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27728

Sigma-Aldrich

Oleic acid

meets analytical specification of Ph, Eur., 65.0-88.0% (GC)

Synonym(s):
cis-9-Octadecenoic acid, Elainic acid
Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
282.46
Beilstein:
1726542
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

vapor pressure

1 mmHg ( 176 °C)

assay

65.0-88.0% (GC)

form

liquid

quality

meets analytical specification of Ph, Eur.

composition

fatty acids w. 1 chain > C18, ≤4.0% GC
linoleic acid, ≤18.0% GC
linolenic acid, ≤4.0% GC
margaric acid, ≤4.0% GC
myristic acid, ≤5.0% GC
oleic acid, 65.0-88.0% GC
palmitic acid, ≤16.0% GC
palmitoleic acid, ≤8.0% GC
stearic acid, ≤6.0% GC

peroxide value

≤10

impurities

residual solvents, complies

ign. residue

≤0.1%

color

clear

refractive index

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

acid value

195‑204

iodine value

89‑105

density

0.89 g/mL at 25 °C (lit.)

suitability

complies for appearance of solution
in accordance for fatty acid composition
passes test for identity

SMILES string

CCCCCCCC\C=C/CCCCCCCC(O)=O

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-KTKRTIGZSA-N

Gene Information

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General description

Oleic acid (OA) is a fatty acid. OA is widely used as a surfactant for the stabilization of magnetic nanoparticles synthesized by the traditional coprecipitation method. Monodisperse magnetite nanoparticles (diameter = 7 and 19nm) coated with oleic acid (OA) have been prepared.

Application

Oleic acid may be used in the preparation of 10-hydroxyoctadecanoic acid and methyl ester of 10-hydroxyoctadecanoic acid.

Biochem/physiol Actions

Uncouples oxidative phosphorylation. Inhibits 2,4-dinitrophenol−stimulated ATPase. Action reversed by adding serum albumin.
Activates protein kinase C in hepatocytes.

Other Notes

The article number 27728-6X1L-R will be discontinued. Please order the single bottle 27728-1L-R which is physically identical with the same exact specifications.

Certificate of Analysis

Certificate of Origin

The stereospecific conversion of stearic acid to oleic acid.
Schroepfer GJ and Bloch K.
The Journal of Biological Chemistry, 240(1), 54-63 (1965)
Oleic acid coating on the monodisperse magnetite nanoparticles
Zhang L, et al.
Applied Surface Science, 235(5), 2611-2617 (2006)
Marta Estrader et al.
Nanoscale, 7(7), 3002-3015 (2015-01-21)
The intimate relationship between stoichiometry and physicochemical properties in transition-metal oxides makes them appealing as tunable materials. These features become exacerbated when dealing with nanostructures. However, due to the complexity of nanoscale materials, establishing a distinct relationship between structure-morphology and
Stefan Freigang et al.
Nature immunology, 14(10), 1045-1053 (2013-09-03)
Chronic inflammation is a fundamental aspect of metabolic disorders such as obesity, diabetes and cardiovascular disease. Cholesterol crystals are metabolic signals that trigger sterile inflammation in atherosclerosis, presumably by activating inflammasomes for IL-1β production. We found here that atherogenesis was
Joyce Wang et al.
BMC genomics, 15, 415-415 (2014-06-03)
Mycobacterium avium subsp. paratuberculosis (MAP) is an obligate intracellular pathogen that infects many ruminant species. The acquisition of foreign genes via horizontal gene transfer has been postulated to contribute to its pathogenesis, as these genetic elements are absent from its

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