Mannide oleate

Scheme 1-Separation and characterization of adjuvant oligosaccharide oleate ester derived from product mixture of mannitol oleate acid esterification

Synthesis: The adjuvant-active product mixture was chemically synthesized by esterification between sugar and fatty acid under strongly acidic conditions using concentrated phosphoric acid (Fig 1). One hundred and eighty grams of d-(−)-mannitol was fused at 220 ℃ for 1 h. Concentrated phosphoric acid and 280 g of oleate acid were gradually dropped into the fused mannitol being mixed slowly. The mixture was stirred and heated continuously at 220 ℃ for 2 h. The reaction mixture was then cooled to room temperature and extracted with methanol. The methanol extract (355 g) was neutralized with aqueous NaOH and washed with distilled water to remove the phosphates and free mannitol residues. It was further washed with n-hexane to remove free oleate acid and dried to give the adjuvant-active product mixture as MMO fraction (285 g). It was a brown viscous paste, had a slightly ester fragrance, and was easily dispersed in water to yield a milky white suspension. It was used in the following experiments.

Preparative normal-phase liquid chromatography (normal LC) and reverse-phase high performance liquid chromatography (RP-HPLC): The normal LC was performed on Silica gel 60 column (50 mm i.d., 500 mm length) using n-hexane/ethylacetate (1:1) at a flow rate of 10 ml/min. When the front of the solvent flow reached the bottom of the column tube after the loading of 50 g of the adjuvant-active product mixture mentioned above, the whole gel bed was smoothly pushed out of the column tube retaining the shape of the gel bed. The ejected gel bed was separated into three sections equally in order of the solvent flow. The separated gel sections were extracted with n-hexane/ethylacetate (1:1) individually, and the extracts were dried as the three fractions for the following experiment and chromatography. Preparative RP-HPLC was performed on Vydac-C4 HPLC column (22 mm i.d.,250 mm length) using a liner gradient of acetonitrile (20–80%) with 0.1% trifluoroacetic acid (TFA) over 60 min at a flow rate of 1 ml/min. The peaks were detected by absorbance at a wavelength of 215 nm.

Preparation and screening process of adjuvant-active product mixture. (Oda, Kenji., et al., 2004)

Case Study 1-Preparation and characterization of polyoxyethylene dehydrated mannitol oleate as hydrophilic emulsifier potentially used in w/o/w type adjuvants

Adjuvants play an important role in improving vaccine efficacy. In this study, polyoxyethylene dehydrated mannitol oleate was used as a hydrophilic emulsifier in w/o/w type adjuvants. A series of w/o/w emulsions with various combinations of mannitol oleate, containing different numbers of ethylene oxides, were prepared. The molecular structure of the mannitol oleate was characterized by Fourier transform infrared spectroscopy and 1H nuclear magnetic resonance spectra. Conductivity testing and microscopic image confirmed the emulsion type. The results of the stability test were satisfactory, and the prepared emulsion remained stable for up to 35 days at 37 ℃. The w/o/w emulsion vaccine was prepared as a potential candidate for Foot-and-Mouth disease vaccines in the appropriate proportions. Following the immunization of mice, antibody titers were measured.

Stability of w/o/w emulsions synthesized with different emulsifiers with various numbers of ethylene oxide ranging from 7–14. Data presents means ± standard error of triplicate samples (Zhou, Mengmeng., et al., 2016)

Case Study 2-Water/Oil Emulsions Prepared by Low Pressure Capillary Homogenization I: Effects of Emulsator and Composition Variables on Mannide Mono-Oleate Stabilized Systems

An automated reciprocating capillary emulsator is described which duplicates the low-pressure homogenization principle of the interconnected glass syringe method used to prepare repository w/o emulsions. The w/o emulsions produced by this emulsator were evaluated by rotational viscometry and optical microscopy. Rheological flow curves of concentrated emulsions could be correlated with the extent of dispersion and degree of coalescence. Coalescence rates were found to be an inverse function of the surfactant concentration, with 20 per cent mannitol oleate furnishing the best relative stability for water-in-mineral oil emulsions. The rate of shear was found to govern the degree of emulsification, with a short capillary of large diameter producing the finest dispersion.

Mannide oleate is a compound that has garnered attention in various fields of study due to its unique properties and potential applications. Below is a detailed description of Mannide oleate across different domains:

Drug Delivery: Mannide oleate can serve as a surfactant in drug formulations, enhancing solubility and bioavailability of poorly soluble drugs. Its ability to form stable emulsions and micelles is beneficial for the delivery of hydrophobic compounds. Due to its biodegradable nature, mannide oleate can be utilized in controlled release formulations, allowing for the gradual release of therapeutic agents. It may also act as an adjuvant in vaccine formulations, promoting a more robust immune response.

Food Science: In the food industry, mannide oleate is utilized as an emulsifier, stabilizing oil-in-water and water-in-oil emulsions. This property is particularly significant in products like dressings, sauces, and dairy items. It is generally recognized as safe (GRAS) and can be used to improve texture and mouthfeel in various food products.

Cosmetic and Personal Care Products: In cosmetics, mannide oleate is used for its emulsifying properties, helping to blend oil and water phases in creams and lotions. Its hydrophilic nature allows it to provide moisturizing benefits, making it a common ingredient in skin and hair care products.

Material Science: Mannide oleate can be incorporated into biodegradable polymer matrices, contributing to the development of eco-friendly materials. In nanotechnology, it can stabilize nanoparticles, ensuring their uniform distribution in various mediums.Environmental Applications. Its natural origin and biodegradable properties make mannide oleate an interesting candidate for environmentally friendly formulations, such as biopesticides and bioherbicides. It has potential uses in oil spill remediation by acting as an emulsifier to disperse oil in water, facilitating microbial degradation.

Analytical Chemistry: Mannide oleate can be used in chromatography as a stationary phase modifier or a solvent additive, enhancing separation efficiency for various compounds.

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