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MilliporeSigma

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/REAXYS Number:
1798411
MDL number:
MFCD00036967
UNSPSC Code:
12352106
PubChem Substance ID:
24894432
NACRES:
NA.77

Key Documents

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
088K37972V
088K37972
088K37971
129H3853
100K3854

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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
Günther F E Scherer et al.
FEBS letters, 581(22), 4205-4211 (2007-08-19)
Auxin increases phospholipase A(2) activity within 2min (Paul, R., Holk, A. and Scherer, G.F.E. (1998) Fatty acids and lysophospholipids as potential second messengers in auxin action. Rapid activation of phospholipase A(2) activity by auxin in suspension-cultured parsley and soybean cells.
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
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
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
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