Jump to content

Sesamin: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
Flopster2 (talk | contribs)
423 edits
m fixed typo and added full page number to reference
move systematic name
 
(44 intermediate revisions by 32 users not shown)
Line 1: Line 1:
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 408462978
| verifiedrevid = 408462978
| ImageFile = Sesamin acsv.svg
| ImageFile = Sesamin acsv.svg
| ImageSize =
| ImageSize =
| IUPACName = (7α,7′α,8α,8′α)-3,4:3′,4′-Bis[methylenebis(oxy)]-7,9′:7′,9-diepoxylignane
| IUPACName = 5,5'-(1''S'',3a''R'',4''S'',6a''R'')-tetrahydro-1''H'',3''H''- furo[3,4-''c'']furan-1,4-diylbis(1,3-benzodioxole)
| SystematicName = 5,5′-[(1''S'',3a''R'',4''S'',6a''R'')-Tetrahydro-1''H'',3''H''-furo[3,4-''c'']furan-1,4-diyl]bis(2''H''-1,3-benzodioxole)
| OtherNames = Sesamin
| OtherNames = Fagarol<br />Sezamin<br />Pseudocubebin<br />Episesamin<br />Asarinin<br />Eleutheroside B4<br /><small>D</small>-(+)-Sesamin<br />''d''-Sesamin<br />(+)-Sesamin<br />l-Sesamin
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 607-80-7
| CASNo = 607-80-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S7946O4P76
| PubChem = 5204
| PubChem = 5204
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C10882
| KEGG = C10882
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 66470
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 252915
| ChEMBL = 252915
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| SMILES = C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6
| ChemSpiderID = 65258
| SMILES = c1cc2c(cc1[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)c5ccc6c(c5)OCO6)OCO2
| 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
| InChIKey = PEYUIKBAABKQKQ-AFHBHXEDBX
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PEYUIKBAABKQKQ-AFHBHXEDSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>20</sub>H<sub>18</sub>O<sub>6</sub>
| Formula = C<sub>20</sub>H<sub>18</sub>O<sub>6</sub>
| MolarMass = 354.35 g/mol
| MolarMass = 354.35 g/mol
| ExactMass = 354.110338 u
| Appearance =
| Appearance =
| Density =
| Density =
Line 25: Line 38:
| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}

'''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.<ref name="pmid21114470">{{cite journal |author=Kamal-Eldin A, Moazzami A, Washi S |title=Sesame seed lignans: potent physiological modulators and possible ingredients in functional foods & nutraceuticals |journal=Recent Pat Food Nutr Agric |volume=3 |issue=1 |pages=17–29 |year=2011 |month=January |pmid=21114470 }}</ref> Its major metabolite is [[enterolactone]], which has an elimination half life of less than 6 hours.<ref name="pmid15867281">{{cite journal |author=Peñalvo JL, Heinonen SM, Aura AM, Adlercreutz H |title=Dietary sesamin is converted to enterolactone in humans |journal=J. Nutr. |volume=135 |issue=5 |pages=1056–1062 |year=2005 |month=May |pmid=15867281 |url=http://jn.nutrition.org/content/135/5/1056.long }}</ref>
'''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.<ref name="pmid15867281">{{cite journal |author1=Peñalvo JL |author2=Heinonen SM |author3=Aura AM |author4=Adlercreutz H |title=Dietary sesamin is converted to enterolactone in humans |journal=J. Nutr. |volume=135 |issue=5 |pages=1056–1062 |date=May 2005 |pmid=15867281 |doi=10.1093/jn/135.5.1056 |doi-access=free }}</ref> Sesamin and [[sesamolin]] are minor components of sesame oil,<ref>{{cite journal | pmid = 17217563 |vauthors=Lim JS, Adachi Y, Takahashi Y, Ide T | doi=10.1017/S0007114507252699 | volume=97 | issue=1 | title=Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. | date=Jan 2007 | journal=Br J Nutr | pages=85–95| doi-access=free }}</ref> on average comprising only 0.14% of the oil by mass.<ref>{{cite book|last=Ikan|first=Raphael|title=Natural Products: A Laboratory Guide 2nd Ed.|year=1991|publisher=Academic Press, Inc.|location=San Diego|isbn=978-0123705518|page=50|url=https://books.google.com/books?id=B7P8HQimBAIC&q=Natural+Products%3A+A+Laboratory+Guide+2nd+Ed.}}</ref>

== See also ==
* [[Sesamol]], another phenolic component of sesame oil


== References ==
== References ==
{{reflist}}
{{reflist}}


{{Lignans}}
== External links ==
{{Xenobiotic-sensing receptor modulators}}
*[http://dx.doi.org/10.1007/s00394-006-0617-8 Effect of sesamin on serum cholesterol and triglycerides levels in LDL receptor-deficient mice]
*[http://dx.doi.org/10.1016/S0040-4039(00)01698-1 A short and stereoselective total synthesis of (±)-sesamin by radical cyclisation of an epoxide using a transition-metal radical source]
*[http://sesaminfatloss.com/sesamin-and-episesamin-induce-apoptosis-in-human-lymphoid-leukemia-molt-4b-cells/ Sesamin and episesamin induce apoptosis in human lymphoid leukemia Molt 4B cells.]


[[Category:CYP3A4 inhibitors]]
{{lignan}}
⚫
[[Category:Phenol antioxidants]]

⚫
[[Category:Natural phenol antioxidants]]
[[Category:Lignans]]
[[Category:Lignans]]
[[Category:Benzodioxoles]]

[[Category:Sesame]]
[[ja:セサミン]]

Latest revision as of 01:41, 7 May 2023

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.124.366 Edit this at Wikidata
KEGG
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 ☒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
  • 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).
☒N verify (what is checkY☒N ?)

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

[edit]
  • Sesamol, another phenolic component of sesame oil

References

[edit]
  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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Sesamin&oldid=1153547937"