18465-50-4, 4,6-O-Ethylidene-alpha-D-glucopyranose,
CAS:18465-50-4
C8H14O6/206.19
MFCD09039288
4,6-O-乙叉-alpha-D-吡喃葡萄糖,
4, 6-O-Ethylidene-D-glucopyranose is a glucose analogue that inhibits sugar transport. It has been shown to inhibit glucose transport by binding to the hydroxyl group on the red cell membrane. This binding prevents the sugar from entering the cell and as a result, glucose accumulates in the blood. 4, 6-O-Ethylidene-D-glucopyranose also binds to tryptophan fluorescence and inhibits cytochalasin B binding to tryptophans that are located on the plasma membrane of eukaryotic cells.
4,6-O-Ethylidene-D-glucopyranose, also known as EDGP or ethylidene glucoside, is a chemical compound that has gained attention in scientific research due to its potential applications in various fields. In this paper, we will explore the definition and background of EDGP, its physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research and potential implications in various fields of research and industry. We will also discuss the limitations of EDGP research and future directions.
Definition and Background:
4,6-O-Ethylidene-D-glucopyranose is a sugar derivative that belongs to the family of glucopyranoses. It is a white solid that is soluble in water. 4,6-O-Ethylidene-D-glucopyranose has been commonly used as a reagent for the chemical modification of biomolecules. The chemical structure of 4,6-O-Ethylidene-D-glucopyranose consists of a six-membered pyranose ring with an ethylidene substituent group attached to the 4th and 6th carbons of the ring.
Synthesis and Characterization:
4,6-O-Ethylidene-D-glucopyranose can be synthesized through various methods such as the condensation reaction between D-glucose and ethylidene glycol, and the reaction between D-glucose and ethylidene acetone. The purity and identity of 4,6-O-Ethylidene-D-glucopyranose can be characterized using techniques such as nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), and mass spectrometry.
Analytical Methods:
Analytical methods such as high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE) have been commonly used to detect and quantify 4,6-O-Ethylidene-D-glucopyranose in biological and chemical samples. These techniques allow for the separation, identification, and quantification of 4,6-O-Ethylidene-D-glucopyranose and its derivatives.
Biological Properties:
4,6-O-Ethylidene-D-glucopyranose has been found to have various biological properties such as antioxidant, anti-inflammatory, and antitumor effects. 4,6-O-Ethylidene-D-glucopyranose has been shown to protect cells from oxidative stress and reduce the production of pro-inflammatory cytokines. In vitro studies have also demonstrated that 4,6-O-Ethylidene-D-glucopyranose can inhibit the growth of cancer cells.
Toxicity and Safety in Scientific Experiments:
Studies have shown that 4,6-O-Ethylidene-D-glucopyranose is relatively safe and non-toxic in scientific experiments. Animal studies have demonstrated that 4,6-O-Ethylidene-D-glucopyranose has low acute toxicity and does not cause adverse effects on organs or tissues.
Applications in Scientific Experiments:
4,6-O-Ethylidene-D-glucopyranose has been widely used as a reagent for the chemical modification of biomolecules such as proteins, peptides, and carbohydrates. 4,6-O-Ethylidene-D-glucopyranose can be used to introduce functional groups into biomolecules for the purpose of studying their structure and function. 4,6-O-Ethylidene-D-glucopyranose has also been used as a calibration standard in HPLC and CE experiments.
Current State of Research:
Research on 4,6-O-Ethylidene-D-glucopyranose is still ongoing, and new applications and functions of this compound continue to be discovered. Researchers are exploring the potential use of 4,6-O-Ethylidene-D-glucopyranose in drug delivery systems, as well as in the synthesis of new biomolecules with improved properties.
Potential Implications in Various Fields of Research and Industry:
4,6-O-Ethylidene-D-glucopyranose has potential implications in various fields of research and industry such as drug discovery, food science, and biotechnology. 4,6-O-Ethylidene-D-glucopyranose can be used as a platform to develop new drugs with improved properties and for the modification of food ingredients to enhance their health benefits.
Limitations and Future Directions:
Despite the potential applications of 4,6-O-Ethylidene-D-glucopyranose, research on this compound has several limitations. Currently, there is limited information on the toxicity and safety of 4,6-O-Ethylidene-D-glucopyranose in long-term exposure studies, and its biodegradability and environmental impact remain unclear. Future research should focus on investigating these aspects of 4,6-O-Ethylidene-D-glucopyranose. Additionally, more research is needed to explore the potential use of 4,6-O-Ethylidene-D-glucopyranose in new applications such as drug delivery and biotechnology.
Future Directions:
1. Investigating the use of 4,6-O-Ethylidene-D-glucopyranose as a template for the synthesis of new biomolecules.
2. Developing new methods for the synthesis of 4,6-O-Ethylidene-D-glucopyranose and its derivatives.
3. Exploring the potential use of 4,6-O-Ethylidene-D-glucopyranose in the development of drug delivery systems.
4. Investigating the biodegradability and environmental impact of 4,6-O-Ethylidene-D-glucopyranose.
5. Developing new analytical methods for the detection and quantification of 4,6-O-Ethylidene-D-glucopyranose.
6. Investigating the potential anti-cancer properties of 4,6-O-Ethylidene-D-glucopyranose and its derivatives.
7. Developing new applications of 4,6-O-Ethylidene-D-glucopyranose in food science and the food industry.
8. Investigating the potential use of 4,6-O-Ethylidene-D-glucopyranose as a catalyst in organic synthesis reactions.
9. Developing new methods for the modification of biomolecules using 4,6-O-Ethylidene-D-glucopyranose.
10. Investigating the mechanisms responsible for the biological properties of 4,6-O-Ethylidene-D-glucopyranose and its derivatives.
CAS Number | 18465-50-4 |
Product Name | 4,6-O-Ethylidene-D-glucopyranose |
IUPAC Name | (4aR,7R,8R,8aS)-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol |
Molecular Formula | C8H14O6 |
Molecular Weight | 206.19 g/mol |
InChI | InChI=1S/C8H14O6/c1-3-12-2-4-7(13-3)5(9)6(10)8(11)14-4/h3-11H,2H2,1H3/t3?,4-,5-,6-,7-,8?/m1/s1 |
InChI Key | VZPBLPQAMPVTFO-DBVAJOADSA-N |
SMILES | CC1OCC2C(O1)C(C(C(O2)O)O)O |
Synonyms | 4,6-O-ethylidene glucose, ethylidene glucose |
Canonical SMILES | CC1OCC2C(O1)C(C(C(O2)O)O)O |
Isomeric SMILES | CC1OC[C@@H]2[C@@H](O1)[C@@H]([C@H](C(O2)O)O)O |
COA:
Product name: 4,6-O-Ethylidene-alpha-D-glucopyranose
M.F.: C8H14O6 M.W.: 206.19 Batch No: 20140707 Quantity:178g
Items | Standards | Results |
Appearance | White crystal powder | Complies |
NMR and MS | Should comply | Complies |
Water | Max. 0.5% | 0.2% |
TCL | Should be one spot | One spot |
Assay | Min.98% | 99.9% |
References:
1. Mueckler M, Weng W, Kruse M, J. Biol. Chem. 1994, Vol269, Issue 32, 20533-20538 08
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