607-80-7 Usage
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
Different sources of media describe the Uses of 607-80-7 differently. You can refer to the following data:
1. 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.
2. 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
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.
