5-MeO,2-Me-IAA is a substituted indole-3-acetic acid (IAA) derivative bearing methoxy and methyl substituents on the indole ring, placing it in the category of non-proteinogenic, structurally modified amino-acid-like carboxylic acids. The molecule retains the characteristic amino-acid motif of a carboxyl group and a side-chain framework derived from IAA, while the aromatic indole substitution pattern modulates electronic properties and can influence conjugation and binding behavior in chemical biology contexts. As a ring-substituted IAA analogue, it is used in studies that examine structure-activity relationships, receptor or binding-site interactions, and analytical method development for auxin-like small molecules, including preparation of labeled or further derivatized indole carboxylic acid building blocks for synthesis of more complex analogues.
CAT No: CP25710
CAS No:2882-15-7
Synonyms/Alias:5-Methoxy-2-methyl-3-indoleaceticacid;2882-15-7;5MIAA;(5-Methoxy-2-methyl-1H-indol-3-yl)aceticacid;2-(5-methoxy-2-methyl-1H-indol-3-yl)aceticacid;1H-Indole-3-aceticacid,5-methoxy-2-methyl-;TXWGINUZLBAKDF-UHFFFAOYSA-N;DESCHLOROBENZOYLINDOMETHACIN;5-Methoxy-2-methylindoleaceticacid;5-methoxy-2-methylindole-3-aceticacid;2-(5-methoxy-2-methylindol-3-yl)aceticacid;PubChem16841;AC1Q5VLC;AC1L2QA4;AC1Q4F1C;CHEMBL1058;Oprea1_768754;N-Deschlorobenzoylindomethacin;KSC204E7R;SCHEMBL454792;105171_ALDRICH;STOCK1N-17012;CTK1A4278;ZINC56398;5-Methoxy-methylindoleaceticacid
Chemical Name:5-Methoxy-2-methylindole-3-acetic acid, 98%
5-MeO,2-Me-IAA is a substituted indole-3-acetic acid (IAA) derivative featuring two ring substitutions (5-methoxy and 2-methyl) that modulate aromatic electronics and steric environment while retaining the acetic acid side chain used for auxin-related chemical biology workflows. This non-proteinogenic amino acid analog is commonly handled as a defined small-molecule building block for structure-activity relationship studies, receptor-binding/uptake assays, and auxin-responsive pathway experiments where controlled chemical structure is required. Researchers also use it as a reference compound to benchmark analytical methods targeting substituted IAA derivatives in complex matrices.
1. Auxin Chemical Biology Studies
5-MeO,2-Me-IAA is used in auxin-focused chemical biology to interrogate how indole substitution patterns influence auxin-like behavior in receptor binding, transport, and downstream transcriptional response assays. Plant biology and chemical genetics groups typically select this defined analog to separate effects of side-chain identity from those of indole ring electronics and sterics, enabling more interpretable SAR comparisons across substituted IAA series. In these workflows, the presence of the carboxylic acid functionality supports consistent dosing and extraction behavior, while the 2-methyl and 5-methoxy substitutions help maintain a stable, non-ambiguous chemical identity for mechanistic interpretation.
2. Structure-Activity Relationship Building Block
5-MeO,2-Me-IAA serves as a practical SAR building block for medicinal chemistry and agrochemical lead optimization programs exploring auxin-mimetic scaffolds. Medicinal chemistry teams use it to populate structure-activity matrices where small changes on the indole ring are expected to alter physicochemical properties and molecular recognition. Because the molecule is a single, well-defined substituted IAA analog rather than a mixture of related auxins, it is frequently incorporated into comparative studies alongside other 2- and 5-substituted IAA derivatives to map trends in activity proxies, uptake, and metabolic handling in assay systems.
3. Analytical Standard For IAA Derivatives
5-MeO,2-Me-IAA is frequently employed as an analytical reference standard for LC-MS and related quantitative workflows that measure substituted IAA derivatives in extracts from biological or environmental samples. Analytical chemists and metabolomics groups use it to confirm retention time and mass spectral features for the specific 5-methoxy/2-methyl substitution pattern and to support calibration or verification of method performance when targeting auxin-like compounds. The carboxylic acid group also makes it compatible with common derivatization and ionization strategies used for acidic indole metabolites, improving confidence when distinguishing closely related IAA analogs in complex matrices.
4. Pharmaceutical Intermediate Development
5-MeO,2-Me-IAA is also relevant as a defined intermediate building block for downstream synthesis of substituted indoleacetic acid derivatives used in research-grade discovery libraries. Synthetic chemistry teams leverage its established substitution pattern to rapidly access analogs that retain the acetic acid handle while varying other functional elements later in the route. This positioning is particularly useful when a program requires a consistent indole substitution motif (2-methyl and 5-methoxy) to support parallel library generation for SAR, formulation screening, or stability studies of auxin-mimetic chemical series.
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