Sesamin

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]

Sesamin

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
CAS Number	607-80-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:66470 N
ChEMBL	ChEMBL252915 N
ChemSpider	65258 N
ECHA InfoCard	100.124.366
KEGG	C10882 N
PubChem CID	5204
UNII	S7946O4P76 Y
CompTox Dashboard (EPA)	DTXSID80231219
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
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

See also

• Sesamol, another phenolic component of sesame oil

References

1. 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.
2. 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.
3. Ikan, Raphael (1991). Natural Products: A Laboratory Guide 2nd Ed. San Diego: Academic Press, Inc. p. 50. ISBN 978-0123705518.