3-インドール酢酸

Indole-3-Acetic Acid

HCID 802CAS 87-51-4

基本情報

標準SMILES
O=C(O)Cc1c[nH]c2ccccc12
InChIKey
SEOVTRFCIGRIMH-UHFFFAOYSA-N
分子式
C10H9NO2
平均分子量
175.18 g/mol
単同位体質量
175.06332853

概要

Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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

名称と識別子

優先名称
Indole-3-Acetic Acid
IUPAC
2-(1H-indol-3-yl)acetic acid
現地名
3-インドール酢酸
英語名
Indole-3-acetic acid
分子式
C10H9NO2
分子量
175.18

名称と別名

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
名称をさらに表示
3-インドール酢酸ノクロサンインドール-3-イル酢酸1H-インドール-3-酢酸2-(1H-インドール-3-イル)酢酸β-インドール酢酸インドール-3-酢酸スカトール-ω-カルボン酸ビオエンライズ(1H-インドール-3-イル)酢酸リゾピンヘテロオーキシンインド-ル-3-酢酸3-インドール酢酸(β-〃)3‐インドール酢酸3-インドール酢酸IAACS_N-10727-250MG_3-インドール酢酸IAA3-インドール酢酸(Β-)3- インドール酢酸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

データベース識別子

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

物性

構造計算による物性

XLogP
1.4
極性表面積
53.1 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
2
重原子数
13

実験および物理化学的性質

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

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Plant Growth Regulators

LogP · 2 件

1.41

1.41

Solubility · 2 件

1.5 mg/mL

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

Melting Point168.5 °C

物理化学的性質

融点
165 · 165-169 °C (lit.)
沸点
306.47 °C · 306.47°C (rough estimate)
比重(密度)
1.1999 · 1.1999 (rough estimate)
屈折率
1.546 · 1.5460 (estimate)
闪点
171 °C · 171°C
貯蔵温度
-20 °C · -20°C

化学的性質

化学的特性white to tan crystals

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 4 件

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%)

毒性情報

Treatment · 1 件

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 件

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 件

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 件

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).

安全データ

F
8-10-23
wgk
3
tsca
TSCA listed
rtecs
NL3150000
毒性
LD50 intraperitoneal in mouse: 150mg/kg
hs_code
29339990

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

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

用途と製造

Uses · 3 件

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
応用分野 · 3 件

解説植物の成長促進に働くホルモン物質はオーキシンとよばれる.その化学的実体はインドール-3-酢酸かその類縁化合物である.生体内ではトリプトファンからつくられる.

使用Plant growth regulator.

一般的な説明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.

調製方法 · 1 件

純化方法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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補足説明

定義本品は、次の化学式で表される複素環式化合物である。

定義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.

関連反応

78 件

関連ノート

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