| Identification | More | [Name]
Indole-3-acetic acid | [CAS]
87-51-4 | [Synonyms]
(1H-INDOL-3-YL)-ACETIC ACID
1H-INDOLE-3-ACETIC ACID
2-(1H-INDOL-3-YL)ACETIC ACID
3-INDOLEACETIC ACID
3-INDOLYLACETIC ACID
AKOS NCG1-0097
HETERAUXIN
HETEROAUXIN
HETEROAUXINE
HETEROAUXIN SODIUM SALT
IAA
IAA SODIUM SALT
INDOL-3-YLACETIC ACID
INDOLE-3-ACETIC ACID
INDOLE-3-ACETIC ACID SODIUM SALT
INDOLEACETIC ACID
INDOLYL-3-ACETIC ACID
JAA
LABOTEST-BB LT00044476
RARECHEM AL BO 0204 | [EINECS(EC#)]
201-748-2 | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD00005636 | [Molecular Weight]
175.18 | [MOL File]
87-51-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to tan crystals | [Melting point ]
165-169 °C (lit.) | [Boiling point ]
306.47°C (rough estimate) | [density ]
1.1999 (rough estimate) | [refractive index ]
1.5460 (estimate) | [Fp ]
171°C | [storage temp. ]
−20°C
| [solubility ]
DMSO:30.0(Max Conc. mg/mL);171.25(Max Conc. mM) | [form ]
crystalline
| [pka]
4.75(at 25℃) | [color ]
off-white to tan
| [Stability:]
Stable. Incompatible with strong oxidizing agents. Light sensitive. | [Water Solubility ]
Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water. | [Decomposition ]
167 ºC | [Sensitive ]
Light Sensitive | [Detection Methods]
HPLC | [Merck ]
14,4964 | [BRN ]
143358 | [LogP]
1.410 | [CAS DataBase Reference]
87-51-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Indole-3-acetic acid(87-51-4) | [Storage Precautions]
Air sensitive;Light sensitive | [EPA Substance Registry System]
87-51-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
NL3150000
| [F ]
8-10-23 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29339990 | [Toxicity]
LD50 intraperitoneal in mouse: 150mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
white to tan crystals | [Uses]
Plant growth regulator. | [Definition]
ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group. | [Biosynthesis]
3-Indolylacetic acid is biosynthesised in plants from tryptophan by two pathways, the indolylpyruvic acid pathway being quantitatively the more important. Experiments with tomato shoots have shown the existence of a tryptophan transaminase, which catalyses the formation of indolylpyruvic acid, and a tryptophan decarboxylase, which catalyses the formation of tryptamine. The decarboxylation of indolylpyruvic acid is catalysed by indolylpyruvate decarboxylase, while indolylacetaldehyde dehydrogenase catalyses the oxidation of indolylacetaldehyde to indolylacetic acid.
The biosynthesis of 3-indolylacetic acid
| [Biological Functions]
3-Indolylacetic acid (indole-3-acetic acid, IAA) is one of the auxins, which together with the gibberellins and abscisic acid, cyto- kinins and ethylene are hormones regulating the growth and development of plants. IAA is a ubiquitous constituent of higher plants and the most important auxin. Some other, non-indolic compounds, including phenyl- acetic acid biosynthesised in plants from phenylalanine, have similar properties and synthetic auxins have also been prepared.
In the plant, IAA conjugates with many compounds, including glucose and other sugars, and with aspartic and glutamic acids. This is probably a way of storing the hormone for future use.
IAA initiates many growth effects in plants, including geotropism and phototropism, development of the ovary, division of cells, enlargement in callus tissue, root formation and apical dominance. When fed to plants, the hormone causes growth up to a maximum, which depends on the type of tissue being fed, and thereafter inhibits further growth, probably through the formation of ethylene, which is growth-inhibitory. Stern tissues tolerate the highest levels of IAA and root tissues the lowest. In the plant, the most active sites of IAA synthesis are the young, expanding leaves. | [General Description]
3-Indoleacetic acid is a highly effective, growth promotor in lower plant life, formed by a variety of fungi, including yeast and has been isolated from Aspergillus niger and Rhizopus sp. It is commonly employed in horticulture and industry. | [Agricultural Uses]
Indoleacetic acid (IAA), synthesized in the plant shoot tips, is a naturally occurring auxin. It is a plant growth promoter. | [storage]
Store at -20°C | [Purification Methods]
Recrystallise heteroauxin from EtOH/water [James & Ware J Phys Chem 89 5450 1985]. [Beilstein 22 III/IV 65.] Alternatively recrystallise 30g of the acid with 10g of charcoal in 1L of hot water, filter and cool when 22g of colourless acid separate. Dry it and store it in a dark bottle away from direct sunlight [Johnson & Jacoby Org Synth Coll Vol V 654 1973]. The picrate has m 178-180o. [Beilstein 22 H 66, 22 I 508, 22 II 50, 22 III/IV 1088.] It is a plant growth substance. |
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