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O1383

Oleic acid

Name: Oleic acid
Brand: SIGMA

BioReagent, suitable for cell culture

Synonym(s):

cis-9-Octadecenoic acid, Elainic acid

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About This Item

Linear Formula:

CH₃(CH₂)₇CH=CH(CH₂)₇COOH

CAS Number:

112-80-1

Molecular Weight:

282.46

UNSPSC Code:

12352211

NACRES:

NA.75

PubChem Substance ID:

24897941

EC Number:

204-007-1

Beilstein/REAXYS Number:

1726542

MDL number:

MFCD00064242

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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.)

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 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.

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.

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

Sealed ampule.

Disclaimer

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

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Storage Class

10 - Combustible liquids

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

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Articles

脂质诱导的胰岛素耐受性

脂肪组织中的胰岛素耐受性减少了循环游离脂肪酸的摄入，并增加了脂肪酶对储存甘油三酯的水解。了解与胰岛素耐受性相关的激素、细胞因子和脂肪因子。

Lipid-induced Insulin Resistance

Lipid Induced Insulin Resistance

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)

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)

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Global Trade Item Number

SKU	GTIN
O1383-1G	04061834216346
O1383-25G	04061834216353
O1383-5G	04061834216360