(+/-)5,6-EPOXYEICOSA-8Z,11Z,14Z-TRIENOIC ACID

Base Information

• Chemical Name: (+/-)5,6-EPOXYEICOSA-8Z,11Z,14Z-TRIENOIC ACID
• CAS No.: 87173-80-6
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Mol file: 87173-80-6.mol

Synonyms:

Chemical Property of (+/-)5,6-EPOXYEICOSA-8Z,11Z,14Z-TRIENOIC ACID

Chemical Property:

• Boiling Point: 456.7±25.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• Density: 0.983±0.06 g/cm3(Predicted)

Purity/Quality:

≥95% (mixture of free acid and lactone) ^*data from raw suppliers

5'',6''-Epoxyeicosatrienoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5'',6''-Epoxyeicosatrienoic acid is a potent vasodilator and TRPV4 agonist.

Technology Process of (+/-)5,6-EPOXYEICOSA-8Z,11Z,14Z-TRIENOIC ACID

There total 25 articles about (+/-)5,6-EPOXYEICOSA-8Z,11Z,14Z-TRIENOIC 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: 47.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid (184488-43-5,81246-84-6,87173-80-6) + 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)

Guidance literature:

With human recombinant cytochrome P₄₅₀ 2D₆; stereoselective reaction; Enzymatic reaction;

DOI:10.1194/jlr.M003061

Reference yield:

2-arachidonoyl glycerol (53847-30-6) → all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + 2-11,12-EG + 2-14,15-EG + 4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid (184488-43-5,81246-84-6,87173-80-6) + 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)

Guidance literature:

With cytochrome P₄₅₀ reductase; Human CYP₂J₂ epoxygenase; NADPH; In aq. phosphate buffer; at 37 ℃; for 0.0833333h; pH=7.4; Kinetics; Enzymatic reaction;

DOI:10.1124/jpet.114.216598

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid (184488-43-5,81246-84-6,87173-80-6) + 8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid (184488-44-6,81246-85-7) + 14(S),15(R)-Epoxyeicosatrienoic acid (105304-92-5,81276-03-1) + 14(R),15(S)-Epoxyeicosatrienoic acid (98103-48-1,81276-03-1) + 11,12-cis-epoxyeicosatrienoic acid (200960-01-6,81276-02-0,87173-81-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1194/jlr.M054072

upstream raw materials:

6-((3Z,6Z,9Z)-1-iodopentadeca-3,6,9-trien-1-yl)tetrahydro-2Hpyran-2-one

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

anandamide

2-arachidonoyl glycerol

Refernces

• 1、 El-Sherbeni, Ahmed A.,El-Kadi, Ayman O. S.. "Repurposing Resveratrol and Fluconazole to Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism". . p. 1278 - 1288. Retrieved 2016/04/26.
• 2、 Teder, Tarvi,Boeglin, William E.,Brash, Alan R.. "Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: A potential P450 and lipoxygenase interaction". . p. 2587 - 2596. Retrieved 2015/02/19.