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O1383

Sigma-Aldrich

Oleic acid

BioReagent, suitable for cell culture

Synonym(s):

cis-9-Octadecenoic acid, Elainic acid

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100 ML
CN¥242.76

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100 ML
CN¥242.76

About This Item

Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOH
CAS Number:
112-80-1
Molecular Weight:
282.46
Beilstein:
1726542
EC Number:
204-007-1
MDL number:
MFCD00064242
UNSPSC Code:
12352211
PubChem Substance ID:
24897941
NACRES:
NA.75

CN¥242.76

Available to ship onApril 27, 2025Details

Request a Bulk Order

biological source

palm oil

Quality Level

200

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.)

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SML0191

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assay

≥98% (HPLC)

assay

-

assay

-

assay

≥98% (HPLC)

Quality Level

100

Quality Level

300

Quality Level

300

Quality Level

100

form

solid

form

-

form

-

form

powder

storage temp.

room temp

storage temp.

2-8°C

storage temp.

-

storage temp.

−20°C

solubility

H2O: >20 mg/mL

solubility

-

solubility

-

solubility

H2O: ≥8 mg/mL

color

white

color

-

color

-

color

white to tan

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.[1] 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.[2]

Application

Oleic acid has been used:
  • in fatty acid oxidation rate experiments in myotubes and in Sirt1 enzyme assay[1]
  • to determine quantitatively its effect on lipid droplets by optical diffraction tomography[3]
  • as a fatty acid source in the medium for primary hepatocyte culture[4]

Packaging

Sealed ampule.

Caution

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000434959
    0000434959
    0000402713
    0000387135
    0000387134

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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)
    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
    View All Related Papers

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