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

Base Information

• Chemical Name: 11-hydroxy-5Z,8Z,11E,14Z-eicosatetraenoic acid
• CAS No.: 71030-38-1
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• ChEMBL ID: CHEMBL458854
• DSSTox Substance ID: DTXSID701017293
• Metabolomics Workbench ID: 2693
• Wikidata: Q27140010
• Mol file: 71030-38-1.mol

Synonyms:11-HETE;11-hydroxy-5,8,12,14-eicosatetraenoic acid;11-hydroxy-5,8,12,14-eicosatetraenoic acid, (E,Z,Z,Z)-isomer;11-hydroxy-5,8,12,14-eicosatetraenoic acid, (R)-(E,Z,Z,Z)-isomer;11-hydroxy-5,8,12,14-eicosatetraenoic acid, (S)-(E,Z,Z,Z)-isomer

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

Chemical Property:

• PSA: 57.53000
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CC(CC=CCC=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 11-hydroxy-5Z,8Z,11E,14Z-eicosatetraenoic acid

There total 7 articles about 11-hydroxy-5Z,8Z,11E,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) → 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3) + (Z,E,Z,Z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid (70968-93-3,79495-84-4) + (+/-)-5-HETE (71030-39-2) + (±)-11-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid (71030-38-1,73804-65-6) + icomucret (54845-95-3,73945-47-8,83603-31-0) + 15(R)-HETE (73945-47-8,83603-31-0)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With Physcomitrella patens lipoxygenase PpLOX₂; oxygen; for 0.5h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;

With sodium tetrahydroborate; In methanol; for 0.5h; enantiospecific reaction;

DOI:10.1016/j.phytochem.2008.11.012

upstream raw materials:

11,12-cis-epoxyeicosatrienoic acid

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

14,15-Epoxyeicosatrienoic acid methylester

(5Z,8Z)-10-[3-((2S,3S)-3-Bromo-2-hydroxy-octyl)-oxiranyl]-deca-5,8-dienoic acid methyl ester

Refernces

• 1、 Anterola, Aldwin,G?bel, Cornelia,Hornung, Ellen,Sellhorn, George,Feussner, Ivo,Grimes, Howard. "Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways". experimental part. p. 40 - 52. Retrieved 2009/07/11.
• 2、 Corey,Marfat,Falck,Albright. "Controlled chemical synthesis of the enzymatically produced eicosanoids 11-, 12-, and 15-HETE from arachidonic acid and conversion into the corresponding hydroperoxides (HPETE)". . p. 1433 - 1435. Retrieved 2007/10/02.