Sesamin Chemical Properties

Melting point:

121.0 to 125.0 °C

Boiling point:

504.4±50.0 °C(Predicted)

Density 

1.385±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in DMSO (>25 mg/ml)

form 

crystalline

color 

White

Merck 

14,8470

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

InChIKey

PEYUIKBAABKQKQ-AFHBHXEDSA-N

LogP

4.064 (est)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29329990

MSDS

• Language:English Provider:Sesamin
• Language:English Provider:SigmaAldrich

Sesamin Usage And Synthesis

Description

Sesamin (607-80-7) is a natural product derived from sesame seeds with anticancer1, antioxidant2, anti-inflammatory/immunomodulatory3, and antidiabetic4,5 effects. It also displayed effects on cholesterol and fatty acid metabolism.6? Sesamin was recently found to inhibit bacterial L-tryptophan indole lyase (Ki = 7 μM).7 This enzyme reacts with dietary tryptophan to produce the uremic toxin indoxyl sulfate which exacerbates chronic kidney disease.

Chemical Properties

White powder

Uses

A lignan isolated from the bark of Fagara plants and from sesame oil. Studies show that it has has multiple functions such as cholesterol-lowering and anti-hypertensive activities. It induces the expr ession of the gene for aldehyde dehydrogenase, an alcohol-metabolizing enzyme suggesting it regulates the metabolism of lipids, xenobiotics, and alcohol at the mRNA level.

Uses

Sesamin has been used:

• as a lignan to study its effects on the osteoblastic differentiation of rat bone marrow stromal cells (BMSCs)
• as a standard for the isolation of sesamin from sesame oil
• as an enterolignan to study its effects on the proliferation of estrogen-receptor (ER)-positive human breast cancer MCF-7 cells

Definition

ChEBI: A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR

General Description

Sesamin is a fat-soluble furfuran lignan present in Sesamum indicum?L seeds.

Biochem/physiol Actions

Non-competitive Δ5-desaturase inhibitor.

References

Majdalawieh et al. (2017) A comprehensive review on the anti-cancer properties and mechanisms of action of sesamin, a lignan in sesame seeds (Sesamum indicum); Eur.? J. Pharmacol.?815 512 Kiso (2004) Antioxidative role of sesamin, a functional lignan in sesame seed, and its effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study; Biofactors 21 191 Majdalawieh et al. (2021) Immunomodulatory and anti-inflammatory effects of sesamin: mechanisms of action and future directions; Crit.? Rev. Food Sci. Nutr.?5 1 Shahi et al. (2017) Effect of Sesamin Supplementation on Glycemic Status, Inflammatory Markers, and Adiponectin Levels in Patients with Type 2 Diabetes Mellitus; J. Diet. Suppl.?14 65 Farbood et al. (2019) Sesamin: A promising protective agent against diabetes-associated cognitive decline in rats; Life Sci. 230 169 Majdalawieh et al. (2020) Effects of sesamin on fatty acid and cholesterol metabolism, macrophage cholesterol homeostasis and serum lipid profile: a comprehensive review; Eur. J. Pharmacol. 173417 Oikawa et al. (2022) (+)-Sesamin, a sesame lignan, is a potent inhibitor of gut bacterial tryptophan indole-lyase that is a key enzyme in chronic kidney disease pathogenesis; Biochem. Biophys. Res. Commun.?590 158

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