Synonyms
1-Monooleate glycerol
Description
DryPowder; Liquid; OtherSolid;OtherSolid;Liquid;pale yellow viscous oily liquid with a faint fatty odour
IUPAC Name
2,3-dihydroxypropyl (Z)-octadec-9-enoate
Molecular Formula
C21H40O4
Canonical SMILES
CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)O
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-
InChI Key
RZRNAYUHWVFMIP-KTKRTIGZSA-N
Density
0.9420 @ 20 °C/4 °C;0.925-0.935
Solubility
INSOL IN WATER; SOL IN ETHANOL, ETHER, CHLOROFORM;insoluble in water; soluble in hot organic solvents;soluble in hot alcohol (in ethanol)
Application
1-monoolein serves a vital role in various applications due to its unique amphiphilic properties. As a polar lipid primarily accessed through glycerolysis or esterification of oleic acid, 1-monoolein manifests in different physical forms, from waxy solids to oily liquids, depending on its di- and tri-glyceride content. Notably characterized by its ability to swell in water and form multiple phases with distinct rheological properties, 1-monoolein is widely utilized in drug delivery systems for its biocompatibility, biodegradability, and minimal toxicity, earning it a status of 'generally recognized as safe' (GRAS). It facilitates the sustained release of water-soluble drugs, enhances transdermal and buccal drug absorption, and forms the basis of mucoadhesive drug delivery systems. Additionally, it is instrumental in the synthesis of cubosomes and serves as an effective emulsifier and stabilizer in both water-in-oil and oil-in-water emulsions. Its mucoadhesive properties and ability to form structured gel phases further extend its utility in optimizing drug administration and skincare formulations.
Color/Form
PLATES FROM ETHANOL;YELLOW OIL OR SOFT SOLID
Covalently-Bonded Unit Count
1
EC Number
203-827-7;247-038-6;266-951-0
MeSH Entry Terms
1-oleoyl monoglyceride;1-oleoyl-2-glycerol;glycerol monooleate;glyceryl monooleate;glycerylmonooleate;mono-oleoylglycerol;monoelaidin;monolein;monoolein;myverol 18-99;oleic acid monoglyceride;sn-1-O-(cis-9)octadecenylglycerol
Monoisotopic Mass
356.29266g/mol
Other Experimental
MELTING POINT: 32 °C (UNSTABLE) /PRIMARY BETA FORM/; 35.5 °C (STABLE) /BETA FORM/;IODINE VALUE 65-80
Refractive Index
INDEX OF REFRACTION: 1.4626 @ 40 °C/D;1.462-1.468