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O1008

Oleic acid

≥99% (GC)

Synonym(s):

9Z-Octadecenoic acid, cis-Oleic acid, 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.25
PubChem Substance ID:
24278605
EC Number:
204-007-1
Beilstein/REAXYS Number:
1726542
MDL number:
MFCD00064242
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biological source

plant (Sunflower)

Quality Level

200

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

Gene Information

human ... PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584), SOAT1(6646), SOAT2(8435)

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.

Other Notes

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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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Certificates of Analysis (COA)

Lot/Batch Number
0000527720
0000522140
0000525569
0000525568
0000525568

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Protocols

Protocol for In-vitro Permeation Testing Using Strat-M® Membranes

Strat-M® synthetic membrane mimics the human skin for In-vitro permeation testing (IVPT) of topical and transdermal formulations

Articles

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

Oleic Acid in Cell Culture

How the unsaturated fatty acid, oleic acid and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

Stearic Acid in Cell Culture

Supplement cell culture systems with fatty acids for biomanufacturing heterologous proteins like monoclonal antibodies.

View All Articles
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)
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)
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
View All Related Papers

Global Trade Item Number

SKUGTIN
O1008-25G04061835507085
O1008-5G04061835547142
O1008-1G04061835547135