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
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
Assay
~98%
concentration
~75 μg/mL in ethanol
shipped in
dry ice
storage temp.
−20°C
SMILES string
CCCCC\C=C/C\C=C/C/C=C\C=C\[C@@H](O)CCCC(O)=O
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class Code
3 - Flammable liquids
WGK
WGK 1
Flash Point(F)
57.2 °F
Flash Point(C)
14 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
W S Powell et al.
The Journal of biological chemistry, 267(27), 19233-19241 (1992-09-25)
Human polymorphonuclear leukocytes (PMNL) convert 6-trans isomers of leukotriene B4 (LTB4) to dihydro metabolites (Powell, W.S., and Gravelle, F. (1988) J. Biol. Chem. 263, 2170-2177). In the present study we investigated the mechanism for the initial step in the formation
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
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
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