Leukotriene B4 (HCID 5280492)

Overview

Leukotriene B4 is a leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway. It has a role as a vasoconstrictor agent, a mouse metabolite, a plant metabolite and a human metabolite. It is a hydroxy polyunsaturated fatty acid, a long-chain fatty acid, a leukotriene and a dihydroxy monocarboxylic acid. It is functionally related to an icosa-6,8,10,14-tetraenoic acid. It is a conjugate acid of a leukotriene B4(1-).

Names & identifiers

Preferred name: Leukotriene B4
IUPAC: (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
English name: Leukotriene B4
Molecular formula: C20H32O4
Molecular weight: 336.47

Names & synonyms

LEUKOTRIENE B4LTB471160-24-25,12-Hete(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acidLEUKOTRIENE_B41HGW4DR56D5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid5S,12R-diHETEDTXSID4037162CHEBI:15647(6z,8e,10e,14z)-(5s,12r)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate

Show more names

Leukotriene B?LTB4 (Leukotriene B4)VNYSSYRCGWBHLG-AMOLWHMGSA-NLeukotriene B4 MaxSpecStandardleukotriene B4 ethanol solutionLeukotriene B4 Lipid Maps MS StandardLeukotriene B - CAS 71160-24-2 - Calbiochem

Leukotriene B5,12 diHETELeukotriene B 4Leukotriene B-4B-4, LeukotrieneRefChem:1531495,12 HETEDTXCID401765891

Database identifiers

CAS: 71160-24-2
PubChem CID: 5280492
DTXSID: DTXSID4037162
ChEMBL: CHEMBL65061
ChEBI: CHEBI:15647
UNII: 1HGW4DR56D
Nikkaji: J240.041C

Properties

Computed structural properties

XLogP: 4.1
Topological polar surface area: 77.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 14
Heavy atoms: 24
Formal charge: 0
Complexity: 421

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biochemical Research

DrugsPharmaceuticals -> Listed in ZINC15

LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Leukotrienes [FA0302]

Physical Description · 2 items

Colorless liquid; [Fisher Scientific MSDS]

Solid

Collision Cross Section · 3 items

185.3 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

187.44 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

186.8 Å² [M-H]-

Physicochemical properties

Boiling point: 536.4 · 536.4±50.0 °C(Predicted)
Density: 1.04 · 1.040±0.06 g/cm3(Predicted)
Flash point: 14 °C · 14 °C
storage temp.: -20 °C · -20°C
solubility: Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 50μg/ml)
form: Clear oil
pka: 4.66 · 4.66±0.10(Predicted)
color: Colorless to light yellow
InChIKey: VNYSSYRCGWBHLG-AMOLWHMGSA-N
SMILES: CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
CAS DataBase Reference: 71160 · 71160-24-2(CAS DataBase Reference)
FDA UNII: 1 HGW4DR56D · 1HGW4DR56D
UNSPSC Code: 12352211 · 12352211
NACRES: 77 · NA.77
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger
Hazard statements: 225 · H225-H319
Precautionary statements: 210 · P210-P233-P240-P241-P242-P305+P351+P338
Hazard Codes: F
Risk Statements: 11 · 11
Safety Statements: 7 · 7-16
RIDADR: 1170 · UN 1170 3/PG 2
WGK Germany: 1 · 1
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Flam · Eye Irrit. 2Flam. Liq. 2

Safety & regulation

Hazard information

Hazards SummaryAn irritant; Inhalation of high concentrations may cause bronchospasm and delayed pulmonary edema; [Fisher Scientific MSDS]

Toxicology

Adverse EffectsToxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

Safety data

wgk: 1
ridadr: UN 1170 3/PG 2
risk_code: 11
Signal word: Danger
Symbol(GHS): GHS02,GHS07
hazard_code: F
safety_code: 7-16
Storage Class: 3 - Flammable liquids
Hazard statements: H225-H319
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2
Precautionary statements: P210-P233-P240-P241-P242-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsEpidermis

Cellular LocationsCytoplasm

Metabolite PathwaysAcetaminophen Action Pathway

Uses & manufacturing

Uses · 1 item

Leukotrienes are metabolites of arachidonic acid that are chemically related to prostaglandins and thromboxanes; They are potent bronchoconstrictors that serve an important role in immediate hypersensitivity reactions; [Merck Index] The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990) [ChemIDplus]

Applications · 2 items

DescriptionLeukotriene 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.

UsesLTB4 (Leukotriene B4) is a potent chemokine with roles in inflammation, immunology, the nervous system, brain and skin.