Merck
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O1383

Sigma-Aldrich

Oleic acid

suitable for cell culture, BioReagent

Sinónimos:
cis-9-Octadecenoic acid, Elainic acid
Fórmula lineal:
CH3(CH2)7CH=CH(CH2)7COOH
Número de CAS:
Peso molecular:
282.46
Beilstein:
1726542
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.75

Nivel de calidad

200

origen biológico

palm oil

presión de vapor

1 mmHg ( 176 °C)

línea de producto

BioReagent

ensayo

≥99% (GC)

formulario

viscous liquid

technique(s)

cell culture | mammalian: suitable

índice de refracción

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

solubilidad

ethanol: soluble

densidad

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

temp. de almacenamiento

−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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Descripción general

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.

Aplicación

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

Envase

1, 5, 25 g in ampule
Sealed ampule.

Acciones bioquímicas o fisiológicas

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

Precaución

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

Código de clase de almacenamiento

10 - Combustible liquids

WGK

WGK 1

Punto de inflamabilidad F

159.8 °F - closed cup

Punto de inflamabilidad C

71 °C - closed cup

Equipo de protección personal

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificado de Análisis

Introduzca el número de lote para buscar un certificado de análisis (COA).

Certificado de origen

Introduzca el número de lote para buscar un Certificado de origen (COO).

Beneficial effect of fish oil on human brain (2009)
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)
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)
Joyce Wang et al.
BMC genomics, 15, 415-415 (2014-06-03)
Mycobacterium avium subsp. paratuberculosis (MAP) is an obligate intracellular pathogen that infects many ruminant species. The acquisition of foreign genes via horizontal gene transfer has been postulated to contribute to its pathogenesis, as these genetic elements are absent from its

Artículos

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