5S-HpETE

Base Information

• Chemical Name: 5S-HpETE
• CAS No.: 71774-08-8
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.472
• ChEMBL ID: CHEMBL1743204
• DSSTox Substance ID: DTXSID701017279
• Metabolomics Workbench ID: 2638
• Nikkaji Number: J360.970G
• Pharos Ligand ID: R18BA23UYH6N
• Wikidata: Q2823231
• Wikipedia: Arachidonic_acid_5-hydroperoxide
• Mol file: 71774-08-8.mol

Synonyms:5-HPETE;5-hydroperoxy-6,8,11,14-eicosatetraenoic acid;6,8,11,14-eicosatetraenoic acid 5-hydroperoxide;arachidonic acid 5-hydroperoxide;cis,trans-5-hydroperoxy-6,8,11,14-eicosatetraenoic acid

Chemical Property of 5S-HpETE

Chemical Property:

• Vapor Pressure: 6.75E-13mmHg at 25°C
• Boiling Point: 518°C at 760 mmHg
• Flash Point: 175.6°C
• PSA: 66.76000
• Density: 1.013g/cm³
• LogP: 5.68480
• Storage Temp.: −20°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 408

Purity/Quality:

98%Min ^*data from raw suppliers

5(S)-HpETE ≥98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CC=CC(CCCC(=O)O)OO
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C=C\[C@H](CCCC(=O)O)OO

Technology Process of 5S-HpETE

There total 15 articles about 5S-HpETE 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:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 5(S)-HPETE (71774-08-8)

Guidance literature:

With oxygen; potassium carbonate; potato lipoxygenase; Yield given. Multistep reaction; 1.) CH₃OH, 2.) 60 atm, 4 min;

DOI:10.1021/ja00186a046

Reference yield:

ammonium arachidonate (49664-88-2) → 5(S)-HPETE (71774-08-8)

Guidance literature:

With TEMPOL; lipoxygenase from potato tubers; oxygen; Triton X-100; Antifoam B; In water; for 0.2h; pH 9 - 6.4;

DOI:10.1021/ja00524a044

Reference yield:

(7R)-deuterioarachidonic acid (85735-74-6) → C20H31(2)HO4 (71774-08-8)

Guidance literature:

With ammonium hydroxide; TEMPOL; 5-lipoxygenase from Potato; Triton X-100; at 20 ℃; for 0.5h;

DOI:10.1021/ja00350a059

upstream raw materials:

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

ammonium arachidonate

(S)-5-hydroperoxy-6-trans,8,11,14-cis-eicosatetraenoic acid methyl ester

(7R)-deuterioarachidonic acid

Downstream raw materials:

(7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Leukotriene A₄ methyl ester

(5S)-(6E,8Z,11Z,14Z)-5-hydroxy-eicosa-6,8,11,14-tetraenoic acid, methyl ester

C₂₀H₃₁⁽²⁾HO₃

Refernces

• 1、 Corey, E. J.,Wright, Stephen W.,Matsuda, Seiichi P. T.. "Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate". . p. 1452 - 1455. Retrieved 2007/10/02.
• 2、 Porter, Ned A.,Lehman, Laura S.,Weber, Bruce A.,Smith, Karl J.. "Unified Mechanism for Polyunsaturated Fatty Acid Autooxidation. Competition of Peroxy Radical Hydrogen Atom Abstraction, β-Scission, and Cyclization". . p. 6447 - 6455. Retrieved 2007/10/02.