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Indole-3-acetic acid

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Indole-3-acetic acid Basic information

Product Name:
Indole-3-acetic acid
CAS:
87-51-4
MF:
C10H9NO2
MW:
175.18
EINECS:
201-748-2
Mol File:
87-51-4.mol
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Indole-3-acetic acid Chemical Properties

Melting point:
165-169 °C(lit.)
Boiling point:
306.47°C (rough estimate)
Density 
1.1999 (rough estimate)
refractive index 
1.5460 (estimate)
Flash point:
171°C
storage temp. 
−20°C
pka
4.75(at 25℃)
form 
crystalline
color 
off-white to tan
Water Solubility 
Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water.
Sensitive 
Light Sensitive
Decomposition 
167 ºC
Merck 
14,4964
BRN 
143358
Stability:
Stable. Incompatible with strong oxidizing agents. Light sensitive.
CAS DataBase Reference
87-51-4(CAS DataBase Reference)
NIST Chemistry Reference
Indole-3-acetic acid(87-51-4)
EPA Substance Registry System
Indole-3-acetic acid (87-51-4)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
NL3150000
8-10-23
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29339990
Toxicity
LD50 intraperitoneal in mouse: 150mg/kg

MSDS

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Indole-3-acetic acid Usage And Synthesis

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ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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
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.

Agricultural Uses

Indoleacetic acid (IAA), synthesized in the plant shoot tips, is a naturally occurring auxin. It is a plant growth promoter.

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.

Indole-3-acetic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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Alfa Aesar Gold
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