15-Oxo-ETE

Base Information

• Chemical Name: 15-Oxo-ETE
• CAS No.: 81416-72-0
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• ChEMBL ID: CHEMBL418941
• Metabolomics Workbench ID: 2660
• Nikkaji Number: J716.153K
• Pharos Ligand ID: 6QNR2HRAZHWD
• Mol file: 81416-72-0.mol

Synonyms:15-KETE;15-keto-5,8,11,13-eicosatetraenoic acid

Chemical Property of 15-Oxo-ETE

Chemical Property:

• Vapor Pressure: 3.79E-11mmHg at 25°C
• Boiling Point: 495°C at 760 mmHg
• Flash Point: 267.3°C
• PSA: 54.37000
• Density: 0.98g/cm³
• LogP: 5.39570
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 428

Purity/Quality:

98%Min ^*data from raw suppliers

15-KETE(15-oxo-ETE) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C=CC=CCC=CCC=CCCCC(=O)O
• Isomeric SMILES: CCCCCC(=O)/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O
• Uses: 15-KETE (15-oxo-ETE) is a major metabolite of arachidonic acid that is formed through the Lipoxygenase pathway.

Technology Process of 15-Oxo-ETE

There total 17 articles about 15-Oxo-ETE 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: 95.0%

icomucret (54845-95-3,73945-47-8,83603-31-0) → (5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-eicosatetraenoic acid (81416-72-0)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; at 85 ℃; for 1h;

DOI:10.1016/j.chemphyslip.2006.02.015

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3) + (R)-12-HETE (82337-46-0) + (Z,E,Z,Z)-8-hydroxyeicosa-5,9,11,14-tetraenoic acid (70968-93-3,79495-84-4) + 5(S)-HETE (61641-47-2,70608-72-9,71030-39-2,71774-09-9,72255-35-7,73307-52-5,74080-72-1,88588-79-8) + (5R)-HETE (61641-47-2) + (R)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (73347-43-0,73804-65-6) + icomucret (54845-95-3,73945-47-8,83603-31-0) + (5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-eicosatetraenoic acid (81416-72-0) + (S)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (54886-50-9,73804-65-6)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With Physcomitrella patens lipoxygenase PpLOX₇; oxygen; for 0.5h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;

With sodium tetrahydroborate; In methanol; for 0.5h; enantiospecific reaction;

DOI:10.1016/j.phytochem.2008.11.012

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → C20H30O3 (135200-65-6) + 15-HPETE (69371-38-6) + 5-HPETE (70968-82-0) + 8-5Z,9E,11Z,14Z-hydroperoxyeicosatetraenoic acid (70968-80-8) + (±)-12-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (71030-35-8) + 11-5Z,8Z,12E,14Z-hydroperoxyeicosatetraenoic acid (70968-78-4) + (5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-eicosatetraenoic acid (81416-72-0)

Guidance literature:

With Physcomitrella patens lipoxygenase PpLOX₇; oxygen; for 0.5h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.phytochem.2008.11.012

upstream raw materials:

(+/-)-15-HETE

icomucret

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

15-HPETE

Refernces

• 1、 Armstrong, Michelle M.,Diaz, Giovanni,Kenyon, Victor,Holman, Theodore R.. "Inhibitory and mechanistic investigations of oxo-lipids with human lipoxygenase isozymes". . p. 4293 - 4297. Retrieved 2014/08/18.
• 2、 Zheng, Yuxiang,Brash, Alan R.. "Formation of a cyclopropyl epoxide via a leukotriene A synthase-related pathway in an anaerobic reaction of soybean lipoxygenase-1 with 15S-hydroperoxyeicosatetraenoic acid: Evidence that oxygen access is a determinant of secondary reactions with fatty acid hydroperoxides". . p. 13427 - 13436. Retrieved 2011/03/22.