Indole-3-Acetic Acid

HCID 802CAS 87-51-4

Basic information

Standard SMILES
O=C(O)Cc1c[nH]c2ccccc12
InChIKey
SEOVTRFCIGRIMH-UHFFFAOYSA-N
Molecular formula
C10H9NO2
Average molar mass
175.18 g/mol
Monoisotopic mass
175.06332853

Overview

Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group. It has a role as an auxin, a plant hormone, a mouse metabolite, a plant metabolite and a human metabolite. It is a member of indole-3-acetic acids and a monocarboxylic acid. It is a conjugate acid of an indole-3-acetate.

Names & identifiers

Preferred name
Indole-3-Acetic Acid
IUPAC
2-(1H-indol-3-yl)acetic acid
English name
Indole-3-acetic acid
Molecular formula
C10H9NO2
Molecular weight
175.18

Names & synonyms

indole-3-acetic acid87-51-43-Indoleacetic acidindoleacetic acidHeteroauxin1H-Indole-3-acetic acid2-(1H-Indol-3-yl)acetic acid1H-indol-3-ylacetic acidRhizopinRhizopon A3-Indolylacetic acid3-Iaa
Show more names
IAAGapIndolylacetic acidINDOL-3-YLACETIC ACIDHETEROAUXINEIndoleacetateindole-3-acetic
3-(Carboxymethyl)indolebeta-Indoleacetic acidbeta-Indolylacetic acidIndolyl-3-acetic acidindole acetic acidKyselina 3-indolyloctovaDTXSID50207382-(indol-3-yl)ethanoic acid

Database identifiers

CAS
87-51-4
PubChem CID
802
DTXSID
DTXSID5020738
ChEMBL
CHEMBL82411
ChEBI
CHEBI:16411
UNII
6U1S09C61L
EC Number
201-748-2
Nikkaji
J5.156J

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
53.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
Pesticides · 3 items

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Plant Growth Regulators

LogP · 2 items

1.41

1.41

Solubility · 2 items

1.5 mg/mL

>26.3 [ug/mL] (The mean of the results at pH 7.4)

Melting Point168.5 °C

Physicochemical properties

Melting point
165 · 165-169 °C (lit.)
Boiling point
306.47 °C · 306.47°C (rough estimate)
Density
1.1999 · 1.1999 (rough estimate)
bulk density
620 kg/m3 · 620kg/m3
refractive index
1.546 · 1.5460 (estimate)
Flash point
171 °C · 171°C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 8.9% (5 of 56) of reports.

Warning

H302 (58.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 56 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 1H-Indole-3-acetic acid

2008/941

Status: Active Update: 29-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34003

Indole-3-acetic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant; [PhytoTechnology Laboratories MSDS] See Indole. See Indole-3-butyric acid.
Hazard Classes and CategoriesAcute Tox. 4 (58.9%)

Toxicology

Treatment · 1 item

Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.

Health Effects · 1 item

Indoleacetic acid is listed in its MSDS as potentially mutagenic to mammalian somatic cells. It is also identified as a potential skin, eye, and respiratory irritant, and users are warned not to ingest it. Acute exposure to Indoleacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of Indoleacetic acid are associated with the inborn error of metabolism known as Hartnup disease.

Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as indole-3-acetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869)

Signs and Symptoms · 1 item

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F
8-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
NL3150000
hs_code
29339990

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Indole-3-acetic-acid has known human metabolites that include Indole-3-acetic-acid-O-glucuronide.

Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism

Uses & manufacturing

Uses · 3 items

Used as a plant growth regulator; [Merck Index] Active product registrations in the US; [NPIRS]

Farming (Pesticides) [Category: Industry]

Naturally produced by the body (endogenous). Also a plant growth hormone (auxin).

General Manufacturing Information1H-Indole-3-acetic acid: ACTIVE
Applications · 3 items

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

UsesPlant growth regulator.

General Description3-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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海金试生化科技有限公司18601717983 18601717983 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

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

Related reactions

78 records

Linked notes

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