2-Hexadecenoic acid

Base Information

• Chemical Name: 2-Hexadecenoic acid
• CAS No.: 929-79-3
• Molecular Formula: C16H30O2
• Molecular Weight: 254.413
• Hs Code.: 2916190090
• European Community (EC) Number: 679-899-2
• DSSTox Substance ID: DTXSID201312626
• Nikkaji Number: J150.285I,J95.437C
• Wikidata: Q27117081
• Metabolomics Workbench ID: 488
• ChEMBL ID: CHEMBL4285532
• Mol file: 929-79-3.mol

Synonyms:2-hexadecenoic acid;629-56-1;(E)-hexadec-2-enoic acid;Gaidic acid;trans-hexadec-2-enoic acid;929-79-3;trans-2-Hexadecenoic acid;2-palmitoleic acid;25447-95-4;(2E)-hexadec-2-enoic acid;2t-Hexadecenoic acid;Caswell No. 481;(E)-2-hexadecenoic acid;Trans-Hexa-dec-2-enoic acid;Delta2-trans-Hexadecenoic Acid;CHEMBL4285532;EPA Pesticide Chemical Code 045401;hexadec-2-enoic acid;C16:1n-14;2-trans-hexadecenoic acid;?2-trans-Hexadecenoic Acid;t-2-hexadecenoic acid;Hexadecenoic acid (ACN;(2E)-hexadecenoic acid;SCHEMBL189080;(2E)-2-Hexadecenoic acid #;2-Hexadecenoic acid, AldrichCPR;CHEBI:37252;AMY6908;trans-Delta(2)-hexadecenoic acid;ZVRMGCSSSYZGSM-CCEZHUSRSA-N;DTXSID201312626;BCP14571;CAA82568;BDBM50466176;LMFA01030054;MFCD00045907;t-16:1D2;AKOS015839097;HY-131306B;AS-58805;CS-0168998;H0428;C16116;A868301;Q27117081;(R)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRICACIDHCL;10B54E76-29DB-4830-BC82-772EB20A8FEB

Chemical Property of 2-Hexadecenoic acid

Chemical Property:

• Boiling Point: 373.684 °C at 760 mmHg
• Flash Point: 273.444 °C
• PSA: 37.30000
• Density: 0.906 g/cm³
• LogP: 5.32830
• XLogP3: 7
• 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:

99% ^*data from raw suppliers

Δ2-trans-Hexadecenoic Acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(=O)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/C(=O)O
• Uses: (2E)-2-Hexadecenoic acid is a trans-fatty acid which is used in the stereoselective preparation of azirine carboxylic esters via chiral thiourea-catalystic asymmetric Neber reaction of sulfonyloxyimines. It is also a component found in Axinelloside A, a lipopolysaccharide isolated from the Japanese marine sponge Axinella infundibula and a strong human telomerase inhibitor.

Technology Process of 2-Hexadecenoic acid

There total 20 articles about 2-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: 83.0%

malonic acid (141-82-2) + myristylaldehyde (124-25-4,511542-15-7) → (2E)-hexadecenoic acid (929-79-3)

Guidance literature:

With piperidine; In pyridine; 1.) 50-60 deg C, 1 h, 2.) reflux, 4 h;

Reference yield: 81.0%

1-hexadecylcarboxylic acid (57-10-3) → (2E)-hexadecenoic acid (929-79-3)

Guidance literature:

1-hexadecylcarboxylic acid; With Zn(2,2,6,6-tetramethylpiperidine)_2*2LiCl; zinc(II) chloride; In tetrahydrofuran; at -40 ℃; for 1.5h; Inert atmosphere; Sealed tube;

With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate; In tetrahydrofuran; at -40 - 60 ℃; for 12h; diastereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201706893

Reference yield:

(R)-β-hydroxypalmitic acid (928-17-6,2398-34-7,83780-74-9,20595-04-4) → (2E)-hexadecenoic acid (929-79-3)

Guidance literature:

With TEA; benzotriazol-1-ol; In tetrahydrofuran;

DOI:10.1016/S0960-894X(00)00613-2

upstream raw materials:

2-bromopalmitic acid

malonic acid

myristylaldehyde

α-iodopalmitic acid

Downstream raw materials:

(2E)-ethyl 2-hexadecenoate

tunicamycin VIII

1-pentadecene