5,8,11,14-Eicosatetraynoic acid

Base Information

• Chemical Name: 5,8,11,14-Eicosatetraynoic acid
• CAS No.: 1191-85-1
• Molecular Formula: C20H24 O2
• Molecular Weight: 296.409
• Hs Code.: 2916190090
• UNII: 5FEJ8J06DR
• DSSTox Substance ID: DTXSID20152318
• Nikkaji Number: J353.502I
• Wikidata: Q27077167
• Pharos Ligand ID: KQHQXAST5TAF
• Metabolomics Workbench ID: 1045
• ChEMBL ID: CHEMBL458328
• Mol file: 1191-85-1.mol

Synonyms:5,8,11,14 Eicosatetraynoic Acid;5,8,11,14-Eicosatetraynoic Acid;ETYA;Ro 3 1428;Ro 3-1428;Ro 31428

Chemical Property of 5,8,11,14-Eicosatetraynoic acid

Chemical Property:

• Vapor Pressure: 5.93E-11mmHg at 25°C
• Melting Point: 79-81oC
• Boiling Point: 490.3oC at 760 mmHg
• Flash Point: 226.6oC
• PSA: 37.30000
• Density: 1.034g/cm3
• LogP: 4.00550
• Storage Temp.: −20°C
• Solubility.: ≤10mg/ml in ethanol;100mg/ml in DMSO;100mg/ml in dimethyl formamide
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 296.177630004
• Heavy Atom Count: 22
• Complexity: 586

Purity/Quality:

98%,99%, ^*data from raw suppliers

ETYA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
• Uses: ETYA is a Cox, LO, and PLA2 inhibitor.

Technology Process of 5,8,11,14-Eicosatetraynoic acid

There total 21 articles about 5,8,11,14-Eicosatetraynoic 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: 66.3%

Eicosa-5,8,11,14-tetrain-1-saeuremethylester (102471-97-6) → eicosa-5,8,11,14-tetraynoic acid (1191-85-1)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 3h;

Reference yield:

undeca-2,5-diyn-1-ol (35378-79-1) → eicosa-5,8,11,14-tetraynoic acid (1191-85-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 81.9 percent / PPh₃, CBr₄ / CH₂Cl₂ / 0.67 h / 0 °C

2: K₂CO₃, NaI, CuI / dimethylformamide / 5 h / 20 °C

3: p-toluenesulfonic acid / methanol / 1 h / 20 °C

4: 79.2 percent / PPh₃, CBr₄ / CH₂Cl₂ / 0.67 h / 0 °C

5: 0.89 g / K₂CO₃, NaI, CuI / dimethylformamide / 5 h / 20 °C

6: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C

With sodium hydroxide; copper(l) iodide; carbon tetrabromide; potassium carbonate; toluene-4-sulfonic acid; triphenylphosphine; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

1-bromo-2,5-undecadiyne (34498-24-3) → eicosa-5,8,11,14-tetraynoic acid (1191-85-1)

Guidance literature:

Multi-step reaction with 5 steps

1: K₂CO₃, NaI, CuI / dimethylformamide / 5 h / 20 °C

2: p-toluenesulfonic acid / methanol / 1 h / 20 °C

3: 79.2 percent / PPh₃, CBr₄ / CH₂Cl₂ / 0.67 h / 0 °C

4: 0.89 g / K₂CO₃, NaI, CuI / dimethylformamide / 5 h / 20 °C

5: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C

With sodium hydroxide; copper(l) iodide; carbon tetrabromide; potassium carbonate; toluene-4-sulfonic acid; triphenylphosphine; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

hex-5-ynoic acid

1-bromo-2,5,8-tetradecatriyne

1-bromooct-2-yne

5,8,11-Dodecatriinsaeure

Downstream raw materials:

arachidonyl alcohol

<5,6,8,9,11,12,14,15-3H8>arachidonic acid

all cis 5,8,11,14-eicosatetraenoic acid

methyl arachidonate

Refernces

• 1、 Qi, Longwu,Meijler, Michael M.,Lee, Sang-Hyeup,Sun, Chengzao,Janda, Kim D.. "Solid-phase synthesis of anandamide analogues". . p. 1673 - 1675. Retrieved 2004.
• 2、 Ivanov, I. V.,Groza, N. V.,Mnasina, E. E.,Myagkova, G. I.. "Synthesis of Arachidonic Acid and Its Acetylenic Precursor". . p. 696 - 699. Retrieved 2007/10/03.