66432-53-9 , 2,3,4,6-Tetra-O-acetyl linamarin,
四乙酰亚麻苦甙,
CAS:66432-53-9
C18H25NO10 / 415.39
MFCD07369654
四乙酰亚麻苦甙,
2,3,4,6-Tetra-O-acetyl Linamarin (TAL) is a natural glucoside found abundantly in cassava roots (Manihot esculenta Crantz), a staple food for over half a billion people worldwide. TAL has been extensively studied due to its potential role as a precursor of cyanogenic glycosides, particularly hydrogen cyanide. Cassava, a tropical tuber, is a carbohydrate-rich food and is an essential component of food security in developing countries. However, cassava roots have high levels of cyanogenic glycosides, which can be toxic if not adequately processed before consumption. TAL plays a crucial role in the detoxification of cyanogenic glycosides present in the cassava plant.
Synthesis and Characterization:
TAL synthesis involves the acetylation of Linamarin, a cyanogenic glycoside that is found in high levels in cassava roots. TAL purification can be achieved through crystallization, which results in a highly pure product of TAL crystalline powder. The purity of TAL can be characterized using various analytical methods, including nuclear magnetic resonance (NMR), high-performance liquid chromatography (HPLC), and infrared spectroscopy (IR).
Analytical Methods:
Analytical methods such as HPLC, NMR, and IR spectroscopy can be used to identify and quantify TAL in cassava roots, cassava products, and other sources. These methods offer high accuracy and precision and are widely used to analyze TAL content.
Biological Properties:
Studies have identified TAL as a potential antitumor, anti-inflammatory, and anti-proliferative agent. TAL exhibited significant anti-cancer activity against several human cancer cell lines, including lung, colorectal, breast, and brain cancer. TAL also showed potent anti-inflammatory activity by suppressing the production of inflammatory cytokines and chemokines.
Toxicity and Safety in Scientific Experiments:
Studies have demonstrated that TAL is safe and non-toxic at therapeutic doses. However, excessive consumption of cassava products containing high levels of cyanogenic glycosides can lead to the production of toxic hydrogen cyanide, which can cause acute and chronic toxicity. Therefore, it is critical to process and prepare cassava products adequately before consumption to eliminate the toxic effects of cyanogenic glycosides, particularly when consumed in large quantities.
Applications in Scientific Experiments:
TAL has a diverse range of applications in scientific experiments, including as a precursor for the synthesis of cyanogenic glycosides and as a substrate for the enzymatic hydrolysis of glucosidases. Moreover, TAL is used in various assays involving oxidative enzymes such as peroxidases.
Current State of Research:
Research on TAL has gained significant attention due to its potential applications in various fields, including health and environmental sciences. Numerous studies have been conducted to explore the therapeutic effects of TAL in various diseases, including cancer, cardiovascular diseases, and inflammatory disorders.
Potential Implications in Various Fields of Research and Industry:
TAL has potential implications in various fields of research and industry, including medicinal chemistry, agriculture, food science, and environmental sciences. TAL can be used as a precursor for the synthesis of various compounds, including cyanogenic glycosides, and as a substrate for enzymatic hydrolysis of glucosidases. Moreover, TAL has potential applications as an anticancer and anti-inflammatory agent.
Limitations and Future Directions:
The current research on TAL is limited to preclinical studies, and further clinical trials are required to validate the clinical efficacy of TAL. Moreover, the safety of TAL consumption in humans needs to be further investigated using well-designed clinical trials. The future direction of TAL research includes exploring its potential as a therapeutic agent for various diseases, identifying its mechanism of action and developing synthetic analogs with improved efficacy and safety.
List of Future Directions:
1. Develop TAL as a therapeutic agent for cancer and inflammatory disorders.
2. Investigate the mechanism of action of TAL as a potential therapeutic agent.
3. Develop synthetic analogs of TAL with improved efficacy and safety.
4. Study the safety of TAL consumption in humans using well-designed clinical trials.
5. Identify the potential clinical applications of TAL.
6. Investigate the effect of TAL on gut microbiota.
7. Study the role of TAL in the detoxification of cyanogenic glycosides.
8. Develop TAL as a substrate for enzymatic hydrolysis of glucosidases.
9. Explore the applications of TAL in agriculture and food science.
10. Investigate the role of TAL in the environmental sciences.
CAS Number | 66432-53-9 |
Product Name | 2,3,4,6-Tetra-O-acetyl Linamarin |
IUPAC Name | [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-cyanopropan-2-yloxy)oxan-2-yl]methyl acetate |
Molecular Formula | C18H25NO10 |
Molecular Weight | 415.39 |
InChI | InChI=1S/C18H25NO10/c1-9(20)24-7-13-14(25-10(2)21)15(26-11(3)22)16(27-12(4)23)17(28-13)29-18(5,6)8-19/h13-17H,7H2,1-6H3/t13-,14-,15+,16-,17+/m1/s1 |
InChI Key | LKTQBMQWABNFQQ-UUAJXVIYSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)OC(C)(C)C#N)OC(=O)C)OC(=O)C)OC(=O)C |
Synonyms | 2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyronitrile; Linamarin Tetraacetate; |
CAS No: 66432-53-9 Synonyms: 2-(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyloxy)isobutyronitrile MDL No: MFCD07369654 Chemical Formula: C18H25NO10 Molecular Weight: 415.39 |
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