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L0517

Sigma-Aldrich

Leukotriene B4

~100 μg/mL in ethanol, ≥97%

Synonym(s):

[5S,12R]-Dihydroxy-[6Z,8E,10E,14Z]-eicosatetraenoic acid

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About This Item

Empirical Formula (Hill Notation):
C20H32O4
CAS Number:
71160-24-2
Molecular Weight:
336.47
EC Number:
200-578-6
MDL number:
MFCD00135630
UNSPSC Code:
12352200
PubChem Substance ID:
24896256
NACRES:
NA.77

Quality Level

200

Assay

≥97%

form

liquid

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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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.
Shyam Panthi et al.
Eye & contact lens, 45(3), 171-181 (2018-10-12)
Lipid mediators of inflammation are a group of signaling molecules produced by various cells under physiological conditions and modulate the inflammatory process during various pathologic conditions. Although eicosanoids and F2-isoprostanes are recognized lipid mediators of inflammation, there is no consensus
Preeti Subramanian et al.
Investigative ophthalmology & visual science, 57(11), 4581-4588 (2016-09-17)
5-Lipoxygenase (5-LOX) oxygenates arachidonic acid to form 5-hydroperoxyeicosatetraenoic acid, which is further converted into biologically detrimental leukotrienes, such as leukotriene B4 (LTB4). The RPE and retina express the PNPLA2 gene for pigment epithelium-derived factor receptor (PEDF-R), a lipase involved in
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