Glyceryl monooleate Chemical Properties

Melting point:

35-37 °C

Boiling point:

449.35°C (rough estimate)

Density 

0.96 g/cm³ (25 ºC)

refractive index 

1.4626 (589.3 nm 40℃)

FEMA 

2526 | GLYCERYL MONOOLEATE

storage temp. 

−20°C

solubility 

chloroform: 50 mg/mL, clear, colorless

Water Solubility 

<3.57mg/L(30 ºC)

Stability:

Hygroscopic

InChI

InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

InChIKey

RZRNAYUHWVFMIP-KTKRTIGZSA-N

SMILES

O(C(=O)CCCCCCC/C=C\CCCCCCCC)CC(CO)O

CAS DataBase Reference

25496-72-4(CAS DataBase Reference)

EPA Substance Registry System

Glyceryl monooleate (25496-72-4)

Safety Information

WGK Germany 

1

F 

3

HS Code 

3822000002

Hazardous Substances Data

25496-72-4(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Glyceryl monooleate Usage And Synthesis

Description

Glyceryl monooleate (GMO), generally referred to as monoolein (MO), is FDA approved amphiphilic lipid that is widely used during the synthesis of cubosomes. Glyceryl monooleate is a waxy material, but its physical form is dependent on the content of di- and triglyceride. GMO is a polar unsaturated monoglyceride that can self-assemble in water into bicontinuous cubic structures. The amphiphilic chemical structure of GMO with hydrophilic polar head (hydroxyl groups) and hydrophobic chains in the tail facilitates H-bond formation with water. GMOs are classified as GRAS (generally recognized as safe) due to their biodegradability, biocompatibility, and minimal toxicity. The biodegradability was attributed to the lipolysis of GMOs in different tissues via esterase activity. The GMO-based systems, especially bicontinuous cubic and hexagonal LC phases, were highly reported as promising drug delivery. Thanks to their unique features, which include their minimal toxicity, prolonged release rate, and thermodynamic stability upon exposure to excess water.

Chemical Properties

Glyceryl monooleate is a polar lipid with a faint fatty odor. It is a mixture of glycerides, primarily consisting of monooleate, derived from oleic acid and other fatty acids. This compound is characterized by its ability to swell in water, forming several phases with varying rheological properties. It is composed mainly of monoacylglycerols, with monooleoylglycerol being the predominant form, along with varying amounts of di- and triacylglycerols. The composition is defined by the nominal content of monoacylglycerols and is typically obtained through partial glycerolysis of vegetable oils rich in triacylglycerols of oleic acid or by the esterification of glycerol with oleic acid, which can be sourced from either vegetable or animal origins. Glyceryl monooleates are often amber oily liquids that may be partially solid at room temperature and are known for their characteristic odor. An appropriate antioxidant may be added to the formulation.

Uses

93% 1-Oleoyl, 7% 2-oleoyl

Uses

Glycerol Monoleate is used to synthesize water soluble drugs in need of sustained-release for drug delivery.

Definition

An antifog agent and dispersant.

Production Methods

Glyceryl monooleate is prepared by the esterification of glycerol with fatty acids, chiefly oleic acid. As the fatty acids are not pure substances, but rather a mixture of fatty acids, the product obtained from the esterification will contain a mixture of esters, including stearic and palmitic. Di- and triesters may also be present. The composition and, therefore, the physical properties of glyceryl monooleate may thus vary considerably from manufacturer to manufacturer; e.g. the melting point may vary from 10–35°C.

Pharmaceutical Applications

Glyceryl monooleate is a polar lipid that swells in water to give several phases with different rheological properties. It is available in both nonemulsifying (n/e) and self-emulsifying (s/e) grades, the self-emulsifying grade containing about 5% of an anionic surfactant.
The nonemulsifying grade is used in topical formulations as an emollient and as an emulsifying agent for water-in-oil emulsions. It is also a stabilizer for oil-in-water emulsions. The self-emulsifying grade is used as a primary emulsifier for oil-in-water systems.
Glyceryl monooleate gels in excess water, forming a highly ordered cubic phase that can be used to sustain the release of various water-soluble drugs.It is also the basis of mucoadhesive drug delivery systems.
Glyceryl monooleate is reported to enhance transdermal and buccal penetration.

Safety Profile

When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Glyceryl monooleate is used in oral and topical pharmaceutical formulations and is generally regarded as a relatively nonirritant and nontoxic excipient.

storage

Glyceryl monooleate should be stored in an airtight container, protected from light in a cool, dry place.

Incompatibilities

Glyceryl monooleate is incompatible with strong oxidizing agents. The self-emulsifying grade is incompatible with cationic surfactants.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (oral capsules, oral powder, oral tablets; creams, controlled-release transdermal films). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Glyceryl monooleate(25496-72-4)Related Product Information

• decaglycerol
• POLYGLYCERYL-6 PENTASTEARATE
• POLYGLYCERYL-2 DIOLEATE
• POLYGLYCERYL-3 DIOLEATE
• hexaglycerol
• Triglycerol monostearate
• POLYGLYCERYL-10 STEARATE
• POLYGLYCERYL-6 STEARATE
• stearic acid, monoester with oxybis(propanediol)
• oleic acid, monoester with triglycerol
• POLYGLYCERYL-3 DISTEARATE
• DIGLYCEROL
• 1,2-DIOLEOYL-RAC-GLYCEROL
• 1,2-DISTEAROYL-RAC-GLYCEROL
• Monostearin
• TRIOLEIN
• Glycerol
• Glyceryl Monooleate