(5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid

Base Information

• Chemical Name: (5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid
• CAS No.: 128914-46-5
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• DSSTox Substance ID: DTXSID501192263
• Nikkaji Number: J608.787F
• Wikidata: Q27070786
• Metabolomics Workbench ID: 63080
• Mol file: 128914-46-5.mol

Synonyms:16(R)-hydroxyeicosatetraenoic acid;16-HETE;16-hydroxy-5,8,11,14-eicosatetraenoic acid

Chemical Property of (5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid

Chemical Property:

• Vapor Pressure: 4.1E-11mmHg at 25°C
• Boiling Point: 477.3°Cat760mmHg
• Flash Point: 256.6°C
• PSA: 57.53000
• Density: 0.984g/cm³
• LogP: 5.18750
• XLogP3: 4.8
• 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:

≥98% ^*data from raw suppliers

(±)16-HETE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C=CCC=CCC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC(/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• Description: Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)16-HETE is the racemic version of a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation. The biological activity of 16-HETE is stereospecific. 16(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, however 16(S)-HETE does not affect perfusion pressure. At a concentration of 2 μM the (S)-enantiomer of 16-HETE inhibits proximal tubule ATPase activity by as much as 60%, whereas the (R)-isomer has negligible effects on ATPase activity.

Technology Process of (5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic acid

There total 38 articles about (5Z,8Z,11Z,14Z)-16-hydroxyicosa-5,8,11,14-tetraenoic 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%

methyl (16S,5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoate (175443-67-1) → (16S,5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoic acid (128914-46-5)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃;

DOI:10.1016/S0968-0896(02)00024-X

Reference yield: 87.0%

methyl (16R,5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoate (175443-68-2) → (16R,5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoic acid (128914-46-5)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃;

DOI:10.1016/S0968-0896(02)00024-X

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

upstream raw materials:

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

methyl (16R,5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoate

Benzoic acid (2Z,5Z,8Z,11Z)-(R)-1-butyl-15-methoxycarbonyl-pentadeca-2,5,8,11-tetraenyl ester

Benzoic acid (R)-1-formyl-pentyl ester

Refernces

• 1、 Nilsson,Ivanov,Oliw. "LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22". experimental part. p. 64 - 71. Retrieved 2011/02/21.
• 2、 Ivanov, Igor V.,Romanov, Stepan G.,Groza, Nataliya V.,Nigam, Santosh,Kuhn, Hartmut,Myagkova, Galina I.. "A simple method for the preparation of (5Z,8Z,11Z,14Z)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid enantiomers and the corresponding 14,15-Dehydro analogues: Role of the 16-Hydroxy group for the lipoxygenase reaction". . p. 2335 - 2343. Retrieved 2007/10/03.