けい皮酸エチル
けい皮酸エチル · 3-フェニルプロペン酸エチル · 3-フェニルアクリル酸エチル · ベンゼンアクリル酸エチル · ベンゼンプロペン酸エチル · けいひ酸エチル · 桂皮酸エチル · trans-3-フェニルアクリル酸エチル
識別子と物理属性
| CAS No. | 103-36-6 |
|---|---|
| 分子式 | C11H12O2 |
| 平均分子量 | 176.21 g/mol |
| 単同位体質量 | 176.08372962 g/mol |
| SMILES | CCOC(=O)C=Cc1ccccc1 |
| InChIKey | KBEBGUQPQBELIU-UHFFFAOYSA-N |
| PubChem CID | 7649 |
| ChEMBL | CHEMBL3182745 |
| DTXSID | DTXSID9022520 |
| 現地名 | けい皮酸エチル |
化学・物理的性質
| XLogP | 3 |
|---|---|
| 極性表面積 | 26.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 179 |
| 融点 | 6-8 °C (lit.) |
| 沸点 | 271 °C (lit.) |
| 密度 | 1.049 g/mL at 20 °C (lit.) |
| 蒸気圧 | 6Pa at 20℃ |
| 屈折率 | n20/D 1.558(lit.) |
| FEMA | 2430 | ETHYL CINNAMATE |
| 引火点 | >230 °F |
| 貯蔵条件 | 2-8°C |
| 溶解度 | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.不溶性 |
| 外観・状態 | 液体 |
| 色 | 無色透明～淡黄色 |
| 臭い | 100.00%で。スイートバルサム フルーティー スパイシー パウダリー ベリー プラム |
| においのタイプ | バルサミコ |
| 由来生物 | synthetic |
| Merck | 14,2299 |
| JECFA Number | 659 |
| BRN | 1238804 |
| ヘンリー定数 | 2.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 5.3(19℃) |
| 安定性 | 安定。強力な酸化剤、酸、塩基、還元剤とは相容れない。可燃性。 |
| 主な用途 | フレーバーそして香料 |
| 化粧品成分の機能 | 紫外線吸収剤香料 |
| InChI | 1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+ |
| InChIKey | KBEBGUQPQBELIU-CMDGGOBGSA-N |
| SMILES | CCOC(=O)\C=C\c1ccccc1 |
| LogP（分配係数） | 3.01 at 23.6℃ |
| CAS データベース | 103-36-6(CAS DataBase Reference) |
| NISTの化学物質情報 | trans-Ethyl cinnamate(103-36-6) |
| EPAの化学物質情報 | Ethyl cinnamate (103-36-6) |
化学的特性
Ethyl Cinnamate, ethyl 3-phenylacrylate, C6H5CH=CHCOOC2H5.Occurs naturally in storax and the volatile oil of Koempferia galanga.The commercial product is a colourless liquid, invariably prepared artificially. Has a sweet balsami honey-note odor of great persistence. Ethyl cinnamate is useful in Oriental bouquets, and in combination with clary sage and citrus oils will make delightful amber colognes.
安全性と法規制
| 水環境危害等級（WGK） | 1 |
|---|---|
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | GD9010000 |
| 毒性 | The acute oral LD50 value in rats was reported as 7.8 g/kg (7.41-8.19 g/kg) (Russell, 1973). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Russell, 1973). |
| 税関コード | 29163990 |
| 危険文句（R） | 20-22 |
| 化審法 | (3)-1750 |
| 消防法 | 危険物第4類第三石油類(非水溶性) |
| 安全措置（S） | 23-24/25 |
| 貯蔵分類 | 10 - Combustible liquids |
用途
説明
Ethyl cinnamate is the ester of cinnamic acid and ethanol, and is typically found in the essential oil of cinnamon. It is noteworthy that pure ethyl cinnamate has an aroma of cinnamon, complicated by balsamic and red fruit nuances,all of which can be characteristic of a fine Nebbiolo wine's aromatics.
天然物の起源
Normally occurring in the trans-form; a cis-form also exists. Reported found in Oriental styrax, in the oil of Campheria galanga and in the rhizomes of Hedychium spicatum. Also reported found in cherry, American cranberry, pineapple, guava, strawberry, fresh blackberry, strawberry jam, soybean, yellow passion fruit juice, hybrid passion fruit juice, apple brandy, quince, prickly pear, strawberry wine, Bourbon vanilla, sea buckthorn, cinnamon leaf and root bark, clove, brandy, rum, sherry, grape wines, cocoa, soybean and other natural sources.
使用
Ethyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.
一般的な説明
Ethyl cinnamate can be used as a flavoring and fragrance ingredient. It is one of the key odor components reported in Burgundy Pinot noir wines.
製法・合成法
調製方法
Ethyl cinnamate is found in storax oil, Kaempferia galanga, and several other oils. It is produced by the direct esterification esterification of ethanol with cinnamic acid under azeotropic conditions or by Claisen-type condensation of ethyl acetate and benzaldeyde in the presence of sodium metal .
製造方法
By heating to 100°C cinnamic acid, alcohol and sulfuric acid in the presence of aluminum sulfate; also by Claisen condensation of benzaldehyde and ethyl acetate
純化方法
Wash the ester with aqueous 10% Na2CO3, then water, dry (MgSO4), and distil it. The purified ester is saponified with aqueous KOH, and, after acidifying the solution, cinnamic acid is isolated, washed and dried. The ester is reformed by refluxing for 15hours the cinnamic acid (25g) with absolute EtOH (23g), conc H2SO4 (4g) and dry *benzene (100mL), after which it is isolated, washed, dried and distilled under reduced pressure [Jeffery & Vogel J Chem Soc 658 1958]. [Beilstein 9 IV 2006.]