leukotriene E4

Base Information

• Chemical Name: leukotriene E4
• CAS No.: 75715-89-8
• Molecular Formula: C23H37 N O5 S
• Molecular Weight: 439.61
• UNII: 8EYT8ATL7G
• ChEMBL ID: CHEMBL509456
• DSSTox Substance ID: DTXSID20897510
• Metabolomics Workbench ID: 2562
• NCI Thesaurus Code: C129009
• Nikkaji Number: J264.600E
• Pharos Ligand ID: AVT4X7W62AXM
• Wikidata: Q2705859
• Wikipedia: Leukotriene_E4
• Mol file: 75715-89-8.mol

Synonyms:Leukotriene E;Leukotriene E 4;Leukotriene E-4;Leukotriene E4;Leukotrienes E;LTE4

Chemical Property of leukotriene E4

Chemical Property:

• Vapor Pressure: 4.63E-21mmHg at 25°C
• Boiling Point: 674.1°C at 760 mmHg
• Flash Point: 361.5°C
• PSA: 146.15000
• Density: 1.132g/cm³
• LogP: 5.01140
• Storage Temp.: −20°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 18
• Exact Mass: 439.23924445
• Heavy Atom Count: 30
• Complexity: 586

Purity/Quality:

≥97% ^*data from raw suppliers

LeukotrieneE4 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11
• Safety Statements: 7-16-23-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)O)N
• Isomeric SMILES: CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@@H](C(=O)O)N
• General Description: Leukotriene E4 (LTE4) is a cysteinyl leukotriene involved in inflammatory and allergic responses, derived from the metabolism of leukotriene C4 (LTC4). It plays a role in bronchoconstriction, vascular permeability, and immune regulation, and its metabolites are significant in studying leukotriene pathways in vivo. The synthesis of LTE4 metabolites and radiolabeled precursors facilitates research into their biological roles and metabolic fate.

Technology Process of leukotriene E4

There total 27 articles about leukotriene E4 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: 82.0%

leukotriene E4 dimethyl ester (74448-22-9) → leukotriene E4 (75715-89-8)

Guidance literature:

With potassium carbonate; In methanol; water; at 0 ℃; for 3.5h;

DOI:10.1002/1099-0690(200009)2000:17<2991::AID-EJOC2991>3.0.CO;2-H

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (7E,9E,11Z,14Z)-(5R,6S)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid (75443-89-9,75715-88-7,75715-89-8,82468-17-5,84823-21-2,84823-22-3,84823-23-4,84823-24-5,84823-25-6,92009-31-9,130010-34-3,130010-35-4)

Guidance literature:

Multi-step reaction with 10 steps

1: dimsyl sodium

2: PhSSPh / cyclohexane / 4 h / Irradiation

4: m-CPBA / CH₂Cl₂

5: NaIO₄, H₂O / acetic acid

6: 84 percent / benzene / Heating

7: 34 percent / benzene / Heating

8: 56 percent

9: (C₂H₅)3N / methanol

10: K₂CO₃ / methanol; H₂O

With sodium periodate; water; sodium methylsulfinylmethanide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; diphenyldisulfane; In methanol; dichloromethane; cyclohexane; water; acetic acid; benzene;

DOI:10.1016/S0040-4039(01)82844-6

Reference yield:

(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-[2-methoxycarbonyl-2-(2,2,2-trifluoro-acetylamino)-ethylsulfanyl]-icosa-7,9,11,14-tetraenoic acid methyl ester (75415-34-8,78419-55-3,80657-04-1,80657-05-2,80657-06-3,80657-07-4,80657-08-5,80657-09-6) → (7E,9E,11Z,14Z)-(5R,6S)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid (75443-89-9,75715-88-7,75715-89-8,82468-17-5,84823-21-2,84823-22-3,84823-23-4,84823-24-5,84823-25-6,92009-31-9,130010-34-3,130010-35-4)

Guidance literature:

With potassium carbonate; In methanol; water;

DOI:10.1016/S0040-4039(01)82844-6

upstream raw materials:

(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-[2-methoxycarbonyl-2-(2,2,2-trifluoro-acetylamino)-ethylsulfanyl]-icosa-7,9,11,14-tetraenoic acid methyl ester

(4-carboxybutyl)triphenylphosphonium bromide

methyl 6-formyl-5,6-trans-epoxyhexanoate

(Z)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid

Downstream raw materials:

Leukotriene E4 sulfone

Refernces

Total synthesis of leukotriene E₄ metabolites and precursors to radiolabeled forms of those metabolites

10.1021/jo00276a025

The research focuses on the total synthesis of leukotriene E4 metabolites and precursors to radiolabeled forms of those metabolites. The purpose of this study was to prepare four novel 8-oxidation products of peptido leukotrienes, which were used to identify unknown polar metabolites derived from leukotriene C4 (LTC4) in rats and primates. The synthesis involved forming the C-11-C-12 cis double bond using the Wittig reaction on chiral diene aldehyde epoxide. The study concluded that the synthesized metabolites correspond to the polar rat biliary metabolites after administration of [3H]LTC4, and the strategy of making the corresponding acetylenic precursors allows access to the isotopically labeled forms of these important metabolites in substantial quantities.

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