8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

Base Information

• Chemical Name: 8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid
• CAS No.: 70968-93-3
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• DSSTox Substance ID: DTXSID401347449
• Wikidata: Q27140041
• Metabolomics Workbench ID: 2694
• Mol file: 70968-93-3.mol

Synonyms:8-HETE;8-hydroxyeicosatetraenoic acid;8-hydroxyeicosatetraenoic acid, (E,Z,Z,Z)-(+-)-isomer;8-hydroxyeicosatetraenoic acid, (E,Z,Z,Z)-isomer

Chemical Property of 8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

Chemical Property:

• Vapor Pressure: 7.45E-11mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 471.1°C at 760 mmHg
• Flash Point: 252.8°C
• PSA: 57.53000
• Density: 0.984g/cm³
• LogP: 5.18750
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 392

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC(CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C=C\C(C/C=C\CCCC(=O)O)O

Technology Process of 8-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

There total 5 articles about 8-hydroxy-5Z,9E,11Z,14Z-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:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → +/-9-HETE (70968-92-2,107656-13-3,79495-85-5,107656-14-4) + (Z,E,Z,Z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid (70968-93-3,79495-84-4) + 12-Hydroxyeicosatetraenoic acid (71030-37-0,59985-28-3) + (±)-11-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid (71030-38-1,73804-65-6)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With oxygen; Tocopherol; at 20 ℃; for 42h;

With sodium tetrahydroborate; In ethanol; for 1h; Further byproducts given;

DOI:10.1016/S0968-0896(00)00246-7

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → (+/-)-15-HETE (71030-36-9,73945-47-8,83603-31-0) + 17-hydroxyeicosatetraenoic acid + 19-Hydroxyarachidonic acid (79551-85-2,115461-39-7,115461-40-0) + +/-9-HETE (70968-92-2,107656-13-3,79495-85-5,107656-14-4) + 4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid (184488-43-5,81246-84-6,87173-80-6) + (Z,E,Z,Z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid (70968-93-3,79495-84-4) + 12-Hydroxyeicosatetraenoic acid (71030-37-0,59985-28-3) + (+/-)-5-HETE (71030-39-2) + (5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid (79551-86-3) + 8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid (184488-44-6,81246-85-7) + cis-14,15-epoxyeicosatrienoic acid (197508-62-6,81276-03-1) + 11,12-cis-epoxyeicosatrienoic acid (200960-01-6,81276-02-0,87173-81-7) + (±)-11-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid (71030-38-1,73804-65-6) + rac-(5Z,8Z,11Z,14Z)-18-hydroxyeicosa-5,8,11,14-tetraenoic acid (133268-58-3,21914-83-0) + (5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoic acid (128914-46-5)

Guidance literature:

With magnesium(II) chloride hexahydrate; nicotinamide adenine dinucleotide phosphate-P₄₅₀ reductase; recombinant human cytochrome P₄₅₀ CYP₂C₁₉ enzyme; NADH; cytochrome b₅; In aq. phosphate buffer; at 37 ℃; for 0.25h; pH=7.4; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/acs.molpharmaceut.5b00873

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → (Z,E,Z,Z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid (70968-93-3,79495-84-4) + (+/-)-5-HETE (71030-39-2) + 6-((1E,3Z,6Z,9Z)-pentadeca-1,3,6,9-tetraen-1-yl)tetrahydro-2Hpyran-2-one (81517-87-5)

Guidance literature:

With oxygen; NADPH; at 25 ℃; for 0.25h; cytochrome P-450, hepatic microsomes;

DOI:10.1016/S0040-4039(01)80185-4

upstream raw materials:

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

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