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Sigma-Aldrich® Oleic acid

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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

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)

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.[1] 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.[2]

Application

Oleic acid has been used:


  • in fatty acid oxidation rate experiments in myotubes and in Sirt1 enzyme assay[1]
  • to determine quantitatively its effect on lipid droplets by optical diffraction tomography[3]
  • as a fatty acid source in the medium for primary hepatocyte culture[4]

 

Packaging

Sealed ampule.

Disclaimer

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