12-Oxo-ltb4

Base Information

• Chemical Name: 12-Oxo-ltb4
• CAS No.: 136696-10-1
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• DSSTox Substance ID: DTXSID10869862
• Metabolomics Workbench ID: 2582
• Nikkaji Number: J662.082E
• Wikidata: Q27103352
• Mol file: 136696-10-1.mol

Synonyms:12-oxo-LTB4;12-oxoleukotriene B4

Chemical Property of 12-Oxo-ltb4

Chemical Property:

• Vapor Pressure: 3.52E-13mmHg at 25°C
• Boiling Point: 524.2°Cat760mmHg
• PKA: 4.66±0.10(Predicted)
• Flash Point: 284.9°C
• PSA: 74.60000
• Density: 1.036g/cm³
• LogP: 4.36650
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 334.21440943
• Heavy Atom Count: 24
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

12-OxoleukotrieneB4inacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(=O)C=CC=CC=CC(CCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O
• Description: Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway. It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. 12-oxo LTB4 is an initial metabolite of LTB4 formed via the LTB4 12-hydroxydehydrogenase pathway. It is rapidly converted to 10,11-dihydro-12-oxo-LTB4, followed by reduction of the 12-oxo group to give 10,11-dihydro-LTB4. 12-oxo-LTB4 (EC50 = 33 nM) is about 70-fold less potent than LTB4 (EC50 = 0.46 nM) at stimulating Ca2+ mobilization in human neutrophils. It is also significantly less potent than LTB4 at stimulating neutrophil migration with EC50 values of 170 and 2.7 nM for 12-oxo-LTB4 and LTB4, respectively.

Technology Process of 12-Oxo-ltb4

There total 4 articles about 12-Oxo-ltb4 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: 55.0%

5(S)-Hydroxy-12,12-(trimethylenedithio)-6(E),8(E),10(E),14(Z)-eicosatetraenoic acid → 5(S)-Hydroxy-12-oxo-6(E),8(E),10(E),14(Z)-eicosatetraenoic acid (136696-10-1)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; In methanol; water; for 0.0333333h; Ambient temperature;

DOI:10.1021/jo00111a044

Reference yield:

5(S)-Hydroxy-12,12-(trimethylenedithio)-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid → 12-keto-leukotriene B4 (136696-10-1) + 5(S)-Hydroxy-12-oxo-6(E),8(E),10(E),14(Z)-eicosatetraenoic acid (136696-10-1)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; In methanol; water; for 0.0333333h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00111a044

Reference yield:

5(S)-Hydroxy-12,12-(trimethylenedithio)-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid → 12-keto-leukotriene B4 (136696-10-1) + 5(S)-Hydroxy-12-oxo-6(E),8(E),10(E),14(Z)-eicosatetraenoic acid (136696-10-1)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; In methanol; water; for 0.0333333h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00111a044

upstream raw materials:

Leukotriene B

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