15-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid

Base Information

• Chemical Name: 15-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
• CAS No.: 71030-36-9
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Wikidata: Q27132968
• Metabolomics Workbench ID: 2695
• Mol file: 71030-36-9.mol

Synonyms:15-HETE;15-hydroxy-5,8,11,13-eicosatetraenoic acid;15-hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(E,Z,Z,Z))-isomer

Chemical Property of 15-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid

Chemical Property:

• Boiling Point: 487.7±45.0 °C(Predicted)
• PKA: 4.75±0.10(Predicted)
• Flash Point: 10℃ (tag closed test)
• PSA: 57.53000
• Density: 0.984±0.06 g/cm3(Predicted)
• LogP: 5.18750
• XLogP3: 5.1
• 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

(±)15-HETE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCCC(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• Description: (±)15-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. The biological activity of (±)15-HETE is similar to that of its constituent enantiomers (Item Nos. 34720 and 34710).(±)15-HETE MaxSpec? standard is a quantitative grade standard of (±)15-HETE that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This (±)15-HETE MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

Technology Process of 15-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid

There total 4 articles about 15-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic 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: 70.0%

cis-14,15-epoxyeicosatrienoic acid (197508-62-6,81276-03-1) → (+/-)-15-HETE (71030-36-9,73945-47-8,83603-31-0)

Guidance literature:

With N-cyclohexylisopropylamine; methylmagnesium bromide; In tetrahydrofuran; 1.) 0 deg C, 10 min, 2.) 0-23 deg C, 2 h, 3.) 23 deg C, 3,5 h;

DOI:10.1021/ja00524a043

Reference yield: 35.0%

15-HPETE (69371-38-6) → (+/-)-15-HETE (71030-36-9,73945-47-8,83603-31-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

DOI:10.1039/a902084e

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:

cis-14,15-epoxyeicosatrienoic acid

15-HPETE

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

Downstream raw materials:

15-oxoeicosatetraenoic acid

15-HPETE

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