Sesamin

Sesamin

Names
IUPAC name 5,5'-(1S,3aR,4S,6aR)-tetrahydro-1H,3H- furo[3,4-c]furan-1,4-diylbis(1,3-benzodioxole)
Other names Fagarol Sezamin pseudocubebin Episesamin Asarinin D-(+)-Sesamin d-Sesamin (+)-Sesamin l-sesamin
Identifiers
CAS Number	607-80-7 Y
ChEBI	CHEBI:66470 N
ChEMBL	ChEMBL252915 N
ChemSpider	65258 N
Jmol 3D model	Interactive image
KEGG	C10882 N
PubChem	5204
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 N Key: PEYUIKBAABKQKQ-AFHBHXEDSA-N N InChI=1/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 Key: PEYUIKBAABKQKQ-AFHBHXEDBX
SMILES c1cc2c(cc1[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)c5ccc6c(c5)OCO6)OCO2
Properties
Chemical formula	C20H18O6
Molar mass	354.35 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Sesamin is a lignan isolated from the bark of Fagara plants and from sesame oil. It has been used as a dietary fat-reduction supplement, although no controlled studies on this application have been performed. Its major metabolite is enterolactone, which has an elimination half life of less than 6 hours. Sesamin and sesamolin are minor components of sesame oil, on average comprising only 0.14% of the oil by mass.

See also

• Sesamol, another phenolic component of sesame oil

External links

• Effect of sesamin on serum cholesterol and triglycerides levels in LDL receptor-deficient mice
• A short and stereoselective total synthesis of (±)-sesamin by radical cyclisation of an epoxide using a transition-metal radical source
• Sesamin and episesamin induce apoptosis in human lymphoid leukemia Molt 4B cells.