E1768
5,8,11,14-Eicosatetraynoic acid
≥97%
Synonym(s):
ETYA, Octadehydroarachidonic acid
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About This Item
Empirical Formula (Hill Notation):
C20H24O2
CAS Number:
Molecular Weight:
296.40
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1798411
InChI
1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
SMILES string
CCCCCC#CCC#CCC#CCC#CCCCC(O)=O
InChI key
MGLDCXPLYOWQRP-UHFFFAOYSA-N
biological source
synthetic (organic)
assay
≥97%
form
powder
mp
78-80 °C
solubility
ethanol: 50 mg/mL, clear, colorless to yellow
storage temp.
−20°C
Quality Level
Gene Information
human ... ALOX15(246)
Related Categories
Biochem/physiol Actions
Eicosatetraynoic acid (ETYA) is a non-metabolizable analog of ω-6 arachidonic acid. ETYA is a strong activator of the human peroxisome proliferator-activated receptor α (PPARα). It acts as an inhibitor of lipoxygenases (LOX) and cyclooxygenases (COX).
Eicosatetraynoic acid is a lipoxygenase and cyclooxygenase inhibitor.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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A S Taylor et al.
Prostaglandins, 29(3), 449-458 (1985-03-01)
5,8,11,14-eicosatetraynoic acid (ETYA), a widely used inhibitor of cyclooxygenase and lipoxygenase, inhibited the incorporation of 14C-arachidonic acid into cell lipids of the murine thymoma EL4 whereas oleic acid had no effect. Inhibition appeared to result from the ability of ETYA
Parissa Taheri et al.
Journal of plant physiology, 167(3), 201-208 (2009-09-05)
Vitamins are plant growth regulators and activators of defense responses against pathogens. The cytomolecular mechanisms involved in the induction of resistance by chemicals especially vitamins on monocotyledonous plants are largely unknown. Here, we show that riboflavin, which acts as a
Kazuhiro Tamura et al.
Vascular pharmacology, 44(6), 411-416 (2006-05-03)
To address the role of prostaglandin E2 (PGE2) in tube formation of endothelial cells and the relationships between the action of PGE2 and vascular endothelial growth factor (VEGF), cultured human umbilical vein endothelial cells (HUVECs) were used to evaluate tube
Marcelo D Carattino et al.
The Journal of biological chemistry, 278(38), 36202-36213 (2003-07-03)
Epithelial Na+ channels (ENaCs) are regulated by the phospholipase A2 (PLA2) product arachidonic acid. Pharmacological inhibition of PLA2 with aristolochic acid induced a significant increase in amiloride-sensitive currents in Xenopus oocytes expressing ENaC. Arachidonic acid or 5,8,11,14-eicosatetraynoic acid (ETYA), a
Miriam Guizy et al.
American journal of physiology. Cell physiology, 289(5), C1251-C1260 (2005-07-01)
Dietary polyunsaturated fatty acids (PUFAs) have been reported to exhibit antiarrhythmic properties, which have been attributed to their availability to modulate Na(+), Ca(2+), and several K(+) channels. However, their effects on human ether-a-go-go-related gene (HERG) channels are unknown. In this
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