1,2-O-cyclohexylidene-alpha-D-glucofuranose

1,2-O-环己叉-alpha-D-呋喃葡萄糖,

1,2-O-Cyclohexylidene-alpha-D-glucofuranose (known as Cyclohexylidene-Glucose or CG) is a chemical compound that has attracted attention in the scientific community due to its various potential applications. CG is a cyclic acetal, which is a molecule with a ring structure that forms when two alcohols react in the presence of an acid. The molecule has a six-membered ring attached to a furanose sugar moiety, where the O atom of the furanose ring forms a bridge with the carbonyl group of the acetal.

Definition and Background

CG was first synthesized by Bergmann and Samuel in 1940 as an intermediate in the synthesis of glucose derivatives. It was later used as a protecting group for the primary alcohol in the synthesis of oligosaccharides and glycoconjugates. Since then, CG has been used in various chemical and biological applications due to its unique properties and versatility.

Synthesis and Characterization

CG can be synthesized by reacting D-glucose with cyclohexanone in the presence of an acid catalyst such as p-toluenesulfonic acid. The reaction yields CG as a white crystalline solid that can be purified via recrystallization.

The purity and identity of CG can be characterized using various methods such as proton nuclear magnetic resonance (1H NMR) spectroscopy, infrared (IR) spectroscopy, and high-performance liquid chromatography (HPLC). The 1H NMR spectrum of CG shows the characteristic peaks for the cyclohexylidene group and the furanose sugar moiety, while the IR spectrum shows the absorption bands for the carbonyl group and the O bridge. HPLC can be used to separate and quantify the CG from other impurities in the sample.

Analytical Methods

CG can be analyzed using various analytical methods such as gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS), and capillary electrophoresis (CE). These techniques can be used to detect and quantify CG in complex mixtures of other compounds.

Biological Properties

CG has been shown to have various biological properties such as anti-inflammatory, antioxidant, and anticancer activities. CG has been found to inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6 in macrophages, which are key mediators of inflammation. Additionally, CG has been found to scavenge free radicals and protect cells from oxidative damage. CG has also been found to induce apoptosis and inhibit proliferation in several cancer cell lines, suggesting its potential as a chemotherapeutic agent.

Toxicity and Safety in Scientific Experiments

CG has a low toxicity profile and has been shown to be safe in scientific experiments. In a 28-day oral toxicity study in rats, CG was found to have no adverse effects on body weight, food consumption, or blood and organ parameters. CG has also been found to have no mutagenic or genotoxic effects in in vitro assays.

Applications in Scientific Experiments

CG has various applications in scientific experiments such as the synthesis of glycoconjugates, as a protecting group for carbohydrates, and as a chiral auxiliary in asymmetric synthesis. CG has been used to protect the primary alcohol of D-glucose in the synthesis of oligosaccharides and glycoconjugates. Additionally, CG has been used as a chiral auxiliary in asymmetric aldol reactions, where it selectively catalyzes the formation of the desired enantiomer.

Current State of Research

Research on CG is ongoing, with new applications and potential uses being discovered. Recent studies have focused on the use of CG in drug delivery systems, as well as its potential as a radiolabeled imaging agent for cancer diagnosis.

Potential Implications in Various Fields of Research and Industry

CG has the potential to impact various fields of research and industry. In the pharmaceutical industry, CG can be used in drug delivery systems to improve the solubility and stability of drugs. In the food industry, CG can be used as a flavor enhancer or as a sugar substitute. In the chemical industry, CG can be used as a starting material for the synthesis of various compounds.

Limitations and Future Directions

Despite its potential applications, CG has some limitations. CG is a relatively expensive compound, which limits its use in large-scale applications. Additionally, the synthesis of CG can be challenging due to the low yield and long reaction times.

Future directions for research on CG include the development of more efficient and cost-effective synthesis methods, as well as the exploration of new applications in drug delivery, imaging, and materials science. Additionally, in-depth studies on the mechanisms of CG's biological activities can help shed light on its potential as a therapeutic agent.