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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H18O6
Molecular Weight 354.3533
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SESAMIN

SMILES

[H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2C5=CC6=C(OCO6)C=C5

InChI

InChIKey=PEYUIKBAABKQKQ-AFHBHXEDSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H18O6
Molecular Weight 354.3533
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Sesamin is a naturally occurring compound found in sesame oil and in the bark and fruit of certain plant species. SESAMIN, (±)- is a racemic dl-form. The dl-form is also known as fagarol, and may be isolated from the bark of various fagara species. Sesamin, either as the d-form or the dl-form, has now been found to possess psychotropic activity, i.e., administration of appropriate dosages to a human or animal subject elicits a psychotropic response. Sesamin is catered to be a nutritional supplement that confers antioxidant and antiinflammatory effects (if touting its health properties) or possibly being an estrogen receptor modulator and fat burner (if targeting athletes or persons wishing to lose weight). Sesamin has a few mechanisms, and when looking at it holistically it can be summed up as a fatty acid metabolism modifier. It appears to inhibit an enzyme known as delta-5-desaturase (Δ5-desaturase) which is a rate-limiting enzyme in fatty acid metabolism; inhibiting this enzyme results in lower levels of both eicosapentaenoic acid (EPA, one of the two fish oil fatty acids) as well as arachidonic acid, and this mechanism appears to be relevant following oral ingestion. The other main mechanism is inhibiting a process known as Tocopherol-ω-hydroxylation, which is the rate-limiting step in the metabolism of Vitamin E; by inhibiting this enzyme, sesamin causes a relative increase of vitamin E in the body but particularly those of the gamma subset (γ-tocopherol and γ-tocotrienol) and this mechanism has also been confirmed to be active following oral ingestion. Sesamin is a potent and specific inhibitor of delta 5 desaturases in polyunsaturated fatty acid biosynthesis. Sesamin inhibits particular CYP3A enzymes that are involved in vitamin E metabolism, where the enzyme initially ω-hydroxylates vitamin E (required step) and then the rest of vitamin E is subject to fat oxidation. By inhibiting this step, sesamin causes an increase in circulating and organ concentrations of vitamin E. Sesamin is thought to have PPARα activating potential in the liver, but it is uncertain how much practical relevance this has in humans due to this being a mechanism that differs between species.

CNS Activity

Curator's Comment: Sesamin, either as the d-form or the dl-form, has now been found to possess psychotropic activity, i.e., administration of appropriate dosages to a human or animal subject elicits a psychotropic response.

Approval Year

TargetsConditions
OverviewDrug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
major
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Synthesis of DL-asarinin and DL-sesamin].
1957 Jan
Differential in vitro anti-HIV activity of natural lignans.
1990 Nov-Dec
Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides.
2003 Apr
Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes.
2003 Dec
Antifungal constituents of Melicope borbonica.
2004 Jul
Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats.
2005 Jan
Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress.
2008 Oct-Dec
Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats.
2010 Jan 5
Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system.
2012
Sesamin protects mouse liver against nickel-induced oxidative DNA damage and apoptosis by the PI3K-Akt pathway.
2013 Feb 6
Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.
2013 Mar 7
Sesamin ameliorates doxorubicin-induced cardiotoxicity: involvement of Sirt1 and Mn-SOD pathway.
2014 Jan 13
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In humans oral ingestion of around 100-150mg of sesamin is sufficient to raise bodily sesamin stores to the level where it can preserve Vitamin E in the body. https://examine.com/supplements/sesamin/
There are limited human studies on sesamin, but it appears that oral ingestion of around 100-150mg of sesamin is sufficient to raise bodily sesamin stores to the level where it can preserve Vitamin E in the body; this indirect antioxidative effect may be the most practical reason to supplement sesamin.
Route of Administration: Oral
When HAECs were pretreated with sesamin (10 or 100 uM), the TNF-alpha-induced expression of intercellular cell adhesion molecule-1 (ICAM-1) was significantly reduced (35 or 70% decrease, respectively) by Western blotting.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:39:39 GMT 2023
Edited
by admin
on Fri Dec 15 20:39:39 GMT 2023
Record UNII
S7946O4P76
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SESAMIN
MI  
Common Name English
FAGAROL
Common Name English
Sesamin [WHO-DD]
Common Name English
D-(+)-SESAMIN
Common Name English
D-SESAMIN
Common Name English
5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-1,3-BENZODIOXOLE
Systematic Name English
1,3-BENZODIOXOLE, 5,5'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS-, (1S-(1.ALPHA.,3A .ALPHA.,4.ALPHA.,6A .ALPHA.))-
Common Name English
SEZAMIN
Common Name English
(+)-SESAMIN
Common Name English
SESAMIN, (+)-
Common Name English
SESAMIN D-FORM [MI]
Common Name English
1H,3H-FURO(3,4-C)FURAN, TETRAHYDRO-1,4-BIS(3,4-(METHYLENEDIOXY)PHENYL)-, (1S,3AR,4S,6AR)-
Common Name English
TETRAHYDRO-1,4-BIS(3,4-(METHYLENEDIOXY)PHENYL)-1H,3H-FURO(3,4-C)FURAN
Systematic Name English
NSC-36403
Code English
SESAMIN [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 298400
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
Code System Code Type Description
PUBCHEM
72307
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
DAILYMED
S7946O4P76
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
RXCUI
2593413
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
CAS
7076-24-6
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
MESH
C054125
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
WIKIPEDIA
SESAMIN
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
EVMPD
SUB120775
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
SMS_ID
100000144024
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
CAS
607-80-7
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
MERCK INDEX
m9879
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY Merck Index
MERCK INDEX
m9879
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY Merck Index
NSC
36403
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID301030528
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
CHEBI
66470
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
FDA UNII
S7946O4P76
Created by admin on Fri Dec 15 20:39:39 GMT 2023 , Edited by admin on Fri Dec 15 20:39:39 GMT 2023
PRIMARY
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