(+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid

Base Information

• Chemical Name: (+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid
• CAS No.: 141110-17-0
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID80694002
• Metabolomics Workbench ID: 2736
• Nikkaji Number: J2.411.280B
• Wikidata: Q27140156
• Mol file: 141110-17-0.mol

Synonyms:141110-17-0;(+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid;(+/-)18-HEPE;18-HEPE;(5Z,8Z,11Z,14Z,16E)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid;(+/-)-18-HEPE;5,8,11,14,16-Eicosapentaenoic acid, 18-hydroxy-, (5Z,8Z,11Z,14Z,16E)-;SCHEMBL31991;CHEBI:72802;(??)18-HEPE;(+-)-18-HEPE;LMFA03070033;AKOS022180447;J-007461;Q27140156;(+-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid;18-hydroxy-5(Z),8(Z),11(Z),14(Z),16(E)-eicosapentaenoic acid

Chemical Property of (+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid

Chemical Property:

• Boiling Point: 488.0±45.0 °C(Predicted)
• PKA: 4.75±0.10(Predicted)
• PSA: 57.53000
• Density: 0.997±0.06 g/cm3(Predicted)
• LogP: 4.96350
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 428

Purity/Quality:

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

18-Hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C=CC=CCC=CCC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• Description: (±)18-HEPE is produced by non-enzymatic oxidation of eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908). 18-HEPE levels are increased in the plasma and heart, as well as in the supernatant of cultured peritoneal macrophages isolated from fat-1 transgenic mice that are capable of endogenously producing ω-3 fatty acids from ω-6 fatty acids. It reduces increases in cardiac fibrosis and the expression of Nppa, Col1a1, Tgfb1, Cx3cl1, and Adgre1 induced by transverse aortic constriction in a mouse model of cardiac hypertrophy when administered at doses of 1 and 5 μg.
• Uses: 18-Hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoic Acid is produced by non-enzymatic oxidation of Eicosapentaenoic Acid (E477800).

Technology Process of (+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid

There total 1 articles about (+/-)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic 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:

C14H21BrO2 + C13H24OSi → (±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid (141110-17-0)

Guidance literature:

C₁₄H₂₁BrO₂; C₁₃H₂₄OSi; With copper(l) iodide; potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

With tetrabutyl ammonium fluoride; Further stages;

DOI:10.1055/s-0037-1610194

Reference yield:

(±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid (141110-17-0) → 5S-hydroperoxy,18R/S-hydroxy-EPE

Guidance literature:

With sodium tetrahydroborate; boric acid; potato 5-lipoxygenase; In ethanol; at 0 - 4 ℃; for 0.333333 - 0.5h; pH=9.2; borate buffer;

Reference yield:

(±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid (141110-17-0) → 5S-hydroperoxy, 18R/S-hydroxy-EPE (865532-69-0)

Guidance literature:

With potato 5-lipoxygenase; In ethanol; at 0 - 4 ℃; for 0.0833333 - 0.166667h; pH=9.2; Borate buffer;

Downstream raw materials:

5S-hydroperoxy, 18R/S-hydroxy-EPE