12-Hydroxyeicosatetraenoic acid

Base Information

• Chemical Name: 12-Hydroxyeicosatetraenoic acid
• CAS No.: 71030-37-0
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Hs Code.: 2918199090
• UNII: Q6F9H3VPC0
• DSSTox Substance ID: DTXSID101344765
• Metabolomics Workbench ID: 2696
• NCI Thesaurus Code: C959
• Nikkaji Number: J356.364B
• Wikidata: Q27157768
• Wikipedia: 12-Hydroxyeicosatetraenoic_acid
• Mol file: 71030-37-0.mol

Synonyms:12 S Hydroxyeicosatetraenoic Acid;12-HETE;12-Hydroxy-5,8,10,14-eicosatetraenoic Acid;12-R-HETE;12-S-HETE;12-S-Hydroxyeicosatetraenoic Acid;Acid, 12-S-Hydroxyeicosatetraenoic

Chemical Property of 12-Hydroxyeicosatetraenoic acid

Chemical Property:

• Boiling Point: 464.5 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 155.7 °C
• PSA: 17.07000
• Density: 0.983 g/cmºC
• LogP: 6.96710
• 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

(±)12-HETE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(C=CC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\CC(/C=C/C=C\C/C=C\CCCC(=O)O)O
• Description: (±)12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. The biological activity of (±)12-HETE is similar to that of its constituent enantiomers (Item Nos. 34560 and 34570). It aggregates neutrophils with an EC50 value of 40 nM.

Technology Process of 12-Hydroxyeicosatetraenoic acid

There total 41 articles about 12-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: 100.0%

(5Z,8Z,10E,14Z)-12-Acetoxy-icosa-5,8,10,14-tetraenoic acid methyl ester (98678-66-1) → 12-Hydroxyeicosatetraenoic acid (71030-37-0,59985-28-3)

Guidance literature:

With lithium hydroxide; In water; isopropyl alcohol;

DOI:10.1021/jo00222a054

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

upstream raw materials:

(6Z,10E,12Z,15Z)-19-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-6,10,12,15-tetraen-9-ol

11,12-cis-epoxyeicosatrienoic acid

(5Z,8Z,10E)-12-Hydroxy-13-(3-pentyl-oxiranyl)-trideca-5,8,10-trienoic acid

methyl 12-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoate

Refernces

• 1、 Easton, Christopher J.,Robertson, Thomas A.,Pitt, Michael J.,Rathjen, Deborah A.,Ferrante, Antonio,Poulos, Alfred. "Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase". . p. 317 - 322. Retrieved 2007/10/03.
• 2、 Gunn, Bruce P.,Brooks, Dee W.. "Total Synthesis of (+/-)-12-Hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic Acid (12-HETE)". . p. 4417 - 4418. Retrieved 2007/10/02.