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25496-72-4

25496-72-4 Structure

25496-72-4 Structure
IdentificationMore
[Name]

MONOOLEIN
[CAS]

25496-72-4
[Synonyms]

1-(CIS-9-OCTADECENOYL)-RAC-GLYCEROL
1-MONO[CIS-9-OCTADECENOYL]-RAC-GLYCEROL
1-MONOLEIN
1-MONOOLEIN
1-MONOOLEOYL-RAC-GLYCEROL
1-OLEOYL-RAC-GLYCEROL
1-O-OLEYL-RAC-GLYCEROL
DELTA 9 CIS MONOOLEIN
DL-ALPHA-MONOOLEIN
GLYCEROL-1-MONOOLEATE
GLYCEROL ALPHA-MONOOLEATE
GLYCEROL MONOOLEATE
GLYCERYL CIS-9-OCTADECENOATE
GLYCERYL MONOOLEATE
MONOOLEIN
RAC-GLYCEROL 1-MONOOLEATE
9-Octadecenoicacid(Z)-,monoesterwith1,2,3-propanetriol
adchemgmo
ajaxgmo
aldo40
[EINECS(EC#)]

203-827-7
[Molecular Formula]

C21H40O4
[MDL Number]

MFCD00042735
[Molecular Weight]

356.54
[MOL File]

25496-72-4.mol
Chemical PropertiesBack Directory
[Definition]

An antifog agent and dispersant.
[Appearance]

Colourless Solid
[Melting point ]

35-37 °C
[Boiling point ]

449.35°C (rough estimate)
[density ]

0.96 g/cm3 (25 ºC)
[FEMA ]

2526 | GLYCERYL MONOOLEATE
[refractive index ]

1.4626 (589.3 nm 40℃)
[storage temp. ]

−20°C
[solubility ]

chloroform: 50 mg/mL, clear, colorless
[form ]

neat
[Water Solubility ]

<3.57mg/L(30 ºC)
[Usage]

93% 1-Oleoyl, 7% 2-oleoyl
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H319
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P
[WGK Germany ]

1
[F ]

3
[TSCA ]

TSCA listed
[HS Code ]

3822000002
[Storage Class]

11 - Combustible Solids
[Safety Profile]

When heated to decomposition it emits acrid smoke and irritating fumes.
[Hazardous Substances Data]

25496-72-4(Hazardous Substances Data)
Hazard InformationBack Directory
[Description]

§ 184.1323(a) Glyceryl monooleate is prepared by esterification of commercial oleic acid that is derived either from edible sources or from tall oil fatty acids meeting the requirements of §172.862. It contains glyceryl monooleate (C21H40O4 and glyceryl esters of fatty acids present in commercial oleic acid.
[Chemical Properties]

Colourless Solid
[Chemical Properties]

Glyceryl monooleate has a faint fatty odor It is a polar lipid that swells in water to give several phases with different rheological properties Glyceryl monooleate is a mixture of the glycerides of oleic acid and other fatty acids, consisting mainly of monooleate.
[Chemical Properties]

The PhEur 6.3 describes glyceryl monooleate as being a mixture of monoacylglycerols, mainly monooleoylglycerol, together with variable quantities of di- and triacylglycerols. They are defined by the nominal content of monoacylglycerols and obtained by partial glycerolysis of vegetable oils mainly containing triacylglycerols of oleic acid or by esterification of glycerol by oleic acid, this fatty acid being of vegetable or animal origin. A suitable antioxidant may be added.
Glyceryl monooleates occur as amber oily liquids, which may be partially solidified at room temperature and have a characteristic odor.
[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.
[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]

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.
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