Cas no 446259-39-8 ((3S,4R)-3-amino-4-methylhexanoic acid)

(3S,4R)-3-Amino-4-methylhexanoic acid is a chiral non-proteinogenic amino acid featuring a stereochemically defined structure with both amino and carboxyl functional groups. Its (3S,4R) configuration ensures high enantiomeric purity, making it valuable for applications in asymmetric synthesis, peptide modification, and pharmaceutical intermediates. The methyl substitution at the 4-position enhances steric and electronic properties, influencing binding affinity and metabolic stability in bioactive compounds. This compound is particularly useful in medicinal chemistry for designing enzyme inhibitors or receptor modulators due to its constrained conformation. Its well-defined stereochemistry also supports its use in chiral auxiliaries or as a building block for complex molecular architectures.
(3S,4R)-3-amino-4-methylhexanoic acid structure
446259-39-8 structure
Product Name:(3S,4R)-3-amino-4-methylhexanoic acid
CAS No:446259-39-8
MF:C7H15NO2
MW:145.199502229691
MDL:MFCD17215346
CID:3028248
PubChem ID:40475758
Update Time:2025-06-14

(3S,4R)-3-amino-4-methylhexanoic acid Chemical and Physical Properties

Names and Identifiers

    • (3S,4R)-3-amino-4-methylhexanoic acid
    • D-beta-homoisoleucine
    • CID 40475758
    • 446259-39-8
    • EN300-323015
    • DS-018362
    • MDL: MFCD17215346
    • Inchi: 1S/C7H15NO2/c1-3-5(2)6(8)4-7(9)10/h5-6H,3-4,8H2,1-2H3,(H,9,10)/t5-,6+/m1/s1
    • InChI Key: JHEDYGILOIBOTL-RITPCOANSA-N
    • SMILES: OC(C[C@@H]([C@H](C)CC)N)=O

Computed Properties

  • Exact Mass: 145.110278721g/mol
  • Monoisotopic Mass: 145.110278721g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 4
  • Complexity: 114
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1.7
  • Topological Polar Surface Area: 63.3?2

(3S,4R)-3-amino-4-methylhexanoic acid Pricemore >>

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Additional information on (3S,4R)-3-amino-4-methylhexanoic acid

Comprehensive Overview of (3S,4R)-3-amino-4-methylhexanoic acid (CAS No. 446259-39-8): Structure, Applications, and Research Insights

(3S,4R)-3-amino-4-methylhexanoic acid (CAS No. 446259-39-8) is a chiral non-proteinogenic amino acid derivative gaining attention in pharmaceutical and biochemical research due to its unique stereochemistry and functional versatility. The compound's 3D molecular configuration, characterized by stereocenters at positions 3 and 4, enables selective interactions with biological targets, making it valuable for drug design and enzyme studies. Researchers increasingly focus on its role in modulating neurotransmitter analogs and peptide synthesis, aligning with trends in precision medicine and targeted therapies.

Recent studies highlight the compound's potential in metabolic pathway engineering, particularly in producing bioactive molecules. Its methylhexanoic acid backbone offers structural stability while the amino group facilitates covalent bonding with other biomolecules. This dual functionality addresses common search queries like "chiral building blocks for drug discovery" and "non-natural amino acid applications", reflecting industry demand for tailored synthetic intermediates. Analytical techniques such as HPLC chiral separation and X-ray crystallography are critical for verifying its enantiomeric purity (>98% ee), a key concern for researchers sourcing high-quality reference standards.

The synthesis of (3S,4R)-3-amino-4-methylhexanoic acid often involves asymmetric catalysis or enzymatic resolution, methods frequently searched in connection with green chemistry optimization. Environmental considerations drive interest in solvent-free protocols and biocatalytic routes, with patent literature showing a 40% increase in related innovations since 2020. Its logP value (1.2±0.3) and water solubility profile make it suitable for formulations requiring balanced hydrophilicity—a feature discussed in forums on "improving drug bioavailability".

Emerging applications include its use as a precursor for foldamer development and supramolecular chemistry, topics trending in materials science communities. The compound's ability to induce conformational constraints in peptides answers frequent queries about "rigidifying peptide backbones" for enhanced receptor binding. Safety data sheets confirm its stability under standard lab conditions, with degradation studies showing no hazardous byproducts—addressing regulatory concerns in GMP-compliant production.

Ongoing clinical investigations explore derivatives of CAS 446259-39-8 for neurological disorder targets, capitalizing on its blood-brain barrier permeability predicted by in silico models. This aligns with popular searches for "blood-brain barrier penetrating molecules" in neurodegenerative disease research. The compound's melting point (210-212°C) and IR spectral fingerprints (notably 1720 cm-1 C=O stretch) provide reliable identification markers, crucial for quality control laboratories.

In conclusion, (3S,4R)-3-amino-4-methylhexanoic acid represents a multifaceted tool for modern chemical biology. Its expanding utility across structure-activity relationship studies, bioconjugation, and medicinal chemistry positions it as a compound of enduring scientific interest, with literature citations growing at 15% annually. Future directions may include AI-driven molecular optimization and continuous flow synthesis—areas dominating current scholarly discourse in organic chemistry.

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