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Merck

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

Key Documents

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InChI key

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

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-

SMILES string

CCCCCCCC\C=C/CCCCCCCC(O)=O

biological source

plant (Sunflower)

vapor pressure

1 mmHg ( 176 °C)

assay

≥99% (GC)

form

viscous liquid

color

colorless to very faintly yellow

Quality Level

200

Gene Information

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

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

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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
WXBD6763V
BCBV8502
BCBV4725
BGBC5673V
BGBC5672V

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Oleic acid coating on the monodisperse magnetite nanoparticles.
Zhang L, et al.
Applied Surface Science, 253(5), 2611-2617 (2006)
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)
P Belfrage et al.
Journal of lipid research, 10(3), 341-344 (1969-05-01)
Oleic acid has a partition coefficient, upper phase/lower phase, of 1.9 (22 degrees C) in the liquid-liquid partition system described herein. Tri-, di-, and monoolein are found almost exclusively in the lower (organic) phase. Oleic acid can be quantitatively removed
Yasutaka Kuwahara et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(2), 380-389 (2016-11-26)
One-pot reaction involving Pd-catalyzed H
Qingwen Qian et al.
Cellular and molecular gastroenterology and hepatology, 8(1), 95-110 (2019-03-31)
The lysosome is an acidic organelle that is important for maintaining cellular and metabolic homeostasis in hepatocytes. Lysosomal dysfunction and chronic inflammation coexist, and both contribute to obesity-associated hepatic insulin resistance. However, in the context of obesity, the interplay between
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