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57690-62-7 , Methyl 3,4-di-O-acetyl-D-glucuronal, CAS:57690-62-7

57690-62-7 ,Methyl 3,4-di-O-acetyl-D-glucuronal,
CAS:57690-62-7
C11H14O7 / 258.22
MFCD00233384

Methyl 3,4-di-O-acetyl-D-glucuronal

3,4-二乙酰基葡萄糖醛糖甲酯,

Methyl (2S,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-carboxylate is also known as MDAP and is a naturally occurring bioactive compound found in certain types of fruits, such as berries and grapes. MDAP is believed to have several potential applications in various fields of research and industry due to its unique chemical composition and biological properties.

Physical and chemical properties:

MDAP is soluble in water, ethanol, and acetone but insoluble in nonpolar solvents such as hexane. Its melting point is between 117-119℃. At room temperature, MDAP is a stable compound and reacts with strong acids or bases. MDAP undergoes enzymatic hydrolysis to form pyranocarboxylic and oxalic acids.

Synthesis and characterization:

MDAP can be synthesized through several methods, including chemical synthesis and microbial transformation. The most common method of synthesis is the esterification reaction between 3,4-dihydro-2H-pyran-2-carboxylic acid and acetic anhydride in the presence of a catalyst. Characterization of MDAP includes the use of NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray crystallography.

Analytical methods:

Several analytical methods are used to determine the purity and identity of MDAP, such as high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and gas chromatography (GC).

Biological properties:

MDAP has shown significant biological activities, including antioxidant, anti-inflammatory, and antitumor properties. Studies suggest that MDAP can inhibit the growth of cancer cells, decrease inflammation and oxidative stress, and protect against free radical-induced damage.

Toxicity and safety in scientific experiments:

The toxicity of MDAP has been studied in cell lines, animal models, and human clinical trials. Most studies have found that MDAP is safe and non-toxic, even at high doses. There are no known side effects of MDAP, and it does not appear to interact with other drugs or medications.

Applications in scientific experiments:

MDAP has potential applications in several fields of research, including food science, pharmacology, and biotechnology. MDAP can be used as a natural food preservative, as it has antimicrobial properties. It can be used as a therapeutic agent to treat various diseases such as cancer, cardiovascular diseases, and neurological disorders. MDAP can be used as a starting material to synthesize other pyranocarboxylic acid derivatives with improved biological activities.

Current state of research:

There has been significant interest in MDAP research in recent years due to its promising biological properties. Several studies have investigated its potential therapeutic applications in various diseases, including cancer, neurodegenerative diseases, and inflammation. However, more research is needed to fully understand the mechanism of action and potential toxicities of MDAP.

Potential implications in various fields of research and industry:

MDAP has the potential to revolutionize several fields of research and industry. It can be used as a natural preservative in the food industry, replacing traditional chemical preservatives. MDAP can be used as a therapeutic agent in the pharmaceutical industry, providing a natural alternative to synthetic drugs. MDAP can also be used in biotechnology to synthesize new compounds with improved biological activities.

Limitations and future directions:

One limitation of MDAP research is the lack of human clinical trials. Although MDAP has been shown to be safe in animal models, more research is needed to fully understand its toxicity and safety in humans. Future research directions include investigating the mechanism of action of MDAP and its potential applications in the treatment of various diseases. Additionally, more research is needed to develop efficient and cost-effective methods for the synthesis of MDAP and its derivatives.

Future Directions:

- Evaluation of MDAP's potential to prevent and treat autoimmune diseases

- Investigation of the effect of MDAP on the gut microbiome

- Development of MDAP-based nutraceuticals and functional foods

- Study of MDAP's molecular targets and signaling pathways

- Evaluation of MDAP's potential to enhance cognitive function and memory.

- Identification of MDAP's effect on gene expression and epigenetic modification.

- Investigation of MDAP's potential utility in wastewater treatment

- Development of targeted-delivery systems for MDAP

- Investigation of the interaction between MDAP and certain disease-causing organisms

- Study of the effect of MDAP on different types of amino acids and enzymes.

CAS Number57690-62-7
Product Namemethyl (2S,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-carboxylate
IUPAC Namemethyl (2S,3S,4R)-3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-carboxylate
Molecular FormulaC11H14O7
Molecular Weight258.22 g/mol
InChIInChI=1S/C11H14O7/c1-6(12)17-8-4-5-16-10(11(14)15-3)9(8)18-7(2)13/h4-5,8-10H,1-3H3/t8-,9+,10+/m1/s1
InChI KeyQYYMNOQXLQYOFN-UTLUCORTSA-N
SMILESCC(=O)OC1C=COC(C1OC(=O)C)C(=O)OC
Synonyms2,6-Anhydro-5-deoxy-D-lyxo-hex-5-enonic Acid Methyl Ester Diacetate
Canonical SMILESCC(=O)OC1C=COC(C1OC(=O)C)C(=O)OC
Isomeric SMILESCC(=O)O[C@@H]1C=CO[C@@H]([C@H]1OC(=O)C)C(=O)OC


CAS No: 57690-62-7 Synonyms: D-lyxo-Hex-5-enonic acid, 2,6-anhydro-5-deoxy-, methyl ester, 3,4-diacetate   MDL No: MFCD00233384 Chemical Formula: C11H14O7 Molecular Weight: 258.22

References: 1. Lundt I, Thiem J, Prahst A, J. Org. Chem. 1984, Vol49, p3063-3069


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