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O1008

Sigma-Aldrich

Oleic acid

≥99% (GC)

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Synonym(s):
9Z-Octadecenoic acid, cis-Oleic acid, cis-9-Octadecenoic acid, Elainic acid
Linear Formula:
CH3(CH2)7CH=CH(CH2)7COOH
CAS Number:
Molecular Weight:
282.46
Beilstein:
1726542
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

plant (Sunflower)

Quality Level

vapor pressure

1 mmHg ( 176 °C)

Assay

≥99% (GC)

form

viscous liquid

color

colorless to very faintly yellow

refractive index

n20/D 1.459 (lit.)

bp

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

solubility

H2O: insoluble (practically)
alcohol: soluble
benzene: soluble
chloroform: soluble
oil: soluble (fixed and volatile)

density

0.89 g/mL at 25 °C (lit.)

application(s)

life science and biopharma
lipidomics

functional group

oleic acid

lipid type

unsaturated FAs

shipped in

ambient

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

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1 of 4

This Item
27728O1383W281506
vibrant-m

O1008

Oleic acid

vibrant-m

27728

Oleic acid

vibrant-m

O1383

Oleic acid

vibrant-m

W281506

Oleic acid

functional group

oleic acid

functional group

-

functional group

-

functional group

-

biological source

plant (Sunflower)

biological source

-

biological source

palm oil

biological source

-

color

colorless to very faintly yellow

color

clear

color

-

color

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

400

solubility

H2O: insoluble (practically), benzene: soluble, oil: soluble (fixed and volatile), alcohol: soluble, chloroform: soluble

solubility

-

solubility

ethanol: soluble

solubility

-

General description

Oleic acid (OA), a non-essential fatty acid, is classified as monounsaturated fatty acid (MUFA) richly present in olive oil. Its quantitative removal from the mixtures of triglyceride and partial glycerides has been reported. OA is widely used as a surfactant for the stabilization of magnetic nanoparticles. Monodisperse magnetite nanoparticles (7 and 19nm) coated with OA have been prepared.

Application

Oleic acid has been used:
  • to study the effects of fatty acids on gastric cancer (GC)
  • to induce lipid droplet formation in cell culture
  • as an additive in the magnetorheological fluid preparation.
Oleic acid may be used in the preparation of 10-hydroxy octadecanoic acid and methyl ester of the 10-hydroxy octadecanoic acid.

Biochem/physiol Actions

Oleic acid is known to improve immune function and health. Dietary supplement of this fatty acid contributes to the reduction in cholesterol levels, atherogenesis risk, blood pressure, and host versus graft response. Oleic acid has been proven to benefit autoimmune diseases by exhibiting anti-inflammatory action. It also ameliorates the condition of breast cancer. Oleic acid produces physiological effects such as protein kinase C activation in hepatocytes, uncoupling oxidative phosphorylation, and 2,4-dinitrophenol−stimulated ATPase inhibition. This action can be reversed by adding serum albumin.
Activates protein kinase C in hepatocytes.
Uncouples oxidative phosphorylation. Inhibits 2,4-dinitrophenol−stimulated ATPase. Action reversed by adding serum albumin.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

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Description
Pricing

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Description
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Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Oleic acid meets analytical specification of Ph, Eur., 65.0-88.0% (GC)

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THE STEREOSPECIFIC CONVERSION OF STEARIC ACID TO OLEIC ACID.
G J SCHROEPFER et al.
The Journal of biological chemistry, 240, 54-63 (1965-01-01)
CD36 mediates palmitate acid-induced metastasis of gastric cancer via AKT/GSK-3?/?-catenin pathway
Pan J, et al.
Journal of Experimental & Clinical Cancer Research, 38 (2019)
Oleic acid coating on the monodisperse magnetite nanoparticles.
Zhang L, et al.
Applied Surface Science, 253(5), 2611-2617 (2006)
Influence of graphite flakes on the strength of magnetorheological fluids at high temperature and its rheology
Thakur MK and Sarkar C
IEEE Transactions on Magnetics, 56(5) (2020)
Kun Huang et al.
Journal of hepatology, 66(5), 962-977 (2016-12-17)
PARP1 is a key mediator of cellular stress responses and critical in multiple physiological and pathophysiological processes of cells. However, whether it is involved in the pathogenesis of non-alcoholic fatty liver disease (NAFLD) remains elusive. We analysed PARP1 activity in

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