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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
W C Johnson et al.
Life sciences, 51(15), 1229-1236 (1992-01-01)
A two step fractionation of conditioned media made from the darkly pigmented dorsal skin of the channel catfish, Ictalurus punctatus, has produced fractions that contain a melanization stimulating factor (MSF). Isolated neural tubes of Xenopus laevis embryos exposed to conditioned
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Today's OR nurse, 14(3), 48-48 (1992-03-01)
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
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
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