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
Certificates of Analysis (COA)
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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
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
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
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
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