Eicosa-11,14,17-trienoic acid

Base Information

• Chemical Name: Eicosa-11,14,17-trienoic acid
• CAS No.: 2091-27-2
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.489
• DSSTox Substance ID: DTXSID301346579
• Wikidata: Q27164838
• Mol file: 2091-27-2.mol

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

Chemical Property of Eicosa-11,14,17-trienoic 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: 322.40000
• Density: 0.917g/cm³
• LogP: -4.12700
• 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:

Analysis control,GC≥98% ^*data from raw suppliers

11C,14C,17C-EICOSATRIENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCCCCCCCCCC(=O)O

Technology Process of Eicosa-11,14,17-trienoic acid

There total 6 articles about Eicosa-11,14,17-trienoic 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

Downstream raw materials:

11,14,17-eicosatrienoic acid methyl ester

Refernces

• 1、 Kuklev, Dmitry V.,Smith, William L.. "Chemical C2-elongation of polyunsaturated fatty acids". . p. 172 - 177. Retrieved 2007/10/03.