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L0517

Leukotriene B₄

Name: Leukotriene B<SUB>4</SUB>
Brand: SIGMA

~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

GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Precautionary Statements

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

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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Ellen Tufvesson et al.

International journal of chronic obstructive pulmonary disease, 12, 3211-3219 (2017-11-16)

The presence of bacteria in the lower airways in COPD results in inflammation, further airway structural damage, and might lead to repeated exacerbations. We have previously shown that chronic colonization of

Leukotriene B4 in the immune system.

H E Claesson et al.

International journal of immunopharmacology, 14(3), 441-449 (1992-04-01)

Leukotriene (LT) B4 is a biologically active molecule derived from arachidonic acid via the 5-lipoxygenase pathway. It mediates certain inflammatory and immunological reactions. The role of LTB4 in the immune system has been questioned since lymphocytes have been regarded to

A Novel Inhibitor of 5-Lipoxygenase (5-LOX) Prevents Oxidative Stress-Induced Cell Death of Retinal Pigment Epithelium (RPE) Cells.

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

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)

Quantification and Potential Functions of Endogenous Agonists of Transient Receptor Potential Channels in Patients With Irritable Bowel Syndrome.

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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