Monoolein

• CAS: 25496-72-4
• Catalog Number: ACM25496724-2
• Category: Main Products
• Molecular Weight: 356.54
• Molecular Formula: C21H40O4
• Synonyms: Monoolein; Monooleate Glycerol; 2,3-dihydroxypropyl (E)-octadec-9-enoate; Glycerol .alpha.-monooleate
• IUPAC Name: Glycerol mono-oleate
• Boiling Point: 483.3ºC at 760 mmHg
• Melting Point: 35-37°C
• Flash Point: 425°F
• Density: 0.96 g/cm³ (25 ºC)
• Appearance: white waxy paste
• Storage: Freezer
• Alpha Sort: Glycerol monooleate
• Exact Mass: 356.29300
• Physical State: Liquid

Case Study

Monoolein for the preparation of quercetin-loaded liquid crystalline nanoparticles (LCNs)

Yong DOC, et al. Journal of Drug Delivery Science and Technology, 2019, 54, 101297.

Monoolein (MO) plays a crucial role in the formulation of liquid crystalline nanoparticles (LCNs) for the encapsulation of quercetin, leveraging its ability to form a liquid crystalline cubic phase. In the described process, MO is melted with quercetin at 45°C, forming a mixture that is then combined with a P 407 solution, also heated to the same temperature. This mixture undergoes vortex mixing, followed by ultrasonication for 10 minutes at 60% amplitude to stabilize the liquid crystalline structure. The resulting LCNs exhibit potential for drug delivery, particularly for the controlled release of quercetin. Monoolein's role as a surfactant and matrix-forming agent enhances the stability and encapsulation efficiency of bioactive compounds, making it highly suitable for pharmaceutical and biotechnological applications in nanocarrier-based drug delivery systems.

Monoolein as a Template for the Synthesis of Gold Nanoparticles

Park SC, et al. Journal of Industrial and Engineering Chemistry, 2023, 121, 2023, 132-141.

Monoolein (MO) has been utilized as a template for the preparation of gold nanoparticles (AuNPs) through a melt and hydration method. In this process, a solution of gold(III) chloride trihydrate is introduced into molten MO, with the gold ions forming nanoparticles within the cubic phase structure. The synthesis process involves the careful addition of gold ion solution to the MO melt, followed by incubation at 25°C for one week, leading to the formation of a clear gel. The concentration of gold ions, ranging from 1 to 5 mM, influences the final cubic phase (CP), with varying concentrations of gold resulting in different nanoparticle characteristics. The resulting gold nanoparticles can be employed in a variety of applications, including catalysis, drug delivery, and sensing, where the cubic phase of MO provides a stable, organized environment for nanoparticle growth. This method demonstrates the versatility of MO as a template material for the controlled synthesis of metal nanoparticles with potential applications in nanomedicine and materials science.

Phase diagram analysis of monoolein/water system

Qiu, Hong, and Martin Caffrey. Biomaterials 21.3 (2000): 223-234.

Monoolein is also an important homologue in a series of monoacylglycerols for deciphering information about lipid molecular structure. To intelligently utilize the monoolein/water system, a reliable and detailed temperature composition phase diagram is required. The system can be reset to a lamellar crystalline phase by implementing sub-zero sample incubation prior to data collection in the heating direction. The low temperature portion of the phase diagram was re-examined and the new equilibrium phase was structurally characterized by static and time-resolved low-angle and wide-angle X-ray distributions and bidirectional scanning calorimetry. A more complete phase diagram encompassing the new equilibrium behavior at low temperatures is reported.
Dry solid monoolein was mechanically mixed with an appropriate amount of water in a syringe-based mixing device to obtain the desired sample composition. Mixing was performed at room temperature while hydrated samples with compositions ranging from 0 to 50% water were prepared. The homogenously mixed samples were transferred to quartz capillaries and bonded with 5-min epoxy and stored for several days to 4 weeks prior to data collection.

Study on the properties of aqueous monoolein dispersions

Wörle, G., et al. International journal of pharmaceutics 329.1-2 (2007): 150-157.

Colloidal cubic phase particles formed in monoolein/poloxamer/water systems are being investigated as potential drug carriers for intravenous administration, among others. The effects of different composition and preparation parameters on the properties of monoolein dispersions prepared by high pressure homogenization were investigated. High pressure homogenization of monoolein/water mixtures stabilized with poloxamer 407 resulted in the dispersion of mostly micron-sized particles at low poloxamer concentrations. The homogenization temperature had a much greater effect on the dispersion properties than the homogenization pressure or the type of homogenizer used. Temperatures around 40-60 degrees Celsius produced the most favorable dispersion properties.
Different ratios of monoolein and poloxamer were mixed in the melt, and the molten mixture was added dropwise to water with stirring at room temperature. Unless otherwise stated, the resulting crude dispersions were equilibrated at room temperature for at least about 1 day before being homogenized in a microfluidizer. The dispersions were filled into glass bottles, flushed with nitrogen and stored at 23°C protected from light.

Monoolein nanoparticles as novel drug carriers

Dawoud, Mohamed, Mohammed AS Abourehab, and Randa Abdou. Journal of Drug Delivery Science and Technology 56 (2020): 101501.

Docetaxel is considered to be an effective anticancer drug. Despite these advantages, docetaxel still has some limitations. Incorporating docetaxel into nanoparticles (e.g., cubic nanoparticles) can overcome these limitations. Monoolein cubic nanoparticles containing docetaxel were prepared with different amphiphile concentrations using a top-down approach using a homogenization technique. Docetaxel-loaded monoolein nanoparticles slowly released the drug over 24 h. Docetaxel cubes showed a higher tumor inhibition rate compared to docetaxel solution. Monoolein cubic nanoparticles appear to be a good carrier for docetaxel due to their particle size and release behavior.
Monoolein cubic nanoparticles with different concentrations of amphiphiles (monoolein and poloxamer) were prepared by mixing different concentrations of molten monoolein with poloxamer. These mixtures were added to stirring water at room temperature using a dropper. These preparation steps resulted in a crude dispersion that was stored at room temperature with magnetic stirring and protected from light for at least 1 day and then homogenized in a microfluidizer at 350 bar for 15 min at 40 °C. The homogenized dispersion was placed in a laboratory autoclave and autoclaved at 121 °C for 15 min and equilibrated for 5 min.

In vitro study using monooleic acid as a penetration enhancer

Lopes, Luciana B., John H. Collett, and M. Vitória LB Bentley. European journal of pharmaceutics and Biopharmaceutics 60.1 (2005): 25-30.

Topical delivery of cyclosporin A (CysA) is of great interest for the treatment of autoimmune skin diseases, but it is often ineffective due to poor permeation of the drug into the skin. This study investigated whether the presence of monooleic acid, a lipid permeation enhancer, in a propylene glycol formulation could improve the delivery of CysA to the skin. It was concluded that monoolein (in a propylene glycol formulation) could enhance the topical delivery of CysA while reducing transdermal delivery.
Various amounts of molten monoolein were added to propylene glycol. Immediately thereafter, CysA was incorporated into the formulation to achieve a concentration of 4% (w/w). CysA was used for topical administration at similar concentrations. Since the phase behavior of monooleic acid systems can be affected by temperature, propylene glycol formulations containing monoolein were analyzed by polarizing microscopy at different temperatures. The formulations were examined using polarized light microscopy.

Custom Q&A

What is the molecular formula of monoolein?

The molecular formula of monoolein is C21H40O4.

What are some synonyms for monoolein?

Some synonyms for monoolein include glyceryl monooleate, 1-monoolein, and oleoylglycerol.

What is the Chemical Abstracts Service (CAS) number for monoolein?

The CAS number for monoolein is 111-03-5.

What is the three-dimensional structure of monoolein?

The three-dimensional structure of monoolein is not provided in the reference.

What are some common applications or uses of monoolein?

The reference does not provide information on the applications or uses of monoolein.

What is the safety information for monoolein?

The reference does not provide specific safety information for monoolein.

What are some other chemicals or compounds that monoolein can be synthesized into?

The reference does not provide information on other chemicals or compounds synthesized from monoolein.

What is the International Union of Pure and Applied Chemistry (IUPAC) name for monoolein?

The IUPAC name for monoolein is not provided in the reference.

Are there any known hazards or risks associated with handling or using monoolein?

The reference does not provide information on specific hazards or risks associated with monoolein.

What physical properties or characteristics does monoolein have?

The reference does not provide information on the specific physical properties or characteristics of monoolein.