Glyceryl monooleate

Catalog Number	ACM111035-2
CAS	111-03-5
Structure
Synonyms	Glycerol-1-oleate
IUPAC Name	2,3-Dihydroxypropyl (Z)-octadec-9-enoate
Molecular Weight	356.54
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
Boiling Point	409.35 °C
Melting Point	35-37 °C
Flash Point	180 °C
Purity	98%
Density	0.9407 g/cm³ at 35 °C
Solubility	Insoluble in water, soluble in hot organic solvents
Appearance	Solid
Storage	2-8 °C
Complexity	315
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	356.29265975
Heavy Atom Count	25
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	2
Isomeric SMILES	CCCCCCCC/C=C\CCCCCCCC(=O)OCC(CO)O
Monoisotopic Mass	356.29265975
Physical State	Liquid
Rotatable Bond Count	19
Topological Polar Surface Area	66.8 Ų

Knowledge & Learning Case Study Q&A

Glyceryl Monooleate (GMO) in the Nanonization and Bioavailability Enhancement of Rivaroxaban Tablets

Al-Shoubki AA, et al. Pharmaceutical Science Advances, 2024, 2, 100015.

The bioavailability of Rivaroxaban (RXB), an anticoagulant, is often limited due to its poor solubility. This study explores the potential of Glyceryl Monooleate (GMO) and Sucrose Acetate Isobutyrate (SAIB) as co-formers in developing nanodispersions to enhance RXB's solubility and bioavailability. These findings suggest that incorporating GMO into RXB formulations can lead to more efficient drug delivery, potentially reducing the required dosage for therapeutic efficacy.
Methodology:
The study utilized a modified melt dispersion technique, incorporating varying polymer-to-drug ratios (0.5:1, 0.75:1, and 1:1) while maintaining a constant polymer-to-poloxamer 407 ratio (0.1:1). The resulting formulations were characterized by particle size (PS), polydispersity index (PDI), zeta potential (ZP), and entrapment efficiency (EE). The best-performing lyophilized formulations were further analyzed using Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), dissolution testing, and pharmacokinetic (PK) studies.
Effect of GMO Concentration:
Increasing GMO concentration resulted in smaller particle sizes and lower PDI values, indicating a more uniform particle distribution. Higher GMO levels improved ZP and EE, enhancing the stability and drug loading capacity of the nanoparticles. Increased GMO concentration also improved the yield of the nanodispersions, contributing to more efficient formulation processes.
Dissolution & Bioavailability:
The dissolution tests revealed that the best lyophilized cubosome (L4) and SAIB-based nanodispersion (L8) significantly outperformed the commercially available XARELTO® in terms of drug release rates. The pharmacokinetic studies further confirmed that L4 and L8 exhibited superior bioavailability compared to XARELTO®, likely due to the enhanced solubility provided by GMO and SAIB.

Glyceryl Monooleate Used for Modified Corn Fiber Gum Emulsifier

Wei Y, et al. Food Chemistry, 2021, 343, 128416.

Glyceryl monooleate (GMO) can be used to prepare GMO-modified corn fiber gum (CFG) emulsifier (GMO-CFG).
The preparation method of GMO-CFG is as follows:
CFG powder (5.00 g) was dissolved in anhydrous DMSO, and 0.30 g EDC and 0.19 g DMAP were added to the solution. The solution was stirred for 1 hour to activate the carboxyl groups of CFG. Different amounts of GMO (e.g., 1%, 3%, and 5% based on the weight of dry CFG) were added to the above solution. The reaction mixture was stirred at 40 °C for 24 hours. The obtained solution was purified by dialyzing against DMSO for one day and deionized water for four days using a dialysis membrane (MWCO3000 Da). The GMO-CFG sample was obtained after freeze-drying.

Glyceryl Monooleate (GMO) Used in the Development of Nanoformulations based on the GMO/Chitosan System

Patil P, et al. Heliyon, 2021, 7(3), e06526.

Glyceryl monooleate (GMO), along with poloxamer 407 and chitosan, can be utilized to prepare gallic acid nanoparticles through a combination of probe sonication and high-pressure homogenization. The preparation method is as follows:
Gallic acid (100 mg) was extracted from amla and dissolved in 1.75 mL of molten GMO. To this, 12.5 mL of a 0.1% poloxamer 407 solution was added dropwise while sonication was performed at 18 W for 3 minutes, creating a primary emulsion. Next, a 2.4% chitosan solution (low molecular weight, in acetic acid) was introduced into the emulsion. The resulting mixture underwent nine cycles of high-pressure homogenization (HPH) at 15,000 psi, followed by drying using a rotary evaporator to form the nanoemulsion. The product was purified using a dialysis membrane, and the dialyzed product was freeze-dried for 48 hours with 2% mannitol as a cryoprotectant to yield a fine powder of nanoparticles. The resulting whitish lyophilized product was stored at 4°C.

Glyceryl Monooleate for the Synthesis of a Novel Copolymer Chitosan Grafted Glycerol Monooleate (CS-GM)

Wang L, et al. International Journal of Pharmaceutics, 2014, 471(1-2), 391-399.

Glyceryl monooleate (GM) can be utilized to synthesize a novel copolymer, chitosan grafted glyceryl monooleate (CS-GM), which serves as an effective nanocarrier for enhancing the oral delivery of enoxaparin.
The synthesis method for the CS-GM copolymer is as follows:
First, glyceryl monooleate (GM) is reacted with succinic anhydride at 170°C for 10 hours to produce succinyl-GM. This succinyl-GM is then treated with EDC and NHS in methanol at 50°C for 2 hours to activate its carboxyl group. Finally, a chitosan (CS) solution with a molecular weight of 50 kDa is mixed with the activated succinyl-GM solution and reacted at 50°C for 24 hours, resulting in the formation of the CS-GM copolymer.

Glyceryl Monooleate for the Synthesis of Hollow Bioadhesive Microspheres for Gastric-specific Drug Delivery

Liu Y, et al. International Journal of Pharmaceutics, 2011, 413(1-2), 103-109.

Glyceryl monooleate (GMO) is an in situ bioadhesive polymer that can be used to prepare hollow bioadhesive microspheres to prolong the retention time of drugs in the stomach.
Step 1: Preparation of Psoralen-Containing Hollow Microspheres Psoralen-containing hollow microspheres were synthesized using the emulsion solvent diffusion method. The polymer matrix was a blend of ethyl cellulose (EC, 0.4 g) and Eudragit® EPO (0.2 g) in a 2:1 ratio. A mixture of 0.06 g of psoralen and 0.6 g of the polymer was dissolved in 2 ml dichloromethane and 2 ml ethanol. This solution was then gradually added dropwise into 30 ml of a 1.5% polyvinyl alcohol (PVA) solution containing 0.3% Tween-80. The resulting emulsion was stirred at 350 rpm using a propeller-type agitator for 2 hours, maintaining the system at a temperature of 15°C throughout the process. The hollow microspheres were then isolated by filtration, washed with water, and vacuum-dried at room temperature for 24 hours.
Step 2: Preparation of Hollow-Bioadhesive Microspheres
The hollow-bioadhesive microspheres were prepared using a coating method. Initially, 0.1 g of the hollow microspheres were introduced into a coating solution containing 0.25 g of glyceryl monooleate (GMO) dissolved in 10 ml of petroleum ether at a concentration of 25 mg/ml. The mixture was dispersed for 3 minutes using magnetic agitation at room temperature. The microspheres were then filtered using a Büchner flask under agitation, allowing the GMO to coat the microspheres. Finally, the coated hollow-bioadhesive microspheres were vacuum-dried at room temperature for 24 hours.

Glyceryl Monooleate in Liquid Embolic Agents

Du L-R, et al. International Journal of Pharmaceutics, 2014, 471(1-2), 285-296.

Glyceryl monooleate (GMO) has emerged as a promising material for developing liquid embolic agents used in vascular embolization.
Researchers developed a series of liquid embolic agents using a GMO, water, and ethanol system. Three formulations with different ratios of GMO, ethanol, and water (49:21:30, 60:20:20, and 72:18:10 by weight) were identified as isotropic liquids (ILs) that could transition into a viscous gel upon contact with physiological fluids or water. This transition is critical as it allows the ILs to effectively block blood flow once delivered to the target site via microcatheters.
Injectability and Microcatheter Deliverability: The low viscosity of the GMO-based ILs ensured smooth delivery through microcatheters, which is crucial for precise embolization in clinical settings.
In Vitro Efficacy: When tested in vitro, the ILs successfully obstructed the flow of saline, simulating their potential to block blood vessels during embolization procedures.
Cytocompatibility: The ILs exhibited good cytocompatibility, as demonstrated in tests with L929 mouse fibroblast cells, indicating that the materials are safe for use in the body.
In Vivo Evaluation: The efficacy of the GMO-based ILs was further evaluated in vivo using rabbit kidney models. The embolization of renal arteries was performed under digital subtraction angiography (DSA) monitoring. Results showed that the degree of embolization was influenced by the formulation and volume used. At five weeks post-embolization, DSA and computed tomography (CT) scans confirmed that the embolized renal arteries remained occluded, leading to significant atrophy of the kidney, with no evidence of recanalization.
Conclusion: GMO-based liquid embolic agents demonstrate significant potential in clinical interventional therapy due to their excellent deliverability, biocompatibility, and effectiveness in permanently occluding blood vessels. These findings support further development and possible clinical application of GMO as a liquid embolic agent in vascular embolization procedures.

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