4-アミノフェニル酢酸
4-アミノフェニル酢酸 · p-アミノフェニル酢酸 · (4-アミノフェニル)酢酸 · 2-(4-アミノフェニル)酢酸 · 4-アミノベンゼン酢酸 · p-アミノ-α-トルイル酸 · P‐アミノフェニル酢酸 · 4-アミノフェニル酢酸, 98%
識別子と物理属性
| CAS No. | 1197-55-3 |
|---|---|
| 分子式 | C8H9NO2 |
| 平均分子量 | 151.16 g/mol |
| 単同位体質量 | 151.06332853 g/mol |
| SMILES | Nc1ccc(CC(=O)O)cc1 |
| InChIKey | CSEWAUGPAQPMDC-UHFFFAOYSA-N |
| PubChem CID | 14533 |
| ChEMBL | CHEMBL3278327 |
| EC No. | 214-828-7 |
| DTXSID | DTXSID1061609 |
| 現地名 | 4-アミノフェニル酢酸 |
化学・物理的性質
| XLogP | 0.9 |
|---|---|
| 極性表面積 | 63.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 139 |
| 物質分類 | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| Physical Description | Solid[Merck Index] Tan powder[Alfa Aesar MSDS] |
| 融点 | 201 °C (dec.) (lit.) |
| 沸点 | 273.17°C (rough estimate) |
| 密度 | 1.2023 (rough estimate) |
| 屈折率 | 1.5635 (rough estimate) |
| 引火点 | 201°C |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | pK1: 3.60pK2: 5.26 (20°C) |
| 外観・状態 | 粉 |
| 色 | ライトイエローからベージュ |
| 溶解度 | 水に非常に溶けやすい。 |
| Decomposition | 201 ºC |
| Merck | 14,463 |
| BRN | 2208094 |
| InChI | 1S/C8H9NO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5,9H2,(H,10,11) |
| InChIKey | CSEWAUGPAQPMDC-UHFFFAOYSA-N |
| SMILES | Nc1ccc(CC(O)=O)cc1 |
| LogP（分配係数） | 0.220 (est) |
| CAS データベース | 1197-55-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzeneacetic acid, 4-amino-(1197-55-3) |
| EPAの化学物質情報 | Benzeneacetic acid, 4-amino- (1197-55-3) |
化学的特性
light yellow to beige powder. Soluble in alcohols and alkalis, slightly soluble in hot water.
安全性と法規制
| GHS 分類 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 9 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzeneacetic acid, 4-amino-Benzeneacetic acid, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A skin and strong eye irritantMay induce methemoglobinemia[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| F | 13 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | AF3550000 |
| 毒性 | mouse,LD50,intraperitoneal,3500mg/kg (3500mg/kg),Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958. |
| 税関コード | 29224995 |
| 危険文句（R） | 36/37/38-20/21/22 |
| 危険表示 | Xi,Xn |
| 安全措置（S） | 22-24/25-36-26 |
| 危険等級 | IRRITANT |
| 貯蔵分類 | 13 - Non Combustible Solids |
用途
使用
4-Aminophenylacetic acid is used as a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1. It can be detected using HPLC, NMR techniques.
製法・合成法
製造方法
p-aminophenylacetic acid is obtained by the reduction of 4-nitrophenylacetic acid. In a reactor, water, 4-nitrophenylacetic acid, and acetic acid are added. The mixture is stirred and heated to 90-95℃. Iron powder is added in portions and refluxed for 2 hours. The mixture is cooled to 40-50℃ and neutralized with sodium carbonate to pH=9, then filtered. The filtrate is further neutralized with acetic acid until pH=4, resulting in the precipitation of 4-aminophenylacetic acid. The yield is 95%.
純化方法
Crystallise the acid from hot water (60-70mL/g). [Beilstein 14 III 1182.]