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O1383

Oleic acid

Name: Oleic acid
Brand: SIGMA

BioReagent, suitable for cell culture

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

UNSPSC Code:

12352211

NACRES:

NA.75

PubChem Substance ID:

24897941

EC Number:

204-007-1

Beilstein/REAXYS Number:

1726542

MDL number:

MFCD00064242

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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.)

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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Biochemicals

Oleic Acid

General description

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.

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.

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.

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

Storage Class

10 - Combustible liquids

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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)

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)

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)

Origin of the large dispersion of magnetic properties in nanostructured oxides: Fe(x)O/Fe3O4 nanoparticles as a case study.

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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Global Trade Item Number

SKU	GTIN
O1383-1G	04061834216346
O1383-25G	04061834216353
O1383-5G	04061834216360

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