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Glyceryl monooleate

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CAS:25496-72-4
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CAS:25496-72-4
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CAS:25496-72-4
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CAS:25496-72-4
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Glyceryl monooleate manufacturers

  • Glyceryl Monooleate
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  • 2024-09-19
  • CAS:25496-72-4
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  • 2024-05-16
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Glyceryl monooleate Basic information
Product Name:Glyceryl monooleate
Synonyms:DL-ALPHA-MONOOLEIN;DELTA 9 CIS MONOOLEIN;GLYCERYL CIS-9-OCTADECENOATE;GLYCEROL ALPHA-MONOOLEATE;GLYCEROL-1-MONOOLEATE;oleic acid, monoester with glycerol;9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol;CIS-9-OCTADECENYLGLYCEROL
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 Structure
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
InChIInChI=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-
InChIKeyRZRNAYUHWVFMIP-KTKRTIGZSA-N
SMILESO(C(=O)CCCCCCC/C=C\CCCCCCCC)CC(CO)O
CAS DataBase Reference25496-72-4(CAS DataBase Reference)
EPA Substance Registry SystemGlyceryl monooleate (25496-72-4)
Safety Information
WGK Germany 1
3
HS Code 3822000002
Hazardous Substances Data25496-72-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
Glyceryl monooleate Usage And Synthesis
DescriptionGlyceryl 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 PropertiesGlyceryl 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.
UsesGlycerol Monoleate is used to synthesize water soluble drugs in need of sustained-release for drug delivery.
Uses93% 1-Oleoyl, 7% 2-oleoyl
DefinitionAn antifog agent and dispersant.
Production MethodsGlyceryl 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 ApplicationsGlyceryl 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 ProfileWhen heated to decomposition it emits acrid smoke and irritating fumes.
SafetyGlyceryl monooleate is used in oral and topical pharmaceutical formulations and is generally regarded as a relatively nonirritant and nontoxic excipient.
storageGlyceryl monooleate should be stored in an airtight container, protected from light in a cool, dry place.
IncompatibilitiesGlyceryl monooleate is incompatible with strong oxidizing agents. The self-emulsifying grade is incompatible with cationic surfactants.
Regulatory StatusGRAS 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 Preparation Products And Raw materials
Raw materialsGlycerol-->Oleic acid
Tag: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