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68539-16-2, 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate, Cas:68539-16-2

68539-16-2,
2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate,
Cas:68539-16-2
MFCD00150517
C12H18O7·H2O / 292.28

(-)-2,3:4,6-二-O-异亚丙基-2-酮-L-古洛糖酸一水合物,

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate,

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate, also known as Isovitamin C, is a synthetic compound that mimics the biological activity of naturally occurring Vitamin C. In this regard, it has garnered significant scientific interest due to its potential implications in various fields such as pharmaceuticals, cosmetics, and food additives. This paper aims to provide an overview of the physicochemical properties, synthesis, characterization, analytical methods, biological properties, toxicity, safety, and potential applications of Isovitamin C in scientific experiments.

Definition and Background

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C is a synthetic compound that has an L-ascorbic acid-like structure. The compound was first synthesized in the 1950s by a group of chemists led by Tadeusz Reichstein, who were attempting to develop a more stable form of Vitamin C. 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C comprises two components: an isopropylidene group and a diketone structure. These groups are responsible for the compound's increased stability and biological activity compared to naturally occurring Vitamin C.

Synthesis and Characterization

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C is synthesized from L-gulonic acid lactone in a multistep reaction. The initial step of the synthesis involves converting L-gulonic acid lactone to L-gulono-3,6-lactone, which is then converted to 2-keto-L-gulonic acid. The final step is to react an excess of acetone with 2-keto-L-gulonic acid, resulting in 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C.

The characterization of 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C is achieved through various techniques such as NMR, x-ray diffraction, and vibrational spectroscopy. These techniques provide insight into the compound's structural properties, purity, and stability.

Analytical Methods

Various analytical methods are utilized to determine the quality and purity of 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C, such as HPLC and GC-MS. The methods involve separating and detecting the compound within a complex matrix, which can be challenging due to the presence of other compounds. Several factors contribute to the analytical methods' reliability, such as the sensitivity of the instrument, the stationary phase used, the injection volume, and the mobile phase composition.

Biological Properties

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C exhibits several biological properties that make it useful in various fields such as pharmaceutical, food additives, and cosmetics. In particular, the compound is a potent antioxidant, a property that is beneficial in preventing oxidative stress and reducing inflammation. Additionally, 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C has been reported to improve skin health, promote hair growth, and boost the immune system.

Toxicity and Safety in Scientific Experiments

Toxicity studies show that 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C has low toxicity at acute and subchronic exposure levels. Nonetheless, the compound should be handled with caution, considering its potential to induce skin irritation and inhalation risk. Safety in scientific experiments involving 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C requires the proper handling and disposal of the compound, adherence to good laboratory practices, and the use of personal protective equipment.

Applications in Scientific Experiments

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C has a broad range of applications in scientific experiments due to its biological properties. In particular, the compound is useful in the production of pharmaceutical formulations, food additives, and cosmetics. 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C can provide protection against oxidative stress in the body, which can then prevent a range of chronic diseases and conditions. Moreover, the compound acts as a preservative in food items, particularly in juices, which tend to lose their nutritional value due to exposure to heat and air.

Current State of Research

Research on 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C is ongoing, focusing on its potential applications in various fields such as cardiovascular health, cancer therapy, and neurodegeneration. Recent studies have highlighted the compound's antioxidant activity, which can prevent the progression of atherosclerosis, a condition characterized by the buildup of fatty deposits in the arteries. Studies on cancer have shown that 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C can act as an adjuvant therapy in combination with chemotherapy, resulting in improved therapeutic outcomes. Additionally, 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C shows neuroprotective effects that can mitigate the development and progression of neurodegenerative diseases such as Alzheimer's.

Potential Implications in Various Fields of Research and Industry

2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C's potential implications in various fields of research and industry include its application as a natural preservative in food items, a functional ingredient in cosmeceuticals, and a therapeutic agent in pharmaceuticals. The compound can also have implications in the energy sector, particularly in the development of efficient solar cells with high conversion rates.

Limitations and Future Directions

One limitation of 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate C is its poor solubility in aqueous systems, which can limit its potential applications in various fields. Future research should focus on improving the compound's solubility to enable its use in more extensive applications. Additionally, research should focus on investigating the compound's potential applications in other fields such as agriculture and biotechnology. Finally, the development of efficient and sustainable synthesis routes is critical for the compound's widespread use in industry.

In conclusion, 2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate has significant potential implications in various fields, including food additives, cosmeceuticals, pharmaceuticals, and energy, due to its biological, chemical, and physical properties. Ongoing research on the compound's potential applications and synthesis routes will enable its wider application in industry.

CAS Number68539-16-2
Product Name2,3:4,6-Di-o-isopropylidene-2-keto-L-gulonic acid monohydrate
IUPAC Name(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane-6-carboxylic acid;hydrate
Molecular FormulaC12H20O8
Molecular Weight292.28 g/mol
InChIInChI=1S/C12H18O7.H2O/c1-10(2)15-5-6-7(17-10)8-12(16-6,9(13)14)19-11(3,4)18-8;/h6-8H,5H2,1-4H3,(H,13,14);1H2/t6-,7+,8-,12+;/m0./s1
InChI KeyZFQRGFMVXLSLKZ-QCILGFJPSA-N
SMILESCC1(OCC2C(O1)C3C(O2)(OC(O3)(C)C)C(=O)O)C.O
Synonyms(-)-2,3:4,6-DI-O-ISOPROPYLIDENE-2-KETO-L-GULONIC ACID MONOHYDRATE;2,3:4,6-DI-O-ISOPROPYLIDENE-2-KETO-L-GULONIC ACID MONOHYDRATE;(-)-2,3:4,6-DI-O-ISOPROPYLIDENE-ALPHA-L-XYLO-2-HEXULOFURANOSONIC ACID MONOHYDRATE;2,3:4,6-DI-O-ISOPROPYLIDENE-ALPHA-L-XYLO
Canonical SMILESCC1(OCC2C(O1)C3C(O2)(OC(O3)(C)C)C(=O)O)C.O
Isomeric SMILESCC1(OC[C@H]2[C@@H](O1)[C@H]3[C@@](O2)(OC(O3)(C)C)C(=O)O)C.O


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