Glyceryl monooleate CAS 25496-72-4
Introduction：Basic information about Glyceryl monooleate CAS 25496-72-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Glyceryl monooleate Basic information
| Product Name: | Glyceryl monooleate |
| Synonyms: | DL-ALPHA-MONOOLEIN;DELTA 9 CIS MONOOLEIN;GLYCERYL CIS-9-OCTADECENOATE;GLYCEROL MONOOLEATE;GLYCEROL ALPHA-MONOOLEATE;GLYCEROL-1-MONOOLEATE;oleic acid, monoester with glycerol;9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol |
| CAS: | 25496-72-4 |
| MF: | C21H40O4 |
| MW: | 356.54 |
| EINECS: | 247-038-6 |
| Product Categories: | Cosmetic Ingredients & Chemicals;Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols |
| Mol File: | 25496-72-4.mol |
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 |
| Major Application | pharmaceutical (small molecule) |
| Cosmetics Ingredients Functions | SURFACTANT - EMULSIFYING PERFUMING SKIN CONDITIONING - EMOLLIENT |
| 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 |
| TSCA | TSCA listed |
| HS Code | 3822000002 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 25496-72-4(Hazardous Substances Data) |
| 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 glycerolwith fatty acids, chiefly oleic acid. As the fatty acids are not puresubstances, but rather a mixture of fatty acids, the product obtainedfrom the esterification will contain a mixture of esters, includingstearic and palmitic. Di- and triesters may also be present. Thecomposition and, therefore, the physical properties of glycerylmonooleate may thus vary considerably from manufacturer tomanufacturer; e.g. the melting point may vary from 10–35°C. |
| Pharmaceutical Applications | Glyceryl monooleate is a polar lipid that swells in water to giveseveral phases with different rheological properties. It is availablein both nonemulsifying (n/e) and self-emulsifying (s/e) grades, theself-emulsifying grade containing about 5% of an anionic surfactant. The nonemulsifying grade is used in topical formulations as anemollient and as an emulsifying agent for water-in-oil emulsions. Itis also a stabilizer for oil-in-water emulsions. The self-emulsifyinggrade is used as a primary emulsifier for oil-in-water systems. Glyceryl monooleate gels in excess water, forming a highlyordered cubic phase that can be used to sustain the release ofvarious water-soluble drugs.It is also the basis of mucoadhesivedrug delivery systems. Glyceryl monooleate is reported to enhance transdermal andbuccal penetration. |
| Safety Profile | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Safety | Glyceryl monooleate is used in oral and topical pharmaceuticalformulations and is generally regarded as a relatively nonirritantand 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-releasetransdermal films). Included in nonparenteral medicines licensed inthe UK. Included in the Canadian List of Acceptable Non-medicinalIngredients. |
Glyceryl monooleate Preparation Products And Raw materials
| Raw materials | Glycerol-->Oleic acid |
