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| | Sesamin Basic information |
| Product Name: | Sesamin | | Synonyms: | [1S-(1BETA,3ALPHA-BETA,4BETA,6ALPHA-BETA)]-5,5'-(TETRAHYDRO-1H,3H-FURO[3,4-C]FURAN-1,4-DIYL)BIS-1,3-BENZODIOXOLE;SesameP.E.;Sesamine70%;SESAMIN(P);SESAMIN(RG);1,3-Benzodioxole,5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-,[1S-(1α,3aα,4α, 6aα)]-;1,3-Benzodioxole, 5,5'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis-, [1S-(1a,3aa,4a,6aa)]-;Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan | | CAS: | 607-80-7 | | MF: | C20H18O6 | | MW: | 354.35 | | EINECS: | | | Product Categories: | Aromatics;Heterocycles;D5-DesaturaseArachidonic Acid Cascade;D to;Intermediates & Fine Chemicals;Pharmaceuticals;Natural Plant Extract;Enzyme Inhibitors;Enzyme Inhibitors by Enzyme;Other;chemical reagent;pharmaceutical intermediate;natural product;Inhibitors;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract | | Mol File: | 607-80-7.mol |  |
| | 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 Statements | 22-24/25 | | WGK Germany | 3 | | HS Code | 29329990 |
| | 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 |
| | Sesamin Preparation Products And Raw materials |
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