L0517

Sigma-Aldrich

Leukotriene B4

~100 μg/mL in ethanol, ≥97%

Synonym(s):
[5S,12R]-Dihydroxy-[6Z,8E,10E,14Z]-eicosatetraenoic acid
Empirical Formula (Hill Notation):
C20H32O4
CAS Number:
Molecular Weight:
336.47
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥97%

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O

InChI

1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

InChI key

VNYSSYRCGWBHLG-AMOLWHMGSA-N

Gene Information

human ... LTB4R(1241)
rat ... Ltb4r(59264)

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Biochem/physiol Actions

Proinflammatory agent. Stimulates c-Fos and c-Jun proto-oncogene transcription in human monocytes. Stimulates chemotaxis, aggregation, and degranulation of polymorphonuclear leukocytes.

Features and Benefits

This compound is featured on the Leukotriene Receptors and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

Data sheet which accompanies each product includes special handling instructions. Except where noted, method for hydrolysis of methyl esters is also described.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

RIDADR

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

L Iversen et al.
The Journal of investigative dermatology, 100(3), 293-298 (1993-03-01)
In the present study, keratinocytes were coincubated with human neutrophils to determine whether or not an increase in leukotriene B4 formation can occur. Human keratinocytes used were cultured in serum-free, low-calcium medium, whereas neutrophils were purified from heparinized venous blood....
Romy R M C Keijsers et al.
The Journal of investigative dermatology, 134(5), 1276-1284 (2013-12-10)
Clinical trials successfully using antibodies targeting IL-17 in psoriasis support the importance of IL-17 in the pathophysiology of this disease. However, there is a debate concerning the source and dynamics of IL-17 production in inflamed skin. Here we characterized IL-17-producing...
Leukotriene A4 hydrolase and leukotriene B4 metabolism.
T Yokomizo et al.
Journal of lipid mediators and cell signalling, 12(2-3), 321-332 (1995-10-01)
Leukotriene A4 hydrolase/aminopeptidase, the gatekeeper of chemotactic leukotriene B4 biosynthesis.
Jesper Z Haeggström
The Journal of biological chemistry, 279(49), 50639-50642 (2004-09-02)
Nicolas Cenac et al.
Gastroenterology, 149(2), 433-444 (2015-04-26)
In mice, activation of the transient receptor potential cation channels (TRP) TRPV1, TRPV4, and TRPA1 causes visceral hypersensitivity. These receptors and their agonists might be involved in development of irritable bowel syndrome (IBS). We investigated whether polyunsaturated fatty acid (PUFA)...
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