Methyl 3-oxohexadecanoate

Base Information

• Chemical Name: Methyl 3-oxohexadecanoate
• CAS No.: 14427-53-3
• Molecular Formula: C17H32 O3
• Molecular Weight: 284.439
• Hs Code.: 2918300090
• European Community (EC) Number: 238-399-0
• NSC Number: 157678
• UNII: U864V86N9H
• DSSTox Substance ID: DTXSID50162662
• Nikkaji Number: J183.105D
• Wikidata: Q63398289
• Mol file: 14427-53-3.mol

Synonyms:Methyl 3-oxohexadecanoate;14427-53-3;Hexadecanoic acid, 3-oxo-, methyl ester;U864V86N9H;EINECS 238-399-0;NSC-157678;C17H32O3;NSC157678;methyl-3-oxohexadecanoate;UNII-U864V86N9H;SCHEMBL3187580;3-Ketopalmitic acid methyl ester;DTXSID50162662;AKOS030255085;NSC 157678;BS-48573;FT-0778182;E84866;Q63398289

Chemical Property of Methyl 3-oxohexadecanoate

Chemical Property:

• Vapor Pressure: 0.000302mmHg at 25°C
• Boiling Point: 321.2°Cat760mmHg
• Flash Point: 131.9°C
• PSA: 43.37000
• Density: 0.918g/cm³
• LogP: 4.81970
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 284.23514488
• Heavy Atom Count: 20
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-Oxohexadecanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)CC(=O)OC
• Uses: Methyl 3-Oxohexadecanoate is an intermediate in the synthesis of 3-Hydroxyhexadecanoic Acid Methyl Ester (H825380), which is a fatty acid ester extracted from the flowers of Trollius chinensis Bunge.

Technology Process of Methyl 3-oxohexadecanoate

There total 17 articles about Methyl 3-oxohexadecanoate 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: 94.0%

monomethyl monopotassium malonate (38330-80-2) + tetradecanoyl chloride (112-64-1) → methyl 3-oxohexadecanoate (14427-53-3)

Guidance literature:

monomethyl monopotassium malonate; With triethylamine; magnesium chloride; In acetonitrile; at 20 ℃; for 3h;

tetradecanoyl chloride; With triethylamine; In acetonitrile; at 20 ℃; for 20h; Further stages.;

DOI:10.1002/adsc.200600504

Reference yield: 84.0%

1-dodecylbromide (143-15-7) + acetoacetic acid methyl ester (105-45-3) → methyl 3-oxohexadecanoate (14427-53-3)

Guidance literature:

acetoacetic acid methyl ester; With n-butyllithium; sodium hydride; In tetrahydrofuran; at 0 ℃;

1-dodecylbromide; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield: 78.0%

magnesium monomethyl malonate + n-tetradecanoic acid (544-63-8) → methyl 3-oxohexadecanoate (14427-53-3)

Guidance literature:

n-tetradecanoic 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

upstream raw materials:

2,4-dioxo-heptadecanoic acid methyl ester

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

sodium methylate

sodium ethyl acetylacetate enolate

Downstream raw materials:

β-hydroxypalmitic acid

5-oxostearic acid methyl ester

(S)-β-hydroxyhexadecanoic acid methyl ester

(R)-β-hydroxyhexadecanoic acid methyl ester

Refernces

• 1、 Sieben, Daniela,Santana, Alexander,Nowka, Paul,Weber, Sven,Funke, Kai,Hüttenhain, Stefan H.. "Preparation of the even-numbered 3-oxo fatty acid nicotinyl esters from C6:0 to C18:0". . p. 808 - 810. Retrieved 2016.
• 2、 Dessert,Halverstadt. "-". . p. 2595. Retrieved 1948.
• 3、 -. "BETA-LACTONE COMPOUNDS". Page/Page column 11-12. . Retrieved 2009/05/28.
• 4、 Blanc, Delphine,Madec, Jonathan,Popowyck, Florence,Ayad, Tahar,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre. "General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS-catalyzed hydrogenation reactions". . p. 943 - 950. Retrieved 2008/03/27.