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
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) |
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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