Methyl vaccenate

Base Information

• Chemical Name: Methyl vaccenate
• CAS No.: 6198-58-9
• Molecular Formula: C₁₉H₃₆O₂
• Molecular Weight: 296.494
• European Community (EC) Number: 228-251-3
• UNII: 6O9MGA9PP2
• DSSTox Substance ID: DTXSID301316726
• Nikkaji Number: J211.449F,J110.840I
• Wikidata: Q27265228
• Mol file: 6198-58-9.mol

Synonyms:methyl vaccenate;methyl vaccenate, (E)-isomer;vaccenic acid methyl ester

Chemical Property of Methyl vaccenate

Chemical Property:

• Melting Point: 10°C(lit.)
• Refractive Index: 1.4500 to 1.4540
• Boiling Point: 154°C/1mmHg(lit.)
• Flash Point: -4 °C
• PSA: 26.30000
• Density: 0.873±0.06 g/cm3(Predicted)
• LogP: 6.19690
• Storage Temp.: −20°C
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 296.271530387
• Heavy Atom Count: 21
• Complexity: 246

Purity/Quality:

98%,99%, ^*data from raw suppliers

VaccenicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,Xn,F
• Hazard Codes: Xi,N,Xn,F
• Statements: 36/37/38-67-65-50/53-38-11
• Safety Statements: 26-36-62-61-60-33-29-16-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCC=CCCCCCCCCCC(=O)OC
• Isomeric SMILES: CCCCCC/C=C/CCCCCCCCCC(=O)OC

Technology Process of Methyl vaccenate

There total 39 articles about Methyl vaccenate 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: 91.0%

11-octadecynoic acid, methyl ester (26543-37-3) → methyl (Z)-vaccenate (6198-58-9,52380-33-3,1937-63-9)

Guidance literature:

With hydrogen; ethylenediamine; In ethanol; water; stereoselective reaction;

DOI:10.1055/s-0030-1259912

Reference yield: 50.0%

11-(1-phenyl-1H-tetrazole-5-sulfonyl)undecanoic acid methyl ester (892501-15-4) + heptanal (111-71-7) → methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) + methyl (Z)-vaccenate (6198-58-9,52380-33-3,1937-63-9)

Guidance literature:

11-(1-phenyl-1H-tetrazole-5-sulfonyl)undecanoic acid methyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -55 ℃; for 0.666667h;

heptanal; In tetrahydrofuran; toluene; at -55 ℃; for 1h;

DOI:10.1016/j.tet.2006.03.006

Reference yield: 50.0%

11-(1-phenyl-1H-tetrazole-5-sulfonyl)undecanoic acid methyl ester (892501-15-4) + heptanal (111-71-7) → methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) + methyl (Z)-vaccenate (6198-58-9,52380-33-3,1937-63-9)

Guidance literature:

11-(1-phenyl-1H-tetrazole-5-sulfonyl)undecanoic acid methyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -55 ℃; for 0.666667h;

heptanal; In tetrahydrofuran; toluene; at -55 ℃; for 1h;

DOI:10.1016/j.tet.2006.03.006

upstream raw materials:

methyl 12-hydroxyoctadecanoate

methyl (Z)-vaccenate

11-(1-phenyl-1H-tetrazole-5-sulfonyl)undecanoic acid methyl ester

heptanal

Downstream raw materials:

methyl (Z)-vaccenate

methyl vaccenate

methyl 12-hydroxyoctadecanoate

ethyl (11Z)-octadec-11-enoate

Refernces

• 1、 Giner, José-Luis,Ceballos, Harriette,Tang, Ying-Zhong,Gobler, Christopher J.. "Sterols and Fatty Acids of the Harmful Dinoflagellate Cochlodinium polykrikoides". . p. 249 - 252. Retrieved 2016/02/27.
• 2、 Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava. "Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27". . p. 7880 - 7890. Retrieved 2013/01/15.