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Merck
CN

O1383

Sigma-Aldrich

Oleic acid

suitable for cell culture, BioReagent

Synonym(s):

cis-9-Octadecenoic acid, Elainic acid

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About This Item

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
UNSPSC Code:
12352211
PubChem Substance ID:
24897941
NACRES:
NA.75

Key Documents

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biological source

palm oil

Quality Level

200

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

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

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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

Packaging

Sealed ampule.

Disclaimer

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000471739
0000471738
0000471738
0000471739
0000469302

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Three-dimensional label-free imaging and quantification of lipid droplets in live hepatocytes
Kim K, et al.
Scientific Reports, 6(10), 36815-36815 (2016)
Beneficial effect of fish oil on human brain (2009)
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)
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)
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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