9-Hexadecenoic acid

Base Information

• Chemical Name: 9-Hexadecenoic acid
• CAS No.: 373-49-9
• Molecular Formula: C16H30O2
• Molecular Weight: 254.413
• Hs Code.: 29161995
• European Community (EC) Number: 606-666-4
• NSC Number: 277452
• UNII: 65DJ825A3Z
• DSSTox Substance ID: DTXSID7021603
• Nikkaji Number: J14.574B,J146.389F
• Wikidata: Q27139858,Q27888066
• Metabolomics Workbench ID: 491
• ChEMBL ID: CHEMBL3182018
• Mol file: 373-49-9.mol

Synonyms:C16:1 trans-9;C16:1n7;palmitelaidic acid;palmitoleate;palmitoleic acid;palmitoleic acid, (E)-isomer;palmitoleic acid, (Z)-isomer;palmitoleic acid, potassium salt, (Z)-isomer;palmitoleic acid, sodium salt, (Z)-isomer

Chemical Property of 9-Hexadecenoic acid

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 2.82E-06mmHg at 25°C
• Melting Point: 0.5 °C
• Refractive Index: 1.457-1.459
• Boiling Point: 363.6 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 239.2 °C
• PSA: 37.30000
• Density: 0.905 g/cm³
• LogP: 5.32830
• Storage Temp.: −20°C
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 6.4
• 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:

Palmitoleic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CCCCCCC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCC/C=C/CCCCCCCC(=O)O
• Description: Palmitoleic acid, or (Z)-9-hexadecenoic acid, is an omega - 7 mono unsaturated fatty acid with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues, but generally found in higher concentrations in the liver. It is biosynthesized from palmitic acid by the action of the enzyme delta-9 desaturase. A beneficial fatty acid, it has been shown to increase insulin sensitivity by suppressing inflammation, as well as inhibit the destruction of insulin-secreting pancreatic beta cells.
• Uses: Palmitoleic Acid is a polyunsaturated fatty acid which contributes to reduced protein oxidation in mammals when added as a dietary supplement. Palmitoleic acid is used in organic synthesis, and as a standard in chromatographic analysis. Palmitoleic Acid is a polyunsaturated fatty acid which contributes to reduced protein oxidation in mammals.

Technology Process of 9-Hexadecenoic acid

There total 45 articles about 9-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: 95.0%

(Z)-9-hexadecenal (56219-04-6) → cis-9-hexadecenoic acid (373-49-9,2091-29-4)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃;

DOI:10.3762/bjoc.14.276

Reference yield: 62.0%

methyl-5-thiastearate (114119-34-5) → cis-9-hexadecenoic acid (373-49-9,2091-29-4) + cis-Octadecenoic acid (112-80-1,2027-47-6) + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4)

Guidance literature:

With Saccharomyces cerevisiae NR₂₃₃₅; In ethanol; at 30 ℃; for 48h;

DOI:10.1016/S0040-4039(01)81007-8

Reference yield: 6.0%

methyl-5-thiastearate (114119-34-5) → cis-9-hexadecenoic acid (373-49-9,2091-29-4) + cis-Octadecenoic acid (112-80-1,2027-47-6) + methyl 5-thiaoleate + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4)

Guidance literature:

With Saccharomyces cerevisiae NRC₂₃₃₅; In ethanol; at 30 ℃; for 48h; Product distribution;

DOI:10.1016/S0040-4039(01)81007-8

upstream raw materials:

15-ethoxy-pentadecane-7,8-diol

heptanal

cis-9-hexadecenoic acid ethyl ester

16-Iodo-(Z)-9-hexadecenoic acid

Downstream raw materials:

(Z)-hexadec-9-enylamine

9,10-dihydroxy-hexadecanoic acid

(+/-)-threo-9,10-Dihydroxy-hexadecansaeure

hexadecen-(7c)-oic acid-⁽¹⁶⁾-(4-bromo-phenacyl ester)

Refernces

• 1、 Bruns, Hilke,Ziesche, Lisa,Taniwal, Nargis Khakin,Wolter, Laura,Brinkhoff, Thorsten,Herrmann, Jennifer,Müller, Rolf,Schulz, Stefan. "N-Acylated amino acid methyl esters from marine Roseobacter group bacteria". . p. 2964 - 2973. Retrieved 2018/12/13.
• 2、 -. "PROCEDURE FOR THE OBTAINMENT OF FATTY ACIDS OF PHARMACOLOGICAL AND NUTRITIONAL INTEREST". Paragraph 0161-0170. . Retrieved 2013/08/14.