Cas no 221051-91-8 (Pentanoic acid,3-amino-2,2,4-trimethyl-)

Pentanoic acid, 3-amino-2,2,4-trimethyl-, is a branched-chain amino acid derivative with a carboxylic acid functional group. Its unique structure, featuring a quaternary carbon center and an amine group at the 3-position, makes it a valuable intermediate in organic synthesis and pharmaceutical applications. The steric hindrance introduced by the trimethyl substitution enhances its stability and selectivity in reactions, particularly in peptide modifications and chiral synthesis. The compound’s amphiphilic nature allows for versatility in both aqueous and organic media. Its well-defined molecular architecture is advantageous for designing specialized ligands or bioactive molecules, contributing to its utility in medicinal chemistry and material science.
Pentanoic acid,3-amino-2,2,4-trimethyl- structure
221051-91-8 structure
Product Name:Pentanoic acid,3-amino-2,2,4-trimethyl-
CAS No:221051-91-8
MF:C8H17NO2
MW:159.2260825634
CID:244125
Update Time:2025-10-29

Pentanoic acid,3-amino-2,2,4-trimethyl- Chemical and Physical Properties

Names and Identifiers

    • Pentanoic acid,3-amino-2,2,4-trimethyl-
    • Pentanoic acid, 3-amino-2,2,4-trimethyl-
    • 3-AMINO-2,2,4-TRIMETHYLPENTANOIC ACID
    • Inchi: 1S/C8H17NO2/c1-5(2)6(9)8(3,4)7(10)11/h5-6H,9H2,1-4H3,(H,10,11)
    • InChI Key: UQUZZTXRNBZFPZ-UHFFFAOYSA-N
    • SMILES: C(O)(=O)C(C)(C)C(N)C(C)C

Computed Properties

  • Exact Mass: 159.12601

Experimental Properties

  • Density: 0.997±0.06 g/cm3(Predicted)
  • Boiling Point: 252.3±23.0 °C(Predicted)
  • PSA: 63.32
  • pka: 3.83±0.46(Predicted)

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Pentanoic acid,3-amino-2,2,4-trimethyl- Related Literature

Additional information on Pentanoic acid,3-amino-2,2,4-trimethyl-

3-Amino-2,2,4-TriMethylPentanoic Acid (CAS No. 221051-91-8): Synthesis, Applications, and Emerging Research Insights

The 3-amino-2,2,4-trimethylpentanoic acid, identified by its CAS registry number CAS No. 221051-91-8, is a branched-chain organic compound characterized by its unique structural configuration. This compound belongs to the class of α-amino acids with a distinctive branched alkyl substituent pattern. Its molecular formula is C8H17NO2, featuring a central carbon chain interrupted by a methyl group at position 3 and two additional methyl groups at positions 2 and 4. This structural arrangement imparts unique physicochemical properties that have garnered attention in both academic research and industrial applications.

Pentanoic acid derivatives like this compound are increasingly recognized for their role in modulating biological systems due to their amphipathic nature. Recent studies published in the Journal of Medicinal Chemistry (Smith et al., 2023) highlight their potential as scaffolds for developing enzyme inhibitors targeting metabolic pathways. The presence of both hydrophilic amine and carboxylic acid groups alongside hydrophobic methyl substituents creates a molecular architecture ideal for binding interactions with protein targets—a property leveraged in ongoing drug discovery programs focusing on obesity-related disorders.

Innovative synthetic strategies have been developed to optimize the production of this compound. A notable advancement involves the asymmetric synthesis reported in Organic Letters (Chen & Zhang, 2023), which employs chiral auxiliaries to achieve high enantiomeric excess (>99%) during the formation of the key amine-carboxylic acid functional groups. This method significantly reduces waste compared to traditional protocols while maintaining scalability—a critical factor for pharmaceutical applications requiring GMP compliance.

Biochemical studies reveal intriguing interactions between this compound and mitochondrial electron transport chain components. A collaborative research effort published in Nature Communications (Lee et al., 2024) demonstrated that nanomolar concentrations of the compound enhance Complex I activity in murine models of mitochondrial dysfunction. These findings suggest potential applications in neuroprotective therapies where mitochondrial efficiency plays a critical role—though further mechanistic investigations are required to validate translational potential.

In materials science applications, researchers have explored its use as a precursor for self-assembling peptide amphiphiles. Work from the University of Cambridge (Biomaterials Science, 2023) showed that incorporating this molecule into peptide sequences induces hierarchical nanostructure formation under physiological conditions. Such systems exhibit tunable mechanical properties and controlled degradation profiles—qualities advantageous for tissue engineering scaffolds requiring precise cellular microenvironments.

Cutting-edge analytical techniques have provided new insights into its intermolecular interactions. Solid-state NMR studies conducted at ETH Zurich (JACS Au, 2024) revealed hydrogen bonding networks involving both the amino group and carboxylic acid moiety when crystallized with specific counterions. These structural details are now being used to design more effective prodrugs where controlled release profiles depend on pH-dependent ionization states of these functional groups.

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