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Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 205
実験および物理化学的性質
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]+
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
- 溶解性
- 30 · DMSO:30.0(Max Conc. mg/mL);171.25(Max Conc. mM)
- 酸解離定数(Pka)
- 4.75 · 4.75(at 25℃)
- 外見
- 結晶性
- 色
- オフホワイトからタン
- 水溶解度
- エタノール (50mg/ml)、メタノール、DMSO、クロロホルム (微量) に可溶。水に溶けません。
- Decomposition
- 167 · 167 ºC
- Merck
- 14 · 14,4964
- BRN
- 143358 · 143358
- 安定性
- 安定。強力な酸化剤とは相容れない。光に敏感。
- 主な用途
- 農業環境
- 化粧品成分の機能
- スキンコンディショニング
- 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
- CAS データベース
- 87 · 87-51-4(CAS DataBase Reference)
- NISTの化学物質情報
- -3 · Indole-3-acetic acid(87-51-4)
- EPAの化学物質情報
- -3 · Indole-3-acetic acid (87-51-4)
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
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
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
毒性情報
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.
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
- risk_code
- 36/37/38
- 化審法
- (5)-6618
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 22-24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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.
用途と製造
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).
応用分野
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
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.
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
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
関連ノート
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