Icomucret

Base Information

• Chemical Name: Icomucret
• CAS No.: 54845-95-3
• Molecular Formula: C20H32O3
• Molecular Weight: 320.472
• Hs Code.: 2918199090
• European Community (EC) Number: 688-204-1
• UNII: 44JHK6G39Q
• ChEMBL ID: CHEMBL594621
• DSSTox Substance ID: DTXSID101031956
• Metabolomics Workbench ID: 2628
• NCI Thesaurus Code: C80608
• Nikkaji Number: J303.917J
• Pharos Ligand ID: 6QVFLKU7BC85
• Wikidata: Q21099561
• Wikipedia: 15-Hydroxyeicosatetraenoic_acid
• Mol file: 54845-95-3.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 Icomucret

Chemical Property:

• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 487.7 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 262.8 °C
• PSA: 57.53000
• Density: 0.984 g/cm³
• LogP: 5.18750
• Storage Temp.: −20°C
• 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:

98%,99%, ^*data from raw suppliers

15(S)-HETE ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 7-16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• Description: 15(S)-HETE is a major arachidonic acid metabolite from the 15-lipoxygenase pathway. In mammals, 15(S)-HETE is synthesized in the respiratory epithelium, leukocytes, and reticulocytes. 15(S)-HETE is present in μg/ml concentrations in the nasal secretions of allergic rhinitis.
• Uses: 15(S)-HETE is a major arachidonic acid metabolite from the 15-lipoxygenase pathway. In mammals, 15(S)-HETE is synthesized in the respiratory epithelium, leukocytes, and reticulocytes. 15(S)-HETE is present in μg/ml concentrations in the nasal secretions of allergic rhinitis. 15(S)-HETE is an arachidonic acid metabolite with immunosuppressive activity.

Technology Process of Icomucret

There total 18 articles about Icomucret 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%

(5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester (70946-44-0) → icomucret (54845-95-3,73945-47-8,83603-31-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃;

DOI:10.1039/c39850001580

Reference yield: 80.0%

(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid (70981-96-3) → icomucret (54845-95-3,73945-47-8,83603-31-0)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1021/jm00385a005

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) + 8(S)-hydroxyeicosatetraenoic acid (98462-03-4,79495-84-4) + (8R)-hydroxyeicosatetraenoic acid (105500-09-2,79495-84-4) + (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) + 15(R)-HETE (73945-47-8,83603-31-0) + (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 8R-lipoxygenase A₅₈₉M mutant; sodium chloride; calcium chloride; In ethanol; at 20 ℃; pH=8; Enzymatic reaction;

With triphenylphosphine; In methanol; at 20 ℃; for 0.5h; Reagent/catalyst; Kinetics;

DOI:10.1074/jbc.M114.599662

upstream raw materials:

(5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid

(5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester

5-hexyl-1-ol

tert-butyldimethylsilyl hex-5-yn-1-yl ether

Downstream raw materials:

(5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester

(2E,4S)-4-hydroxy-2-nonenal

(5Z,8Z,11Z,13E,15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt

15(S)-hydroxy-eicosa-5Z,8Z,11Z,13E-tetraenoyl-N-(2-hydroxyethyl)amine

Refernces

• 1、 Martini, Dominique,Buono, Gerard,Lacazio, Gilles. "Regiocontrol of soybean lipoxygenase oxygenation. Application to the chemoenzymatic synthesis of methyl 15(S)-HETE and Methyl 5(S),15(S)-diHETE". . p. 9062 - 9064. Retrieved 1996.
• 2、 Neau, David B.,Bender, Gunes,Boeglin, William E.,Bartlett, Sue G.,Brash, Alan R.,Newcomer, Marcia E.. "Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase". . p. 31905 - 31913. Retrieved 2015/02/19.
• 3、 Anterola, Aldwin,G?bel, Cornelia,Hornung, Ellen,Sellhorn, George,Feussner, Ivo,Grimes, Howard. "Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways". experimental part. p. 40 - 52. Retrieved 2009/07/11.