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4954

Sigma-Aldrich

Oleic Acid

Synonyma:

Oleic Acid, cis-9-Octadecenoic Acid, 18:1

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About This Item

Empirický vzorec (Hillův zápis):
C18H34O2
Číslo CAS:
112-80-1
Molekulová hmotnost:
282.46
MDL number:
MFCD00064242
UNSPSC Code:
12352211
NACRES:
NA.77

assay

≥99% (GC)

Quality Level

100

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

colorless

solubility

chloroform: 10 mg/mL
ethanol: 5 mg/mL

density

0.89 g/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

OC(=O)CCCCCCC\C=C\CCCCCCCC

InChI

1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+

InChI key

ZQPPMHVWECSIRJ-MDZDMXLPSA-N

General description

A cis-unsaturated fatty acid that has been shown to activate protein kinase C in hepatocytes. Potentiates acetylcholine receptor currents by activating CaM kinase II, independent of the PKC pathway.
Unsaturated fatty acid that has been shown to activate protein kinase C in hepatocytes. Density: 0.89 g/ml.

Biochem/physiol Actions

Cell permeable: no
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Other Notes

Nishizaki, T., et al. 1997. NeuroReport 8, 597.
Bessesen, D.H., et al. 1993. J. Lipid Res.34, 229.
Felden, F., et al. 1993. Biochem. Biophys. Res. Commun.190, 602.
Williams, L.L., et al. 1993. Proc. Soc. Exp. Biol. Med.202, 239.
Diaz-Guerra, M.J. 1991. J. Biol. Chem.266, 23568.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

Osvědčení o analýze (COA)

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M J Díaz-Guerra et al.
The Journal of biological chemistry, 266(35), 23568-23576 (1991-12-15)
The effect of oleate on the subcellular distribution of protein kinase C (PKC) was studied in isolated hepatocytes and in perfused rat liver in the presence of physiological concentrations of serum albumin. A time- and dose-dependent translocation of PKC from
F Felden et al.
Biochemical and biophysical research communications, 190(2), 602-608 (1993-01-29)
The free fatty acid (FFA) concentration in the epididymal cytosol of the adult rat was found to be 20-fold higher than in the serum. The binding of [3H] dihydrotestosterone to epididymal rat androgen binding protein (rABP) was modified by physiological
T Nishizaki et al.
Neuroreport, 8(3), 597-601 (1997-02-10)
Oleic acid, a cis-unsaturated free fatty acid, is proposed to be involved in the protein kinase C (PKC) activation pathway. Its biological actions, however, have not been well-characterized. We examined the effects of oleic acid on acetylcholine (ACh)-gated channel currents
D H Bessesen et al.
Journal of lipid research, 34(2), 229-238 (1993-02-01)
Lipoprotein lipase (LPL) is important for the delivery of triglyceride fatty acids (TGFA) to a variety of tissues. We have used measurements of heparin-releasable LPL activity, immunohistochemistry, in situ hybridization, and Northern analysis to more fully characterize the location of
L L Williams et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 202(2), 239-245 (1993-02-01)
The polyunsaturated omega-6 fatty acid, arachidonic acid ([AA] 20:4n-6), is both the key of the immunoregulatory substances, prostaglandins, and leukotrienes, and an essential component of immune cell membrane phospholipids, providing stability and flexibility to ensure cellular function. To explore possible

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