8Z,11Z,14Z,17Z-eicosatetraenoic acid

Base Information

• Chemical Name: 8Z,11Z,14Z,17Z-eicosatetraenoic acid
• CAS No.: 24880-40-8
• Molecular Formula: C20H32 O2
• Molecular Weight: 304.47
• Hs Code.: 2916190090
• UNII: 2K2DJ01BB7
• DSSTox Substance ID: DTXSID00920517
• Metabolomics Workbench ID: 602,1157
• Nikkaji Number: J381.481E
• Wikidata: Q27139653
• Mol file: 24880-40-8.mol

Synonyms:8,11,14,17-eicosatetraenoic acid;8,11,14,17-eicosatetraenoic acid, Z-isomer

Chemical Property of 8Z,11Z,14Z,17Z-eicosatetraenoic acid

Chemical Property:

• Flash Point: 14 °C
• PSA: 37.30000
• LogP: 6.21670
• Storage Temp.: −20°C
• 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:

98%Min ^*data from raw suppliers

(all-cis)-8,11,14,17-EicosatetraenoicAcid(10mg/mLethanol) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCCCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
• Description: ω-3 Arachidonic acid is a rare PUFA found in trace amounts in dietary sources. ω-3 Fatty acids are now known to be essential for infant growth and development and protect against heart disease, thrombosis, hypertension, and inflammatory and autoimmune disorders. In human platelet membranes, ω-3 arachidonic acid inhibits arachidonoyl-CoA synthetase with a Ki of 14 μM. It also inhibits arachidonoyl-CoA synthetase in calf brain extracts with an IC50 value of about 5 μM.
• Uses: (all-cis)-8,11,14,17-Eicosatetraenoic Acid (ω-3 Arachidonic acid) is a rare PUFA found in trace amounts in dietary sources. ω-3 Fatty acids are known to be essential for infant development and protect against heart disease, hypertension, thrombosis, and autoimmune and inflammatory disorder. In human platelet membranes, ω-3 Arachidonic acid inhibits arachidonoyl-CoA synthetase.

Technology Process of 8Z,11Z,14Z,17Z-eicosatetraenoic acid

There total 19 articles about 8Z,11Z,14Z,17Z-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: 93.0%

8Z,11Z,14Z,17Z-eicosatetraenoic acid methyl ester (132712-70-0) → eicosatetraenoic acid (24880-40-8)

Guidance literature:

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

DOI:10.1016/j.chemphyslip.2006.09.002

Reference yield:

6,9,12,15-cis-octadecanetetraenoic acid methyl ester (73097-00-4) → eicosatetraenoic acid (24880-40-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C

2.1: 88 percent / Ph₃PBr₂ / CH₂Cl₂ / 0.5 h / 20 °C

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

3.2: 2.686 g / hexane; tetrahydrofuran / 2.33 h / -78 °C

4.1: 91 percent / AcCl / 12 h / Heating

5.1: 93 percent / 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:

1-bromo-6Z,9Z,12Z,15Z-octadecatetraene (181213-46-7) → eicosatetraenoic acid (24880-40-8)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 2.686 g / hexane; tetrahydrofuran / 2.33 h / -78 °C

2.1: 91 percent / AcCl / 12 h / Heating

3.1: 93 percent / aq. KOH / ethanol / 16 h / 20 °C

With potassium hydroxide; n-butyllithium; acetyl chloride; In tetrahydrofuran; ethanol; hexane;

DOI:10.1016/j.chemphyslip.2006.09.002

upstream raw materials:

8Z,11Z,14Z,17Z-eicosatetraenoic acid methyl ester

4,4-Dimethyl-2-((7Z,10Z,13Z,16Z)-nonadeca-7,10,13,16-tetraenyl)-4,5-dihydro-oxazole

6,9,12,15-cis-octadecanetetraenoic acid methyl ester

1-bromo-6Z,9Z,12Z,15Z-octadecatetraene

Refernces

• 1、 Jakobsen, Martin Gjerde,Vik, Anders,Hansen, Trond Vidar. "Concise syntheses of three ω-3 polyunsaturated fatty acids". supporting information. p. 5837 - 5839. Retrieved 2013/01/13.
• 2、 Kuklev,Popkov,Kas'yanov,Akulin,Bezuglov. "Synthesis of C2-elongated polyunsaturated fatty acids". . p. 192 - 195. Retrieved 2007/10/03.