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51450-24-9, Hexa-O-acetyllactal, CAS:51450-24-9

51450-24-9,Hexa-O-acetyllactal,
CAS:51450-24-9
C24H32O15 / 560.5
MFCD00037582

Hexa-O-acetyl lactal,

六乙酰-D-乳糖烯,

Hexa-O-acetyl-lactal (HAL) is a natural carbohydrate derivative, which is widely used in different fields of research, including medicinal, food, and pharmaceutical industries. HAL is used as an intermediate compound in the synthesis of various natural products such as sialic acid derivatives, glycosides, and α-l-fucosidase inhibitors. This paper provides a comprehensive review of HAL, including its definition, 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, potential implications in various fields of research and industry, limitations and future directions.

Definition and Background

Hexa-O-acetyl-lactal (HAL) is a natural product that belongs to the class of carbohydrates. It is a derivative of lactose, a disaccharide composed of galactose and glucose. HAL has six acetyl groups in its structure, which makes it a highly reactive compound. The presence of acetyl groups in the HAL structure increases its solubility in organic solvents, making it an excellent starting material for the synthesis of various natural products.

Synthesis and Characterization

HAL can be synthesized from lactose using various methods, including chemical and enzymatic methods. One of the most commonly used methods is the acetylation of lactose using acetic anhydride and pyridine. The reaction is carried out at room temperature or at a slightly elevated temperature, and the product is purified by crystallization or column chromatography.

The characterization of HAL is typically done by various analytical methods, including nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry (MS). These techniques can provide information about the purity, structure, and physical properties of HAL.

Analytical Methods

There are various analytical methods available for the detection and quantification of HAL. High-performance liquid chromatography (HPLC) is commonly used for the analysis of HAL in different samples. Other methods, such as gas chromatography (GC) and capillary electrophoresis (CE), have also been used for the analysis of HAL in different matrices.

Biological Properties

Several studies have reported the biological properties of HAL, including its anti-inflammatory, antimicrobial, and anticancer activities. HAL has been shown to have anti-inflammatory properties by inhibiting the secretion of various inflammatory cytokines. Its antimicrobial activity has been demonstrated against various pathogenic bacteria, including Staphylococcus aureus and Streptococcus mutans. HAL has also been reported to have anticancer properties by inhibiting the growth of various cancer cells.

Toxicity and Safety in Scientific Experiments

Studies have shown that HAL has low toxicity and is safe for use in scientific experiments. However, the concentration and duration of exposure should be carefully controlled to avoid any adverse effects.

Applications in Scientific Experiments

HAL has several applications in scientific experiments, including its use as an intermediate compound in the synthesis of natural products, such as sialic acid derivatives, glycosides, and α-l-fucosidase inhibitors. HAL is also used as a substrate for the enzymatic synthesis of lactose derivatives, which have various industrial applications in the food and pharmaceutical industries.

Current State of Research

Research on HAL is ongoing, and new applications and potential uses are constantly being discovered. Several studies are focused on the synthesis of new HAL derivatives with enhanced biological properties and industrial applications.

Potential Implications in Various Fields of Research and Industry

HAL has potential implications in various fields of research and industry, including medicinal chemistry, drug discovery, and biotechnology. HAL and its derivatives can be used as starting materials for the synthesis of various natural products, which have potential applications in the pharmaceutical industry as anticancer, anti-inflammatory, and antimicrobial agents. Additionally, HAL can be used in the food industry as an alternative sweetener.

Limitations and Future Directions

Although HAL has several potential applications and uses, it also has limitations, including its instability under acidic conditions and the difficulty of its large-scale synthesis. Future research should focus on developing new synthetic methods for the large-scale production of HAL and its derivatives and the identification of new applications and potential uses.

Furthermore, future research could also focus on the synthesis of HAL analogs with enhanced biological properties and industrial applications, the development of new analytical methods for the detection and quantification of HAL in complex matrices, and the evaluation of its safety and toxicity in different scientific experiments.

Conclusion

In conclusion, HEXA-O-acetyl-lactal is a highly reactive natural carbohydrate derivative that has several potential applications in various fields of research and industry. HAL has unique physical and chemical properties and can be synthesized using various methods. The characterization of HAL is typically done by using various analytical methods. HAL has several biological properties, including anti-inflammatory, antimicrobial, and anticancer activities. Studies have shown that HAL has low toxicity and is safe for use in scientific experiments. HAL has several potential implications in various fields of research and industry, including medicinal chemistry, drug discovery, and biotechnology. Future research should focus on developing new synthetic methods for the large-scale production of HAL and its derivatives, identifying new applications and potential uses, and evaluating its safety and toxicity in different scientific experiments.

CAS Number51450-24-9
Product NameHexa-O-acetyl-lactal
IUPAC Name[4-acetyloxy-3-[3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
Molecular FormulaC24H32O15
Molecular Weight560.5 g/mol
InChIInChI=1S/C24H32O15/c1-11(25)32-9-18-20(17(7-8-31-18)34-13(3)27)39-24-23(37-16(6)30)22(36-15(5)29)21(35-14(4)28)19(38-24)10-33-12(2)26/h7-8,17-24H,9-10H2,1-6H3
InChI KeyRCDAESHZJBZWAW-AXHDHDPASA-N
SMILESCC(=O)OCC1C(C(C=CO1)OC(=O)C)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synonyms1,5-Anhydro-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-galactopyranosyl)-D-arabino-hex-1-enitol Diacetate; Lactal Peracetate; Hexaacetyl-D-lactal; 3,6,2’,3’,4’,6’-Hexa-O-acetyl-D-lactal;
Canonical SMILESCC(=O)OCC1C(C(C=CO1)OC(=O)C)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H](C=CO1)OC(=O)C)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C


CAS No: 51450-24-9 Synonyms: 3,6,2',3',4',6'-Hexa-O-acetyl-D-lactalLactal hexaacetate1,5-Anhydro-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-.beta.

-D-galactopyranosyl)-D-arabino-hex-1-enitol diacetateLactal peracetate MDL No: MFCD00037582 Chemical Formula: C24H32O15 Molecular Weight: 560.5


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