페닐 아세트알데히드
α-톨루익알데히드 · α-톨루알데히드 · 페닐아세트알데히드 · 페닐아세트알데하이드 · Benzeneacetaldehyde · 2-PHENYLACETALDEHYDE · Hyacinthin · Phenylethanal
식별자 및 물리적 특성
| CAS No. | 122-78-1 |
|---|---|
| 분자식 | C8H8O |
| 평균 분자량 | 120.15 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 페닐 아세트알데히드 |
화학 및 물리적 성질
| XLogP | 1.8 |
|---|---|
| 극성 표면적 | 17.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 82 |
| 녹는점 | −10 °C(lit.) |
| 끓는 점 | 195 °C |
| 밀도 | 1.079 g/mL at 20 °C |
| 증기압 | 2.09hPa at 20℃ |
| FEMA | 2874 | PHENYLACETALDEHYDE |
| 굴절률 | n20/D 1.535(lit.) |
| 인화점 | 188 °F |
| 저장 조건 | 2-8°C |
| 용해도 | 2.21g/l 약간 용해됨 |
| 물리적 상태 | 액체 |
| 비중 | 1.075 (20/4℃) |
| 색상 | 무색~담황색 투명 |
| 냄새 | 디프로필렌 글리콜 중 10.00%. 녹색 달콤한 꽃 히아신스 클로버 꿀 코코아 |
| 향취 유형 | 녹색 |
| 생물학적 소스 | synthetic |
| 용해도 | 2.210g/L(25℃) |
| Merck | 14,7265 |
| JECFA Number | 1002 |
| BRN | 385791 |
| 헨리 상수 | 1.6×100 mol/(m3Pa) at 25℃, Dupeux et al. (2022) |
| 유전율 | 4.8(20℃) |
| 안정성 | 안정적인. 타기 쉬운. 강한 산화제, 강한 염기와 호환되지 않습니다. |
| 화장품 원료 기능 | 향수향료향기 |
| 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(분배 계수) | 1.44 at 25℃ |
| NIST | Benzeneacetaldehyde(122-78-1) |
| EPA | Phenylacetaldehyde (122-78-1) |
화학적 성질
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.
안전 및 규제
| 수질 위해 등급(WGK) | 2 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | CY1420000 |
| 운송 번호(UN) | UN 1170 3/PG 2 |
| 독성 | LD50 orl-rat: 1550 mg/kg FCTXAV 17,377,79 |
| 관세 코드 | 29122990 |
| 위험 문구(R) | 22-36/37/38-43-11 |
| 위험 표시 | Xn,F |
| 안전 문구(S) | 26-36-37-24-16-7 |
| 기존화학 물질 | KE-28263 |
| 위험 등급 | Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1Skin Corr. 1BSkin Sens. 1A |
| 저장 분류 | 8A - Combustible corrosive hazardous materials |
용도
개요
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.
출처
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.
용도
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.
일반 설명
Phenylacetaldehyde is an important aroma volatile found in tomato and roses. It has also been identified in potato, roasted cocoa beans and honey. Phenylacetaldehyde is also a potent moth attractant.
제조 및 합성 방법
생산 방법
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.