IBA contains an indole-3-butyric acid framework, classifying it as an amino acid derivative in which a carboxylic acid is tethered to an indole ring via a butyl side chain rather than a canonical α-amino acid backbone. The molecule bears a terminal carboxyl functional group and an indole aromatic system, providing distinct sites for acid-base behavior and for derivatization or conjugation chemistry, while no amino (α-NH2) stereocenter is implied by the name. IBA is used as a chemical biology and synthetic chemistry building block for preparing indole-containing conjugates, probing structure-activity relationships, and supporting analytical method development where indole carboxylic acid motifs are required.
CAT No: CP25317
CAS No:133-32-4
Synonyms/Alias:Indole-3-butyricacid;3-Indolebutyricacid;133-32-4;4-(1H-Indol-3-yl)butanoicacid;Indolebutyricacid;Hormodin;Seradix;1H-INDOLE-3-BUTANOICACID;Indole-3-butanoicacid;Jiffygrow;4-(3-Indolyl)butyricacid;4-(Indol-3-yl)butyricacid;Hormexrootingpowder;1H-Indole-3-butyricacid;IBA;Indolbutyricacid;Seradix2;Seradix3;SeradixB2;SeradixB3;3-Indolylbutyricacid;beta-Indolebutyricacid;4-(3-Indolyl)butanoicacid;Butyricacid,4-(indolyl)-;Indol-3,4'-ylbutyricacid
Chemical Name:Indole-3-butyric acid, 4-(3-Indolyl)butyric acid, horticultural grade, 99%
IBA is an amino acid derivative commonly encountered as an indole-3-butyric acid (IBA) scaffold bearing a carboxylic acid functionality and a chiral, side-chain stereochemical motif that can be leveraged as a functionalized carbonyl-bearing intermediate. The indole ring provides a planar, aromatic heterocycle with nitrogen for electronic and coordination behavior, while the butanoic acid side chain supports controlled derivatization through carboxyl activation and ester formation. The molecule's stereochemical integrity is relevant when IBA is used as a chiral precursor for downstream analogs or when side-chain configuration must be retained during peptide-adjacent coupling chemistry. The presence of a free acid also enables protection-group strategies (e.g., esterification or temporary acid masking) to tune reactivity during multi-step syntheses and to support conversion into activated intermediates for further functional group installation.
1. Plant Growth Research
IBA is applied in plant hormone and chemical biology research where indole-containing carboxylic acid motifs are used to probe auxin-related signaling and structure-activity relationships. The indole heterocycle and the carboxyl group together enable derivatization into ester or activated acid forms that can be used to generate labeled or modified analogs for uptake and metabolic studies. Side-chain stereochemistry can be preserved or deliberately inverted when preparing configuration-defined derivatives to assess stereochemical effects on biological processing. Downstream work often uses IBA-derived intermediates to build analog libraries for mechanistic studies and comparative chemical profiling in agrochemical discovery programs.
2. Peptidomimetic Linkers
IBA is used in synthetic organic chemistry and peptidomimetic construction where the indole-bearing acid can function as a fragment for amide coupling or as a scaffold for tethered bioactive analogs. The carboxylic acid group enables conversion to activated derivatives compatible with peptide coupling chemistry, while the aromatic indole can serve as a hydrophobic/aromatic recognition element in molecular design. Protecting-group strategies that mask the acid during intermediate assembly can help control chemoselectivity when additional nucleophilic sites are introduced. Resulting IBA-containing amide or ester linkers can be carried into SAR studies and medicinal chemistry workflows as chiral or conformationally constrained building blocks.
3. Chiral Intermediate Synthesis
IBA is suitable for chiral building block development and stereoselective synthesis because the side-chain carbon framework can be retained through protection-group cycling and controlled functional group interconversions. The carboxylic acid functionality supports temporary protection (commonly via ester formation) to enable selective transformations on other parts of the molecule, followed by deprotection to regenerate the reactive acid handle. The indole nitrogen and aromatic system can influence reaction conditions and selectivity during derivatization, supporting reproducible intermediate preparation. IBA-derived chiral intermediates can then be used to access configuration-defined analogs for fine chemical synthesis and structure-driven library generation.
4. Chemical Manufacturing Intermediates
IBA is employed as a manufacturing-oriented intermediate in specialty chemical production where the acid functionality supports scalable conversion into activated species for downstream functionalization. The indole core can be carried through multi-step routes with controlled chemoselectivity, while the carboxyl group provides a reliable handle for forming amides, esters, or salt forms used in further processing. Process chemistry workflows can incorporate protection-group strategies to manage reactivity during sequential installations of functional groups and to align intermediate stability with purification requirements. The resulting IBA-based derivatives can feed into industrial synthesis of functionalized heteroaromatic acids and related fine chemical intermediates.
5. Analytical Standards And Labeling
IBA is utilized in analytical research and chemical characterization workflows where indole-carboxylic acid standards enable method development for separation, quantification, and metabolite profiling. The presence of a defined aromatic heterocycle and a carboxyl group supports derivatization approaches for chromatographic detectability and for generating reference compounds used in LC-MS or GC-MS method validation. Carboxyl activation chemistry can be applied to prepare labeled or structurally modified analogs for tracking transformation pathways while maintaining the indole scaffold for consistent analytical behavior. IBA-derived analytical materials can also support impurity mapping and stability studies across amino acid and heteroaromatic acid derivative chemistries.
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