3-Hydroxy-4-aminophenylbutyric acid is an aromatic, non-proteinogenic amino acid derivative featuring a phenylbutyric acid backbone with a phenolic hydroxyl group and a primary amino group on the side chain, along with a free amino and carboxyl functionality characteristic of amino acid building blocks. The molecule bears an additional hydroxyl substituent on the aromatic ring that can participate in hydrogen bonding and can undergo typical phenol reactivity under derivatization conditions, while the amino and carboxyl groups enable salt formation and coupling chemistry in peptide-related syntheses. In research and synthesis contexts, it is used as a substrate for preparing modified peptides, bioconjugates, or structure-activity probes where an aniline-like amino handle and a phenolic hydroxyl group provide orthogonal functional handles for further derivatization and analytical characterization.
CAT No: CP17301
3-Hydroxy-4-aminophenylbutyric acid is an aromatic amino acid derivative featuring a phenylbutyric acid backbone with an aniline-type primary amino group and a phenolic hydroxyl group. This combination of orthogonally addressable functionalities makes it a useful building block for constructing bioactive scaffolds and for preparing labeled or derivatized intermediates used in chemical biology and medicinal chemistry workflows. Its non-proteinogenic substitution pattern supports downstream functionalization rather than direct incorporation into standard peptide synthesis.
1. Medicinal Chemistry Intermediates
3-Hydroxy-4-aminophenylbutyric acid is used by medicinal chemistry teams as a versatile intermediate for assembling substituted aromatic pharmacophore fragments. The primary amine enables formation of amides, ureas, and other nitrogen-containing linkages, while the phenolic hydroxyl supports etherification, esterification, or protective-group strategies to tune physicochemical properties during SAR (structure-activity relationship) studies. In practice, researchers select this scaffold-building reagent when they need a ready-to-functionalize aromatic "handle" that can be carried through multi-step synthesis toward small-molecule candidates or tool compounds.
2. Peptidomimetic And Conjugate Building
3-Hydroxy-4-aminophenylbutyric acid is applied in peptidomimetic and conjugate development where an amino acid-like carboxylic acid and a reactive aniline-type amine provide controlled attachment points. The phenylbutyric acid motif supports the design of non-natural backbone elements that can be appended to peptides, linkers, or carrier molecules through amide or other coupling strategies. Chemical biology groups often use this type of aromatic amino acid derivative to introduce a defined aromatic/phenolic functionality into larger constructs, enabling subsequent derivatization for binding studies, labeling workflows, or affinity reagent generation.
3. Analytical Derivatization Standards
3-Hydroxy-4-aminophenylbutyric acid is commonly leveraged as a derivatization substrate and reference material in analytical method development targeting aromatic amine/phenol-containing compounds. The presence of both an amine and a phenolic hydroxyl supports derivatization approaches that improve detectability or chromatographic behavior, which is valuable when developing LC-MS or HPLC workflows for structurally related intermediates and metabolites. Laboratories also use this compound to verify derivatization performance and to support identification strategies for reaction monitoring in synthetic and medicinal chemistry programs where aromatic amino/phenol motifs are expected.
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