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Indole acetic acid

Catalog Number
ACM87514-1
CAS
87-51-4
Structure
IUPAC Name
IUPAC Name: 2-(1H-indol-3-yl)acetic acid
Synonyms
1H-Indole-3-acetic acid
Molecular Weight
175.18
Molecular Formula
C10H9NO2
Canonical SMILES
Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)O
InChI
InChIKey: SEOVTRFCIGRIMH-UHFFFAOYSA-N
InChI Key
InChI: InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
Boiling Point
306.5°C
Melting Point
165-169 °C (lit.)
Density
1.20g/ml
Active Content
95%
Physical State
Solid
Typical Applications
Auxin
Spec Sheet
Case Study

Indole Acetic Acid Used for the Enhancement of Phenolic Biosynthesis and Bioactivity in Mentha rotundifolia L.

Indole Acetic Acid Used for the Enhancement of Phenolic Biosynthesis and Bioactivity in Mentha rotundifolia L. Kecis, Hadjer, et al. Process Biochemistry (2025).

Indole acetic acid (IAA), a naturally occurring auxin, was investigated for its role in promoting the biosynthesis of polyphenolic compounds and enhancing biological activities in Mentha rotundifolia L. plants. The study evaluated combined treatments of IAA with adenine-type cytokinin (AD) at 10 and 20 mg/L (T1-T4) to assess effects on plant growth, phenolic accumulation, and pharmacological potential.
Experimental Approach:
Aerial and root tissues of treated and control plants were analyzed for fresh and dry weight, total phenolic content, flavonoid and flavonol levels, and specific phenolic acids using HPLC. Bioactivity assays included antioxidant capacity and inhibition of acetylcholinesterase (AChE) and α-glucosidase. Molecular docking studies were conducted to correlate phenolic composition with enzyme inhibition.
Results and Implications:
IAA in combination with AD significantly increased biomass and total phenolic contents, reaching up to 252.69 µg GAE/mL in roots. Treatments T1 and T4 markedly enhanced the levels of rosmarinic acid, salvianolic acid, and quinic acid in aerial parts, while individual flavonoids were primarily elevated in T4-treated tissues. Extracts from treated plants exhibited stronger antioxidant activity and enzyme inhibitory effects. Docking studies revealed that major phenolics, including naringin and rosmarinic acid, contributed effectively to AChE and α-glucosidase inhibition, with low binding energies (-8.4 to -10.5 kcal/mol).
This study demonstrates that indole acetic acid, when applied in combination with adenine-type cytokinin, can strategically enhance secondary metabolite biosynthesis in M. rotundifolia, improving both phenolic content and bioactivity. The findings highlight IAA's potential as a bio-stimulant for optimizing the pharmacological properties of medicinal plants through controlled phytohormone application.

Indole Acetic Acid Used for Mitigation of Cadmium Stress and Enhancement of Growth in Daucus carota L.

Indole Acetic Acid Used for Mitigation of Cadmium Stress and Enhancement of Growth in Daucus carota L. Faiz, Samia, et al. Chemosphere 290 (2022): 133200.

Indole acetic acid (IAA), a key phytohormone, was investigated for its role in alleviating cadmium (Cd) toxicity and enhancing growth in carrot (Daucus carota L.) plants. Cadmium is a highly toxic heavy metal that impairs plant physiological mechanisms, reducing root and shoot development and overall biomass accumulation.
Experimental Approach:
Three genotypes of D. carota were exposed to Cd stress, with treatments including IAA, silver nanoparticles (AgNPs), and their combination. Growth parameters such as root diameter, root length, root and shoot weight, shoot length, and leaf fresh and dry weight were measured. Biochemical assays were conducted to evaluate reactive oxygen species (ROS) levels, malondialdehyde (MDA) content, and the activity of phenol-synthesizing enzymes including peroxidase (POX), polyphenol oxidase (PPO), and phenylalanine ammonia-lyase (PAL).
Results and Implications:
Cd stress significantly decreased growth attributes, with reductions up to 85.38% in leaf dry weight in local genotypes. IAA application mitigated these effects, increasing root diameter, root length, and shoot weight by 12-73% compared to Cd-only treated plants. IAA enhanced the activity of antioxidant and phenol biosynthetic enzymes (POX, PPO, PAL), reduced MDA accumulation, and contributed to ROS detoxification, indicating a protective effect against oxidative stress. The combined treatment of IAA and AgNPs further improved growth and stress tolerance. Notably, genotype Pre breed 22 exhibited superior Cd tolerance, highlighting genotypic variability in response to IAA-mediated amelioration.
These findings demonstrate that indole acetic acid can serve as an effective bio-stimulant for mitigating heavy metal stress, enhancing growth, and regulating antioxidant defense systems in D. carota, providing a promising strategy for sustainable crop production under metal-contaminated conditions.

Indoleacetic Acid Used for the Functional Modification of Cellulose Nanocrystals in Pectin-Based Antibacterial Films

Indoleacetic Acid Used for the Functional Modification of Cellulose Nanocrystals in Pectin-Based Antibacterial Films Han, R., Li, Y., Li, H., Song, Y., Yu, J., Duan, J., & Ai, S. (2025). International journal of biological macromolecules, 146053.

Indoleacetic acid (IAA) was applied as a chemical modifier for cellulose nanocrystals (CNCs) to enhance their functionality in bio-based materials. CNCs are widely used in biodegradable and bioactive applications due to their high aspect ratio, mechanical strength, and biocompatibility. The present study reports an efficient, environmentally friendly method for IAA modification of CNCs under mild reaction conditions.
Experimental Approach:
CNCs were first oxidized using a sodium bisulfite (NaHSO₃)-activated potassium permanganate system at room temperature for 3 hours. Indoleacetic acid was dissolved in acetic acid, activated with EDC and DMAP, and reacted with CNCs for 36 hours to form IAA-modified CNCs (CNCI). The CNCI products were purified with ethanol and deionized water, followed by drying at 50 °C. The chemical and physical properties of CNCI were characterized using SEM, XRD, FT-IR, TGA, and XPS.
Results and Implications:
IAA modification successfully introduced bioactive functional groups to CNCs, broadening their chemical versatility. Incorporation of CNCI into pectin-based films improved mechanical strength, UV resistance, and hydrophobicity while imparting antibacterial activity, making the films suitable for food preservation applications such as strawberry packaging. The mild, aqueous-based reaction minimized energy consumption and chemical hazards, providing an efficient and scalable strategy for producing advanced functional bio-based materials.
This study demonstrates the practical application of indoleacetic acid in functionalizing cellulose nanocrystals, enhancing both physicochemical and bioactive properties, and expanding their use in sustainable, biodegradable, and antibacterial materials for food and biomedical industries.

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