E3140
5,8,11-Eicosatriynoic acid
≥98%
Synonym(s):
ETI
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About This Item
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
UNSPSC Code:
12352202
PubChem Substance ID:
MDL number:
InChI
1S/C20H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-8,11,14,17-19H2,1H3,(H,21,22)
SMILES string
CCCCCCCCC#CCC#CCC#CCCCC(O)=O
InChI key
OWYNLPMPYBYKJP-UHFFFAOYSA-N
assay
≥98%
form
powder
solubility
methanol: 10 mg/mL, clear, colorless to light yellow
storage temp.
−20°C
Biochem/physiol Actions
The acetylenic analog of 5,8,11-eicosatrienoic acid is an inhibitor of 12-lipoxygenase and, in MDCK cells, triggers release of Ca2+ from endoplasmic reticulum and other intracellular stores.
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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L Orning et al.
The Journal of biological chemistry, 255(17), 8023-8026 (1980-09-10)
Leukotriene C4 and leukotriene D4 are slow reacting substances produced by mouse mastocytoma cells and rat basophilic leukemia cells, respectively. Serine x borate complex, an inhibitor of glutamyl transpeptidase (EC 2.3.2.2), prevented the formation of the biologically more potent leukotriene
J Nakao et al.
Atherosclerosis, 43(2-3), 143-150 (1982-06-01)
The migration of rat aortic smooth muscle cells was measured in modified Boyden chambers. Smooth muscle cells were motile in vitro and their migration was stimulated (time- and dose-dependently) by a platelet-derived factor. Treatment of platelets with indomethacin resulted in
R S Barlow et al.
The American journal of physiology, 275(4 Pt 2), H1283-H1289 (1998-09-24)
It has been known for a number of years that neutrophils and macrophages secrete H2O2 while fighting disease, and the levels obtained within the vasculature under these conditions can reach several hundred micromolar. Because the effect of H2O2 on vascular
F Saito et al.
Hypertension (Dallas, Tex. : 1979), 20(2), 138-143 (1992-08-01)
Previous studies have shown that inhibition of the lipoxygenase pathway of arachidonic acid metabolism can prevent the development of elevated blood pressure in renin-dependent models of hypertension. Agents that inhibit the lipoxygenase pathway such as phenidone and the flavonoid baicalein
S J Craib et al.
British journal of pharmacology, 134(1), 30-37 (2001-08-28)
1. In the absence of indomethacin, anandamide did not contract the guinea-pig bronchus at concentrations up to 100 microM. In the presence of indomethacin (10 microM), anandamide induced concentration-related contractions with a pEC(50) value of 5.18+/-0.11. It was significantly less
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