フェニルアセトアルデヒド
フェニルアセトアルデヒド (30-50%フタル酸ジエチル溶液) · ベンゼンアセトアルデヒド · 2-フェニルエタナール · 2-フェニルアセトアルデヒド · α-トルイルアルデヒド · ベンゼンエタナール · フェニルエタナール · α-トルアルデヒド
識別子と物理属性
| CAS No. | 122-78-1 |
|---|---|
| 分子式 | C8H8O |
| 平均分子量 | 120.15 g/mol |
| 単同位体質量 | 120.05751487 g/mol |
| SMILES | O=CCc1ccccc1 |
| InChIKey | DTUQWGWMVIHBKE-UHFFFAOYSA-N |
| PubChem CID | 998 |
| ChEMBL | CHEMBL1233464 |
| ChEBI | CHEBI:16424 |
| EC No. | 204-574-5 |
| DTXSID | DTXSID3021483 |
| 現地名 | フェニルアセトアルデヒド |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 17.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 2 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 82 |
| 融点 | −10 °C(lit.) |
| 沸点 | 195 °C |
| 密度 | 1.079 g/mL at 20 °C |
| 蒸気圧 | 2.09hPa at 20℃ |
| FEMA | 2874 | PHENYLACETALDEHYDE |
| 屈折率 | n20/D 1.535(lit.) |
| 引火点 | 188 °F |
| 貯蔵条件 | 2-8°C |
| 溶解度 | 2.21g/l 微溶性2.210g/L（25℃） |
| 外観・状態 | 液体 |
| 比重 | 1.075 (20/4℃) |
| 色 | 無色透明～淡黄色 |
| 臭い | ジプロピレングリコール中10.00%。緑の甘い花ヒヤシンスクローバーハニーココア |
| においのタイプ | 緑 |
| 由来生物 | synthetic |
| Merck | 14,7265 |
| JECFA Number | 1002 |
| BRN | 385791 |
| ヘンリー定数 | 1.6×100 mol/(m3Pa) at 25℃, Dupeux et al. (2022) |
| 誘電率 | 4.8(20℃) |
| 安定性 | 安定。可燃性。強酸化剤、強塩基とは相容れない。 |
| 化粧品成分の機能 | 香料香料香料 |
| InChI | 1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2 |
| InChIKey | DTUQWGWMVIHBKE-UHFFFAOYSA-N |
| SMILES | O=CCc1ccccc1 |
| LogP（分配係数） | 1.44 at 25℃ |
| CAS データベース | 122-78-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzeneacetaldehyde(122-78-1) |
| EPAの化学物質情報 | Phenylacetaldehyde (122-78-1) |
化学的特性
Phenylacetaldehyde has a harsh, green odor reminiscent of hyacinth on dilution. It has an unpleasant, pungent, bitter flavor, turning sweet and fruit-like at low levels. Since it readily undergoes oxidation and polymerizes, it must be stabilized by addition of antioxidants and by dilution with, for example, diethyl phthalate before use in compositions.
安全性と法規制
| 水環境危害等級（WGK） | 2 |
|---|---|
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | CY1420000 |
| 輸送番号（UN） | UN 1170 3/PG 2 |
| 毒性 | LD50 orl-rat: 1550 mg/kg FCTXAV 17,377,79 |
| 税関コード | 29122990 |
| 危険文句（R） | 22-36/37/38-43-11 |
| 化審法 | (3)-2656 |
| 安衛法 | 有機溶剤中毒予防規則:第2種有機溶剤,57,57-2 |
| 消防法 | 危-4-3-III |
| 危険表示 | Xn,F |
| 安全措置（S） | 26-36-37-24-16-7 |
| 危険等級 | Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Corr. 1BSkin Sens. 1A |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
用途
解説
フェニルアセトアルデヒド，無色の液体．沸点194～195 ℃．d2041.0319．n20D1.5283．有機溶媒に易溶，水に難溶．ヒヤシンス様の強い花香を有する．空気中では，酸化や重合が起こりやすい．香料として用いられる．森北出版「化学辞典（第2版）
用途
多くの種類の昆虫（チョウ目、ハチ目、甲虫類、アミメカゲロウ目）は、フェニルアセトアルデヒドを交信物質として利用している。マゴットセラピーにおいて抗菌作用を示すことも知られる。タバコの香りを増すために加えられる。純粋なフェニルアセトアルデヒドの匂いは、蜂蜜のよう、甘い、バラの香り、みずみずしい、草の香り、と表現される。ソバやチョコレート[4]などの食品や植物にも含まれる。ヒヤシンス、ナルシサス、アカシア、シクラメンなどのフレグランス、ラズベリー、アンズ、サクランボ、スパイスなどのフレーバーの調合原料として用いられる。
説明
Phenylacetaldehyde is an organic compound which can be naturally found in buckwheat, flowers, and communication pheromones from various insect orders. It is commonly used for the preparation of fragrance as well as flavors, and applied in flavored cigarettes and beverages because of its honey-like sweet character. It is also applied in the synthesis of polymers, such as polyesters, as a rate controlling additive in polymerization reactions and used in the preparation of more complex chemicals like resmethrin, where it acts as a building block.
天然物の起源
Identified among the constituents of several essential oils: neroli, Citrus sinensis leaves, other citrus species (flowers and leaves), narcissus, magnolia, lily, rose and tea. It is reported found in over 170 natural products including apricot, sour cherry, cooked apple, peach, fresh blackberry, crispbread, other types of bread, green tea, unprocessed rice, lemon balm, red sage, black currant, bilberry, cranberry, other berries, grapes, raisins, melon, papaya, guava fruit, pineapple, asparagus, celery leaves, carrot, parsley, peas, bell pepper, sweet pepper, peach, cabbage, peppermint oil, Scotch spearmint oil, mustard, vinegar, onion, cooked potato, tomato, cinnamon bark, cassia leaf, ginger, many cheeses, milk, yogurt, boiled egg, cooked and cured meats, beer, cognac, grape wines, cocoa, coffee, tea, roasted filbert, roasted peanut, soybean, pecans, cauliflower, broccoli, honey, avocado, passion fruit, beans, mushrooms, trassi, mango, tamarind, rice, licorice, buckwheat, lovage root, pumpkin, sweet potato, cassava, corn oil, malt, wort, dried bonito, loquat, pawpaw, maté, sweet grass oil, orange peel oil, grapefruit juice, endive, clam and Chinese quince.
使用
Phenylacetaldehyde is used for the preparation of fragrances and polymers like polyesters, which find application as a rate controlling additive in polymerization reactions. It is an active component of fragrances and floral scent due to its honey-like sweet character and finds application in flavored cigarettes and beverages. It is an insect attractant and utilized in blacklight trap for pests. It is also used as a building block in the synthesis of more complex chemicals, such as resmethrin. Furthermore, it is used in association with acetic anhydride and allyltrimethylsilane in three-component coupling process catalyzed by LiBF4 providing homoallylic acetates.
製法・合成法
調製方法
The most important method industrially is the isomerization of styrene oxide. Ion-exchange resins, catalysis by chromium trioxide–tungsten trioxide on graphite or silicon dioxide–aluminum trioxide, and thermolysis are recommended for the rearrangement. Phenylacetaldehyde can also be synthesized by the direct oxidation of styrene in the presence of palladium salts and copper(II) chloride in aqueous solutions of glycol ethers. Other possibilities include the catalytic dehydrogenation of 2-phenylethanol on silver or gold catalysts, the hydroformylation of benzyl halides in the presence of dicobalt octacarbonyl and sodium carbonate in acetonitrile, and the Darzens glycide ester synthesis from benzaldehyde and alkyl chloroacetates.