Leukotriene B4

Base Information

• Chemical Name: Leukotriene B4
• CAS No.: 71160-24-2
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.472
• UNII: 1HGW4DR56D
• ChEMBL ID: CHEMBL65061
• DSSTox Substance ID: DTXSID4037162
• Metabolomics Workbench ID: 2561
• NCI Thesaurus Code: C609
• Nikkaji Number: J240.041C
• Pharos Ligand ID: VGZ6ZML6THLX
• Wikidata: Q2704449
• Wikipedia: Leukotriene_B4
• Mol file: 71160-24-2.mol

Synonyms:5,12 diHETE;5,12 HETE;5,12-diHETE;5,12-HETE;B-4, Leukotriene;Leukotriene B;Leukotriene B 4;Leukotriene B-4;Leukotriene B4;Leukotrienes B;LTB4

Chemical Property of Leukotriene B4

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 536.37°C at 760 mmHg
• PKA: 4.66±0.10(Predicted)
• Flash Point: 14 °C
• PSA: 77.76000
• Density: 1.04g/cm³
• LogP: 4.15830
• Storage Temp.: −20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 421

Purity/Quality:

98%,99%, ^*data from raw suppliers

Leukotriene B4 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CCCCCC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
• Isomeric SMILES: CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O
• Recent ClinicalTrials: Skin IaM: An Exploratory Clinical Trial to Evaluate Changes in Skin Appearance, Colour, and/or Texture Following the Induction of a Local Inflammatory Skin Response
• 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. In subnanomolar ranges (3.9 x 10?10 M), LTB4 causes chemotaxis and chemokinesis in human polymorphonuclear leukocytes. At higher concentrations, (1.0 x 10?7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production. 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. In subnanomolar ranges (3.9 x 10?10 M), LTB4 causes chemotaxis and chemokinesis in human polymorphonuclear leukocytes. At higher concentrations, (1.0 x 10?7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production. LTB4 MaxSpec? standard is a quantitative grade standard of LTB4 that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This LTB4 MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: LTB4 (Leukotriene B4) is a potent chemokine with roles in inflammation, immunology, the nervous system, brain and skin.

Technology Process of Leukotriene B4

There total 327 articles about 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: 95.0%

Methyl (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate (83058-42-8) → Leukotriene B (71160-24-2)

Guidance literature:

With lithium hydroxide; In water; isopropyl alcohol; at 23 ℃; for 1h;

DOI:10.1021/jo00065a012

Reference yield: 85.0%

5(S),12(R)-bis<(tert-butyldimethylsilyl)oxy>-6(7),8(E),10(E),14(Z)-eicosatetraenoic acid (115418-91-2) → Leukotriene B (71160-24-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 17h; Ambient temperature;

DOI:10.1021/jo00306a007

Reference yield: 82.0%

(5S,6Z,8E,10E,12R,14Z)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-6,8,10,14-eicosatetraenoate (90108-36-4) → Leukotriene B (71160-24-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 14h;

DOI:10.1021/jo00065a012

upstream raw materials:

5(S),12(R)-bis<(tert-butyldimethylsilyl)oxy>-6(7),8(E),10(E),14(Z)-eicosatetraenoic acid

Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester

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

Methyl (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate

Downstream raw materials:

6-trans-Leukotriene B₄

(6E,8Z,10Z,14Z)-(5S,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

LTB_x methyl ester

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