Leukotriene F4

Base Information

• Chemical Name: Leukotriene F4
• CAS No.: 83851-42-7
• Molecular Formula: C₂₈H₄₄N₂O₈S
• Molecular Weight: 568.732
• DSSTox Substance ID: DTXSID901317172
• Metabolomics Workbench ID: 2567
• Wikidata: Q27103162
• Mol file: 83851-42-7.mol

Synonyms:5(S)-hydroxy-6(R)-S-gamma-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acid;leukotriene F-4;LTF4

Chemical Property of Leukotriene F4

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 872.8 °C at 760 mmHg
• Flash Point: 481.6 °C
• PSA: 212.55000
• Density: 1.205 g/cm³
• LogP: 4.75190
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 23
• Exact Mass: 568.28183754
• Heavy Atom Count: 39
• Complexity: 857

Purity/Quality:

99% ^*data from raw suppliers

Leukotriene F4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)O)NC(=O)CCC(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)NC(=O)CC[C@@H](C(=O)O)N
• Uses: Leukotriene F4 is a cysteinyl-leukotriene exhibiting agonistic properties.

Technology Process of Leukotriene F4

There total 3 articles about Leukotriene F4 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:

(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{(R)-2-methoxycarbonyl-2-[(S)-4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester (83851-62-1,84414-54-0) → Leukotriene F4 (83851-42-7)

Guidance literature:

With potassium carbonate; In methanol; for 20h; Ambient temperature;

DOI:10.1248/cpb.30.2453

Reference yield:

Leukotriene A4 methyl ester (73466-12-3) → Leukotriene F4 (83851-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / methanol / 3 h / Ambient temperature

2: aq. potassium carbonate / methanol / 20 h / Ambient temperature

With potassium carbonate; triethylamine; In methanol;

DOI:10.1248/cpb.30.2453

Reference yield:

(S)-4-((R)-2-Mercapto-1-methoxycarbonyl-ethylcarbamoyl)-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester (83851-50-7) → Leukotriene F4 (83851-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / methanol / 3 h / Ambient temperature

2: aq. potassium carbonate / methanol / 20 h / Ambient temperature

With potassium carbonate; triethylamine; In methanol;

DOI:10.1248/cpb.30.2453

upstream raw materials:

(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{(R)-2-methoxycarbonyl-2-[(S)-4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester

Leukotriene A₄ methyl ester

(S)-4-((R)-2-Mercapto-1-methoxycarbonyl-ethylcarbamoyl)-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester

Refernces

Symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as inhibitors of leukotriene biosynthesis

10.1021/jm000180n

The research focuses on the investigation of symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as potent inhibitors of leukotriene biosynthesis, with the aim of developing new drug candidates for the treatment of asthma and related inflammatory disorders. The study centers on the compound 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid sodium salt (47?Na), which demonstrated high selectivity for inhibiting leukotriene C4 (LTC4) over prostaglandin E2 (PGE2) and showed promising pharmacokinetic properties in rat and cynomolgus monkey models. The experiments involved the synthesis of various bis-QMP analogues, their evaluation in vitro using human neutrophils and in vivo using animal models, and the analysis of their inhibitory activity on leukotriene biosynthesis. The research utilized a range of analytical techniques, including NMR spectroscopy, mass spectrometry, and elemental analysis, to characterize the synthesized compounds and assess their potency, selectivity, and pharmacokinetic properties. The main reactants used in the synthesis included commercially available diphenolic acid, quinolylmethoxyphenyl derivatives, and various reagents for the synthesis and modification of the target compounds. The study concluded that 47?Na (ABT-080) met the design parameters for a drug candidate and has proceeded to phase I human studies for safety and pharmacokinetic evaluation.