5-Hydroxyeicosapentaenoic acid

Base Information

• Chemical Name: 5-Hydroxyeicosapentaenoic acid
• CAS No.: 92008-51-0
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• DSSTox Substance ID: DTXSID001258761
• Nikkaji Number: J1.287.337I
• Wikidata: Q27140155
• Metabolomics Workbench ID: 2730
• Mol file: 92008-51-0.mol

Synonyms:5-HEPE;5-hydroxy-6,8,11,14,17-eicosapentaenoic acid;5-hydroxyeicosapentaenoic acid

Chemical Property of 5-Hydroxyeicosapentaenoic acid

Chemical Property:

• Vapor Pressure: 1.42E-11mmHg at 25°C
• Boiling Point: 488°Cat760mmHg
• Flash Point: 263.1°C
• PSA: 57.53000
• Density: 0.997g/cm³
• 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% ^*data from raw suppliers

5(S)-HEPE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CC=CC(CCCC(=O)O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O
• Uses: 5(S)-HEPE is produced by 5-lipoxygenase catalyzed oxidation of eicosapentaenoic acid (EPA). While the synthesis of 5(S)-HEPE from EPA by tissue homogenates has been demonstrated, the biological activity of 5(S)-HEPE is poorly documented. It remains to be determined whether this activity differs substantially from that of 5(S)-HETE .

Technology Process of 5-Hydroxyeicosapentaenoic acid

There total 12 articles about 5-Hydroxyeicosapentaenoic 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: 88.0%

6-[(3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl]-tetrahydro-2H-pyran-2-one → 5-HEPE (92008-51-0)

Guidance literature:

6-[(3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl]-tetrahydro-2H-pyran-2-one; With potassium hydroxide; In methanol; water; at 20 ℃; for 2h;

With hydrogenchloride; In methanol; water;

DOI:10.3987/COM-09-S(S)90

Reference yield: 85.0%

6-((1E,3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl)tetrahydro-2H-pyran-2-one (375387-75-0) → 5-HEPE (83952-40-3,92008-51-0)

Guidance literature:

With potassium hydroxide; In ethanol; at 24 ℃; for 16h;

DOI:10.1016/j.chemphyslip.2004.02.006

Reference yield: 85.0%

→ 5-HEPE (83952-40-3,92008-51-0)

Guidance literature:

upstream raw materials:

6-((1E,3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl)tetrahydro-2H-pyran-2-one

6-[(3Z,6Z,9Z,12Z)-1-iodopentadeca-3,6,9,12-tetraen-1-yl]-tetrahydro-2H-pyran-2-one

5,8,11,14,17-eicosapentaenoic acid