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Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 205
실험 및 물리화학적 성질
Pesticides
Plant Growth Regulators
Active substance -> EU Pesticides database: Not approved
Pesticides -> Plant Growth Regulators
LogP
1.41
1.41
Solubility
1.5 mg/mL
>26.3 [ug/mL] (The mean of the results at pH 7.4)
Physical Description
Solid; [Merck Index] Light tan to light pink flaky powder; Odorless; [PhytoTechnology Laboratories MSDS]
Solid
Collision Cross Section
136.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
138.11 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
143.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
143.6 Ų [M+Na]+
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
- 용해도
- 30 · DMSO:30.0(Max Conc. mg/mL);171.25(Max Conc. mM)
- 산도 계수 (pKa)
- 4.75 · 4.75(at 25℃)
- 물리적 상태
- 수정 같은
- 색상
- 회백색부터 황갈색까지
- 수용성
- 에탄올(50 mg/ml), 메탄올, DMSO 및 클로로포름(드물게)에 용해됩니다. 물에 불용성.
- Merck
- 14 · 14,4964
- BRN
- 143358 · 143358
- 안정성
- 안정적인. 강한 산화제와 호환되지 않습니다. 빛에 민감합니다.
- 주요 응용
- 농업환경
- 화장품 원료 기능
- 피부 컨디셔닝
- InChI
- 1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
- InChIKey
- SEOVTRFCIGRIMH-UHFFFAOYSA-N
- SMILES
- OC(=O)Cc1c[nH]c2ccccc12
- LogP
- 1.41 · 1.410
- NIST
- -3 · Indole-3-acetic acid(87-51-4)
- EPA
- -3 · Indole-3-acetic acid (87-51-4)
화학적 성질
white to tan crystals
안전 및 규제
GHS 분류
GHS Classification
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
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
독성 정보
Treatment
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
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.
Toxicity Summary
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
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.
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NL3150000
- 독성
- LD50 intraperitoneal in mouse: 150mg/kg
- HS 번호
- 29339990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 22-24/25
- 기존화학 물질
- KE-21008
- F 고인화성물질
- 8-10-23
- 위험 참고 사항
- Irritant
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Metabolism/Metabolites
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.
용도 및 제조
Uses
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).
응용 분야
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
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
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