11,14,17-Eicosatrienoic acid

Base Information

• Chemical Name: 11,14,17-Eicosatrienoic acid
• CAS No.: 17046-59-2
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.489
• DSSTox Substance ID: DTXSID60920492
• Wikidata: Q27124062
• NCI Thesaurus Code: C68359
• Metabolomics Workbench ID: 795
• ChEMBL ID: CHEMBL453991
• Mol file: 17046-59-2.mol

Synonyms:11,14,17-eicosatrienoate;11,14,17-eicosatrienoic acid;11,14,17-eicosatrienoic acid, (Z,Z,Z)-isomer

Chemical Property of 11,14,17-Eicosatrienoic acid

Chemical Property:

• Vapor Pressure: 1.07E-08mmHg at 25°C
• Boiling Point: 432.7°Cat760mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 329.4°C
• PSA: 37.30000
• Density: 0.917g/cm³
• LogP: 6.44070
• Storage Temp.: −20°C
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 306.255880323
• Heavy Atom Count: 22
• Complexity: 327

Purity/Quality:

98%Min ^*data from raw suppliers

11(Z),14(Z),17(Z)-Eicosatrienoic Acid ≥98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCCCCCCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O
• Description: Eicosatrienoic Acid (20:3ω-3) is a rare polyunsaturated fatty acid of the ω-3 series. In normal humans, it represents less than 0.25% of serum phospholipid fatty acids. However, it is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors.
• Uses: 11,14,17-Eicosatrienoic Acid is a polysaturated fatt acid compound found in food.

Technology Process of 11,14,17-Eicosatrienoic acid

There total 5 articles about 11,14,17-Eicosatrienoic 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:

(11Z,14Z,17Z)-11,14,17-icosatrienoic acid methyl ester (62472-96-2) → cis-11,14,17-eicosatrienoic acid (2091-27-2,125535-18-4,125535-19-5,125535-20-8,125535-21-9,125535-22-0,125535-24-2,17046-59-2)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1016/j.chemphyslip.2006.09.002

Reference yield:

methyl linolenate (301-00-8) → cis-11,14,17-eicosatrienoic acid (2091-27-2,125535-18-4,125535-19-5,125535-20-8,125535-21-9,125535-22-0,125535-24-2,17046-59-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LiAlH₄ / diethyl ether / 2 h / 20 °C

2.1: Ph₃PBr₂ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 0.08 h / -78 °C

3.2: hexane; tetrahydrofuran / -78 °C

4.1: AcCl / 12 h / Heating

5.1: aq. KOH / ethanol / 16 h / 20 °C

With potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; triphenylphosphine dibromide 1:1 addition complex; acetyl chloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane;

DOI:10.1016/j.chemphyslip.2006.09.002

Reference yield:

linolenyl alcohol (506-44-5,2774-90-5) → cis-11,14,17-eicosatrienoic acid (2091-27-2,125535-18-4,125535-19-5,125535-20-8,125535-21-9,125535-22-0,125535-24-2,17046-59-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Ph₃PBr₂ / CH₂Cl₂ / 0.5 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.08 h / -78 °C

2.2: hexane; tetrahydrofuran / -78 °C

3.1: AcCl / 12 h / Heating

4.1: aq. KOH / ethanol / 16 h / 20 °C

With potassium hydroxide; n-butyllithium; triphenylphosphine dibromide 1:1 addition complex; acetyl chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1016/j.chemphyslip.2006.09.002

upstream raw materials:

(11Z,14Z,17Z)-11,14,17-icosatrienoic acid methyl ester

methyl linolenate

linolenyl alcohol

(Z,Z,Z)-1-Bromooctadeca-9,12,15-triene

Refernces