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Ethyl oleate

Catalog Number

ACM111626-4

CAS

111-62-6

Structure

IUPAC Name

Ethyl (Z)-octadec-9-enoate

Synonyms

Oleic acid, ethyl ester

Molecular Weight

310.5

Molecular Formula

C20H38O2

Canonical SMILES

CCCCCCCCC=CCCCCCCCC(=O)OCC

InChI

InChI=1S/C20H38O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h11-12H,3-10,13-19H2,1-2H3/b12-11-

InChI Key

LVGKNOAMLMIIKO-QXMHVHEDSA-N

Boiling Point

216-218 °C

Melting Point

-32 °C

Flash Point

>230 °F

Purity

98%+

Density

0.87 g/mL at 25 °C(lit.)

Solubility

Insoluble in water; soluble in ether

Appearance

Clear pale yellow oily liquid

Application

Ethyl oleate is a versatile compound primarily utilized as a solvent and carrier in pharmaceutical formulations, particularly for drugs requiring lipophilic delivery. This pale yellow to nearly colorless liquid possesses a mild, olive oil-like taste and is derived from the esterification of oleic acid with ethanol. Recognized for its rapid absorption and lower viscosity compared to fixed oils, ethyl oleate is employed in various drug delivery systems such as self-microemulsifying systems for oral administration, microemulsions for topical and ocular treatments, and vehicles for parenteral preparations, including intramuscular and subdermal applications. It serves as an effective solvent for lipophilic substances like steroids and is regulated by the FDA for use as a food additive. Additionally, ethyl oleate is explored for its potential in targeted drug delivery, including liver targeting, although its safety during pregnancy is not yet established.

Active Content

95%

Physical State

Oily liquid

Typical Applications

Use as lubricant.
Use as dispersing agent, emulsion stabilizer.

MSDS

Download MSDS

COA

Download COA

Spec Sheet

Download Spec Sheet

Case Study

Ethyl Oleate Used for the Preparation of Nanostructured Lipid Carriers to Enhance Oral Bioavailability of trans-Ferulic Acid

Ethyl Oleate Used for the Preparation of Nanostructured Lipid Carriers to Enhance Oral Bioavailability of trans-Ferulic Acid Zhang, Yongtai, et al. International journal of pharmaceutics 511.1 (2016): 57-64.

Ethyl oleate has been effectively utilized as the liquid lipid component in the preparation of nanostructured lipid carriers (NLCs) aimed at enhancing the oral bioavailability of trans-ferulic acid (TFA), a bioactive compound known for its antioxidative, anti-inflammatory, and cardioprotective properties. The clinical potential of TFA has been limited by its poor aqueous solubility and low oral absorption; however, encapsulating TFA within lipid-based nanocarriers addresses these challenges.
In this study, NLCs were fabricated using a microemulsion-based method, where ethyl oleate was combined with glyceryl behenate as the solid lipid matrix. The warm oil-in-water microemulsion was formed by heating the lipid mixture to 70 °C and then introducing water under controlled stirring. Upon rapid cooling at -20 °C, uniform solid nanoparticles were obtained.
Ethyl oleate played a critical role in optimizing the internal structure of the lipid matrix, providing flexibility, reducing crystallinity, and improving drug loading capacity. This approach not only preserved the structural integrity and stability of TFA during processing but also promoted controlled release and enhanced absorption.
The incorporation of ethyl oleate into NLCs highlights its utility as a key formulation component in lipid-based drug delivery systems designed to overcome solubility and bioavailability barriers for poorly water-soluble therapeutic agents.

Ethyl Oleate Used for the Surface Modification of Silica Nanoparticles in Lubricating Oil Applications

Ethyl Oleate Used for the Surface Modification of Silica Nanoparticles in Lubricating Oil Applications Tóth, Álmos Dávid, et al. Ceramics 6.2 (2023): 980-993.

Ethyl oleate plays a pivotal role in enhancing the dispersion stability of silica nanoparticles within lubricating oil formulations, offering a viable solution for reducing wear and friction in tribological systems. While nanosized silica particles are well-regarded for their excellent anti-friction and anti-wear properties, their tendency to aggregate in oil significantly limits their long-term performance. To address this, ethyl oleate was synthesized in situ via the esterification of oleic acid with ethyl alcohol and used as a surface modifier.
In the described procedure, silica nanoparticles were treated with a mixture of oleic acid and ethanol at 75 ± 5 °C for 2 hours, resulting in the formation of ethyl oleate. This ester then precipitated onto the surface of the silica particles during subsequent drying at 80 °C for 16 hours. The resulting ethyl oleate layer effectively prevented particle agglomeration, ensuring stable dispersion within the oil matrix.
This surface-modified nanopowder exhibited enhanced colloidal stability, crucial for maintaining consistent tribological performance over time. Ethyl oleate thus serves not only as a dispersing agent but also as a key functionalizing material that improves the compatibility of inorganic nanoparticles with hydrophobic lubricant environments.
The application underscores ethyl oleate's value in advanced lubrication technologies aimed at reducing dependency on fossil-based oils while improving mechanical durability and efficiency.

Custom Q&A

What is ethyl oleate?

Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol.

How is ethyl oleate produced in the body?

Ethyl oleate is produced by the body during ethanol intoxication.

What is a common use of ethyl oleate in pharmaceutical preparations?

Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.

How is ethyl oleate regulated by the FDA?

Ethyl oleate is regulated as a food additive by the FDA under "Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515.

What has ethyl oleate been identified as in honeybees?

Ethyl oleate has been identified as a primer pheromone in honeybees.

What is the molecular formula of ethyl oleate?

The molecular formula of ethyl oleate is C20H38O2.

What is the boiling point of ethyl oleate?

The boiling point of ethyl oleate is 216-218 °C.

What are some synonyms for ethyl oleate?

Some synonyms for ethyl oleate are Oleic acid, ethyl ester.

What is the flash point of ethyl oleate?

The flash point of ethyl oleate is >230 °F.

Is ethyl oleate currently approved by the FDA for injectable use?

No, ethyl oleate is not currently approved by the FDA for any injectable use.

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