5,8,11,14-Eicosatetraenoic acid

Base Information

• Chemical Name: 5,8,11,14-Eicosatetraenoic acid
• CAS No.: 506-32-1
• Molecular Formula: C20H32O2
• Molecular Weight: 304.473
• Hs Code.: 29161900
• European Community (EC) Number: 208-033-4
• Nikkaji Number: J42.975I,J986.595K
• Wikipedia: Arachidonic_acid
• Wikidata: Q27116784
• Pharos Ligand ID: KQR28J1FQR7Y
• Metabolomics Workbench ID: 809
• ChEMBL ID: CHEMBL267484
• Mol file: 506-32-1.mol

Synonyms:5,8,11,14-Eicosatetraenoic acid;ArachidonicAcid-d11;Icosa-5,8,11,14-tetraenoic acid;5,8,11,14-Icosatetraenoic Acid;CHEMBL267484;all-trans-Arachidonic acid;C20:4n-6,9,12,15;arachidonsaure;Immunocytophyt;Immunocytophyte;Vevodar;ARACHIDONIC_ACID;SCHEMBL16163;SCHEMBL23768;CHEBI:36306;BDBM50546238;eicosa-5,8,11,14-tetraenoic acid;LMFA01030393;AKOS015892940;LS-21530;PD130007;EN300-260389;Arachidonic Acid (winterized to +5 degrees C);C20:4, n-6,9,12,15;Q27116784

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

Chemical Property:

• Appearance/Colour: colorless to light yellow oil
• Vapor Pressure: 8.85E-08mmHg at 25°C
• Melting Point: -49 °C(lit.)
• Refractive Index: n20/D 1.4872(lit.)
• Boiling Point: 407.45 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 336.308 °C
• PSA: 37.30000
• Density: 0.929 g/cm³
• LogP: 6.21670
• Storage Temp.: −20°C
• Solubility.: ethanol: ≥10 mg/mL
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 304.240230259
• Heavy Atom Count: 22
• Complexity: 362

Purity/Quality:

99%, ^*data from raw suppliers

FOXC1 ^*data from reagent suppliers

Safty Information:

• Statements: 19
• Safety Statements: 24/25-19

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O
• Description: Arachidonic acid belongs to a kind of polyunsaturated omega-6 fatty acid, which is highly biologically relevant. It is abundantly distributed in brain, muscles and liver. It is the precursor for all prostaglandins, thromboxanes, and leukotrienes. Most cellular arachidonic acid is esterified in the membrane phospholipids. It is an important second messenger of cellular signalling participating in the regulation of signaling enzymes including PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms. In addition, arachidonic acid acts as key inflammatory intermediate as well as avasodilator. Generally, the body can synthesize the arachidonic acid through linoleic acid. However, upon linoleic acid deficiency, it is necessary to supplement arachidonic acid from the diets. Food sources of arachidonic acid include meat, eggs and some fishes. Alternatively, we can also have arachidonic acid supplements. Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is the counterpart to the saturated arachidic acid found in peanut oil, (L. arachis – peanut.).
• Uses: An unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides. arachidonic acid is an ingredient with skin-smoothing, emollient, and healing properties. Arachidonic acid is an omega-6 essential fatty acid naturally occurring in the skin and considered critical for appropriate skin metabolism. It is a constituent of vitamin F.

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

There total 62 articles about 5,8,11,14-Eicosatetraenoic 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: 78.0%

ethyl arachidonate (95285-77-1,1808-26-0) → all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1)

Guidance literature:

With triethylamine; In water; acetonitrile; at 30 ℃; for 96h; under 7500600 Torr;

DOI:10.1021/jo00020a001

Reference yield: 34.0%

eicosa-5,8,11,14-tetraynoic acid (1191-85-1) → all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1)

Guidance literature:

With sodium tetrahydroborate; hydrogen; ethylenediamine; nickel diacetate; In ethanol; at 20 ℃;

DOI:10.1021/ol049474j

Reference yield:

1,4-decadiyne (929-53-3) → all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) EtMgBr, THF, (ii) /BRN= 1908795/, CuCN

2: H₂ / Lindlar / methanol

With hydrogen; Lindlar's catalyst; In methanol;

upstream raw materials:

arachidonic acid methyl ester

eicosa-5,8,11,14-tetraynoic acid

1-chloro-nonadeca-4c,7c,10c,13c-tetraene

carbon dioxide

Downstream raw materials:

5,6-Epoxyeicosatrienoic acid methyl ester

ethyl arachidonate

Malondialdehyde

prostaglandin H₂

Refernces

• 1、 Wagner,Friedrich. "". . p. 1603. Retrieved 1969.
• 2、 Corey, E. J.,Wright, Stephen W.. "A SIMPLE PROCESS FOR THE PURIFICATION OF ARACHIDONIC ACID". . p. 2729 - 2730. Retrieved 1984.
• 3、 Romero, Oscar,de las Rivas, Blanca,Lopez-Tejedor, David,Palomo, Jose M.. "Effect of Site-Specific Peptide-Tag Labeling on the Biocatalytic Properties of Thermoalkalophilic Lipase from Geobacillus thermocatenulatus". . p. 369 - 378. Retrieved 2018/01/11.