Episesamin

Base Information

• Chemical Name: Episesamin
• CAS No.: 133-05-1
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.359
• Hs Code.: 29329990
• UNII: F6PWY73ZGT,C3RVX72NMG
• DSSTox Substance ID: DTXSID201033462
• Nikkaji Number: J10.014E
• Metabolomics Workbench ID: 134000
• ChEMBL ID: CHEMBL43469
• Mol file: 133-05-1.mol

Synonyms:1-asarinine

Chemical Property of Episesamin

Chemical Property:

• Vapor Pressure: 8.38E-10mmHg at 25°C
• Melting Point: 120-122 °C(lit.)
• Boiling Point: 504.4°Cat760mmHg
• Flash Point: 212.3°C
• PSA: 55.38000
• Density: 1.385g/cm³
• LogP: 3.21920
• Storage Temp.: -20°C
• 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:

99%, ^*data from raw suppliers

Asarinin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 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

Technology Process of Episesamin

There total 163 articles about Episesamin 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:

Piperonylic acid

5-nitro-1,3-benzodioxole

6-nitro-1,3-benzodioxole-5-carbaldehyde

dihydrocubebin

Refernces

HORSFIELDIN, A LIGNAN AND OTHER CONSTITUENTS FROM HORSFIELDIA IRYAGHEDHI

10.1016/0031-9422(82)83106-3

The study focuses on the phytochemical investigation of Horsfieldia iryaghedhi seeds, a plant indigenous to Sri Lanka. The researchers extracted and characterized several constituents from the hot methanol extract of the seeds, including a new lignan named horsfieldin, along with d-asarinin, (-)-dihydrocubebin, dodecanoylphloroglucinol, myristic acid, trimyristin, and sitosterol. The study provides detailed information on the structure elucidation and absolute configuration of the lignans, as well as discussing their chemotaxonomic significance. The findings contribute to the understanding of the chemical composition of H. iryaghedhi and its potential biological activities, as tetrahydrofuran lignans like horsfieldin have been shown to possess insecticidal and medicinal properties.

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