Sesamin

Base Information

• Chemical Name: Sesamin
• CAS No.: 607-80-7
• Deprecated CAS: 10590-92-8
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.359
• Hs Code.: 29329990
• European Community (EC) Number: 612-029-1
• UNII: FY3S29JVC9,S7946O4P76
• DSSTox Substance ID: DTXSID301030528
• Nikkaji Number: J9.612A
• Wikipedia: Sesamin
• Wikidata: Q3511416
• Metabolomics Workbench ID: 67874
• ChEMBL ID: CHEMBL252915
• Mol file: 607-80-7.mol

Synonyms:asarinin;epi-sesamin;episesamin;sesamin;sesamin, (1R-(1alpha,3aalpha,4alpha,6aalpha))-isomer;sesamin, (1R-(1alpha,3aalpha,4beta,6aalpha))-isomer

Chemical Property of Sesamin

Chemical Property:

• Appearance/Colour: crystalline
• Vapor Pressure: 8.38E-10mmHg at 25°C
• Melting Point: 122-124oC
• Refractive Index: 1.622
• Boiling Point: 504.4 °C at 760 mmHg
• Flash Point: 212.3 °C
• PSA: 55.38000
• Density: 1.385 g/cm³
• LogP: 3.21920
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (>25 mg/ml)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 482

Purity/Quality:

Sesamin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(COC2C3=CC4=C(C=C3)OCO4)C(O1)C5=CC6=C(C=C5)OCO6
• Isomeric SMILES: C1[C@H]2[C@H](CO[C@@H]2C3=CC4=C(C=C3)OCO4)[C@H](O1)C5=CC6=C(C=C5)OCO6
• 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.
• 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. 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

Technology Process of Sesamin

There total 163 articles about Sesamin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(1S,3aR,4S,6aR)-1,4-bis(6-bromobenzo[d][1,3]dioxol-5-yl)tetrahydro-1H,3H-furo[3,4-c]furan → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium formate; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.tet.2020.131483

Reference yield: 60.0%

4,8-dihydroxysesamin (63398-39-0) → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.11.007

Reference yield: 12.0%

(3,4-methylenedioxy)phenylmagnesium bromide (17680-04-5) + (+)-samin (166239-82-3) → sesamin (133-03-9,133-04-0,133-05-1,551-30-4,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,607-80-7) + episesamin (133-04-0,133-05-1,551-30-4,607-80-7,7076-24-6,13079-95-3,68509-46-6,81602-22-4,105661-97-0,111465-32-8,111465-33-9,133-03-9)

Guidance literature:

(3,4-methylenedioxy)phenylmagnesium bromide; (+)-samin; In tetrahydrofuran; at 40 ℃; Inert atmosphere;

With pyridine; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/d0cc05640e

upstream raw materials:

sesamin

(3,4-methylenedioxy)phenylmagnesium bromide

(1R,2S,3S,4R)-2,3-bis(hydroxymethyl)-1,4-bis(3,4-methylenedioxyphenyl)butane-1,4-diol

5-[(1E)-3-{(S)-1,3-benzodioxol-5-yl[(2S)-oxiran-2-yl]methoxy}prop-1-enyl]-1,3-benzodioxole

Downstream raw materials:

sesamin

(-)-dihydrocubebin

rac-(1R,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

5-nitro-1,3-benzodioxole

Refernces

• 1、 Zhao, Can,Khan, Ijaz,Zhang, Yong Jian. "Enantioselective total synthesis of furofuran lignans via Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates with 2-nitroacrylates". supporting information. p. 12431 - 12434. Retrieved 2020/10/30.
• 2、 Mori, Naoki,Furuta, Akiko,Watanabe, Hidenori. "Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans". . p. 8393 - 8399. Retrieved 2016/12/06.