H6643
(+)-5(S)-Hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoic acid
~75 μg/mL in ethanol, ~98%
Synonym(s):
(+)-5-HETE, 5(S)-HETE
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About This Item
Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
Molecular Weight:
320.47
UNSPSC Code:
12352211
PubChem Substance ID:
MDL number:
SMILES string
CCCCC\C=C/C\C=C/C/C=C\C=C\[C@@H](O)CCCC(O)=O
assay
~98%
concentration
~75 μg/mL in ethanol
shipped in
dry ice
storage temp.
−20°C
Biochem/physiol Actions
A substrate for hydroxyeicosanoid dehydrogenase in polymorphonuclear (PMN) leucocytes, where it is converted to 5-oxo-ETE. Both compounds are reported to increase the intracellular mobilization of calcium in PMN leucocytes.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk
WGK 1
flash_point_f
57.2 °F
flash_point_c
14 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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E J Goetzl
Nature, 288(5787), 183-185 (1980-11-13)
The arachidonic acid released from cellular phospholipids of specifically stimulated platelets and leukocytes is oxygenated enzymatically by two major pathways. A complex cycloxygenase converts some of the free arachidonic acid to labile endoperoxides that are transformed to prostaglandins, thromboxanes and
Santiago E Farias et al.
The Journal of trauma, 71(5), 1211-1218 (2011-03-24)
Enzymatic and nonenzymatic oxidation of polyunsaturated fatty acids leads to the formation of biologically active products known as lipid mediators. In the brain, lipid mediators play an important role in supporting homeostasis and normal function. Thus, levels of these metabolites
Thorsten J Maier et al.
Biochemical pharmacology, 76(7), 862-872 (2008-08-12)
Celecoxib is a selective cyclooxygenase-2 (COX-2) inhibitor used in the therapy of inflammatory and painful conditions. Various COX-2-independent pharmacological effects, such as a chemo-preventive and tumor-regressive activity have been suggested, but the respective non-COX-2 targets of celecoxib are still a
Stephen R Clark et al.
Blood, 117(6), 2033-2043 (2010-12-24)
5-Lipoxygenase (5-LOX) plays key roles in infection and allergic responses. Herein, four 5-LOX-derived lipids comprising 5-hydroxyeicosatetraenoic acid (HETE) attached to phospholipids (PLs), either phosphatidylethanolamine (PE) or phosphatidylcholine (18:0p/5-HETE-PE, 18:1p/5-HETE-PE, 16:0p/5-HETE-PE, and 16:0a/5-HETE-PC), were identified in primary human neutrophils. They formed
Pranav Patel et al.
The Journal of pharmacology and experimental therapeutics, 329(1), 335-341 (2009-01-24)
5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) is a metabolite of the 5-lipoxygenase (5-LO) product 5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-HETE), formed by the microsomal enzyme 5-hydroxyeicosanoid dehydrogenase (5-HEDH). 5-oxo-ETE is a chemoattractant for neutrophils and eosinophils, both in vitro and in vivo. To examine the substrate
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