Methyl stearidonate

Base Information

• Chemical Name: Methyl stearidonate
• CAS No.: 73097-00-4
• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.446
• DSSTox Substance ID: DTXSID801015995
• Wikidata: Q63392111
• Mol file: 73097-00-4.mol

Synonyms:Methyl stearidonate;73097-00-4;METHYL (6Z,9Z,12Z,15Z)-OCTADECA-6,9,12,15-TETRAENOATE;6,9,12,15-Octadecatetraenoicacid, methyl ester, (6Z,9Z,12Z,15Z)-;Stearidonic Acid methyl ester;Moroctic Acid methyl ester;SCHEMBL7712920;BIRKCHKCDPCDEG-GJDCDIHCSA-N;DTXSID801015995;HMS3649B06;YCA09700;Methyl stearidonate, >=97.0% (GC);Methyl (all-cis)-6,9,12,15-octadecatetraenoate;SR-01000946694;SR-01000946694-1;6Z,9Z,12Z,15Z-octadecatetraenoic acid, methyl ester;Methyl 6(Z),9(Z),12(Z),15(Z)-Octadecatetraenoate;Q63392111;(6Z,9Z,12Z,15Z)-Octadecatetraenoic acid methyl ester;(6Z,9Z,12Z,15Z)-Methyl octadeca-6,9,12,15-tetraenoate;6,9,12,15-Octadecatetraenoic acid, methyl ester, (all-Z)-;(Z,Z,Z,Z)-6,9,12,15-OCTADECATETRAENOIC ACID METHYL ESTER;6,9,12,15-Octadecatetraenoic acid, methyl ester, (6Z,9Z,12Z,15Z)-

Chemical Property of Methyl stearidonate

Chemical Property:

• Boiling Point: 374.5±31.0 °C(Predicted)
• Flash Point: 13 °C
• PSA: 26.30000
• Density: 0.907±0.06 g/cm3(Predicted)
• LogP: 5.52490
• Storage Temp.: −20°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 290.224580195
• Heavy Atom Count: 21
• Complexity: 349

Purity/Quality:

98%Min ^*data from raw suppliers

MethylStearidonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCCCCC(=O)OC
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC
• Uses: Methyl Stearidonate can be isolated from diatom Navicula delognei and has antibacterial activity against Staphylococcus aureus, S. epidermidis, Salmonella typhimurium, and Proteus vulgaris.

Technology Process of Methyl stearidonate

There total 13 articles about Methyl stearidonate 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: 73.0%

methyl 6,9,12,15-octadecatetraynoate → 6,9,12,15-cis-octadecanetetraenoic acid methyl ester (73097-00-4)

Guidance literature:

With sodium tetrahydroborate; hydrogen; nickel diacetate; In ethanol; ethylenediamine; at 10 ℃; for 5h; Inert atmosphere;

DOI:10.1007/s10600-015-1485-3

Reference yield: 70.0%

Methyl (all-Z)-octadeca-2,6,9,12,15-pentaenoate (309728-59-4) → 6,9,12,15-cis-octadecanetetraenoic acid methyl ester (73097-00-4)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.08.009

Reference yield:

methanol (67-56-1) + (2S)-1-O-3,6,9,12,15-octadecapentaenoyl-2-O-6,9,12,15-octadecatetraenoyl-3-O-[α-D-galactopyranosyl)-(1''''->6''')-O-β-D-galactopyranosyl]-sn-glycerol → (2R)-3-O-[α-D-galactopyranosyl-(1''''->6''')-O-β-D-galactopyranosyl]-sn-glycerol (33600-42-9) + 6,9,12,15-cis-octadecanetetraenoic acid methyl ester (73097-00-4) + methyl (3Z,6Z,9Z,12Z,15Z)‐octadeca‐3,6,9,12,15‐pentaenoate (144118-14-9)

Guidance literature:

With sodium methylate; at 20 ℃; for 0.5h;

DOI:10.1021/np0201265

upstream raw materials:

diazomethane

stearidonic acid

methanol

(6Z,9Z,12Z,15Z)-octadeca-6-9-12-15-tetraenoic acid (2R)-3-[(6-O-α-galactopyranosyl-β-D-galactopyranosyl)oxy]-2-hydroxypropyl ester

Downstream raw materials:

(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-1-ol

stearidonic acid

Δ^9.12.15-Octadecatrienol-(1)

eicosatetraenoic acid