19(S)-HETE

Base Information

• Chemical Name: 19(S)-HETE
• CAS No.: 115461-40-0
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol file: 115461-40-0.mol

Synonyms:19(S)-HETE

Chemical Property of 19(S)-HETE

Chemical Property:

• Boiling Point: 477.3±45.0 °C(Predicted)
• PKA: 4.75±0.10(Predicted)
• PSA: 57.53000
• Density: 0.984±0.06 g/cm3(Predicted)
• LogP: 5.18750

Purity/Quality:

99% ^*data from raw suppliers

19(S)-HETE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 19-HETE is one of the major cytochrome P450 (CYP450) metabolites of arachidonic acid that is released from the kidney in response to angiotensin II. When formed by the CYP2E1 isoform, 19-HETE is composed of 70% and 30% of the (S) and (R) stereoisomers, respectively. Both 19(S)- and 19(R)-HETE are potent vasodilators of renal preglomerular vessels. 19(S)-HETE stimulates both renal sodium-potassium ATPase and volume absorption in the rabbit proximal straight tubule.

Technology Process of 19(S)-HETE

There total 37 articles about 19(S)-HETE 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: 94.0%

(5Z,8Z,11Z,14Z)-(S)-19-Hydroxy-icosa-5,8,11,14-tetraenoic acid methyl ester (115461-42-2) → 19(S)-hydroxyeicosatetraenoic acid (115461-39-7,115461-40-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 23 ℃; for 6h;

DOI:10.1016/j.tetlet.2004.01.151

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:

methyl (5Z,8Z,11Z,14Z)-rac-19-(benzoyloxy)eicosa-5,8,11,14-tetraenoate → 19-Hydroxyarachidonic acid (79551-85-2,115461-39-7,115461-40-0)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 30h;

DOI:10.1016/j.chemphyslip.2004.02.008

upstream raw materials:

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

19-Hydroxy-5,8,11,14-eikosatetraensaeure-methylester

methyl hex-5-ynoate

methyl 5-(trimethylsilyl)-4-pentynyl ketone

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、 Romanov, Stepan G.,Ivanov, Igor V.,Shevchenko, Valery P.,Nagaev, Igor Yu.,Pushkov, Alexandr A.,Myasoedov, Nikolai F.,Myagkova, Galina I.,Kuhn, Hartmut. "Synthesis of (5Z,8Z,11Z,14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route". . p. 117 - 126. Retrieved 2007/10/03.