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O1383

Sigma-Aldrich

Oleic acid

suitable for cell culture, BioReagent

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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.75

biological source

palm oil

vapor pressure

1 mmHg ( 176 °C)

product line

BioReagent

Assay

≥99% (GC)

form

viscous liquid

technique(s)

cell culture | mammalian: suitable

refractive index

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

solubility

ethanol: soluble

density

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

storage temp.

−20°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

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This Item
O1008364525W281506
Oleic acid suitable for cell culture, BioReagent

Sigma-Aldrich

O1383

Oleic acid

Oleic acid ≥99% (GC)

Sigma-Aldrich

O1008

Oleic acid

Oleic acid technical grade, 90%

Sigma-Aldrich

364525

Oleic acid

Oleic acid natural, FCC

Sigma-Aldrich

W281506

Oleic acid

assay

≥99% (GC)

assay

≥99% (GC)

assay

90%

assay

-

form

viscous liquid

form

viscous liquid

form

liquid, semisolid, waxy solid

form

liquid

technique(s)

cell culture | mammalian: suitable

technique(s)

-

technique(s)

-

technique(s)

-

refractive index

n20/D 1.459 (lit.)

refractive index

n20/D 1.459 (lit.)

refractive index

n20/D 1.459 (lit.)

refractive index

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

General description

Oleic acid is a mono-unsaturated omega-9 fatty acid created by dehydrogenation of stearic acid. It is then further dehydrogenated and elongated to create members of the n-9 family of fatty acids. Oleic acid is not an essential fatty acid (EFA); however, providing it to cells in culture reduces energy demand.
Oleic acid mediates complete oxidation of fatty acid in sirtuin1- proliferator-activated receptor γ coactivator−1α (SIRT1-PGC-1α) signalling pathway. Oleic acid shows anti-inflammatory properties related to atherosclerosis and insulin resistant state. Oleic acid inhibits permeability in gap junctions and promotes glucose uptake in astrocytes. Oleic acid aids in neural cell proliferation by increasing glucose uptake and by protein kinase C (PKC) activation. Oleic acid is essential for axonal growth and neuronal clustering.

Application

Oleic acid has been used:
  • in fatty acid oxidation rate experiments in myotubes and in Sirt1 enzyme assay
  • to determine quantitatively its effect on lipid droplets by optical diffraction tomography
  • as a fatty acid source in the medium for primary hepatocyte culture

Biochem/physiol Actions

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

Packaging

Sealed ampule.

Caution

Unsaturated fatty acids are subject to oxidation and peroxidation. Consider complexed fatty acid supplements.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

159.8 °F - closed cup

Flash Point(C)

71 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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25G
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705578-5MG-PW

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MMYOMAG-74K-13

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The role of proliferator-activated receptor gamma coactivator-1alpha in the fatty-acid-dependent transcriptional control of interleukin-10 in hepatic cells of rodents
Morari J, et al.
Metabolism, Clinical and Experimental, 59(2), 215-223 (2010)
Beneficial effect of fish oil on human brain (2009)
Three-dimensional label-free imaging and quantification of lipid droplets in live hepatocytes
Kim K, et al.
Scientific Reports, 6(10), 36815-36815 (2016)
Oleic acid stimulates complete oxidation of fatty acids through protein kinase A-dependent activation of SIRT1-PGC1alpha complex
Lim JH, et al.
The Journal of Biological Chemistry, 288(10), 7117-7126 (2013)
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

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