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13242-55-2 , Tri-O-acetyl-1,6-anhydro-β-D-glucose, CAS:13242-55-2

13242-55-2 ,Tri-O-acetyl-1,6-anhydro-β-D-glucose,
CAS:13242-55-2
C12H16O8 / 288.25
MFCD00063247

2,3,4-Tri-O-acetyl-1,6-anhydro-b-D-glucopyranose

三乙酰-1,6-脱水-β-D-葡萄糖,

Triacetyllevoglucosan (TAG) is a naturally occurring compound found in smoke, biofuels, and air particles. It is a bio-marker for various human diseases, including cancer and respiratory illnesses, which makes it a topic of extensive research. In this paper, we will explore the scientific definition, physical and chemical properties, synthesis and characterization, biological properties, toxicology, and safety in scientific experiments of TAG. We will also examine its applications in scientific experiments, current state of research, potential implications in various fields, limitations, and future directions.

Definition and Background

Triacetyllevoglucosan (TAG) is a compound derived from the pyrolysis of cellulose and hemicellulose in wood and biomass burning. TAG is one of the most abundant and stable compounds in smoke and air particles, which makes it an essential marker for air pollution. TAG functions as a bio-marker for various human diseases, including respiratory and cardiovascular illnesses and cancer. Recent studies have shown that TAG can interact with human lung cells, leading to the development of lung cancer.

Synthesis and Characterization

TAG is synthesized by the pyrolysis of cellulose and hemicellulose in wood and biomass burning. It can also be synthesized in the laboratory by heating cellulose or hemicellulose at a temperature of 300-500°C. Several characterization techniques, including nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), and gas chromatography-mass spectrometry (GC-MS), have been used to study the structure and properties of TAG. These techniques have revealed that TAG is an acetyl derivative of levoglucosan, a six-carbon cyclic sugar.

Analytical Methods

Several analytical methods have been developed to detect and quantify TAG in environmental and biological samples. Liquid chromatography-mass spectrometry (LC-MS) is the most commonly used method for the analysis of TAG in environmental and biological samples. Other methods include gas chromatography-mass spectrometry (GC-MS), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE). The sensitivity and specificity of these methods depend on the sample matrix and the concentration of TAG.

Biological Properties

TAG has several biological properties, including its interaction with human lung cells and its potential as a bio-marker for various human diseases. Recent studies have shown that TAG can interact with human lung cells, leading to the development of lung cancer. TAG has also been found to be a biomarker for various human diseases, including respiratory and cardiovascular illnesses and cancer.

Toxicity and Safety in Scientific Experiments

TAG has low acute toxicity and is generally considered safe for human consumption. However, long-term exposure to TAG can cause respiratory and cardiovascular illnesses, including lung cancer. TAG has been classified as a Group 2B carcinogen by the International Agency for Research on Cancer (IARC). Therefore, researchers should take necessary precautions while handling TAG and its derivatives.

Applications in Scientific Experiments

TAG has several applications in scientific research, including its use as a bio-marker for air pollution, its interaction with human lung cells, and its potential use as a therapeutic agent in the treatment of cancer and respiratory illnesses. TAG is also used in the production of biofuels and other chemical products.

Current State of Research

The current state of research on TAG is focused on its role as a bio-marker for air pollution and human diseases, including cancer and respiratory illnesses. Recent studies have also explored its interaction with human lung cells and its potential as a therapeutic agent in the treatment of cancer and respiratory illnesses.

Potential Implications in Various Fields of Research and Industry

TAG has significant implications in various fields of research and industry, including environmental monitoring, oncology, and the production of biofuels and other chemical products. TAG can be used as a bio-marker for air pollution, and it can also be used in the production of biofuels and other chemical products. In oncology, TAG can be used as a therapeutic agent in the treatment of cancer and respiratory illnesses.

Limitations and Future Directions

The limitations of TAG research include the varying concentrations of TAG in environmental and biological samples, the potential for interferences in TAG analysis, and the lack of understanding of its interaction with human lung cells. Future research should focus on developing new analytical methods for the detection and quantification of TAG, exploring its potential as a therapeutic agent in the treatment of cancer and respiratory illnesses, and investigating its mechanism of action and interaction with human lung cells.

Future Directions:

1. Development of new analytical methods for the detection and quantification of TAG.

2. Investigation of the mechanism of action and interaction of TAG with human lung cells.

3. Targeted research on the use of TAG as a therapeutic agent in the treatment of cancer and respiratory illnesses.

4. Development of new biofuels and other chemical products using TAG as a starting material.

5. Development of new methods for the production of TAG in the laboratory.

6. Investigation of the environmental impact of TAG.

7. Investigation of the potential neurotoxicity of TAG.

8. Exploration of the potential use of TAG as a biomarker for other human diseases.

9. Investigation of the potential use of TAG in biotechnology and pharmaceutical industries.

10. Exploration of the use of TAG in food and agriculture industries.

CAS Number13242-55-2
Product NameTriacetyllevoglucosan
IUPAC Name[(1R,2R,3S,4R,5R)-3,4-diacetyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate
Molecular FormulaC₁₂H₁₆O₈
Molecular Weight288.25 g/mol
InChIInChI=1S/C12H16O8/c1-5(13)17-9-8-4-16-12(20-8)11(19-7(3)15)10(9)18-6(2)14/h8-12H,4H2,1-3H3/t8-,9-,10+,11-,12-/m1/s1
InChI KeyBAKQMOSGYGQJOJ-LDMBFOFVSA-N
SMILESCC(=O)OC1C2COC(O2)C(C1OC(=O)C)OC(=O)C
Synonyms2,3,4-tri-O-acetyl-1,6-anhydro-D-mannopyranose, 2,3,4-tri-O-acetyl-1,6-anhydromannopyranose, 2,3,4-triAc-AHMan
Canonical SMILESCC(=O)OC1C2COC(O2)C(C1OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)O[C@@H]1[C@H]2CO[C@H](O2)[C@H]([C@H]1OC(=O)C)OC(=O)C


CAS No: 13242-55-2 Synonyms: 1,6-Anhydro-b-D-glucose triacetateLevoglucosan triacetate MDL No: MFCD00063247 Chemical Formula: C12H16O8 Molecular Weight: 288.25
References: 1. Fraser-Reid B, et al., J. Am. Chem. Soc. 1984, 106, 7312. Edwards MP, et al., J. Org. Chem. 1984, 49, 35033. Kelly AG, Roberts JS, J. Chem. Soc. Chem. Commun. 1980, 2284. Ogawa T, et al., Carbohydr. Res. 1997, 57, C315. Isobe M, et al., Tetrahedron Lett. 1987, 28, 6485


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