Sesamin

Last updated
Sesamin
Sesamin acsv.svg
Names
Preferred 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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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. 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]

See also

Related Research Articles

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Nordihydroguaiaretic acid Chemical compound

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Açaí palm Palm tree with many uses, mainly fruit as cash crop

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Enterolactone Chemical compound

Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

Enterodiol Lignan formed by the action of intestinal bacteria on lignan precursors found in plants.[1]

Enterodiol is an organic compound with the formula [HOC6H4CH2CH(CH2OH)]2.

Pinoresinol Chemical compound

Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

Sesamolin Chemical compound

Sesamolin is a lignan isolated from sesame oil. Sesamin and sesamolin are minor components of sesame oil.

Cooking oil Oil consumed by humans, of vegetable or animal origin

Cooking oil is plant, animal, or synthetic liquid fat used in frying, baking, and other types of cooking. It is also used in food preparation and flavoring not involving heat, such as salad dressings and bread dips, and may be called edible 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.