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2782-07-2 ,D-Galactono-1,4-lactone, CAS:2782-07-2

2782-07-2 ,D-Galactono-1,4-lactone,
CAS:2782-07-2
C6H10O6 / 178.14
MFCD00065019

D-Galactono-1,4-lactone

D-半乳糖酸-1,4-内酯

D-Galactono-1,4-lactone is an intermediate in the galactose catabolism pathway. It is an acidic compound that can be found in plants and bacteria. D-Galactono-1,4-lactone has been shown to inhibit enzyme activities when it is present at high concentrations. This compound also inhibits the enzyme carbon source, which is involved in the conversion of glucose to energy. The deuterium isotope effect on the inhibition of enzyme activity by D-galactono-1,4-lactone has been studied extensively using plant phytochemicals such as triticum aestivum.

D-galactono-1,4-lactone, also known as D-galacturonic acid lactone or DGL, is a cyclic molecule that belongs to the family of sugars. It is a six-membered ring that contains four carbon atoms and two oxygen atoms, with one of the oxygen atoms forming a double bond with a carbon atom. DGL is an important precursor for the synthesis of ascorbic acid or vitamin C, which plays an essential role in various physiological functions in the body.

Physical and Chemical Properties:

DGL is a white crystalline powder that is soluble in water and has a slightly sweet taste. It has a molecular weight of 178.14 g/mol and a melting point of 97-100 °C. The chemical formula of DGL is C6H10O6, and its structure is similar to glucose. It is sensitive to light, heat, and air, and can undergo hydrolysis in the presence of acids or bases to produce galacturonic acid and lactone.

Synthesis and Characterization:

DGL can be synthesized by the oxidation of D-galactose using various chemical reagents, such as nitric acid, potassium permanganate, or hydrogen peroxide. It can also be synthesized enzymatically using galactose oxidase or uronate dehydrogenase. The pure compound can be characterized using different spectroscopic techniques, such as infrared, nuclear magnetic resonance, or mass spectrometry.

Analytical Methods:

Several analytical methods have been employed for the quantification of DGL in various samples, such as food, dietary supplements, and biological fluids. These methods include high-performance liquid chromatography, gas chromatography, capillary electrophoresis, and enzymatic assays.

Biological Properties:

DGL has been demonstrated to possess antioxidant, anti-inflammatory, and immunomodulatory properties. As a precursor of vitamin C, it plays a crucial role in the metabolism of collagen, neurotransmitters, and other important biomolecules. DGL has also been shown to modulate the expression of genes involved in the regulation of apoptosis and cell cycle, suggesting its potential role in cancer prevention and treatment. Furthermore, DGL exhibits neuroprotective effects and may improve cognitive function.

Toxicity and Safety in Scientific Experiments:

Based on available toxicological studies, DGL is considered safe and non-toxic at doses typically used in scientific experiments. Acute toxicity studies have shown that DGL has a low oral toxicity, with no significant adverse effects observed in animals at doses up to 5 g/kg body weight. However, chronic toxicity studies are still limited, and further investigations are needed to determine the safety profile of DGL in long-term exposure.

Applications in Scientific Experiments:

DGL has been widely used as a precursor for the synthesis of vitamin C in scientific experiments. It has also been employed as an antioxidant or reducing agent for the determination of other biomolecules, such as amino acids, proteins, and nucleic acids. DGL can be used as a source of energy for bacteria and fungi, and as a substrate for the production of polysaccharides and other compounds.

Current State of Research:

The current research on DGL mainly focuses on its bioactivity, biosynthesis, and biotechnological applications. There is a growing interest in exploring the potential of DGL as a functional food ingredient or a dietary supplement, due to its health-promoting properties and natural origin. Furthermore, DGL has been investigated as a possible alternative to synthetic antioxidants or reducing agents, which may have adverse effects on human health and the environment.

Potential Implications in Various Fields of Research and Industry:

DGL has potential implications in various fields of research and industry, including food and nutrition, pharmaceuticals, biotechnology, and cosmetics. In the food and nutrition industry, DGL can be used as an ingredient in functional foods or dietary supplements, due to its health benefits and natural origin. In the pharmaceutical industry, DGL may serve as a lead compound for the development of novel drugs for cancer, neurodegenerative, or inflammatory diseases. In the biotechnology industry, DGL may be employed as a platform for the synthesis of various biomolecules or as a substrate for the production of value-added products. In the cosmetic industry, DGL may be used as an active ingredient in skincare or haircare products, due to its antioxidant and anti-aging properties.

Limitations and Future Directions:

Despite the promising applications of DGL, there are several limitations and future directions that need to be addressed. First, the biosynthesis of DGL is still limited to a few microorganisms or enzymatic reactions, and further engineering and optimization are needed to improve its yield and purity. Second, the safety of long-term exposure to DGL needs to be thoroughly investigated, particularly in the context of its potential use as a dietary supplement. Third, more studies are needed to elucidate the molecular mechanisms underlying the biological activities of DGL, and to identify its potential targets and pathways. Fourth, the use of DGL in various industrial applications needs to be evaluated in terms of its efficiency, cost-effectiveness, and environmental impact.

Future Directions:

1. Engineering of microorganisms for the efficient biosynthesis of DGL using metabolic engineering or synthetic biology approaches.

2. Development of novel analytical methods for the sensitive and selective detection of DGL in complex samples, such as food or biological fluids.

3. Elucidation of the molecular mechanisms underlying the antioxidant, anti-inflammatory, and neuroprotective properties of DGL using in vitro and in vivo models.

4. Exploration of the potential of DGL as an alternative to synthetic antioxidants or reducing agents in different industrial applications.

5. Investigation of the synergy or antagonism between DGL and other bioactive compounds, such as polyphenols, carotenoids, or tocopherols, in the modulation of biological functions.

6. Evaluation of the safety and efficacy of DGL in different clinical conditions or populations, particularly in the context of its potential use as a dietary supplement.

7. Optimization of the downstream processing of DGL for the production of high-value products, such as vitamin C, bioplastics, or biofuels.

8. Investigation of the effect of DGL on the gut microbiota and its potential implications for human health and disease.

9. Screening of novel microorganisms or enzymes for the biosynthesis or conversion of DGL, and identification of their genetic and biochemical characteristics.

10. Application of DGL in the field of nanotechnology for the synthesis of biocompatible nanoparticles or for the functionalization of surfaces.

In conclusion, D-galactono-1,4-lactone is a versatile molecule that has attracted substantial attention due to its potential applications in various fields of research and industry. Its properties, synthesis, characterization, analytical methods, biological properties, toxicity and safety, scientific applications, current state of research, and future directions have been comprehensively reviewed in this paper. The identification of future directions will provide researchers and industries with direction and guidance to further explore the potential of this interesting molecule.

CAS Number2782-07-2
Product NameD-galactono-1,4-lactone
IUPAC Name(3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
Molecular FormulaC6H10O6
Molecular Weight178.14 g/mol
InChIInChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3-,4-,5+/m1/s1
InChI KeySXZYCXMUPBBULW-AIHAYLRMSA-N
SMILESC(C(C1C(C(C(=O)O1)O)O)O)O
SynonymsD-Galactonic Acid Gamma-lactone; D-Galactonic Acid γ-Lactone; 1,4-D-Galactonolactone; D-Galactonic Acid 1,4-lactone; D-Galactono-1,4-lactone; D-Galactono-γ-lactone; NSC 102762; γ-D-Galactonolactone
Canonical SMILESC(C(C1C(C(C(=O)O1)O)O)O)O
Isomeric SMILESC([C@H]([C@H]1[C@@H]([C@H](C(=O)O1)O)O)O)O
CAS No: 2782-07-2 Synonyms: D-Galactonic acid gamma-lactone MDL No: MFCD00065019 Chemical Formula: C6H10O6 Molecular Weight: 178.14
References: 1. Huber RE, Brockbank RL, Biochemistry 1987, Vol26, p1526-1531


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