O1383

Oleic acid

suitable for cell culture, BioReagent

• 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: 24897941
• NACRES: NA.75

Properties

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

Description

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.

Safety Information

• 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