4613-78-9, b-Gentiobiose octaacetate,
CAS:4613-78-9
C28H38O19 / 678.59
MFCD00016917
八乙酰龙胆二糖,
Beta-gentiobiose octaacetate, also known as gentiobiose octaacetate, is a chemical compound that belongs to the category of acetylated carbohydrates. It is derived from gentiobiose, which is a disaccharide consisting of two glucose molecules linked together by a beta-1,6-glycosidic bond.
The octaacetylated form of gentiobiose is widely used in various scientific fields due to its unique physical and chemical properties. It is soluble in organic solvents, including chloroform, methanol, and ethyl acetate, and is relatively stable under normal conditions.
The chemical properties of beta-gentiobiose octaacetate are determined by its molecular structure and reactivity. Due to the presence of eight acetate groups, the compound is relatively hydrophobic and less reactive than gentiobiose. However, it can be easily hydrolyzed under acidic or basic conditions, leading to the release of gentiobiose.
Synthesis and Characterization:
Beta-gentiobiose octaacetate can be synthesized by acetylation of gentiobiose using acetic anhydride and a catalyst such as pyridine. The reaction typically occurs at room temperature and takes several hours to complete. The resulting product is then purified using chromatographic techniques, yielding pure beta-gentiobiose octaacetate.
The characterization of beta-gentiobiose octaacetate involves various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry. These techniques can provide detailed information about the molecular structure, purity, and chemical properties of the compound.
Analytical Methods:
Beta-gentiobiose octaacetate can be analyzed using various analytical methods, including high-performance liquid chromatography (HPLC), gas chromatography (GC), and thin-layer chromatography (TLC). These techniques can be used to quantify the amount of beta-gentiobiose octaacetate in a sample and identify any impurities or degradation products.
In addition, other methods such as electrospray ionization mass spectrometry (ESI-MS) and high-resolution mass spectrometry (HRMS) can be used to determine the molecular weight and composition of beta-gentiobiose octaacetate.
Biological Properties:
Beta-gentiobiose octaacetate has been shown to exhibit various biological properties, including anti-inflammatory, anti-oxidant, and anti-cancer activities. In particular, several studies have reported that beta-gentiobiose octaacetate can inhibit the expression of pro-inflammatory cytokines and oxidative stress markers, suggesting its potential therapeutic use in the treatment of inflammatory diseases and cancer.
Moreover, beta-gentiobiose octaacetate has been reported to possess immunomodulatory effects, enhancing the immune response against viral and bacterial infections.
Toxicity and Safety in Scientific Experiments:
Beta-gentiobiose octaacetate has been shown to have low toxicity in scientific experiments, with no reports of adverse effects in animals or humans. However, like any chemical compound, it should be handled with care and appropriate safety measures should be taken. In particular, it is recommended that beta-gentiobiose octaacetate should be stored in a dry and cool place, away from direct sunlight and moisture.
Applications in Scientific Experiments:
Beta-gentiobiose octaacetate has various applications in scientific experiments, including as a substrate for enzymatic and chemical reactions, as a building block for the synthesis of novel carbohydrate derivatives, and as a model compound for studying the physicochemical and biological properties of carbohydrates.
Moreover, beta-gentiobiose octaacetate can be used as a tool for investigating the role of glycans in biological systems, such as glycosylation of proteins and cell signaling.
Current State of Research:
Currently, there is growing interest in the use of beta-gentiobiose octaacetate in various scientific fields, including medicinal chemistry, biochemistry, and biotechnology. Researchers are exploring the potential of beta-gentiobiose octaacetate as a therapeutic agent for various diseases, including cancer, inflammation, and viral infections.
Moreover, there is ongoing research on the development of new synthesis methods and analytical techniques for beta-gentiobiose octaacetate, with a focus on improving yield and purity.
Potential Implications in Various Fields of Research and Industry:
The potential implications of beta-gentiobiose octaacetate in various fields of research and industry are vast. In the field of medicine, beta-gentiobiose octaacetate may be used as a therapeutic agent for various diseases, such as cancer, inflammation, and viral infections.
In the field of biotechnology, beta-gentiobiose octaacetate may be used as a building block for the development of new biopolymers, such as biofuels and biodegradable plastics. Moreover, the unique physical and chemical properties of beta-gentiobiose octaacetate make it a valuable tool for investigating the properties and functions of carbohydrates in biological systems.
Limitations and Future Directions:
Despite its potential applications, there are some limitations and challenges associated with the use of beta-gentiobiose octaacetate. For example, its low solubility in water may limit its use in some biological systems, and its relatively high cost may hinder its large-scale production.
In the future, researchers may focus on developing new synthesis methods and analytical techniques for beta-gentiobiose octaacetate, with the aim of reducing its production cost and improving its yield and purity. Moreover, there may be opportunities for the development of new derivatives and analogs of beta-gentiobiose octaacetate with improved properties and functions.
CAS Number | 4613-78-9 |
Product Name | Beta-gentiobiose octaacetate |
IUPAC Name | [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate |
Molecular Formula | C28H38O19 |
Molecular Weight | 678.59 |
InChI | InChI=1S/C28H38O19/c1-11(29)37-9-19-21(39-12(2)30)23(41-14(4)32)25(43-16(6)34)27(46-19)38-10-20-22(40-13(3)31)24(42-15(5)33)26(44-17(7)35)28(47-20)45-18(8)36/h19-28H,9-10H2,1-8H3/t19-,20-,21-,22-,23+,24+,25-,26-,27-,28-/m1/s1 |
InChI Key | GNTLGGDVHFXGLI-UPIDMYHSSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
Canonical SMILES | CC(=O)OCC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
Isomeric SMILES | CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H](C(O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
CAS No: 4613-78-9 Synonyms: 1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)-b-D-glucopyranose MDL No: MFCD00016917 Chemical Formula: C28H38O19 Molecular Weight: 678.59 |
References: 1. Wolfrom ML, Igarashi K, Koizumi K, J. Org. Chem. 1965, p3841 |
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