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:
Pricing and availability is not currently available.
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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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
François D Graham et al.
Free radical biology & medicine, 47(1), 62-71 (2009-04-21)
Neutrophils spontaneously undergo apoptosis, which is associated with increased oxidative stress. We found that there is a dramatic shift in the formation of 5-lipoxygenase products during this process. Freshly isolated neutrophils rapidly convert leukotriene B(4) (LTB(4)) and 5-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE)
N A Pawlowski et al.
The Journal of experimental medicine, 158(2), 393-412 (1983-08-01)
Purified human monocytes release and metabolize endogenous arachidonic acid (20:4) from phospholipid stores when challenged with particulate inflammatory stimuli or the calcium ionophore A23187. Using radiolabeled cultures, the percentage of total [3H]20:4 released was similar with each type of stimulus.
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