Indole-3-acrylic acid ultra pure

Indole-3-acrylic acid ultra pure is a non-proteinogenic amino acid derivative featuring an indole ring substituted at the 3-position with an acrylic acid side chain, placing it in the indoleacrylic acid family rather than the standard proteinogenic amino acid class. The molecule contains a carboxylic acid functional group and an alkene (acrylate) moiety conjugated to the side chain, enabling chemical reactivity associated with unsaturated carboxylic acids while the indole nitrogen and aromatic system provide distinct polarity and hydrogen-bonding characteristics. In synthetic and chemical biology workflows, it is used as a defined indole-containing building block for preparing more complex indole-acrylate derivatives, for structure-activity studies, and for analytical method development where controlled chemical identity of the unsaturated acid is required.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25726

CAS No:29953-71-7

Synonyms/Alias:3-Indoleacrylicacid;trans-3-Indoleacrylicacid;1204-06-4;29953-71-7;3-Indolylacrylicacid;3-(1H-Indol-3-yl)acrylicacid;INDOLE-3-ACRYLICACID;Indoleacrylicacid;3-(3-Indolyl)acrylicacid;trans-3-(1H-Indol-3-yl)acrylicacid;Indole-3beta-acrylicacid;3-(Indol-3-yl)acrylicacid;Indole-3-crylicacid;Indoleacrylicacid(VAN);(E)-3-(1H-indol-3-yl)acrylicacid;CHEMBL445966;(E)-3-(1H-indol-3-yl)prop-2-enoicacid;(2E)-3-(1H-indol-3-yl)prop-2-enoicacid;PLVPPLCLBIEYEA-AATRIKPKSA-N;UNII-83X500J040;EINECS214-872-7;NSC29428;SBB003692;NSC137806;3-(1H-Indol-3-yl)-2-propenoicacid

Chemical Name:Indole-3-acrylic acid ultra pure, 3-(3-Indolyl)acrylic acid, trans-beta-Indoleacrylic acid, 99,5%

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C11H9NO2
M.W/Mr.
187,2 g/mole

Indole-3-acrylic acid ultra pure is an indole-containing unsaturated carboxylic acid featuring an indole-3-substituted acrylic acid motif, where the side chain bears a conjugated alkene adjacent to the terminal carboxyl group. The molecule combines an aromatic indole system with a reactive α,β-unsaturated acid functionality, enabling chemoselective transformations that preserve the indole core while modifying the acrylic segment. The "ultra pure" grade is typically selected for trace-sensitive studies where impurity profiles can influence downstream derivatization, polymerization, or analytical quantitation. As an amino-acid-like, chiral-agnostic organic acid building block, it functions as a chemically defined intermediate for indole-based scaffold elaboration, conjugation-ready derivatives, and structure-controlled synthesis of indole-acrylate analogs.

1. Peptidomimetic Building Blocks

Indole-3-acrylic acid ultra pure is applied in peptidomimetic and constrained scaffold synthesis where the indole ring serves as a hydrogen-bonding aromatic element and the acrylic acid provides a handle for controlled functionalization. The carboxylic acid can be converted into activated esters or coupling-ready derivatives, enabling amide formation with amine-bearing partners used in peptide analog construction. The α,β-unsaturated system can also participate in selective derivatization strategies that introduce electrophilic or crosslinkable functionality while retaining the indole recognition motif. Downstream, indole-acrylate motifs can be incorporated into libraries for medicinal chemistry and SAR studies focused on indole-containing binding patterns, supporting structure-defined analog generation from a single acid precursor.

2. Side-Chain Functionalization Chemistry

Indole-3-acrylic acid ultra pure is suitable for side-chain functionalization workflows in synthetic organic chemistry where the indole-3 substitution pattern and acrylic acid geometry guide regioselective modification. The terminal carboxyl group enables conversion to esters for temporary protection or to acid derivatives for subsequent coupling, allowing stepwise installation of the indole-acrylate fragment onto larger molecules. The conjugated alkene can be leveraged to generate Michael acceptor derivatives, polymerizable acrylate intermediates, or further functionalized unsaturated products that maintain the indole scaffold. Resulting derivatives can be used to build functionalized small molecules, surface-reactive linkers, or intermediate platforms for downstream transformation into more complex indole-containing architectures.

3. Chemical Biology Labeling

Indole-3-acrylic acid ultra pure is used in chemical biology research as an indole-based functional handle for probe synthesis and biomolecule labeling strategies. The indole aromatic system supports specific noncovalent interactions and can be maintained during derivatization, while the acrylic acid functionality enables formation of conjugation-ready intermediates through carboxyl activation or esterification. The unsaturated acid motif can be incorporated into linker designs that connect to amine-, thiol-, or hydroxyl-bearing targets after conversion to appropriate reactive derivatives. Labeled or conjugated indole-acrylate constructs derived from this acid can then be applied in binding studies, target engagement assays, and analytical tracking of indole-containing molecular interactions.

4. Polymer And Materials Intermediates

Indole-3-acrylic acid ultra pure is relevant to functional materials and polymer modification where the acrylic acid moiety supports incorporation into polymer backbones or side chains. The carboxylic acid functionality can be transformed into acrylic esters or other polymerizable derivatives that allow controlled copolymerization or grafting onto polymer substrates. The indole ring contributes aromatic character that can influence UV absorption, intermolecular interactions, and surface affinity, supporting materials design that relies on aromatic functionality. Downstream, indole-acrylate-derived monomers and crosslinking components can be used in specialty chemical production for coatings, adhesive formulations, and functional polymer intermediates that require defined indole chemistry.

5. Process Chemistry Intermediate

Indole-3-acrylic acid ultra pure is employed as a defined indole-acrylic acid intermediate in process chemistry for manufacturing routes targeting indole-acrylate derivatives and downstream fine chemicals. The presence of a single carboxylic acid group simplifies activation and downstream conversion to esters, amides, or other coupling partners used in multi-step syntheses. The conjugated alkene provides a predictable reactivity profile for controlled transformations that can be tuned by selecting appropriate protecting-group strategies on other functional groups in the reaction partner. Ultra-pure material specifications support reproducible impurity behavior in scale-up, enabling consistent generation of downstream intermediates used for library synthesis, specialty chemical production, and industrial chemical manufacturing where trace impurities can affect analytical endpoints.

6. Analytical Standards And SAR Studies

Indole-3-acrylic acid ultra pure is applicable in analytical research and SAR studies as a chemically defined reference material for quantitation and impurity-aware method development. The indole chromophore and unsaturated acid functionality provide strong analytical detectability, supporting LC/UV or MS-based monitoring of derivatization and degradation pathways in indole-acrylate chemistry. Conversion to labeled or derivatized standards can enable calibration of analytical methods used to evaluate related indole-acrylic acid analogs in synthetic sequences. Structure-anchored use of this acid supports reproducible scaffold comparison across analog series where the indole core and acrylic geometry are held constant while other functional groups are varied for SAR-driven molecular design.

Size
50 g;100 g;
InChI
1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
InChI Key
PLVPPLCLBIEYEA-AATRIKPKSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)C=CC(=O)O

Useful Tools

Peptide Calculator

Abbreviation List

Peptide Glossary

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.

Featured Services
cGMP Peptide ServicePeptide Nucleic Acids SynthesisPeptide CDMOPeptide Modification ServicesPeptide Analysis ServicesPeptide Synthesis ServicesEpitope Mapping ServicesCustom Conjugation Service
Hot Products
About us

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.

Our Customers