化工社化工社 化学情報印刷レポート · 研究参考用
3-インドール酢酸
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
識別子と物理属性
| CAS No. | 87-51-4 |
|---|---|
| 分子式 | C10H9NO2 |
| 平均分子量 | 175.18 g/mol |
| 単同位体質量 | 175.06332853 g/mol |
| SMILES | O=C(O)Cc1c[nH]c2ccccc12 |
| InChIKey | SEOVTRFCIGRIMH-UHFFFAOYSA-N |
| PubChem CID | 802 |
| ChEMBL | CHEMBL82411 |
| ChEBI | CHEBI:16411 |
| EC No. | 201-748-2 |
| DTXSID | DTXSID5020738 |
| 現地名 | 3-インドール酢酸 |
化学・物理的性質
| XLogP | 1.4 |
|---|---|
| 極性表面積 | 53.1 |
| 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 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Angular frequency |
| 農薬 | Plant Growth RegulatorsActive substance -> EU Pesticides database: Not approvedPesticides -> Plant Growth Regulators |
| LogP（分配係数） | 1.41 |
| 溶解度 | 1.5 mg/mL>26.3 [ug/mL] (The mean of the results at pH 7.4)DMSO:30.0(Max Conc. mg/mL)171.25(Max Conc. mM)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。 |
| 融点 | 168.5 °C165-169 °C (lit.) |
| 蒸気圧 | 0.00000526 [mmHg] |
| Physical Description | Solid[Merck Index] Light tan to light pink flaky powderOdorless[PhytoTechnology Laboratories MSDS] |
| Collision Cross Section | 136.2 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]138.11 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]143.5 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]143.6 Ų [M+Na]+ |
| 沸点 | 306.47°C (rough estimate) |
| 密度 | 1.1999 (rough estimate) |
| 屈折率 | 1.5460 (estimate) |
| 引火点 | 171°C |
| 貯蔵条件 | -20°C |
| pKa（酸解離定数） | 4.75(at 25℃) |
| 外観・状態 | 結晶性 |
| 色 | オフホワイトからタン |
| Decomposition | 167 ºC |
| Merck | 14,4964 |
| BRN | 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（分配係数） | 1.410 |
| CAS データベース | 87-51-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Indole-3-acetic acid(87-51-4) |
| EPAの化学物質情報 | Indole-3-acetic acid (87-51-4) |
化学的特性
white to tan crystals
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 8.9% (5 of 56) of reports.WarningH302 (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. |
|---|---|
| 規制情報 | Chemical: 1H-Indole-3-acetic acid2008/941Status: Active Update: 29-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34003Indole-3-acetic acid: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | An irritant[PhytoTechnology Laboratories MSDS] See Indole. See Indole-3-butyric acid. |
| Hazard Classes and Categories | Acute Tox. 4 (58.9%) |
| 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. |
| 健康影響 | 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. |
| 暴露経路 | Endogenous, Ingestion, Dermal (contact) |
| 毒性の概要 | 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. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 8-10-23 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | NL3150000 |
| 毒性 | LD50 intraperitoneal in mouse: 150mg/kg |
| 税関コード | 29339990 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (5)-6618 |
| 危険表示 | Xi |
| hazard_note | Irritant |
| 安全措置（S） | 22-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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.
製法・合成法
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.