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Sigma-Aldrich

Oleic acid

technical grade, 90%

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Synonym(s):
cis-9-Octadecenoic acid, Elainic acid
Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOH
CAS Number:
112-80-1
Molecular Weight:
282.46
Beilstein:
1726542
EC Number:
204-007-1
MDL number:
MFCD00064242
PubChem Substance ID:
24862437
NACRES:
NA.25

biological source

plant

grade

technical grade

vapor pressure

1 mmHg ( 176 °C)

Assay

90%

form

liquid
semisolid
waxy solid

refractive index

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

solubility

alcohol: soluble
benzene: soluble
chloroform: soluble
diethyl ether: soluble
water: insoluble

density

0.887 g/mL at 25 °C
0.89 g/mL at 25 °C (lit.)

application(s)

microbiology

functional group

oleic acid

lipid type

unsaturated FAs

shipped in

ambient

storage temp.

2-8°C

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

human ... SOAT1(6646) , SOAT2(8435)

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Application

Oleic acid has been used as a test reagent for studying its impact on the secretion of apoB from HepG2 cells. It has also been used to study the necrophoric response of the southern harvester ant, Pogonomyrmex badius to oleic acid.

Biochem/physiol Actions

Oleic acid is a colourless, odourless fatty acid that blocks the glucose production and food intake when administered intracerebroventricularly.
Activates protein kinase C in hepatocytes.
Uncouples oxidative phosphorylation. Inhibits 2,4-dinitrophenol−stimulated ATPase. Action reversed by adding serum albumin.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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C R Pullinger et al.
Journal of lipid research, 30(7), 1065-1077 (1989-07-01)
The objective of this study was to establish conditions whereby apoB secreted from HepG2 cells could be regulated over a wide range, and to determine whether changes of output were correlated with the level of apoB mRNA. The presence of
D M Gordon
Journal of chemical ecology, 9(1), 105-111 (1983-01-01)
The response of the southern harvester ant,Pogonomyrmex badius, to oleic acid was found to depend on social context. Social context was specified as the number of ants engaging in each of five categories of behavior. When a large percentage of
Katarzyna Adamala et al.
Nature protocols, 10(6), 927-938 (2015-05-29)
The liposome dialyzer is a small-volume equilibrium dialysis device, built from commercially available materials, that is designed for the rapid exchange of small volumes of an extraliposomal reagent pool against a liposome preparation. The dialyzer is prepared by modification of
Yan Zhang et al.
ACS nano, 11(3), 2846-2857 (2017-02-22)
Nd
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
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