CAS 25496-72-4 Glycerol mono-oleate - Analytical Products / Alfa Chemistry

CAT	APS25496724
CAS	25496-72-4
Structure
Synonyms	Synative ES-GMO, Harowax L 9, Rylo MG 19 Pharma, Oleylmonoglyceride, Glycolube 100, Oleic acid monoglyceride, Mazol GMO, Alkamuls GMO 45LG, Radiasurf 7150, Agnique GMO, Emalsy MO, Excel O 95F, Glycerin monooleate, Poem OL 200V, S 1096R, Canamex Glicepol 182, Monoglyceryl oleate, Rheodol MO 60, Glycerol monooleate, Monomuls 90O18, Monegyl 0100, Priolube 1407, Radiasurf 7149, Esterol 272, Rheodol MO 50, Emasol MO 50, Crossential GMO, Sunsoft 8070, Glyceryl monooleate, Polybatch AF 1085, Rikemal XO 100, Aldo MO, Atsurf 595, Emcol O, Kemester 2000,Glyceryl Monooleate, Kessco GMO, Lumulse GMO, Dimodan LSQK, Glyceryl oleate, Oleic acid glycerol monoester, Atmer 1007, Monooleoylglycerol, GMO 8903, Monoolein, Emasol MO, Olicine, Tegin OV, Excel O 95N, Supeol, Aldo MO-FG, Rikemal OL 100E, Sinnoester OGC, GMOrphic 80, Rikemal OL 100, Emrite 6009, Arlacel 129, Excel O 95R, Emalsy OL 100H, Adchem GMO, Dremulse, OL 100, Oleic monoglyceride, A 300, Dur-Em 204, Emuldan RYLO-MG 90, Sunsoft 8070V, Emalsy OL, Capmul GMO 50, Sunsoft O 30B, Monomuls 90-018, Dimodan GMO 90, Loxiol G 10V, XU 61518.10, Olein, mono- (6CI,8CI), Loxiol G 10, S 1096, Ajax GMO, Emerest 2400, A 300 (ester), Glycerol oleate, Glycerine monooleate, EAR 300, 9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol, Aldo 40, Emerest 2421, 9-Octadecenoic acid (Z)-, monoester with 1,2,3-propanetriol, Glyceromonooleate, S 1097, Edenor GMO, Nikkol MGO, Dur-Em 114, Emalsy OL 100
Molecular Weight	713.08
Molecular Formula	((C21H40O4)c(C21H40O4)c)mix
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-

Accurate Mass	712.5853
API Family	Matrix - API Family See respective official monograph(s)
Format	Neat
Shipping	Room Temperature
Storage Conditions	2-8°C Fridge/Coldroom
Subcategory	European Pharmacopoeia (Ph. Eur.)
Type	Excipient

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Case Study

Glyceryl Monooleate (GMO) for the Synthesis of Modified Corn Fiber Gum as an Emulsifier

Wei, Yue, et al. Food Chemistry 343 (2021): 128416.

Glyceryl monooleate (GMO) has been utilized in the synthesis of GMO-modified corn fiber gum (GMO-CFG) emulsifiers to enhance interfacial properties and improve emulsion stability. By esterifying corn fiber gum (CFG) with GMO at different degrees of substitution (DS: 0-0.039), researchers have demonstrated its significant impact on interfacial rheology and emulsification.
The synthesis involved activating the carboxyl groups of CFG using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and 4-dimethylaminopyridine (DMAP) in an anhydrous DMSO medium, followed by the controlled addition of GMO (1%, 3%, and 5%). Purification through dialysis and lyophilization yielded GMO-CFG emulsifiers with varying DS levels.
The modification led to a substantial reduction in critical micelle concentration, surface tension, and interfacial tension, facilitating rapid adsorption at the oil/water interface. Rheological studies confirmed that GMO-CFG forms a highly viscous interfacial layer, with increased elasticity and improved stability at higher DS levels. Emulsions stabilized by GMO-CFG exhibited smaller droplet sizes and enhanced phase stability, as evidenced by quartz crystal microbalance with dissipation (QCM-D) and confocal laser scanning microscopy (CLSM).

Glyceryl Monooleate (GMO) for the Preparation of Bioadhesive Microspheres in Gastric Drug Delivery

Liu, Yuanfen, et al. "Preparation and evaluation of glyceryl monooleate-coated hollow-bioadhesive microspheres for gastroretentive drug delivery." International journal of pharmaceutics 413.1-2 (2011): 103-109.

Glyceryl monooleate (GMO) has been successfully utilized in the development of bioadhesive microspheres for gastric-specific drug delivery. Due to its amphiphilic nature, GMO forms a unique cubic phase liquid crystal structure upon hydration, enhancing bioadhesion and controlled drug release in the gastrointestinal tract.
In this study, psoralen-containing hollow microspheres were synthesized using the emulsion solvent diffusion method. The polymer matrix consisted of ethyl cellulose (EC) (0.4 g) and EPO (0.2 g) in a 2:1 ratio. To prepare the microspheres, 0.06 g of psoralen and 0.6 g of the polymer (1:10) were dissolved in a solvent mixture of 2 ml dichloromethane and 2 ml ethanol. This dispersion was gradually introduced dropwise into 30 ml of a 1.5% polyvinyl alcohol (PVA) solution containing 0.3% Tween-80 under continuous stirring at 350 rpm using a propeller-type agitator. The temperature was maintained at 15 °C throughout the process. The formed microspheres were collected by filtration, rinsed with water, and vacuum-dried at room temperature for 24 hours. Microspheres within the size range of 500-1000 μm were selected for further processing.
To enhance bioadhesion, the hollow microspheres were coated with glyceryl monooleate (GMO). Specifically, 0.1 g of microspheres was immersed in a GMO solution (0.25 g in 10 ml petroleum ether at 25 mg/ml). After 3 minutes of dispersion via magnetic stirring at room temperature, the coated microspheres were recovered using a Büchner flask under agitation. The final hollow-bioadhesive microspheres were vacuum-dried at room temperature for 24 hours before further analysis.

Glyceryl Monooleate (GMO) as a Versatile Precursor for Injectable Liquid Embolics

Du, L. R., Lu, X. J., Guan, H. T., Yang, Y. J., Gu, M. J., Zheng, Z. Z., ... & Fan, T. Y. (2014). International Journal of Pharmaceutics, 471(1-2), 285-296.

Glyceryl monooleate (GMO) has emerged as a promising biomaterial for vascular embolization due to its unique phase behavior in aqueous environments. Recent studies have demonstrated that GMO-based low-viscosity injectable precursors can spontaneously transition into a bicontinuous cubic phase upon exposure to excess water or physiological fluids. This transformation enables effective occlusion of renal arteries in rabbit models, highlighting GMO's potential as an advanced embolic liquid for clinical applications.
A ternary phase diagram of the GMO-ethanol-water system was constructed at both 25 ± 0.5 °C and 37 ± 0.5 °C to explore its phase behavior. The system's mesophases were identified using polarized light microscopy, allowing researchers to map out suitable compositions for injectable formulations. Notably, isotropic liquid (IL) phases were identified for their low viscosity and injectability. Three specific formulations-IL1 (49:21:30), IL2 (60:20:20), and IL3 (72:18:10)-were selected as potential embolic agents. Ethanol was incorporated at minimal concentrations to reduce vascular irritation and injection-associated pain.
This study underscores the significance of GMO in biomedical applications, particularly in minimally invasive procedures such as vascular embolization. The ability of GMO-based precursors to self-assemble into stable mesophases upon hydration makes them highly adaptable for therapeutic interventions, paving the way for future clinical developments.