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Indole-3-acetic acid

CAS No.
87-51-4
Chemical Name:
Indole-3-acetic acid
Synonyms
IAA;INDOLEACETIC ACID;2-(1H-INDOL-3-YL)ACETIC ACID;3-INDOLEACETIC ACID;Gap;INDOL-3-YLACETIC ACID;HETEROAUXINE;indole-3-acetic;indolyl-aceticaci;Indolylacetic acid
CBNumber:
CB8783347
Molecular Formula:
C10H9NO2
Molecular Weight:
175.18
MDL Number:
MFCD00005636
MOL File:
87-51-4.mol
MSDS File:
SDS
Last updated:2023-09-01 17:37:15

Indole-3-acetic acid 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
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
Water Solubility Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water.
Decomposition 167 ºC
Sensitive Light Sensitive
Merck 14,4964
BRN 143358
Stability Stable. Incompatible with strong oxidizing agents. Light sensitive.
LogP 1.410
CAS DataBase Reference 87-51-4(CAS DataBase Reference)
FDA UNII 6U1S09C61L
NIST Chemistry Reference Indole-3-acetic acid(87-51-4)
EPA Substance Registry System Indole-3-acetic acid (87-51-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
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
NFPA 704
1
2 1

Indole-3-acetic acid price More Price(45)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I3750 3-Indoleacetic acid 98% 87-51-4 5G $28.5 2024-03-01 Buy
Sigma-Aldrich I3750 3-Indoleacetic acid 98% 87-51-4 25g $102 2024-03-01 Buy
Sigma-Aldrich I3750 3-Indoleacetic acid 98% 87-51-4 100g $258 2024-03-01 Buy
Sigma-Aldrich I2886 3-Indoleacetic acid plant cell culture tested, crystalline 87-51-4 5g $34.5 2024-03-01 Buy
Sigma-Aldrich 45533 3-Indoleacetic acid PESTANAL , analytical standard 87-51-4 250mg $53.2 2024-03-01 Buy
Product number Packaging Price Buy
I3750 5G $28.5 Buy
I3750 25g $102 Buy
I3750 100g $258 Buy
I2886 5g $34.5 Buy
45533 250mg $53.2 Buy

Indole-3-acetic acid Chemical Properties,Uses,Production

Chemical Properties

white to tan crystals

Uses

It is applied as plant growth hormone. is an inducer of plant cell elongation and division shown to cause uncontrolled growth.

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.

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.

526-55-6
87-51-4
Synthesis of Indole-3-acetic acid from Tryptophol
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View Lastest Price from Indole-3-acetic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Indole-3-acetic acid pictures 2024-04-12 Indole-3-acetic acid
87-51-4
US $0.00 / kg 1kg 99% 2000ton Shaanxi Haibo Biotechnology Co., Ltd
Indole-3-acetic acid pictures 2023-08-15 Indole-3-acetic acid
87-51-4
US $0.00 / kg 1kg 99% 1000tons Hebei Mojin Biotechnology Co., Ltd
Indole-3-acetic acid pictures 2023-06-20 Indole-3-acetic acid
87-51-4
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
(1H-Indol-3-yl)acetic acid 98% Bioenraiz Noclosan IAA/IUPAC 3-(Carboxymethyl)-1H-indole IAA, 3-Indolylacetic acid NSC 3787 Indole-3-acetic acid (Auxin) 3-(Carboxymethyl)-1H-indole, Heteroauxin, IAA IAA, 3-Indolylacetic acid, Heterauxin IAA, Heteroauxin 3-Indoleacetic acid 98% 3-Indoleacetic Acid, 97+% 2-(3-Indolyl)acetic acid 3-(Carboxymethyl)Indole 3-IAA Acetic acid, indolyl- a-Iaa alpha-IAA alpha-Indol-3-yl-acetic acid alpha-indol-3-yl-aceticacid beta-IAA beta-Indole-3-acetic acid beta-indole-3-aceticacid beta-indoleaceticacid beta-Indolylacetic acid beta-indolylaceticacid b-Iaa b-Indoleacetic acid Heteroauxinhexteroauxiniaa Hexteroauxin Indoleacetate IAA 1H-Indole-3-acetic acid Heteroauxin 2-(1H-indol-3-yl)acetic acid Indole-3-acetic acid IAA Indole-3-acetic acid (indole acetic acid) 2,3-dihydro-1H-indol-3-ylacetic acid Kyselina 3-indolyloctova kyselina3-indolyloctova omega-Skatole carboxylic acid omega-skatolecarboxylicacid Rhizopon A Rhizopon A, AA rhizopona Skatole carboxylic acid INDOLE-3-ACETIC ACID PLANT CELL CULTURE TESTED 3-INDOLYLACETIC ACID PESTANAL, 250 MG 2-(INDOLIN-3-YL)ACETIC ACID 3-IndoleaceticAcid,Indole-3-AceticAcid Indole-3-AceticAcidForBiochemistry Indole-3-acetic acid, 98+% IAA,3-Indoleaceticacid 1H-Indole-3-acetic acid, 99+% INDOLE-3-ACETICACID,(IAA)98%(BULK Indol-3-ylacetic acid 98% 3-INDOLEACCETIC ACID(IAA) INDOLACETICACID 4-(INDOL-3-YL)ACETICACID Indole-3-acetic acid horticultural grade, 99% INDOLE-3-ACETIC AICD