20-Carboxy-leukotriene B4

Base Information

• Chemical Name: 20-Carboxy-leukotriene B4
• CAS No.: 80434-82-8
• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.455
• European Community (EC) Number: 632-880-2
• ChEMBL ID: CHEMBL1592630
• DSSTox Substance ID: DTXSID301313358
• Metabolomics Workbench ID: 2574
• Nikkaji Number: J2.760.808F
• Wikidata: Q27103196
• Mol file: 80434-82-8.mol

Synonyms:20-carboxy-leukotriene B4;20-carboxyleukotriene B4;20-COOH LTB4;5(S),12(R)-dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acid

Chemical Property of 20-Carboxy-leukotriene B4

Chemical Property:

• Vapor Pressure: 2.73E-16mmHg at 25°C
• Boiling Point: 588.3°C at 760 mmHg
• PKA: 4.66±0.10(Predicted)
• Flash Point: 323.6°C
• PSA: 115.06000
• Density: 1.151g/cm³
• LogP: 3.22300
• Storage Temp.: −20°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 366.20423867
• Heavy Atom Count: 26
• Complexity: 504

Purity/Quality:

99% ^*data from raw suppliers

20-COOH-LTB4 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(=O)O)CC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
• Isomeric SMILES: C(CCC(=O)O)C/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O
• Description: 20-carboxy LTB4 is a metabolite of LTB4 in human neutrophils. In human leukocytes, LTB4 is inactivated by the enzyme LTB4 20-hydroxylase. The resulting 20-hydroxy LTB4 is further oxidized to 20-carboxy LTB4. LTB4 metabolism in isolated rat hepatocytes also results in production of 20-carboxy LTB4 along with other ω-oxidation products. The biological activity of 20-carboxy LTB4 is only about 2.6% compared to that of LTB4 in causing PMNL degranulation.
• Uses: 20-COOH-LTB4 is a leukotriene B4 metabolite and substrate for β-oxidation pathways.

Technology Process of 20-Carboxy-leukotriene B4

There total 19 articles about 20-Carboxy-leukotriene B4 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: 70.0%

(6Z,8E,10E,14Z)-(5S,12R)-5-Benzoyloxy-12-hydroxy-icosa-6,8,10,14-tetraenedioic acid 1-ethyl ester 20-methyl ester (85615-54-9) → 20-Carboxyleukotriene B4 (80434-82-8)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)85704-4

Reference yield:

(6Z,8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,10,14-tetraenedioic acid dimethyl ester (106027-35-4) → 20-Carboxyleukotriene B4 (80434-82-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 25 ℃;

DOI:10.1016/S0040-4039(00)84400-7

Reference yield:

5-hexyl-1-ol (928-90-5) → 20-Carboxyleukotriene B4 (80434-82-8)

Guidance literature:

Multi-step reaction with 8 steps

3: imidazole / dimethylformamide / 0 - 25 °C

4: pyridinium p-toluene sulphonate / methanol / 48 °C

5: CrO_3.2pyr., celite / CH₂Cl₂ / 0 °C

6: LDA / tetrahydrofuran / -78 - 25 °C

7: hydrogen / Lindlar

8: nBu₄NF / tetrahydrofuran / 0 - 25 °C

With 1H-imidazole; Celite; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; dipyridine chromium trioxide; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84400-7

upstream raw materials:

(6Z,8E,10E,14Z)-(5S,12R)-5-Benzoyloxy-12-hydroxy-icosa-6,8,10,14-tetraenedioic acid 1-ethyl ester 20-methyl ester

(6Z,8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,10,14-tetraenedioic acid dimethyl ester

6-carboxy hexylidene triphenylphosphorane

(Z)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-dec-6-enoic acid methyl ester

Downstream raw materials:

(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenedioic acid dimethyl ester

Refernces

• 1、 Zamboni, Robert,Rokach, Joshua. "STEREOSPECIFIC SYNTHESIS OF TWO METABOLITES OF LTB4". . p. 4751 - 4754. Retrieved 2007/10/02.