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20-(tert-Butoxy)-20-oxoicosanoic acid
  • Brand:baishixing
  • Origin:sichuanchengdu
  • Code:C150
  • Createtime: 2024-09-06
  • Updatetime: 2024-09-06
Product Details
CAS 683239-16-9
PU 99%
MF C24H46O4
20-(tert-Butoxy)-20-oxoicosanoic acid is a synthetic organic compound featuring a long-chain fatty acid structure with a tert-butoxy protecting group and a ketone functional group (-C=O) at the 20th position. This compound belongs to the class of oxo fatty acids, which are commonly used in organic synthesis, materials science, and lipid research due to their functional diversity and ability to participate in various chemical reactions.

Chemical Structure and Properties
Chemical Formula: C24H46O4
Molecular Weight: 398.63 g/mol
Structure: The molecule consists of a 20-carbon chain (C20), with a ketone group (-C=O) at the 20th position and a tert-butoxy group (-OC(CH3)3), which acts as a protective group for the ketone, enhancing its stability. The terminal carboxyl group (-COOH) adds polarity to the molecule, making it a versatile intermediate in chemical reactions.
Applications in Organic Synthesis
The combination of a long alkyl chain with both ketone and carboxyl functionalities allows 20-(tert-Butoxy)-20-oxoicosanoic acid to be used as an intermediate in the synthesis of complex molecules, including bioactive compounds and lipid derivatives. The tert-butoxy group serves as a protective group that can be easily removed under acidic conditions, exposing the reactive carbonyl group for further reactions.

This compound is particularly valuable in peptide-lipid conjugate synthesis, where lipid chains are attached to peptides for improved membrane interaction, stability, and bioavailability. The long carbon chain can mimic natural lipid tails, enhancing the hydrophobic properties of the target molecule.

Role in Material Science and Lipid Research
In material science, 20-(tert-Butoxy)-20-oxoicosanoic acid can be utilized to develop new surface-active agents or coating materials due to its amphiphilic nature. The long fatty acid chain provides hydrophobic properties, while the carboxyl and ketone groups allow for further functionalization or interaction with hydrophilic substances.

In lipid research, this compound is used in the modification of liposomes and other lipid-based delivery systems. The introduction of functional groups like ketones and carboxyl groups allows for precise chemical modifications, improving the encapsulation and delivery of pharmaceuticals, particularly hydrophobic drugs.

Pharmaceutical and Biomedical Applications
The oxo group at the 20th position introduces reactivity that can be exploited in drug development, especially for creating lipid-based drug carriers. The tert-butoxy group ensures that the ketone functionality remains protected during certain stages of synthesis, offering controlled release and targeted chemical reactions. This is particularly useful for developing prodrugs or modified drug molecules with enhanced stability and delivery profiles.

Additionally, oxo fatty acids like 20-(tert-Butoxy)-20-oxoicosanoic acid are often used in enzyme inhibition studies, metabolic research, and lipid-protein interaction studies, where their unique structure helps elucidate the behavior of natural lipids and fatty acids in biological systems.

Conclusion
20-(tert-Butoxy)-20-oxoicosanoic acid is a valuable compound in organic chemistry and lipid research, providing a flexible structure for the synthesis of bioactive compounds and lipid-based materials. Its long-chain fatty acid backbone, combined with functional ketone and carboxyl groups, allows for diverse applications in pharmaceuticals, material science, and biotechnology. This compound plays a key role in advancing lipid-based drug delivery systems and the development of novel biomaterials.
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