2'-アミノアセトフェノン
2'-アミノアセトフェノン · 2-アセチルアニリン · o-アミノアセトフェノン · 1-(2-アミノフェニル)エタノン · 2′-アミノアセトフェノン · o-アミノアセトフェノン(2′-) · 2′‐アミノアセトフェノン · 2'-アミノアセトフェノン, 98%
識別子と物理属性
| CAS No. | 27941-88-4 |
|---|---|
| 分子式 | C8H9NO |
| 平均分子量 | 135.16 g/mol |
| 単同位体質量 | 135.06841391 g/mol |
| SMILES | CC(=O)c1ccccc1N |
| InChIKey | GTDQGKWDWVUKTI-UHFFFAOYSA-N |
| PubChem CID | 11086 |
| ChEMBL | CHEMBL2251601 |
| ChEBI | CHEBI:91110 |
| EC No. | 209-002-8 |
| DTXSID | DTXSID4052213 |
| 現地名 | 2'-アミノアセトフェノン |
化学・物理的性質
| XLogP | 1.6 |
|---|---|
| 極性表面積 | 43.1 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 133 |
| 物質分類 | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP（分配係数） | 1.63 |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.115-1.1211.112 g/mL at 25 °C(lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | YELLOW OILY LIQUIDYELLOW CRYSTALS |
| 溶解度 | PRACTICALLY INSOL IN WATERSOL IN ALCSOL IN ETHERSoluble in fats, acetoneVery slightly soluble in waterSoluble (in ethanol)ジクロロメタン（少量）、DMSO、メタノール（少量） |
| 沸点 | BP 250-252 °C @ 760 MM HG (SOME DECOMP)85.00 to 90.00 °C. @ 0.50 mm Hg85-90 °C (0.5 mm Hg)85-90 °C0.5 mm Hg(lit.) |
| 融点 | 20 °C |
| 蒸気圧 | 0.00989 [mmHg] |
| 屈折率 | INDEX OF REFRACTION: 1.6160 @ 20 °C/DMAX ABSORPTION (ALC): 226 NM (LOG E= 4.32), 254 NM (LOG E= 3.75), 359 NM (LOG E= 3.64)1.612-1.619n20/D 1.614(lit.) |
| FEMA | 3906 | 2-AMINOACETOPHENONE |
| 引火点 | >230 °F |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 2.31±0.10(Predicted) |
| 外観・状態 | 液体 |
| 色 | 黄色から黄褐色 |
| 臭い | ブドウの甘い |
| 由来生物 | synthetic |
| においのタイプ | 葡萄 |
| JECFA Number | 2043 |
| Merck | 14,413 |
| BRN | 386122 |
| 主な用途 | フレーバーそして香料 |
| InChI | 1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3 |
| InChIKey | GTDQGKWDWVUKTI-UHFFFAOYSA-N |
| SMILES | CC(=O)c1ccccc1N |
| LogP（分配係数） | 1.63 |
| CAS データベース | 551-93-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Ethanone, 1-(2-aminophenyl)-(551-93-9) |
| EPAの化学物質情報 | Ethanone, 1-(2-aminophenyl)- (551-93-9) |
化学的特性
2-Aminoacetophenone, also known as o-aminoacetophenone or 2-AA, is a yellow to yellow-brown liquid that has a grape-like odor. Aminoacetophenone is a pheromone produced by virgin honeybee queens and released in feces. The pheromone repels and is used to terminate agonistic interactions between queens and workers. A grape-like odor of 2-aminoacetophenone is of diagnostic importance in detecting the growth of Pseudomonas aeruginosa in culture and in burn wounds.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 56.9% (78 of 137) of all reports.WarningH302 (13.9%): 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 137 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Ethanone, 1-(2-aminophenyl)-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 15-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20816Ethanone, 1-(2-aminophenyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | An irritantMay induce methemoglobinemia[MSDSonline] |
| Hazard Classes and Categories | Acute Tox. 4 (13.9%) |
| 処分方法 | The following wastewater treatment technologies have been investigated for acetophenone: concentration process: activated carbon. /Acetophenone/The following wastewater treatment technologies have been investigated for acetophenone: concentration process: resin adsorption. /Acetophenone/ |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Non-Human Toxicity Excerpts | Methyl anthranilate is an effective bird repellent at concentrations of 1.0% (g/g). Ortho-aminoacetophenone has an odor similar to that of methyl anthranilate and is chemically (structurally) similar. Coincidentally, ortho-aminoacetophenone is present in the scent gland secretions of mustelid species that prey on birds. For these reasons, ... the bird repellency of this material and 3 isomers to European starlings (Sturnus vulgaris) /were tested/. Ortho-aminoacetophenone was repellent at concentrations 0.01% in both choice and no-choice feeding tests. The other structural isomers (meta-,para-, alpha-) were less effective. Chemically, the results suggest that hydrogen-bonded ring structure formation and basicity predict bird repellent activity. |
用途
用途
有機合成用原料、香料材料。
天然物の起源
Reported present in chestnut honey (>154 ppb)*; green tea and wine (0.7 to 12.8 μg/L).
使用
2′-Aminoacetophenone may be used as an analytical standard for the determination of the analyte in livestock particulate matter, and grape-derived beverages by gas chromatography-mass spectrometry-olfactometry (GC-MS-O) and GC-MS, respectively.
一般的な説明
2′-Aminoacetophenone is one of the key volatile flavor components of masa corn flour products. It is also reported to be responsible for the grape-like odor in culture media growing Pseudomonas aeruginosa.
製法・合成法
製造方法
Synthesis of 2-Aminoacetophenone by reaction of methyl lithium with Isatoic anhydride in an anhydrous or nearly anhydrous solvent at a reaction temperature of -50°C or less.