Sesamin

Last updated
Sesamin
Sesamin acsv.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 X mark.svgN
    Key: PEYUIKBAABKQKQ-AFHBHXEDSA-N X mark.svgN
  • 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
  • c1cc2c(cc1[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)c5ccc6c(c5)OCO6)OCO2
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).
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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 14% of the oil by mass. [3]

See also

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.
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