O1383

Sigma-Aldrich

Oleic acid

suitable for cell culture, BioReagent

Sinônimo(s):
cis-9-Octadecenoic acid, Elainic acid
Fórmula linear:
CH3(CH2)7CH=CH(CH2)7COOH
Número CAS:
Peso molecular:
282.46
Beilstein/REAXYS Number:
1726542
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.75

Nível de qualidade

200

fonte biológica

palm oil

pressão de vapor

1 mmHg ( 176 °C)

linha de produto

BioReagent

teor

≥99% (GC)

forma

viscous liquid

aplicação(ões)

cell culture | mammalian: suitable

índice de refração

n20/D 1.459 (lit.)

pb

194-195 °C/1.2 mmHg (lit.)

pf

13-14 °C (lit.)

solubilidade

ethanol: soluble

densidade

0.89 g/mL at 25 °C (lit.)
0.89 g/mL at 25 °C (lit.)

temperatura de armazenamento

−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

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Descrição geral

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.

Aplicação

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

Embalagem

1, 5, 25 g in ampule
Sealed ampule.

Ações bioquímicas/fisiológicas

Uncouples oxidative phosphorylation. Inhibits 2,4-dinitrophenol−stimulated ATPase. Action reversed by adding serum albumin.
Activates protein kinase C in hepatocytes.

Atenção

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

storage_class_code

10 - Combustible liquids

WGK Alemanha

WGK 1

Ponto de fulgor (ºF)

159.8 °F - closed cup

Ponto de fulgor (ºC)

71 °C - closed cup

Equipamento de proteção individual

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificado de análise

Certificado de origem

Beneficial effect of fish oil on human brain (2009)
Three-dimensional label-free imaging and quantification of lipid droplets in live hepatocytes
Kim K, et al.
Scientific Reports, 6(10), 36815-36815 (2016)
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)
Stefan Freigang et al.
Nature immunology, 14(10), 1045-1053 (2013-09-03)
Chronic inflammation is a fundamental aspect of metabolic disorders such as obesity, diabetes and cardiovascular disease. Cholesterol crystals are metabolic signals that trigger sterile inflammation in atherosclerosis, presumably by activating inflammasomes for IL-1β production. We found here that atherogenesis was...
Artigos
Lipid Induced Insulin Resistance
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