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SMB00705

Sigma-Aldrich

Sesamin

≥98% (HPLC)

Synonym(s):

Fagarol

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About This Item

Empirical Formula (Hill Notation):
C20H18O6
CAS Number:
607-80-7
Molecular Weight:
354.35
MDL number:
MFCD00216134
UNSPSC Code:
12352205
NACRES:
NA.25

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: 10 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

C1Oc2ccc(cc2O1)[C@H]3OC[C@H]4[C@@H]3CO[C@@H]4c5ccc6OCOc6c5

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

InChI key

PEYUIKBAABKQKQ-AFHBHXEDSA-N

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General description

Sesamin is the most abundant lignan isolated from Sesamum indicum or sesame seeds and sesame oil.

Application

Sesamin has been used as a reference standard to study the activity of Cytochrome P450 enzyme sesamin synthase from Sesamum indicum L. in the conversion of pinoresinol to sesamin.

Biochem/physiol Actions

Sesamin presents multiple health benefits including hypocholesterolemic, anti-hypertensive, anti-carcinogenic, anti-aging, immunoregulatory, hypoglycemic, anti-thrombotic, hepatoprotective, and antioxidant activities. It has also been demonstrated to work synergistically with vitamin E against lipid peroxidation. Sesamin was found to be metabolized into several catechol forms in the liver. These cathecols have a potent ability to scavenge superoxide radicals.
Non-competitive Δ5-desaturase inhibitor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yun-Ping Lim et al.
Evidence-based complementary and alternative medicine : eCAM, 2012, 242810-242810 (2012-05-31)
Inconsistent expression and regulation of drug-metabolizing enzymes (DMEs) are common causes of adverse drug effects in some drugs with a narrow therapeutic index (TI). An important cytochrome, cytochrome P450 3A4 (CYP3A4), is predominantly regulated by a nuclear receptor, pregnane X
Colonoscope constriction and laser safety interlock problems investigated.
Today's OR nurse, 14(3), 48-48 (1992-03-01)
Mitsuo Namiki
Critical reviews in food science and nutrition, 47(7), 651-673 (2007-10-19)
The results of recent food chemical and nutraceutical studies on the traditionally well-known health value of sesame are described, including some aspects of the utilization of sesame. The highly antioxidative activity of sesame oil was clarified and found to involve
Sarah Dalibalta et al.
Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society, 28(10), 1276-1289 (2020-11-03)
Sesamin, a major lignin isolated from sesame (Sesamum indicum) seeds and sesame oil, is known to possess antioxidant and anti-inflammatory properties. Several studies have revealed that oxidative stress and inflammation play a major role in a variety of cardiovascular diseases
Kaori Yasuda et al.
Expert opinion on drug metabolism & toxicology, 8(1), 93-102 (2011-11-22)
Sesamin is a major lignan found in sesame and is known to have various biological effects. Some of these biological effects occur following its metabolic conversion to corresponding catechols and, therefore, the study of sesamin metabolism is quite important. There

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