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. Its major metabolite is enterolactone, which has an elimination half life of less than 6 hours.[1] Sesamin and sesamolin are minor components of sesame oil,[2] on average comprising only 0.14% of the oil by mass.[3]
Names | |
---|---|
IUPAC name
(7α,7′α,8α,8′α)-3,4:3′,4′-Bis[methylenebis(oxy)]-7,9′:7′,9-diepoxylignane
| |
Systematic IUPAC name
5,5′-[(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2H-1,3-benzodioxole) | |
Other names
Fagarol
Sezamin Pseudocubebin Episesamin Asarinin Eleutheroside B4 D-(+)-Sesamin d-Sesamin (+)-Sesamin l-Sesamin | |
Identifiers | |
3D model (JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.124.366 |
KEGG | |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C20H18O6 | |
Molar mass | 354.35 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
See also
edit- Sesamol, another phenolic component of sesame oil
References
edit- ^ Peñalvo JL; Heinonen SM; Aura AM; Adlercreutz H (May 2005). "Dietary sesamin is converted to enterolactone in humans". J. Nutr. 135 (5): 1056–1062. doi:10.1093/jn/135.5.1056. PMID 15867281.
- ^ Lim JS, Adachi Y, Takahashi Y, Ide T (Jan 2007). "Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats". Br J Nutr. 97 (1): 85–95. doi:10.1017/S0007114507252699. PMID 17217563.
- ^ Ikan, Raphael (1991). Natural Products: A Laboratory Guide 2nd Ed. San Diego: Academic Press, Inc. p. 50. ISBN 978-0123705518.