607-80-7

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 NO: 607-80-7
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.35
• Product Categories: Natural Plant Extract;D5-DesaturaseArachidonic Acid Cascade;D to;Enzyme Inhibitors;Enzyme Inhibitors by Enzyme;Other;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors
• Mol File: 607-80-7.mol
• Article Data: 32

Chemical Properties

• Melting Point: 121.0 to 125.0 °C
• Boiling Point: 504.4 °C at 760 mmHg
• Flash Point: 212.3 °C
• Appearance: /crystalline
• Density: 1.385 g/cm³
• Vapor Pressure: 8.38E-10mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (>25 mg/ml)
• 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.
• Merck: 14,8470
• CAS DataBase Reference: Sesamin(CAS DataBase Reference)
• NIST Chemistry Reference: Sesamin(607-80-7)
• EPA Substance Registry System: Sesamin(607-80-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 607-80-7(Hazardous Substances Data)

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

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

Upstream product

• 133-03-9 sesamin 
• 17680-04-5 (3,4-methylenedioxy)phenylmagnesium bromide 
• 133-03-9 2-exo,6-exo-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 81581-37-5 2,3-bis(hydroxymethyl)-1,4-bis(3,4-methylenedioxyphenyl)butane-1,4-diol 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 67911-75-5 (E)-5-(3-bromoprop-1-en-1-yl)benzo[d][1,3]dioxole 
• 59901-91-6 3-(3,4-methylenedioxyphenyl)-3-hydroxy-1,2-epoxypropane 
• 551-30-4 2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 111465-33-9 (-)-Epiasarinin 
• 133-04-0 episesamin 
• 166239-82-3 (+)-samin 
• 63398-39-0 4,8-dihydroxysesamin 

Downstream Products

• 133-03-9 sesamin 
• 24563-03-9 (-)-dihydrocubebin 
• 133-03-9 rac-(1R,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 4375-03-5 (–)-eudesmin 
• 526-06-7 eudesmine 
• 133-04-0 episesamin 
• 133-03-9 2-endo,6-endo-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 133-03-9 sesamin 
• 1105568-81-7 (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane 
• 340167-81-9 (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane 
• 551-30-4 2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 133644-85-6 (2S,3R,4R)-3-hydroxymethyl-4-(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)tetrahydrofuran 
• 1105568-81-7 C₁₉H₁₈O₆ 
• 340167-81-9 C₁₈H₁₈O₆ 

Relevant articles and documents

Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes

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

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.

Metal Triflates for the Production of Aromatics from Lignin

The depolymerization of lignin into valuable aromatic chemicals is one of the key goals towards establishing economically viable biorefineries. In this contribution we present a simple approach for converting lignin to aromatic monomers in high yields under mild reaction conditions. The methodology relies on the use of catalytic amounts of easy-to-handle metal triflates (M(OTf)x). Initially, we evaluated the reactivity of a broad range of metal triflates using simple lignin model compounds. More advanced lignin model compounds were also used to study the reactivity of different lignin linkages. The product aromatic monomers were either phenolic C2-acetals obtained by stabilization of the aldehyde cleavage products by reaction with ethylene glycol or methyl aromatics obtained by catalytic decarbonylation. Notably, when the method was ultimately tested on lignin, especially Fe(OTf)3 proved very effective and the phenolic C2-acetal products were obtained in an excellent, 19.3±3.2 wt % yield.