Glyceryl monooleate

• BPGlycerol Mono-oleate
• Ph. Eur.Glycerol Mono-oleate
• USP–NFGlyceryl Monooleate

Capmul GMO; glycerol monooleate; glyceryl oleate; monoolein; Myverol 18-99; Peceol; E471

9-Octadecenoic acid (Z)-, monoester with propane-1,2,3-triol (with di- and triglycerides of oleic acid) · [25496-72-4]

UNII D3AEF6S35P · PubChem CID 5283468

C21H40O4 · 356.54

Surfactant, emulsifier

Typical concentrations: — · Dosage forms: Semi-solid

A non-ionic, polar lipid used as an emulsifier, solubiliser and absorption enhancer in oral lipid-based formulations such as self-emulsifying systems and liquid or semi-solid capsule fills. With water it forms liquid crystalline phases (lamellar and cubic), which are exploited in bioadhesive and sustained-release depots, cubosome dispersions and periodontal or mucosal gels. It is also used as a water-in-oil emulsifier and penetration enhancer in topical products, and in foods.

A pale yellow, oily liquid or soft, waxy solid (depending on monoester content and temperature) with a faint characteristic odour. Pharmacopoeial grades are classified by their monoglyceride content, for example about 40%, 60% and 90%.

HLB

≈ 3–4

Physical state

liquid to soft solid at room temperature; high-monoester grades melt at about 35 °C

Phase behaviour

forms lamellar, cubic and hexagonal liquid crystalline phases with water depending on water content and temperature

Solubility

soluble in chloroform, ethanol, mineral oil and vegetable oils; practically insoluble in water, in which it swells

The unsaturated oleate chain makes it susceptible to oxidation; commercial grades may contain an antioxidant. Store in an airtight container, protected from light, in a cool, dry place.

Incompatible with strong oxidising agents.

Produced by glycerolysis of vegetable oils rich in oleic acid (for example high-oleic sunflower oil), or by direct esterification of glycerol with oleic acid; high-monoester grades are obtained by molecular distillation.

Widely used in foods and in oral and topical pharmaceutical products, and generally regarded as non-toxic. It may be mildly irritant to skin and eyes.

Observe normal precautions for the quantity handled; eye protection and gloves are recommended. Spills are slippery.

Mono- and diglycerides are GRAS listed and accepted as food additives in Europe (E471). Glyceryl monooleate is included in the FDA Inactive Ingredient Database (oral and topical preparations) and in non-parenteral medicines licensed in Europe.

Glyceryl monolinoleate; glyceryl monostearate; oleoyl polyoxylglycerides; oleic acid.

The liquid crystalline cubic phase that forms in excess water is highly viscous and bioadhesive and can hold both water- and oil-soluble drugs, which makes glyceryl monooleate a common material for in-situ forming depots. Grade selection (monoester content) strongly affects phase behaviour and performance.