 external link
Biochem/physiol Actions
Non-competitive Δ5-desaturase inhibitor.
Toronto Research Chemicals - S280500 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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