17651-11-5

Upstream product

• 143-07-7 lauric acid 
• 2280-44-6 D-Glucose 
• 71071-51-7 2,2,2-Trichloroethyl dodecanoate 
• 2146-71-6 vinyl laurate 
• 492-62-6 alpha-D-glucopyranose 
• 13039-40-2 6-O-sucrose monolaurate 
• 492-61-5 β-D-glucose 
• 112-16-3 n-dodecanoyl chloride 
• 530-26-7 D-Mannose 
• 7296-15-3 alpha-D-mannopyranoside 
• 7283-09-2 β-D-allopyranose 
• 50-99-7 D-glucose 
• 10257-28-0 D-Galactose 

Relevant academic research and scientific papers

Factors determining the reaction temperature of the solvent-free enzymatic synthesis of trehalose esters

Solvent-free synthesis encourages the design of processes and products that reduce the use and generation of hazardous chemicals. Given the importance of developing greener methodologies, we sought to determine the factors influencing the reaction temperature required for solvent-free, enzymatic synthesis of sugar esters such as trehalose (TRE) esters, using Novozyme 435 as the enzyme catalyst. The use of lauric acid (La) and ethyl laurate (LaEt) as acyl donors did not affect the activation temperature for the generation of trehalose diesters (TDEs), despite the differences in corresponding by-products (water and ethanol). However, when glucose (GLU) and La were employed as reaction substrates as a comparison, glucose monoester (GME) generation readily occurred at much lower temperatures than with the TRE esters, even without a water collection device. Moreover, when the glass transition temperature (Tg) of the sugar substrates increased, a higher reaction temperature was required. These results suggest that while the activation temperature of the reaction did not correlate with the boiling point of the by-product, it did correlate with the glass transition temperature (Tg) of the trehalose substrates. Thus, our work demonstrates the importance of the physical state of amorphous matrices in determining the optimal reaction temperature of a solvent-free sugar synthesis.

Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids

(Chemical Equation Presented) Glucose fatty acid ester synthesis with poly(ethylene glycol)-modified Candida antarctica lipase B (CAL-B) was performed in pure 1-butyl-3-methyl imidazolium tetrafluoroborate [BMIM][BF4] (30% conversion) and in pure 1-butyl-3-methyl imidazolium hexafluorophosphate [BMIM][PF6] (35% conversion). In a solvent system composed of ionic liquid and 40% t-BuOH conversions up to 90% and isolated yields of up to 89% were achieved using fatty acid vinyl esters as acyl donors and commercial CAL-B.

Solubility of glucose in mixtures containing 2-methyl-2-butanol, dimethyl sulfoxide, acids, esters, and water

Solubility measurements of glucose in a variety of binary, ternary, and multicomponent mixtures containing 2-methyl-2-butanol, dimethyl sulfoxide, acids, esters, and water at different temperatures are presented. The solubilities of crystalline β-glucose,

Lipase-catalysed esterification of some α-D-glucopyranosides in dry media under focused microwave irradiation

Immobilized Candida antarctica lipase (Novozym 435)-catalysed esterifications of methyl α-D-glucopyranoside 1, α-D-glucose 2 and α,α-trehalose 3 with dodecanoic acid in dry media under focused microwave irradiation and classical heating conditions are described, under the same conditions of time and temperature. The advantages of performing the reactions in the microwave reactor are evident in all cases either in terms of yields and (or) purities of products.

Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

As nonionic surfactants derived from naturally renewable resources such as sugars and fatty acids, sugar fatty acid esters have been widely utilized in food, cosmetic and pharmaceutical industries. Our present study has demonstrated that the inexpensive and halogen-free tetraalkylammonium salts (e.g., [Bu4N][Ac], [Et4N][Ac] and [Me4N][Ac]) can act as dual solvents–catalysts for regioselective acylation to produce glucose laurate. This non-enzymatic synthesis can proceed under mild conditions with high specificity, and the conversions obtained were superior to that when an enzyme catalyst (lipase, EC 3.1.1.3) was added. A higher yield was obtained in the ammonium salt with a longer alkyl chain on the cation, while no product was obtained in [Bu4N][HSO4] and [Bu4P][Ac]. A reaction mechanism has been proposed, which is supported by phase-transfer catalysis and law of matching water affinity.

Retarding activity of 6-O-Acyl-D-alloses against plant growth

The retarding activity of 6-O-dodecanoyl-D-allose against rice growth was higher than that of the octanoate and the decanoate. The activities of 6-O-dodecanoyl-D-glucose,-D-mannose, and-D-galactose against rice seedlings were examined. 6-O-Dodecanoyl-D-allose exhibited the highest activity, suggesting the importance of the a-axial hydroxy group at C-3 of D-allose.

Dynamic formation of nanostructured particles from vesicles via invertase hydrolysis for on-demand delivery

The unique multicompartmental nanostructure of lipid-based mesophases can be triggered, on-demand, in order to control the release of encapsulated drugs. In this study, these nanostructured matrices have been designed to respond to a specific enzyme, invertase, an enzyme which catalyses the hydrolysis of sucrose. The effect of two sugar esters upon the phase behaviour of two different lipids which form cubic phases, phytantriol and monolinolein, was investigated. Factors affecting the hydrolysis of the sucrose headgroup are discussed in terms of the molecular structure of the sugar surfactant and also its ability to incorporate into the lipid bilayer. By hydrolysing the incorporated sugar esters, a dynamic change in mesophase nanostructure from vesicles to a cubic phase was observed. This phase change resulted in the triggered release of an encapsulated model drug, fluorescein. This investigation demonstrates, for the first time, that changes on a molecular level by subtly controlling the hydrophilic and hydrophobic features of an amphiphilic additive at the interface by enzymatic hydrolysis can result in a global change in the system and so paves the way towards the design and development of lipid-based matrices which are responsive to specific enzymes for the controlled delivery of pharmaceutically active molecules or functional foods.

One-step synthesis of carbohydrate esters as antibacterial and antifungal agents

Carbohydrate esters are biodegradable, and the degraded adducts are naturally occurring carbohydrates and fatty acids which are environmentally friendly and non-toxic to human. A simple one-step regioselective acylation of mono-carbohydrates has been developed that leads to the synthesis of a wide range of carbohydrate esters. Screening of these acylated carbohydrates revealed that several compounds were active against a panel of bacteria and fungi, including Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), Candida albicans, Cryptococcus neoformans, Aspergillus flavus and Fusarium graminearum. Unlike prior studies on carbohydrate esters that focus only on antibacterial applications, our compounds are found to be active against both bacteria and fungi. Furthermore, the synthetic methodology is suitable to scale-up production for a variety of acylated carbohydrates. The identified lead compound, MAN014, can be used as an antimicrobial in applications such as food processing and preservation and for treatment of bacterial and fungal diseases in animals and plants.

Synthesis of D-allose fatty acid esters via lipase-catalyzed regioselective transesterification

The acylation of the rare sugar, D-allose (the C-3 epimer of D-glucose), with fatty acid vinyl esters was successfully carried out using Candida antarctica lipase in acetonitrile at 45°C to give D-allose 6-alkanoates with high regioselectivity in good yields.

Highly efficient synthesis of glucose fatty acid esters catalyzed by high performance lipase preparations

Glucose fatty acid esters were synthesized using cross-linked enzyme aggregates (CLEAs), protein coated microcrystals (PCMCs) and cross-linked protein coated microcrystals (CLPCMCs) of Candida antarctica lipase B (CALB) as biocatalyst designs in single and mixed solvent systems. Up to 90% conversion and more than 99% regioselectivity were obtained using vinyl acetate as the acyl donor in a solvent system composed of 2-methyl-2-butanol (2M2B) and 30% (v/v) DMSO, with CALB CLEAs within 45 min. Similar results were obtained with CALB CLPCMCs as the biocatalyst under the same reaction conditions. This approach was then extended to the synthesis of glucose esters with higher acyl chain length. The synthetic strategy used in this work can potentially be extended for the fast and regioselective esterification/transesterification of other sugars as well.