H4019

Sigma-Aldrich

8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoic acid

~100 μg/mL in ethanol, ~98% (HPLC)

Synonym(s):
8(S)-HETE
Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
Molecular Weight:
320.47
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

assay

~98% (HPLC)

Quality Level

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C/C=C\C=C\[C@@H](O)C\C=C/CCCC(O)=O

InChI

1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1

InChI key

NLUNAYAEIJYXRB-VYOQERLCSA-N

Packaging

10 μg in glass bottle
Packaged under Argon.

Biochem/physiol Actions

Arachidonic acid metabolite that stimulates epithelial cell migration during wound healing. Activates PPAR-α (peroxisome proliferator-activated receptor-α).

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H4019.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN1170 - class 3 - PG 2 - Ethanol

WGK Germany

WGK 1

M Yamada et al.
Cornea, 19(3 Suppl), S13-S20 (2000-06-01)
We previously found that the inhibition of lipoxygenases resulted in delayed epithelial wound closure in organ-cultured rat corneas. The present study was undertaken to determine the lipoxygenase enzyme and metabolite(s) responsible for regulating reepithelialization and their mechanism of action. The...
Y Guan et al.
The American journal of physiology, 273(6 Pt 2), F1013-F1022 (1998-01-22)
Peroxisome proliferator-activated receptors (PPARs, alpha, beta/delta, and gamma) are members of the nuclear receptor superfamily of ligand-activated transcription factors. PPARs regulate the expression of genes involved in lipid metabolism. 8(S)-hydroxyeicosatetraenoic acid (8-S-HETE), leukotriene B4 (LTB4), and hypolipidemic fibrates activate PPAR...
K Yu et al.
The Journal of biological chemistry, 270(41), 23975-23983 (1995-10-13)
Peroxisome proliferator-activated receptors (PPARs) are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear, however, what naturally occurring compounds...
Janny C de Grauw et al.
Arthritis research & therapy, 13(4), R123-R123 (2011-07-29)
Articular tissues are capable of producing a range of eicosanoid mediators, each of which has individual biological effects and may be affected by anti-inflammatory treatment. We set out to develop and evaluate a high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS)...
Ayako Furugen et al.
Biomedical chromatography : BMC, 29(7), 1084-1093 (2014-12-03)
Leukotrienes (LTs) and hydroxyeicosatetraenoic acids (HETEs) are important bioactive lipid mediators that participate in various pathophysiological processes. To advance understanding of the mechanisms that regulate these mediators in physiological and pathological processes, an analytical method using liquid chromatography/tandem mass spectrometry...

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