2-(1H-indol-3-yl)acetic acid

• ChemBase ID: 5579
• Molecular Formular: C10H9NO2
• Molecular Mass: 175.18396
• Monoisotopic Mass: 175.06332853
• SMILES: c12c(cccc1)c(c[nH]2)CC(=O)O
• Canonical SMILES: OC(=O)Cc1c[nH]c2c1cccc2
• 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)
• InChIKey: SEOVTRFCIGRIMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1H-indol-3-yl)acetic acid
• IUPAC Traditional name: indole-3-acetic acid; β-indole-3-acetic acid
• Synonyms: Heteroauxin; 3-Indoleacetic Acid; Indolyacetic Acid; Rhizopin; INDOLE-3-ACETIC ACID; 3-(Carboxymethyl)-1H-indole; (1H-Indol-3-yl)acetic acid 98%; Heterauxin; Indolyl-3-acetic acid; Indole-3-acetic acid; 1H-INDOL-3-YLACETIC ACID; Indole-3-acetic acid; indolylacetic acid; 1H-Indole-3-acetic acid; indoleacetic acid; IAA; 2-(1H-indol-3-yl)acetic acid; 3-Indoleacetic acid; (1H-Indol-3-yl)acetic Acid; 3-(Carboxymethyl)indole; 3-IAA; 3-Indolylmethylcarboxylic Acid; Bioenraiz; GAP; Noclosan; Indoleacetic Acid; 吲哚-3-乙酸; 杂茁长素; 3-吲哚乙酸

Database IDs

• CAS Number: 87-51-4; 6505-45-9
• EC Number: 201-748-2
• MDL Number: MFCD00005636
• Beilstein Number: 143358
• Merck Index: 144964
• PubChem SID: 160969007; 24896043; 99444421; 24869056; 24896015
• PubChem CID: 802
• CHEBI ID: 16411
• CHEMBL: 82411
• Chemspider ID: 780
• DrugBank ID: DB07950
• KEGG ID: C00954
• Wikipedia Title: Indole-3-acetic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.6618505
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.81362313
• LogD (pH = 7.4): -0.96409625
• Log P: 1.7097561
• Molar Refractivity: 48.4521 cm^3
• Polarizability: 19.722364 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.87
• LOG S: -2.1
• Solubility (Water): 1.38e+00 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; moderate in water
• Apperance: Off-White Solid; off-white to tan crystalline; white solid
• Melting Point: 162-165°C; 165-168°C; 165-169 °C(lit.); 165-169°C; 168-170 °C (441-443 K); ca 167°C dec.
• Flash Point: 171°C(339°F)

Safety Information

• Storage Condition: 0°C, Protect from light; Refrigerator
• Storage Warning: IRRITANT; Irritant/Light Sensitive/Keep Cold/Store under Argon; Light Sensitive
• RTECS: NL3150000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~99%; ≥95% (T); ≥98.0% (T); ≥98.5%; 95%; 98%; 98+%
• Grade: PESTANAL®, analytical standard; SAJ special grade; technical
• Suitability: plant cell culture tested
• Ignition Residue: ≤0.3%
• Empirical Formula (Hill Notation): C10H9NO2

DETAILS

MP Biomedicals - 02102037

Plant Growth Hormone
Off-white to tan crystals
Purity: ~99%

DrugBank - DB07950

Drug information: experimental

Sigma Aldrich - I3750

Packaging
25, 100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 45533

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 57330

Other Notes
Plant growth hormone, review1; Regulates cell membrane electron transport and proton flux2

Sigma Aldrich - I2886

Application
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.