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Merck
CN

H6643

Sigma-Aldrich

(+)-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:
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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.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard 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

Regulatory Information

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William S Powell et al.
Progress in lipid research, 44(2-3), 154-183 (2005-05-17)
5-Oxo-ETE (5-oxo-6,8,11,14-eicosatetraenoic acid) is an arachidonic acid metabolite formed by the oxidation of 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) by 5-hydroxyeicosanoid dehydrogenase (5-HEDH), a microsomal enzyme found in leukocytes and platelets. 5-HEDH is highly selective for 5S-HETE, and displays little activity for other
Gail E Grant et al.
Carcinogenesis, 32(6), 822-828 (2011-03-12)
The 5-lipoxygenase (5-LO) product 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE), which is a potent chemoattractant for myeloid cells, is known to promote the survival of prostate cancer cells. In the present study, we found that PC3 prostate cancer cells and cell lines derived
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
N A Soter
The Journal of investigative dermatology, 96(3), 32S-38S (1991-03-01)
The most frequent site of organ involvement in patients with any form of mastocytosis is the skin. Cutaneous expressions include urticaria pigmentosa, mastocytoma, diffuse and erythrodermic cutaneous mastocytosis, and telangiectasia macularis eruptiva perstans. The cutaneous lesions tend to appear early
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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