5-HO-IAA contains an indole-derived amino acid scaffold consistent with 5-hydroxyindole-3-acetic acid (5-HO-IAA), placing it in the indoleacetic acid family of amino acid derivatives rather than a free proteinogenic amino acid. The molecule bears a carboxylic acid and a side-chain functional framework characteristic of indole-based derivatives, with the 5-hydroxy substituent on the indole ring providing an additional oxygen-bearing handle for hydrogen-bonding and derivatization reactions. In research settings, this compound is used as a chemical biology and analytical probe for studying indole-auxin-related structure-function relationships, preparing conjugates or labeled analogues, and supporting the synthesis of more complex indole-containing amino acid derivatives.
CAT No: CP25887
CAS No:54-16-0
Synonyms/Alias:5-Hydroxyindole-3-aceticacid;5-HIAA;2-(5-hydroxy-1H-indol-3-yl)aceticacid;5-Hydroxyheteroauxin;54-16-0;5-Hydroxyindoleaceticacid;5-Oxyindoleaceticacid;5-Hydroxy-IAA;(5-Hydroxy-1H-indol-3-yl)aceticacid;5-Hydroxyindol-3-ylaceticacid;Hydroxyindoleaceticacid;5-Hydroxyindolaceticacid;5-Hydroxy-1H-indole-3-aceticacid;5-Hydroxyindolylaceticacid;5-Hydroxyindoleacetate;5-Hydroxy-3-indoleaceticacid;1H-Indole-3-aceticacid,5-hydroxy-;Indole-3-aceticacid,5-hydroxy-;5-hydroxy-indole-3-aceticacid;1321-73-9;5-Oxyindoleacetate;Hydroxyindoleacetate;5HIAA;NSC90432;5-Hydroxyindole-3-acetate
Chemical Name:5-Hydroxyindole-3-acetic acid, 98%
5-HO-IAA is an indole-derived amino acid analog related to indole-3-acetic acid (IAA), bearing a phenolic hydroxyl substituent on the indole ring. This functionalized side-chain architecture makes it a useful building block for chemical biology studies where indole auxin-like motifs are needed, and it also provides an additional handle for derivatization and analytical differentiation versus non-hydroxylated IAA analogs. Researchers commonly select 5-HO-IAA when they require a hydroxylated indole scaffold to probe structure-property relationships, prepare labeled or derivatized standards, or generate intermediates for downstream synthesis of auxin-mimetic compounds.
1. Auxin-Mimetic SAR Studies
5-HO-IAA is used in medicinal chemistry and chemical biology workflows focused on structure-activity relationship (SAR) comparisons of indole auxin-like chemotypes. By incorporating a ring hydroxyl functionality, it supports systematic evaluation of how phenolic substitution influences physicochemical behavior and downstream reactivity during lead optimization. Teams in small-molecule discovery and academic research groups often use this scaffold as a reference starting point for synthesizing analog series, enabling controlled variation of indole substitution patterns while keeping the amino acid-like motif consistent.
2. Chemical Biology Probe Intermediates
5-HO-IAA serves as a practical intermediate for constructing indole-based chemical biology probes that rely on a phenolic handle for further functionalization. In probe development pipelines, the additional hydroxyl group can be leveraged to introduce linkers, affinity tags, or other substituents that maintain the indole core while tuning overall probe properties for downstream assays. Researchers in biomolecular interaction studies and pathway-focused chemical biology commonly start from 5-HO-IAA to build probe-ready derivatives that retain the auxin-like indole geometry needed for target engagement experiments.
3. Derivatized Analytical Standards
5-HO-IAA is frequently employed for analytical method development and targeted quantification workflows where hydroxylated indole species must be distinguished from closely related IAA analogs. The defined, functionalized structure supports preparation of derivatized standards and calibration materials used in LC-MS or related analytical platforms to improve identification confidence and reduce ambiguity in chromatographic separation. Analytical chemistry teams and metabolomics method developers use 5-HO-IAA to ensure that hydroxyl-substituted indole metabolites or synthetic analogs can be tracked with consistent reference chemistry.
4. Indole Scaffold Building Block
5-HO-IAA is also used as a specialized indole scaffold building block for downstream synthesis of hydroxylated indole derivatives and auxin-mimetic intermediates. Pharmaceutical intermediate development groups and specialty chemical manufacturers value the compound as a defined starting material for constructing substituted indole products while retaining a functional hydroxyl group for selective downstream transformations. This makes 5-HO-IAA a relevant choice when the project requires a hydroxylated indole motif as a core structural element for library synthesis or process development.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More