Eicosa-8,11,14-trien-5-ynoic acid

Base Information

• Chemical Name: Eicosa-8,11,14-trien-5-ynoic acid
• CAS No.: 58688-54-3
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.457
• Wikidata: Q76386926
• Metabolomics Workbench ID: 1049
• Mol file: 58688-54-3.mol

Synonyms:eicosa-8,11,14-trien-5-ynoic acid;eicosa-cis-8,11,14-trien-5-ynoic acid

Chemical Property of Eicosa-8,11,14-trien-5-ynoic acid

Chemical Property:

• Vapor Pressure: 3.77E-09mmHg at 25°C
• Boiling Point: 444.7°Cat760mmHg
• Flash Point: 212.2°C
• PSA: 37.30000
• Density: 0.952g/cm³
• LogP: 5.66390
• Storage Temp.: −20°C
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 416

Purity/Quality:

98%Min ^*data from raw suppliers

5,6-Dehydroarachidonic acid ≥98%, ethanol solution ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11-16
• Safety Statements: 16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC#CCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CC#CCCCC(=O)O

Technology Process of Eicosa-8,11,14-trien-5-ynoic acid

There total 6 articles about Eicosa-8,11,14-trien-5-ynoic 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: 100.0%

(8Z,11Z,14Z)-Icosa-8,11,14-trien-5-ynoic acid methyl ester (77297-91-7) → 5,6-dehydroarachidonic acid (58688-54-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 1.5h;

DOI:10.1016/S0040-4039(00)92873-9

Reference yield:

1-heptynyllithium (42017-07-2) → 5,6-dehydroarachidonic acid (58688-54-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HMPA, 2.) iodine-silver trifluoracetate / 1.) THF, 2.) CH₂Cl₂, -78 deg C

3: 1.)disiamylborane, 2.) HOAc / 1.) THF, -40 deg C, 2 h , - 20 deg C, 4 h, 0 deg C, 1 h, 2.) 25 deg C, 4 h

4: 1.) t-BuLi, 2.) CuI*Me₂s / ether/THF

5: 100 percent / LiOH / tetrahydrofuran; H₂O / 14 h / 25 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; copper(I) iodide dimethyl sulfide complex; iodine; tert.-butyl lithium; silver trifluoroacetate; bis-(1,2-dimethylpropyl)borane; acetic acid; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)87181-6

Reference yield:

3-iodo-1,2-octadiene (82645-30-5) → 5,6-dehydroarachidonic acid (58688-54-3)

Guidance literature:

Multi-step reaction with 4 steps

2: 1.)disiamylborane, 2.) HOAc / 1.) THF, -40 deg C, 2 h , - 20 deg C, 4 h, 0 deg C, 1 h, 2.) 25 deg C, 4 h

3: 1.) t-BuLi, 2.) CuI*Me₂s / ether/THF

4: 100 percent / LiOH / tetrahydrofuran; H₂O / 14 h / 25 °C

With lithium hydroxide; copper(I) iodide dimethyl sulfide complex; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; acetic acid; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)87181-6

upstream raw materials:

(8Z,11Z,14Z)-Icosa-8,11,14-trien-5-ynoic acid methyl ester

1-heptynyllithium

3-iodo-1,2-octadiene

(1Z,4Z)-1-iodotrideca-1,4-dien-7-yne

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