All Photos(1)

O1008

Sigma-Aldrich

Oleic acid

≥99% (GC)

Synonym(s):
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

Quality Level

vapor pressure

1 mmHg ( 176 °C)

assay

≥99% (GC)

form

viscous liquid

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.)

functional group

oleic acid

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Oleic acid (OA) is a fatty acid. Its quantitative removal from the mixtures of triglyceride and partial glycerides has been reported. OA is widely used as surfactant for the stabilization of magnetic nanoparticles. Monodisperse magnetite nanoparticles (7 and 19nm) coated with OA have been prepared.

Application

Oleic acid may be used in the preparation of 10-hydroxyoctadecanoic acid and methyl ester of the 10-hydroxyoctadecanoic acid.

Packaging

1, 5, 25 g in ampule

Biochem/physiol Actions

Uncouples oxidative phosphorylation. Inhibits 2,4-dinitrophenol−stimulated ATPase. Action reversed by adding serum albumin.
Activates protein kinase C in hepatocytes.

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. You describe Product O1008, Oleic acid, as a liquid in your Specification Sheet, but you do not give its concentration.

    Oleic acid is a liquid at room temperature. Its molarity, calculated from its density and molecular weight (0.89 g/mL at 25 degrees C and 282.46 g/mol, respectively) is approximately 3.15 mol/L.

  4. In what solvents can Product O1008, Oleic acid, be dissolved or diluted?

    Per the chemicals encyclopedia published by the Royal Society of Chemistry, 12th ed., Entry# 6965, oleic acid is soluble in alcohol, benzene, chloroform, ether, fixed and volatile oils, but is practically insoluble in water.

  5. How can one determine whether Product O1008, Oleic acid, has undergone oxidation?

    Sigma's oleic acid is a clear, colorless to very faint yellow viscous liquid. It is sensitive to air and light. When it becomes oxidized, it aquires a much darker yellow to brown color.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
Oleic acid coating on the monodisperse magnetite nanoparticles.
Zhang L, et al.
Applied Surface Science, 253(5), 2611-2617 (2006)
Yasutaka Kuwahara et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(2), 380-389 (2016-11-26)
One-pot reaction involving Pd-catalyzed H
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...
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...

Articles

Stearic Acid in Cell Culture

Fatty acids of the n-3, n-6 and n-9 families are important supplements for cell culture systems. They are important in cell culture systems used to biomanufacture heterologous proteins, such as monoclonal antibodies.

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.

Chemical Synthesis of Monodisperse Magnetic Nanoparticles

Magnetic nanoparticles have attracted tremendous attention due to their novel properties and their potential applications in magnetic recording, magnetic energy storage and biomedicine.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service