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Key Documents

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E1768

Sigma-Aldrich

5,8,11,14-Eicosatetraynoic acid

≥97%

Sinónimos:

ETYA, Octadehydroarachidonic acid

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About This Item

Fórmula empírica (notación de Hill):
C20H24O2
Número de CAS:
1191-85-1
Peso molecular:
296.40
Beilstein/REAXYS Number:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
YiLin Ren et al.
Hypertension (Dallas, Tex. : 1979), 53(2), 319-323 (2008-12-03)
In the renal cortex, the connecting tubule (CNT) returns to the glomerular hilum and contacts the afferent arteriole (Af-Art). Increasing Na delivery to the CNT dilates the Af-Art by activating epithelial Na channels, a process that we call connecting tubule
Enrico Dainese et al.
Journal of molecular biology, 349(1), 143-152 (2005-05-07)
Soybean lipoxygenase-1 (LOX-1) is used widely as a model for studying the structural and functional properties of the homologous family of lipoxygenases. The crystallographic structure revealed that LOX-1 is organized in a beta-sheet N-terminal domain and a larger, mostly helical
Ming-Xiao Wang et al.
American journal of physiology. Renal physiology, 318(6), F1369-F1376 (2020-04-21)
Cytochrome P-450 (Cyp) epoxygenase-dependent metabolites of arachidonic acid (AA) have been shown to inhibit renal Na+ transport, and inhibition of Cyp-epoxygenase is associated with salt-sensitive hypertension. We used the patch-clamp technique to examine whether Cyp-epoxygenase-dependent AA metabolites inhibited the basolateral
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