4-Methy-DL-Phenylalanine is a substituted phenylalanine amino acid derivative featuring a benzyl side chain with an additional methyl substituent at the 4-position of the aromatic ring, classifying it within the aromatic amino acid family. The molecule contains both an amino group and a carboxyl group on the α-carbon, and the "DL" designation indicates a racemic mixture of stereoisomers at the chiral center, with the aromatic ring providing hydrophobic character and potential for π-π and dispersive interactions. As a free amino acid building block, it is used in peptide and amino acid derivative synthesis and in structure-activity or binding studies where altered aromatic substitution patterns are introduced to probe effects on conformation, hydrophobicity, and intermolecular interactions.
CAT No: CP15803
CAS No:4599-47-7
Synonyms/Alias:2-Amino-3-p-tolyl-propionicacid;4599-47-7;DL-4-ME-PHE-OH;2-amino-3-(4-methylphenyl)propanoicacid;4-Methy-DL-Phenylalanine;DL-4-METHYLPHENYLALANINE;2-AMINO-3-P-TOLYLPROPANOICACID;ACMC-20amdc;H-p-Me-D-Phe-OH;Phenylalanine,4-methyl-;AC1L8WML;SCHEMBL44871;CTK4I9059;4-METHYL-DL-PHENYLALANINE;MolPort-003-990-080;6328AB;ANW-59481;AKOS000170686;AKOS016843033;AB21662;AM83429;FS-2553;VC30806;alpha-Amino-4-methylbenzenepropionicacid;AK-35255
4-Methy-DL-Phenylalanine is a DL (racemic) phenylalanine analog featuring a methyl substituent at the 4-position of the aromatic ring, providing a sterically and electronically modified side chain while retaining the amino acid backbone functionality. This non-proteinogenic amino acid is commonly used as a defined building block for synthesis of substituted amino acid derivatives and for structure-property studies where aromatic substitution patterns are varied. Its racemic composition makes it particularly useful for exploratory medicinal chemistry and analytical method development where relative stereochemical purity is not the primary variable.
1. Peptidomimetic Building Block
4-Methy-DL-Phenylalanine is used by medicinal chemistry and chemical biology teams to introduce a para-methyl substituted aromatic residue into peptidomimetics and peptide-like scaffolds. The modified aryl side chain supports SAR workflows aimed at tuning hydrophobic character, steric profile, and aromatic electronics without changing the amino acid backbone. Because the material is supplied as a DL mixture, it is frequently selected for early-stage library synthesis and comparative studies where multiple stereochemical outcomes are acceptable and downstream biological evaluation can be performed after further optimization.
2. Pharmaceutical Intermediate Development
4-Methy-DL-Phenylalanine serves as a practical starting amino acid building block for the preparation of substituted phenylalanine derivatives used in pharmaceutical intermediate pipelines. Process and R&D groups employ it to access aryl-substituted amino acid motifs that can be carried forward into protected amino acid derivatives, coupling-ready intermediates, and analog series for hit-to-lead development. The para-methyl substitution provides a straightforward handle for generating chemical diversity while maintaining an amino acid-compatible functional group pattern for downstream derivatization.
3. SAR and Structure-Property Studies
4-Methy-DL-Phenylalanine is frequently incorporated into small-molecule or peptide-derived analog sets to probe how aromatic ring substitution affects physicochemical behavior and structure-activity relationships. Researchers use this compound to systematically vary substitution on the phenylalanine side chain while keeping the backbone composition consistent, enabling clearer interpretation of trends related to hydrophobicity and steric effects. The DL form supports parallel synthesis and screening approaches where stereochemical resolution is handled later if required for refined SAR conclusions.
4. Analytical Reference Material
4-Methy-DL-Phenylalanine is also used as a defined reference compound in analytical chemistry workflows that require an authentic substituted phenylalanine standard. Laboratories preparing calibration or qualification materials for LC methods, derivatization-based assays, or impurity profiling can use the racemic amino acid to benchmark retention and response for para-methyl substituted aromatic amino acid motifs. This makes it useful for routine method development and characterization of intermediate streams where substituted phenylalanine derivatives are expected.
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