607-80-7 Usage
Description
Sesamin is a fat-soluble furan lignan derived from sesame seeds, specifically from Sesamum indicum L. It is a white powder with various biological activities, including anticancer, antioxidant, anti-inflammatory/immunomodulatory, and antidiabetic effects. Sesamin also plays a role in cholesterol and fatty acid metabolism and has been found to inhibit bacterial L-tryptophan indole lyase, which is involved in the production of uremic toxin indoxyl sulfate, a compound that worsens chronic kidney disease.
Uses
1. Used in Pharmaceutical Applications:
Sesamin is used as a natural product with multiple therapeutic potentials for its cholesterol-lowering, anti-hypertensive, and antidiabetic activities. It also has implications in the regulation of lipid, xenobiotic, and alcohol metabolism at the mRNA level.
2. Used in Cancer Research:
Sesamin is used as a lignan to study its effects on the osteoblastic differentiation of rat bone marrow stromal cells (BMSCs) and as an enterolignan to study its effects on the proliferation of estrogen-receptor (ER)-positive human breast cancer MCF-7 cells.
3. Used in Nutraceutical Applications:
Sesamin is used as a natural compound derived from sesame seeds, with potential benefits for cardiovascular health, immune system modulation, and overall well-being.
4. Used in Chemical Research:
Sesamin is used as a standard for the isolation and study of sesamin from sesame oil, contributing to the understanding of its chemical properties and potential applications in various industries.
5. Used in Agricultural Applications:
Sesamin is used as a natural product derived from sesame seeds, which can be further explored for its potential applications in the agricultural sector, such as enhancing crop resistance or as a natural pesticide.
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
Check Digit Verification of cas no
The CAS Registry Mumber 607-80-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 7 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 607-80:
(5*6)+(4*0)+(3*7)+(2*8)+(1*0)=67
67 % 10 = 7
So 607-80-7 is a valid CAS Registry Number.
InChI:InChI=1/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
607-80-7Relevant articles and documents
Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes
Sato, Ko,Tanaka, Hiroshi
supporting information, p. 9422 - 9428 (2021/05/26)
Lignans are a group of polyphenolic phytochemicals that possess a large spectrum of chemical structures and biological activities. Here the syntheses of lignans – anwulignan, burseran, dehydroxycubebin, ruburisandrin B, and sesamin – are achieved based on a borate-mediated one-pot sequential Suzuki-Miyaura coupling of cis- and trans-fused bicyclic boranes, which were prepared by diastereoselective cyclic hydroboration of exo-cyclic diene with cyclopentyl- and thexylboranes, respectively. A one-pot sequential Suzuki-Miyaura coupling of each cyclic borate with various aryl bromides initiated by activation of the cyclic borane with the carbon nucleophile provided 2,3-dibenzylbutane derivatives with different aromatic substituents. Finally, the syntheses of naturally occurring lignans were accomplished in several steps from the products of Suzuki-Miyaura coupling.
Chromatography-free “two-pots” asymmetric total synthesis of (+)-sesamin and (+)-aschantin
Hajra, Saumen,Garai, Sujay,Sen, Biswajit
, (2020/09/02)
A gram-scale chromatography-free asymmetric total synthesis of both homo- and heterobiaryl furofuran lignans containing at least one methylenedioxy phenyl unit such as (+)-sesamin and (+)-aschantin is accomplished in “two-pots” from easily accessible enantiopure lactone involving four steps in high overall yields. Steps- and pot economy are the key advantages of the protocol. Additionally, the bromo-functionality of the intermediates is useful for late stage functionalization.
Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans
Mori, Naoki,Furuta, Akiko,Watanabe, Hidenori
, p. 8393 - 8399 (2016/12/06)
A new electrochemical method for the asymmetric oxidative dimerization of cinnamic acid derivatives has been developed. This method enabled the enantioselective syntheses of furofuran lignans, yangambin, sesamin and eudesmin.