3-Indoleacetic acid（IAA） - ≥98% , CAS No.87-51-4

CAS: 87-51-4 Cat. No.: I101072 Molecular Weight: 175.18 Beilstein Registry Number: 143358 EC Number: 201-748-2

GRADE & PURITY ≥98%

Synonyms

.beta.-Indoleacetic acid | bmse000177 | 1H-indol-3-ylacetic acid | Tox21_302731 | MLS001331664 | .beta.-IAA | auxin | b-Indolylacetic acid | MLS001332400 | (1H-indol-3-yl)acetate | (1H-Indol-3-yl)-acetate | .alpha.-IAA | 3-Indolylacetic acid | 3-indolyl-a

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Indole-3-acetic acid (IAA) is a natural phytohormone (plant auxin) used as a supplement in media such as Murashige and Skoog media and Gamborg’s B5 media. IAA is a plant signaling molecule involved in plant organogenesis and growth control.

as standard to quantify hormones

to modify MS (Murashige and Skoog) media for the initiation of callus

as an external standard in the analyses of free endogenous growth regulators

Specifications

Synonyms

.beta.-Indoleacetic acid | bmse000177 | 1H-indol-3-ylacetic acid | Tox21_302731 | MLS001331664 | .beta.-IAA | auxin | b-Indolylacetic acid | MLS001332400 | (1H-indol-3-yl)acetate | (1H-Indol-3-yl)-acetate | .alpha.-IAA | 3-Indolylacetic acid | 3-indolyl-a

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Natural phytohormone (plant auxin), synthesized from tryptophan, which induces plant cell elongation and division causing uncontrolled growth. Signaling molecule involved in plant organogenesis and growth control. Used as a supplement in media such as Mur

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC=C2C(=C1)C(=CN2)CC(=O)O
• IUPAC Name: 2-(1H-indol-3-yl)acetic acid
• InChIKey: SEOVTRFCIGRIMH-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)O
• WGK Germany: 3
• RTECS: NL3150000
• Molecular Weight: 175.18
• Beilstein: 143358
• Reaxy-Rn: 143358
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=143358&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indolyl carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indolyl carboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Indole-3-acetic acid derivatives
• Alternative Parents: 3-alkylindoles Substituted pyrroles Benzenoids Heteroaromatic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indole-3-acetic acid derivative - 3-alkylindole - Indole - Substituted pyrrole - Benzenoid - Heteroaromatic compound - Pyrrole - Azacycle - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Carbonyl group - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
• External Descriptors: Indole alkaloids - Auxins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

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PDF Tchem Peptide deformylase mitochondrial (169 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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KYAT1 Tbio Kynurenine--oxoglutarate transaminase I (96 Activities)

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FLT3 Tclin Tyrosine-protein kinase receptor FLT3 (13481 Activities)

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Liver microsomes (16955 Activities)

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Associated Targets(non-human)

def Peptide deformylase (54 Activities)

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Escherichia coli (133304 Activities)

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Bacillus subtilis (32866 Activities)

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Oryza sativa (2923 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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V79 (1637 Activities)

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Lactuca sativa (1092 Activities)

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BCHE Cholinesterase (8742 Activities)

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Avena sativa (212 Activities)

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Cucumis sativus (803 Activities)

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Fusarium culmorum (260 Activities)

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Macrophomina phaseolina (474 Activities)

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Rhizoctonia solani (2251 Activities)

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ftmPT1 Brevianamide F prenyltransferase (40 Activities)

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PDF1A Peptide deformylase 1A, chloroplastic (24 Activities)

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Globisporangium debaryanum (107 Activities)

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clpP ATP-dependent Clp protease proteolytic subunit (245 Activities)

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Laetisaria fuciformis (2 Activities)

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Cryphonectria parasitica (24 Activities)

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Fuchsia (11 Activities)

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Vigna mungo (68 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in Methanol almost transparency;Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water.
• Sensitivity: Air and light sensitive
• Flash Point(°F): 339.8℉
• Flash Point(°C): 171℃
• Melt Point(°C): 167°C
• Molecular Weight: 175.180 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063 Da
• Monoisotopic Mass: 175.063 Da
• Topological Polar Surface Area: 53.100 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 205.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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18. Xin Tan, Renwang Sheng, Weikun Li, Yinghua Tao, Zonghao Liu, Ning Yang, Syeda Safia Hashmi, Feiling Feng, Fangzhou Liu, Liqin Ge.  (2025)  Mannose-Glycated Metal-Phenolic Microcapsules Orchestrate Phenotype Switch of Macrophages for Boosting Tumor Immunotherapy.  Advanced Science,      [PMID:40014038] [10.1002/advs.202415565]

19. Zheng Jianxiu, Wang Liyan, Liu Ahui, Shen Haofei, Wang Bin, Jiang Yanbiao, Jing Panpan, Guan Defeng, Yu Liulin, Zhang Xuehong.  (2024)  Predicting the therapeutic role and potential mechanisms of Indole-3-acetic acid in diminished ovarian reserve based on network pharmacology and molecular docking.  HEREDITAS,  161  (1): (1-17).  [PMID:39568012] [10.1186/s41065-024-00348-6]

20. Yi Hao, Jian Shang, Shuyan Liu, Xuemeng Tian, Xin Yao, Fengjun Liu, Ruizhen Zhu, Yue Wang, Ruixia Gao, Sicen Wang.  (2025)  Preparation of protein-resistant magnetic molecularly imprinted polymers as solid-phase extraction adsorbents via a one-stone-two-birds strategy for selective enrichment of tetracycline in milk.  TALANTA,      [PMID:39904252] [10.1016/j.talanta.2025.127678]

21. Jing Jiang, Chenyang Zhang, Meng Na, Shangqi Xu, Xiaoping Li, Shoubiao Zhou, Jihai Zhou.  (2025)  Regulatory roles of indole-3-acetic acid in the physiological and biochemical responses of Cinnamomum camphora seedlings under cadmium stress.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:40663943] [10.1016/j.ecoenv.2025.118671]

22. Lisi Wang, Xiaoqing Li, Yijing Ai, Brij Mohan, Hongji Li, Zhisong Lu, Baoli Wang, Wei Sun.  (2025)  Sustainable Precursor-Based Titanium Dioxide–Graphene Nanocomposite Electrochemical Sensor for Sensitive Detection of Diuron in Vegetables.  Foods,  14  (17): (2946).  [PMID:40941062] [10.3390/foods14172946]

23. Guannan Kong, Da Song, Chao Zhang, Xinyao Jia, Yingying Ren, Shuhe Wei, Huiping Dai.  (2025)  The Effect of Plant Growth Promoting Rhizobacteria Bacillus thuringiensis LKT25 on Cadmium Accumulation and Physiological Responses in Solanum nigrum L..  Plants-Basel,  14  (18): (2918).  [PMID:41012069] [10.3390/plants14182918]

24. Xiaolei Liu, Xiaoman Jiang, Anjie Li.  (2025)  Bio-entrapment of Chlorella vulgaris mimicking granular sludge: Insights into aggregated microalgae growth and symbiotic bacteria under antibiotic stress.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.163075]

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