5-Oxo-ETE

Base Information

• Chemical Name: 5-Oxo-ETE
• CAS No.: 126432-17-5
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Nikkaji Number: J661.539B
• Wikipedia: 5-Oxo-eicosatetraenoic_acid
• Wikidata: Q25323762
• Pharos Ligand ID: A65ADT6FMRBM
• Metabolomics Workbench ID: 2637
• ChEMBL ID: CHEMBL18028
• Mol file: 126432-17-5.mol

Synonyms:5-oxo-eicosatetraenoic acid;5-oxo-ETE

Chemical Property of 5-Oxo-ETE

Chemical Property:

• Vapor Pressure: 3.79E-11mmHg at 25°C
• Boiling Point: 495°Cat760mmHg
• Flash Point: 267.3°C
• PSA: 0.00000
• Density: 0.98g/cm³
• LogP: 0.00000
• XLogP3: 5.1
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CC=CC(=O)CCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)O

Technology Process of 5-Oxo-ETE

There total 46 articles about 5-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: 86.0%

methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate (74785-00-5) → 5-oxo-ETE (126432-17-5,106154-18-1)

Guidance literature:

With lithium hydroxide; In water; isopropyl alcohol; at 23 ℃; for 0.666667h;

DOI:10.1021/jm00390a010

Reference yield: 77.0%

(+/-)-5-HETE (71030-39-2) → 5-oxo-ETE (126432-17-5,106154-18-1)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h; Product distribution / selectivity;

Reference yield: 69.0%

(7Z,10Z,13Z)-6-Hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-7,10,13-trien-4-one (356070-86-5) → 5-oxo-ETE (126432-17-5,106154-18-1)

Guidance literature:

(7Z,10Z,13Z)-6-Hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-7,10,13-trien-4-one; With sulfuric acid; In methanol; at 0 ℃; for 0.5h;

With potassium carbonate; In methanol; at 0 ℃; for 1h; pH=10;

With lithium hydroxide; In isopropyl alcohol; at 23 ℃; for 12h;

DOI:10.1016/S0040-4039(01)00668-2

upstream raw materials:

methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate

4-[((1E,3Z,6Z,9Z)-2-Pentadeca-1,3,6,9-tetraenyl)-[1,3]dithiolan-2-yl]-butyric acid

(7Z,10Z,13Z)-6-Hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-7,10,13-trien-4-one

undeca-2,5-diyn-1-ol

Refernces

• 1、 Cossette, Chantal,Chourey, Shishir,Ye, Qiuji,Nagendra Reddy, Chintam,Gore, Vivek,Gravel, Sylvie,Slobodchikova, Irina,Vuckovic, Dajana,Rokach, Joshua,Powell, William S.. "Pharmacokinetics and Metabolism of Selective Oxoeicosanoid (OXE) Receptor Antagonists and Their Effects on 5-Oxo-6,8,11,14-eicosatetraenoic Acid (5-Oxo-ETE)-Induced Granulocyte Activation in Monkeys". . p. 10127 - 10146. Retrieved 2016/12/07.
• 2、 Jin, Jing,Zheng, Yuxiang,Boeglin, William E.,Brash, Alan R.. "Biosynthesis, isolation, and NMR analysis of leukotriene A epoxides: Substrate chirality as a determinant of the cis or trans epoxide confi guration". . p. 754 - 761. Retrieved 2013/05/09.