(5Z,8Z,11Z,14Z,19R)-19-hydroxyicosa-5,8,11,14-tetraenoic acid

Base Information

• Chemical Name: (5Z,8Z,11Z,14Z,19R)-19-hydroxyicosa-5,8,11,14-tetraenoic acid
• CAS No.: 115461-39-7
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• DSSTox Substance ID: DTXSID501347559
• Nikkaji Number: J455.067F
• Mol file: 115461-39-7.mol

Synonyms:115461-39-7;19(R)-HETE;(5Z,8Z,11Z,14Z,19R)-19-hydroxyicosa-5,8,11,14-tetraenoic acid;5,8,11,14-Eicosatetraenoic acid, 19-hydroxy-, (5Z,8Z,11Z,14Z,19R)-;DTXSID501347559;AKOS040755127;AT35694;PD020270;HY-118332;CS-0065706;19(R)-hydroxy-5(Z),8(Z),11(Z),14(Z)-eicosatetraenoic acid

Chemical Property of (5Z,8Z,11Z,14Z,19R)-19-hydroxyicosa-5,8,11,14-tetraenoic acid

Chemical Property:

• PSA: 57.53000
• LogP: 5.18750
• XLogP3: 4.6
• 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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC=CCC=CCC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: C[C@H](CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• 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. However, 19(R)-HETE at 1 μM completely blocks 20-HETE-induced vasoconstriction of renal arterioles, whereas 19(S)-HETE remains inactive.

Technology Process of (5Z,8Z,11Z,14Z,19R)-19-hydroxyicosa-5,8,11,14-tetraenoic acid

There total 45 articles about (5Z,8Z,11Z,14Z,19R)-19-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: 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: 94.0%

methyl 19(R)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate (115461-41-1) → 19(R)-hydroxyeicosatetraenoic acid (115461-39-7)

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

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、 Kandel, Sylvie E.,Lampe, Jed N.,Tooker, Brian C.,Work, Hannah M.. "Pseudomonas aeruginosa cytochrome P450 CYP168A1 is a fatty acid hydroxylase that metabolizes arachidonic acid to the vasodilator 19-HETE". . . Retrieved 2022/03/27.
• 2、 McDougle, Daniel R.,Kambalyal, Amogh,Meling, Daryl D.,Das, Aditi. "Endocannabinoids anandamide and 2-arachidonoylglycerol are substrates for human CYP2J2 epoxygenase". . p. 616 - 627. Retrieved 2015/01/16.