10-Oxohexadecanoic acid

Base Information

• Chemical Name: 10-Oxohexadecanoic acid
• CAS No.: 818-26-8
• Molecular Formula: C16H30O3
• Molecular Weight: 270.412
• DSSTox Substance ID: DTXSID70407385
• Metabolomics Workbench ID: 1580
• Nikkaji Number: J206.180E
• Wikidata: Q27464114
• Mol file: 818-26-8.mol

Synonyms:10-oxohexadecanoic acid;818-26-8;10-keto palmitic acid;Hexadecanoic acid, 10-oxo-;10-oxo-hexadecanoic acid;10-Ketopalmitinsaure;SCHEMBL7822442;DTXSID70407385;CHEBI:196126;LMFA01060057;FT-0607196;F74690;Q27464114

Chemical Property of 10-Oxohexadecanoic acid

Chemical Property:

• Melting Point: 75-75.8 °C
• Boiling Point: 418.0±28.0 °C(Predicted)
• PKA: 4.78±0.10(Predicted)
• PSA: 0.00000
• Density: 0.950±0.06 g/cm3(Predicted)
• LogP: 3.64680
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 270.21949481
• Heavy Atom Count: 19
• Complexity: 236

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(=O)CCCCCCCCC(=O)O

Technology Process of 10-Oxohexadecanoic acid

There total 9 articles about 10-Oxohexadecanoic acid 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: 74.0%

methyl 10-oxohexadecanoate (689-69-0) → 10-oxohexadecanoic acid (818-26-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 50 ℃; for 5h;

DOI:10.1002/anie.201702509

Reference yield: 72.0%

16-hydroxyhexadecan-7-one → 10-oxohexadecanoic acid (818-26-8)

Guidance literature:

With Jones reagent; In acetone; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.0c02058

Reference yield:

1,10-decanedioic acid (111-20-6,26776-29-4) → 10-oxohexadecanoic acid (818-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂

2: diethyl ether / folgende Behandlung mit Kalilauge

With thionyl chloride; diethyl ether;

upstream raw materials:

sebacoyl chloride

diethyl ether

n-hexylmagnesium bromide

1,10-decanedioic acid

Downstream raw materials:

stearic acid

10-hydroxy-hexadecanoic acid

Refernces

• 1、 Batsika, Charikleia S.,Mantzourani, Christiana,Gkikas, Dimitrios,Kokotou, Maroula G.,Mountanea, Olga G.,Kokotos, Christoforos G.,Politis, Panagiotis K.,Kokotos, George. "Saturated Oxo Fatty Acids (SOFAs): A Previously Unrecognized Class of Endogenous Bioactive Lipids Exhibiting a Cell Growth Inhibitory Activity". . p. 5654 - 5666. Retrieved 2021/05/31.