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HomeProduct name listSesamin

Sesamin

Synonym(s):Fagarol

  • CAS NO.:607-80-7
  • Empirical Formula: C20H18O6
  • Molecular Weight: 354.35
  • MDL number: MFCD00216134
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
Sesamin Structural

What is Sesamin?

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

The Uses of Sesamin

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

The Uses of Sesamin

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.

What are the applications of Application

Sesamin is a non-competitive inhibitor of Δ5-desaturase

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

Properties of Sesamin

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.

Safety information for Sesamin

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H317:Sensitisation, Skin
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P272:Contaminated work clothing should not be allowed out of the workplace.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention.

Computed Descriptors for Sesamin

InChIKey PEYUIKBAABKQKQ-AFHBHXEDSA-N

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