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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

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

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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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.
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)
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
Lloyd Tanner et al.
Journal of innate immunity, 12(3), 203-225 (2019-09-19)
Chronic obstructive pulmonary disease (COPD) affects the lives of an ever-growing number of people worldwide. The lack of understanding surrounding the pathophysiology of the disease and its progression has led to COPD becoming the third leading cause of death worldwide.
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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