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E1768

Sigma-Aldrich

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:
1191-85-1
Molecular Weight:
296.40
Beilstein:
1798411
MDL number:
MFCD00036967
UNSPSC Code:
12352106
PubChem Substance ID:
24894432
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥97%

form

powder

mp

78-80 °C

solubility

ethanol: 50 mg/mL, clear, colorless to yellow

storage temp.

−20°C

SMILES string

CCCCCC#CCC#CCC#CCC#CCCCC(O)=O

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)

InChI key

MGLDCXPLYOWQRP-UHFFFAOYSA-N

Gene Information

human ... ALOX15(246)

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
088K37972V
088K37972
088K37971
077H3781
075H3806

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Christine L Oltman et al.
American journal of physiology. Heart and circulatory physiology, 285(6), H2309-H2315 (2003-07-19)
Reactive oxygen species (ROS) have been proposed to mediate vasodilation in the microcirculation. We investigated the role of ROS in arachidonic acid (AA)-induced coronary microvascular dilation. Porcine epicardial coronary arterioles (110 +/- 4 microm diameter) were mounted onto pipettes in
Deepti Dabral et al.
Biochemical and biophysical research communications, 515(2), 261-267 (2019-05-28)
The canonical Phospholipase A2 (PLA2) metabolites lysophosphatidylcholine (LPC) and arachidonic acid (ARA) affect regulated exocytosis in a wide variety of cells and are proposed to directly influence membrane merger owing to their respective spontaneous curvatures. According to the Stalk-pore hypothesis
Crystal J J Lee et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(7), 2468-2483 (2011-04-20)
Thalidomide (TD) causes birth defects in humans and rabbits via several potential mechanisms, including bioactivation by embryonic prostaglandin H synthase (PHS) enzymes to a reactive intermediate that enhances reactive oxygen species (ROS) formation. We show herein that TD in rabbit
C Wolfrum et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(5), 2323-2328 (2001-02-28)
Peroxisome proliferator-activated receptor alpha (PPARalpha) is a key regulator of lipid homeostasis in hepatocytes and target for fatty acids and hypolipidemic drugs. How these signaling molecules reach the nuclear receptor is not known; however, similarities in ligand specificity suggest the
Fredrik Elinder et al.
Frontiers in physiology, 8, 43-43 (2017-02-22)
Polyunsaturated fatty acids (PUFAs) act on most ion channels, thereby having significant physiological and pharmacological effects. In this review we summarize data from numerous PUFAs on voltage-gated ion channels containing one or several voltage-sensor domains, such as voltage-gated sodium (NaV)
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