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O1383 Sigma-Aldrich

Oleic acid

suitable for cell culture, BioReagent

Synonym: cis-9-Octadecenoic acid, Elainic acid

  • CAS Number 112-80-1

  • Linear Formula CH3(CH2)7CH=CH(CH2)7COOH

  • Molecular Weight 282.46

  •  Beilstein/REAXYS Number 1726542

  •  EC Number 204-007-1

  •  MDL number MFCD00064242

  •  PubChem Substance ID 24897941

  •  NACRES NA.75

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Properties

Related Categories Allium cepa (Onion), Allium sativum (Garlic), Aloe Vera, Carthamus tinctorius (Safflower oil), Cell Biology,
Quality Level   200
biological source   palm oil
vapor pressure   1 mmHg ( 176 °C)
product line   BioReagent
assay   ≥99% (GC)
form   viscous liquid
application(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

Packaging

1, 5, 25 g in ampule

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 & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
1
RTECS 
RG2275000
Flash Point(F) 
>235.4 °F
Flash Point(C) 
>113 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Lipid Induced Insulin Resistance

Obesity is a well-established risk factor for the development of insulin resistance. Obesity is associated with the increased deposition of lipids in non-adipose tissue with subsequent decreases in i...
Linda Stephenson, Ph.D.
Biofiles v6 n4, 9
Keywords: Angiogenesis, Antivirals, Apoptosis, Biological processes, Cardiovascular, Catalog, Catalysis, Cell culture, Cell proliferation, Deposition, Diabetes, Events, Gene expression, Growth factors, Hormones, Inflammation, Metabolism, Metabolites, Obesity, Phosphorylations, Physiological Processes, Reductions, Transcription, Transduction, Type

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Cell Culture Troubleshooting Guide

Cell culture has become one of the most fundamental techniques for modeling biological systems, and is of increasing importance in the biotechnology and pharmaceutical sectors as well as an essential...
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Peer-Reviewed Papers
15

References

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