20-Hydroxyeicosatetraenoic acid

Base Information

• Chemical Name: 20-Hydroxyeicosatetraenoic acid
• CAS No.: 79551-86-3
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• DSSTox Substance ID: DTXSID601009895
• Nikkaji Number: J455.066H
• Wikipedia: 20-Hydroxyeicosatetraenoic_acid
• Wikidata: Q21099666
• Metabolomics Workbench ID: 2635
• ChEMBL ID: CHEMBL4085458
• Mol file: 79551-86-3.mol

Synonyms:20-HETE;20-hydroxy-5,8,11,14-eicosatetraenoic acid;20-hydroxyeicosatetraenoic acid

Chemical Property of 20-Hydroxyeicosatetraenoic acid

Chemical Property:

• Vapor Pressure: 2.57E-11mmHg at 25°C
• Boiling Point: 482°C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 259.4°C
• PSA: 57.53000
• Density: 0.985g/cm³
• LogP: 5.18910
• Storage Temp.: −20°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 378

Purity/Quality:

99% ^*data from raw suppliers

20-HETE ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CCC=CCC=CCC=CCC=CCCCC(=O)O)CCO
• Isomeric SMILES: C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCO
• Uses: 20-HETE is a cytochrome P450 (CYP450) metabolite that may play an autacoid role in cerebral and renal vasculature.

Technology Process of 20-Hydroxyeicosatetraenoic acid

There total 1 articles about 20-Hydroxyeicosatetraenoic 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) → (+/-)-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:

(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid (79551-86-3) → 20-hydroxy-5,8,11,14-eicosatetraenoic acid ethanolamide (942069-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: 2-hydroxypyridine / 1 h / 50 °C

With 2-hydroxypyridin; In diethyl ether;

DOI:10.1124/mol.54.1.180

upstream raw materials:

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

Downstream raw materials:

20-hydroxy-5,8,11,14-eicosatetraenoic acid ethanolamide

Refernces