trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid - 191282-48-1
trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid
Catalog Number: BT-253740
CAS Number: 191282-48-1
Molecular Formula: C₁₄H₂₂O₄
Molecular Weight: 254.32 g/mol
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Product Introduction
Description
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid, also known as MOTC, is a synthetic compound that has gained attention in the scientific community due to its potential therapeutic and environmental applications. This paper will discuss the methods of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges of MOTC.
Properties
CAS Number
191282-48-1
Product Name
trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid
IUPAC Name
(2R,3S)-4-methylidene-2-octyl-5-oxooxolane-3-carboxylic acid
Molecular Formula
C₁₄H₂₂O₄
Molecular Weight
254.32 g/mol
InChI
InChI=1S/C14H22O4/c1-3-4-5-6-7-8-9-11-12(13(15)16)10(2)14(17)18-11/h11-12H,2-9H2,1H3,(H,15,16)/t11-,12+/m1/s1
InChI Key
VCWLZDVWHQVAJU-NEPJUHHUSA-N
SMILES
CCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
Synonyms
4-methylene-2-octyl-5-oxofuran-3-carboxylic acid
C75 cpd
trans-4-carboxy-5-octyl-3-methylenebutyrolactone
Canonical SMILES
CCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
Isomeric SMILES
CCCCCCCC[C@@H]1[C@H](C(=C)C(=O)O1)C(=O)O
Method of Synthesis or Extraction
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid can be synthesized using various methods, including the reaction of 4-methylene-2-octanone with diethyl oxalate, followed by hydrolysis and decarboxylation. Another method involves the reaction of 4-methylene-2-octanone with ethyl diazoacetate, followed by hydrolysis and decarboxylation. The efficiency and yield of each method vary, with the first method yielding a higher percentage of trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid. However, both methods require careful handling due to the use of hazardous chemicals. Environmental considerations include the disposal of waste products and the potential for air and water pollution.
Chemical Structure and Biological Activity
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has a unique chemical structure, consisting of a tetrahydrofuran ring, a carboxylic acid group, and a methylene group. The compound has been shown to have biological activity, specifically as an inhibitor of the enzyme dihydroorotate dehydrogenase (DHODH). DHODH is involved in the de novo synthesis of pyrimidine nucleotides, which are essential for DNA replication and cell proliferation. Inhibition of DHODH has been shown to have potential therapeutic effects in the treatment of cancer, autoimmune diseases, and viral infections.
Biological Effects
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been shown to have effects on cell function and signal transduction. Inhibition of DHODH by trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid leads to a decrease in pyrimidine nucleotide synthesis, which can result in cell cycle arrest and apoptosis. Additionally, trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been shown to have potential toxic effects, including hepatotoxicity and nephrotoxicity. However, further studies are needed to fully understand the biological effects of trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid.
Applications
In medical research, trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been studied for its potential role in drug development. Clinical trials have shown promising results in the treatment of autoimmune diseases and viral infections. However, further studies are needed to determine the safety and efficacy of trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid in humans. In environmental research, trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been studied for its effects on ecosystems and its potential role in pollution management. The compound has been shown to have low toxicity to aquatic organisms, making it a potential candidate for use in pollution management. In industrial research, trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations include the proper handling and disposal of hazardous chemicals.
Future Perspectives and Challenges
Current limitations in the use and study of trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid include the need for further research to fully understand its biological effects and potential therapeutic applications. Possible solutions and improvements include the development of more efficient and environmentally friendly methods of synthesis or extraction. Future trends and prospects in the application of trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid in scientific research include the continued study of its potential therapeutic effects and its role in pollution management. However, challenges remain in the development of safe and effective treatments using trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid.
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