leukotriene C4

Base Information

• Chemical Name: leukotriene C4
• CAS No.: 72025-60-6
• Molecular Formula: C₃₀H₄₇N₃O₉S
• Molecular Weight: 625.784
• European Community (EC) Number: 686-872-9
• UNII: 2CU6TT9V48
• ChEMBL ID: CHEMBL451509
• DSSTox Substance ID: DTXSID00903946
• Metabolomics Workbench ID: 2563
• Nikkaji Number: J263.860F
• Pharos Ligand ID: XALPRHSY1BMM
• Wikidata: Q2704310
• Wikipedia: Leukotriene_C4
• Mol file: 72025-60-6.mol

Synonyms:Leukotriene C;Leukotriene C 1;Leukotriene C 4;Leukotriene C-1;Leukotriene C-4;Leukotriene C1;Leukotriene C4;Leukotrienes C;LTC4

Chemical Property of leukotriene C4

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 974.3°C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 11 °C
• PSA: 241.65000
• Density: 1.225g/cm³
• LogP: 4.25900
• Storage Temp.: −20°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 25
• Exact Mass: 625.30330126
• Heavy Atom Count: 43
• Complexity: 982

Purity/Quality:

99% ^*data from raw suppliers

Leukotriene C4 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)NCC(=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)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• Description: Leukotriene C4 (LTC4) is the parent cysteinyl leukotriene produced by the LTC4 synthase catalyzed conjugation of glutathione to LTA4. LTC4 is produced by neutrophils, macrophages, mast cells, and by transcellular metabolism in platelets. It is one of the constituents of slow-reacting substance of anaphylaxis (SRS-A) and exhibits potent smooth muscle contracting activity. LTC4-induced bronchoconstriction and enhanced vascular permeability contribute to the pathogenesis of asthma and acute allergic hypersensitivity. The concentration of LTC4 required to produce marked contractions of lung parenchymal strips and isolated tracheal rings is about 1 nM.
• Uses: LTC4 (Leukotriene C4) is a potent agonist for contraction of smooth muscle, wtih many important immunomodulatory functions.

Technology Process of leukotriene C4

There total 65 articles about leukotriene C4 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: 84.0%

Leukotriene C4 methyl ester (73958-10-8) → (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid (73466-14-5,74841-69-3,76738-45-9,79026-71-4,79026-72-5,80629-45-4,82468-64-2,84823-19-8,84823-20-1,87391-79-5,92009-30-8,92418-31-0,92418-46-7,72025-60-6)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃; for 3.5h;

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

Reference yield:

C26H22O8 (55797-81-4,105453-39-2) → leukotriene C1 (72025-60-6,73466-14-5,74841-69-3,76738-45-9,79026-71-4,79026-72-5,80629-45-4,82468-64-2,84823-19-8,84823-20-1,87391-79-5,92009-30-8,92418-31-0,92418-46-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / benzoic acid / 1,2-dimethoxy-ethane / 4 h / Heating

2: 100 percent / H₂SO₄ / 3 h / 23 °C

3: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

4: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

5: 99 percent / dry hydroden chloride / 72 h / 23 °C

6: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

7: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

8: 96 percent / Collins reagent / CH₂Cl₂ / 0.25 h / 23 °C

9: 46 percent / 1.) s-BuLi, 3.) phosphate buffer / diethyl ether / 1.) - 78 deg C, 45 min, 2.) -110 deg C, 15 min; -78 deg C, 30 min

10: 1.) hexamethylphosphoric amide / 1.) THF, -60 deg C, 10 s, 2.) -95 deg C, 20 min

11: Et₃N / methanol / 4 h / 23 °C

12: K₂CO₃ / methanol; H₂O / 3 h / 23 °C

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; amalgamated zinc; phosphate buffer; Collins oxidation agent; sulfuric acid; hydrogen; sec.-butyllithium; potassium carbonate; triethylamine; benzoic acid; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water;

DOI:10.1021/ja00524a045

Reference yield:

C32H30O10 (73957-95-6,74006-65-8) → leukotriene C1 (72025-60-6,73466-14-5,74841-69-3,76738-45-9,79026-71-4,79026-72-5,80629-45-4,82468-64-2,84823-19-8,84823-20-1,87391-79-5,92009-30-8,92418-31-0,92418-46-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

2: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

3: 99 percent / dry hydroden chloride / 72 h / 23 °C

4: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

5: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

6: 96 percent / Collins reagent / CH₂Cl₂ / 0.25 h / 23 °C

7: 46 percent / 1.) s-BuLi, 3.) phosphate buffer / diethyl ether / 1.) - 78 deg C, 45 min, 2.) -110 deg C, 15 min; -78 deg C, 30 min

8: 1.) hexamethylphosphoric amide / 1.) THF, -60 deg C, 10 s, 2.) -95 deg C, 20 min

9: Et₃N / methanol / 4 h / 23 °C

10: K₂CO₃ / methanol; H₂O / 3 h / 23 °C

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; amalgamated zinc; phosphate buffer; Collins oxidation agent; hydrogen; sec.-butyllithium; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/ja00524a045

upstream raw materials:

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

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

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

(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

Downstream raw materials:

Leukotriene C4 sulfone

6-trans-Leukotriene B₄

(5S,12S)-6-trans-leukotriene B

Refernces

• 1、 Rokach, Joshua,Young, Robert N.,Kakushima, Masatoshi,Lau, Cheuk-Kun,Seguin, Rick,at al.. "SYNTHESIS OF LEUKOTRIENES - NEW SYNTHESIS OF NATURAL LEUKOTRIENE A4". . p. 979 - 982. Retrieved 2007/10/02.
• 2、 Baker, S. Richard,Jamieson, William B.,Osborne, David J.,Ross, William J.. "SYNTHESIS OF THE 9Z and 9Z,11E ISOMERS OF LEUKOTRIENE C4". . p. 2505 - 2508. Retrieved 2007/10/02.