5Z-hexadecenoic acid

Base Information

• Chemical Name: 5Z-hexadecenoic acid
• CAS No.: 7056-90-8
• Molecular Formula: C16H30O2
• Molecular Weight: 254.413
• DSSTox Substance ID: DTXSID001313761
• Metabolomics Workbench ID: 1193
• Nikkaji Number: J1.057.569I
• Mol file: 7056-90-8.mol

Synonyms:5Z-hexadecenoic acid;cis-5-hexadecenoic acid;16:1(5Z);C16:1n-11;(Z)-hexadec-5-enoic acid;7056-90-8;SCHEMBL412148;CHEBI:179823;DTXSID001313761;LMFA01030854

Chemical Property of 5Z-hexadecenoic acid

Chemical Property:

• Vapor Pressure: 1.4E-06mmHg at 25°C
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 209

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC=CCCCC(=O)O
• Isomeric SMILES: CCCCCCCCCC/C=C\CCCC(=O)O

Technology Process of 5Z-hexadecenoic acid

There total 5 articles about 5Z-hexadecenoic 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:

undecylaldehyde (112-44-7) + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (Z)-Hexadec-5-enoic Acid (7056-90-8)

Guidance literature:

With potassium tert-butylate; In benzene;

Reference yield:

ethyl 5-oxopentanoate (22668-36-6) → (Z)-Hexadec-5-enoic Acid (7056-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C

2: sodium hydroxide; water / 3 h / 20 °C

With water; sodium hexamethyldisilazane; sodium hydroxide; In tetrahydrofuran; 1: |Wittig Olefination;

DOI:10.1021/acschemneuro.7b00105

Reference yield:

ethyl 4-cyanobutyrate (10444-38-9) → (Z)-Hexadec-5-enoic Acid (7056-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium phosphinate / 2 h / 40 °C

2: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C

3: sodium hydroxide; water / 3 h / 20 °C

With sodium phosphinate; water; sodium hexamethyldisilazane; sodium hydroxide; In tetrahydrofuran; 2: |Wittig Olefination;

DOI:10.1021/acschemneuro.7b00105

upstream raw materials:

undecylaldehyde

(4-carboxybutyl)triphenylphosphonium bromide

ethyl 5-oxopentanoate

ethyl 4-cyanobutyrate

Downstream raw materials:

racemic erythro 6-acetoxy-5-hexadecanolide

(5R*,6S*)-6-hydroxyhexadecan-5-olide

Refernces

• 1、 Mostyn, Shannon N.,Carland, Jane E.,Shimmon, Susan,Ryan, Renae M.,Rawling, Tristan,Vandenberg, Robert J.. "Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2". . p. 1949 - 1959. Retrieved 2017/09/26.
• 2、 -. "SRS-A antagonists". . . Retrieved 2008/06/13.