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O1383

Sigma-Aldrich

Oleic acid

suitable for cell culture, BioReagent

Sinônimo(s):

cis-9-Octadecenoic acid, Elainic acid

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About This Item

Fórmula linear:
CH3(CH2)7CH=CH(CH2)7COOH
Número CAS:
Peso molecular:
282.46
Beilstein:
1726542
Número CE:
Número MDL:
Código UNSPSC:
12352211
ID de substância PubChem:
NACRES:
NA.75

fonte biológica

palm oil

Nível de qualidade

pressão de vapor

1 mmHg ( 176 °C)

linha de produto

BioReagent

Ensaio

≥99% (GC)

forma

viscous liquid

técnica(s)

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

cadeia de caracteres SMILES

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-

chave InChI

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

Informações sobre genes

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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

Sealed ampule.

Atenção

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

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 1

Equipamento de proteção individual

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Three-dimensional label-free imaging and quantification of lipid droplets in live hepatocytes
Kim K, et al.
Scientific Reports, 6(10), 36815-36815 (2016)
Beneficial effect of fish oil on human brain (2009)
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)
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)
Veijo T Salo et al.
Developmental cell, 50(4), 478-493 (2019-06-11)
Seipin is an oligomeric integral endoplasmic reticulum (ER) protein involved in lipid droplet (LD) biogenesis. To study the role of seipin in LD formation, we relocalized it to the nuclear envelope and found that LDs formed at these new seipin-defined

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