3-HO-ICA-OMe is a structurally modified amino acid derivative featuring an indole-containing side chain consistent with an indole-3-acetic acid (IAA) scaffold, presented here as a methyl ester (-COOCH3) and bearing a hydroxyl substituent on the indole ring. The molecule contains an amino group and a carboxylate functionality that is esterified, so it does not exist as a free carboxylic acid, and the hydroxyl-bearing indole moiety provides an additional hydrogen-bonding and aromatic electronic feature for conjugation or analytical differentiation. 3-HO-ICA-OMe is used in chemical biology and peptide/bioconjugation workflows as a protected or functionalized precursor for preparing more complex indole-based amino acid derivatives, as well as a labeled or derivatizable building block in structure-activity studies and analytical method development where ester stability and controlled functional-group presentation are relevant.
CAT No: CP25745
CAS No:31827-04-0
Synonyms/Alias:31827-04-0;3-Hydroxyindole-2-carboxylicacidmethylester;Methyl3-hydroxy-1H-indole-2-carboxylate;METHYL3-HYDROXYINDOLE-2-CARBOXYLATE;3-HYDROXY-1H-INDOLE-2-CARBOXYLICACIDMETHYLESTER;2-[hydroxy(methoxy)methylidene]-1H-indol-3-one;1H-Indole-2-carboxylicacid,3-hydroxy-,methylester;zlchem782;PubChem15863;AC1NYFW9;AC1O0RUM;3-HO-ICA-OME;AC1O9SX8;SCHEMBL4207606;CTK4G7804;ZLD0241;MolPort-000-294-818;ACT06117;ZINC2243036;SBB069251;AKOS002664613;AB01492;VI30203;AJ-34183;AK126588
Chemical Name:3-Hydroxyindole-2-carboxylic acid methyl ester, 98%
3-HO-ICA-OMe is a methyl ester derivative of 3-hydroxy-iso-caproic acid (3-HO-ICA), featuring a carboxylate protected as an O-methyl ester and a free aliphatic secondary alcohol. This functional-group pattern makes the compound a practical intermediate for downstream conversion into activated carboxylic acid derivatives and for building stereochemically defined aliphatic fragments used in medicinal chemistry and chemical biology workflows. Researchers also use such esterified hydroxy-acid building blocks to control reactivity during multi-step synthesis and to enable selective transformations of the hydroxyl group without immediately exposing a free acid.
1. Pharmaceutical Intermediate Synthesis
3-HO-ICA-OMe is used in pharmaceutical intermediate development where a hydroxy-substituted aliphatic acid fragment is required for assembling larger drug-like scaffolds. The methyl ester form provides a convenient handle for iterative coupling and late-stage functional group interconversions, while the secondary alcohol enables branching into ether, ester, or other oxygen-functional derivatives depending on the target series. Medicinal chemistry groups and custom synthesis providers commonly incorporate this type of protected hydroxy-acid building block to streamline route design and improve control over chemoselectivity across sequential steps.
2. Chiral Building Block Derivatization
3-HO-ICA-OMe supports derivatization strategies that benefit from a stable ester-protected carboxyl group paired with a hydroxyl-bearing side chain. In stereochemically guided synthesis, the ester can be maintained during transformations that modify or protect the alcohol, allowing chemists to generate a set of related analogs for structure-property studies. This makes the compound a useful starting point for producing conformationally constrained hydroxy-containing intermediates that are then carried into SAR campaigns, fragment elaboration, or scaffold diversification efforts.
3. Synthesis of Ester-Based Prodrugs
3-HO-ICA-OMe is also used as a hydroxy-acid ester precursor when medicinal chemistry teams design ester-linked motifs intended for controlled release or metabolic conversion concepts in small-molecule candidates. The methyl ester provides a ready platform for exchanging the ester moiety into alternative ester linkages (for example, to introduce different alcohol partners), enabling systematic evaluation of how ester structure affects downstream behavior. Research groups developing prodrug-like or ester-mediated activation strategies often prefer such pre-functionalized hydroxy-acid esters because they reduce the number of protecting-group and activation steps required to reach the desired ester variants.
4. Analytical Reference Material Development
3-HO-ICA-OMe can serve as a chemical reference or starting standard material for method development and impurity profiling in synthetic and analytical laboratories. The combination of a defined hydroxy functionality and an esterified carboxyl group supports robust characterization by chromatographic and spectrometric workflows, including studies focused on ester stability, alcohol derivatization, and related transformation products. Analytical chemistry teams commonly use structurally matched standards like this to support LC/GC method optimization, calibration workflows, and identification of closely related hydroxy-acid ester species arising during process development.
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