인돌-3-아세트산

Indole-3-Acetic Acid

HCID 802CAS 87-51-4

기본 정보

표준 SMILES
O=C(O)Cc1c[nH]c2ccccc12
InChIKey
SEOVTRFCIGRIMH-UHFFFAOYSA-N
분자식
C10H9NO2
평균 분자량
175.18 g/mol
단동위원소 질량
175.06332853

개요

Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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

이름 및 식별자

우선 이름
Indole-3-Acetic Acid
IUPAC
2-(1H-indol-3-yl)acetic acid
현지명
인돌-3-아세트산
영어명
Indole-3-acetic acid
분자식
C10H9NO2
분자량
175.18

이름 및 동의어

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
이름 더 보기
3-인돌아세트산인돌-3-아세트산1H-인돌-3-아세트산3-(카르복시메틸)인돌헤테아욱신인돌아세인돌아세틱애씨드인돌-3-아세트산IAAGapIndolylacetic 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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
1.4
극성 표면적
53.1 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
2
무거운 원자 수
13

실험 및 물리화학적 성질

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

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Plant Growth Regulators

LogP · 2건

1.41

1.41

Solubility · 2건

1.5 mg/mL

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

Melting Point168.5 °C

물리화학적 성질

녹는점
165 · 165-169 °C (lit.)
끓는 점
306.47 °C · 306.47°C (rough estimate)
밀도
1.1999 · 1.1999 (rough estimate)
굴절률
1.546 · 1.5460 (estimate)
인화점
171 °C · 171°C
저장 조건
-20 °C · -20°C

화학적 성질

white to tan crystals

안전 및 규제

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 4건

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%)

독성 정보

Treatment · 1건

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 · 1건

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 · 1건

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 · 1건

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).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
NL3150000
독성
LD50 intraperitoneal in mouse: 150mg/kg
HS 번호
29339990
risk_code
36/37/38

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

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

용도 및 제조

Uses · 3건

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
응용 분야 · 2건

용도Plant growth regulator.

일반 설명3-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.

공급사50 곳

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]

추가 설명

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

관련 반응

78건

연결된 노트

불러오는 중…

Indole-3-Acetic Acid (HCID 802)|Huagongshe