Methyl 3-oxooctadecanoate

Base Information

• Chemical Name: Methyl 3-oxooctadecanoate
• CAS No.: 14531-34-1
• Molecular Formula: C19H36 O3
• Molecular Weight: 312.493
• Hs Code.: 2918300090
• European Community (EC) Number: 238-555-8
• DSSTox Substance ID: DTXSID80162978
• Nikkaji Number: J110.681C
• Wikidata: Q83031804
• Mol file: 14531-34-1.mol

Synonyms:Methyl 3-oxooctadecanoate;14531-34-1;Octadecanoic acid, 3-oxo-, methyl ester;EINECS 238-555-8;SCHEMBL1123664;DTXSID80162978;Octadecanoic acid,3-oxo-,methyl ester

Chemical Property of Methyl 3-oxooctadecanoate

Chemical Property:

• Vapor Pressure: 6.48E-05mmHg at 25°C
• Boiling Point: 344.7°Cat760mmHg
• Flash Point: 141.5°C
• PSA: 43.37000
• Density: 0.911g/cm³
• LogP: 5.59990
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 312.26644501
• Heavy Atom Count: 22
• Complexity: 274

Purity/Quality:

99.9% ^*data from raw suppliers

METHYL 3-OXOOCTADECANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)CC(=O)OC

Technology Process of Methyl 3-oxooctadecanoate

There total 16 articles about Methyl 3-oxooctadecanoate 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: 82.0%

magnesium monomethyl malonate + 1-hexadecylcarboxylic acid (57-10-3) → methyl 3-oxooctadecanoate (14531-34-1)

Guidance literature:

1-hexadecylcarboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 10h;

magnesium monomethyl malonate; In tetrahydrofuran; at 20 ℃; for 18h; Further stages.;

DOI:10.1002/adsc.200390021

Reference yield: 79.0%

monomethyl monopotassium malonate (38330-80-2) + n-hexadecanoyl chloride (112-67-4) → methyl 3-oxooctadecanoate (14531-34-1)

Guidance literature:

monomethyl monopotassium malonate; With triethylamine; magnesium chloride; In acetonitrile; at 10 - 25 ℃; for 2.5h; Inert atmosphere;

n-hexadecanoyl chloride; With triethylamine; In acetonitrile; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.031

Reference yield: 79.0%

1-iodotetradecane (19218-94-1) + acetoacetic acid methyl ester (105-45-3) → methyl 3-oxooctadecanoate (14531-34-1)

Guidance literature:

DOI:10.1039/c39870001368

upstream raw materials:

2-acetyl-3-oxo-octadecanoic acid ethyl ester

sodium methylate

methanol

5-Hexadecanoyl-2,2-dimethyl-[1,3]dioxane-4,6-dione

Downstream raw materials:

methyl 2-hydroxyimino-3-oxo-octadecanoate

(2S,3R)-2-acetylaminooctadecan-1,3-diol

C2-dihydroceramide

N-acetyl-5-benzylidene-3-hexadecanoyltetramic acid

Refernces

• 1、 De Oliveira, Franciele S.,De Oliveira, Patrick M.,Farias, Luana M.,Brinkerhoff, Rafael C.,Sobrinho, Rui Carlos M. A.,Treptow, Tamara M.,Montes D'Oca, Caroline R.,Marinho, Marcelo A. G.,Hort, Mariana A.,Horn, Ana P.,Russowsky, Dennis,Montes D'Oca, Marcelo G.. "Synthesis and antitumoral activity of novel analogues monastrol-fatty acids against glioma cells". . p. 1282 - 1288. Retrieved 2018.
• 2、 Brinkerhoff, Rafael Centuriao,Santa-Helena, Eduarda,Do Amaral, Paulo C.,Cabrera, Diego Da C.,Ongaratto, Renata F.,De Oliveira, Patrick M.,Da Ros Montes D'Oca, Caroline,Neves Gon?alves, Carla A.,Maia Nery, Luiz E.,Montes D'Oca, Marcelo G.. "Evaluation of the antioxidant activities of fatty polyhydroquinolines synthesized by Hantzsch multicomponent reactions". . p. 24688 - 24698. Retrieved 2019/08/22.
• 3、 Gangadhara, Kishore Lingam,Lescrinier, Eveline,Pannecouque, Christophe,Herdewijn, Piet. "Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents". . p. 817 - 820. Retrieved 2014/02/14.