铃兰醛
| 铃兰醛 | |
|---|---|
| |
| IUPAC名 3-(4-tert-Butylphenyl)-2-methylpropanal | |
| 别名 | 4-叔丁基-α-甲基苯丙醛 4-叔丁基-α-甲基氢化肉桂醛 百合醛 2-(4-叔丁苄基)丙醛 α-甲基对叔丁基苯丙醛 4-(1,1-二甲基乙基)-α-甲基苯丙醛 |
| 识别 | |
| CAS号 | 80-54-6（外消旋体）  75166-31-3（2R） 75166-30-2（2S）
|
| PubChem | 1549660（2R） 1715213（2S） 228987 |
| ChemSpider | 1266494 (2R), 1363748 (2S), 199342 |
| SMILES |
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| InChI |
|
| InChIKey | SDQFDHOLCGWZPU-UHFFFAOYSA-N |
| UN编号 | 3082 |
| EINECS | 201-289-8 |
| RTECS | MW4895000 |
| 性质 | |
| 化学式 | C14H20O |
| 摩尔质量 | 204.31 g·mol−1 |
| 外观 | 澄清的粘稠液体 |
| 密度 | 0.94 g/cm3 |
| 熔点 | −20 °C（253 K） |
| 沸点 | 275 °C（548 K）[1] |
| 溶解性（水） | 0.045 g/L（20 °C） |
| log P | 4.36 [1] |
| 药理学 | |
| 给药途径 | 局部 |
| 相关物质 | |
| 相关化合物 | 4-叔丁基苯并醛 异丁醛 2-亚苄基辛醛 2-甲基十一醛 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
铃兰醛又名百合醛，是一种醛类有机化合物，化学式为C14H20O，常用作化妆品或洗衣粉中的香料。
合成
[编辑]BASF公司通过对4-叔丁基甲苯进行双阳极氧化来生产铃兰醛，年产量超过1万吨。[2]
在实验室中，它可由2-甲基烯丙醇和4-叔丁基碘苯在碳酸钠存在下、氯化钯催化下反应制得。[3]
性质
[编辑]铃兰醛以外消旋混合物的形式生成并销售，但它的不同对映异构体对其气味的贡献并不相同。(R)-异构体具有仙客来或铃兰的强烈的花香，而(S)-异构体的气味则比较淡。[4]
(R)-铃兰醛（上图）和(S)-铃兰醛（下图）的结构式
propionaldehyd_Formulae_V.1.svg)
它和乙二醇在二氧化硅负载的硫酸氢铵催化下反应，可以得到相应的缩醛。[5]它和三苯基膦、四溴化碳在二氯甲烷中反应，可以得到4-(4,4-二溴-2-甲基-3-丁烯-1-基)叔丁苯。[6]
安全性
[编辑]欧盟消费者安全科学委员会在2019年认定将铃兰醛应用于冲洗型和免洗型化妆品中是不安全的。[7]由于铃兰醛在动物研究中被发现有生殖毒性，欧盟将其重新划分为禁用物质，并于2022年3月起禁止其在化妆品中使用。[8]
参考文献
[编辑]- ^ 1.0 1.1 Haefliger, Olivier P.; Jeckelmann, Nicolas; Ouali, Lahoussine; León, Géraldine. Real-Time Monitoring of Fragrance Release from Cotton Towels by Low Thermal Mass Gas Chromatography Using a Longitudinally Modulating Cryogenic System for Headspace Sampling and Injection. Analytical Chemistry. 2010, 82 (2): 729–737. ISSN 0003-2700. PMID 20025230. doi:10.1021/ac902460d.
- ^ Möhle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.; Waldvogel, S. R. Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products. Angew. Chem., Int. Ed. 2018, 57: 6018−6041. doi:10.1002/anie.201712732.
- ^ Richard F. Heck. Palladium-Catalyzed Vinylation of Organic Halides. Organic Reactions. 2005. doi:10.1002/0471264180.or027.02.
- ^ Bartschat, Dietmar; Bürner, Susanne; Mosandl, A.; Bats, Jan W. Stereoisomeric flavour compounds LXXVI: direct enantioseparation, structure elucidation and structure-function relationship of 4-tert-butyl-α-methyldihydrocinnamaldehyde. Zeitschrift für Lebensmittel-Untersuchung und -Forschung A. 1997, 205 (1): 76–79. ISSN 1431-4649. S2CID 97399242. doi:10.1007/s002170050127.
- ^ Azzena, Ugo ; Carraro, Massimo; Corrias, Martina; Crisafulli, Rosella; De Luca, Lidia; Gaspa, Silvia; Nuvoli, Luca; Pintus, Salvatore; Pisano, Luisa ; Polese, Riccardo; Sanna, Michela; Satta, Giuseppe ; Senes, Nina; Urtis, Luigi ; Garroni, Sebastiano. Ammonium salts catalyzed acetalization reactions in green ethereal solvents. Catalysts. 2020, 10 (10): 1108. doi:10.3390/catal10101108.
- ^ Liu, Liu; Lv, Ye; Wu, Yile; Gao, Xiang; Zeng, Zhiping; Gao, Yuxing; Tang, Guo; Zhao, Yufen. Experimental and theoretical studies on nickel–zinc-catalyzed cross-coupling of gem-dibromoalkenes with P(O)–H compounds. RSC Advances. 2014, 4 (5): 2322–2326. ISSN 2046-2069. doi:10.1039/C3RA45212C.
- ^
Scientific Committee on Consumer Safety. OPINION ON the safety of Butylphenyl methylpropional (p-BMHCA) in cosmetic products (PDF). 2019-05-10 [2020-05-28] （英语）.
On individual product basis, Butylphenyl methylpropional (p-BMHCA) (CAS 80-54-6) with alpha-tocopherol at 200 ppm, can be considered safe when used as fragrance ingredient in different cosmetic leave-on and rinse-off type products. However, considering the first-tier deterministic aggregate exposure, arising from the use of different product types together, Butylphenyl methylpropional at the proposed concentrations cannot be considered as safe.
- ^ COMMISSION REGULATION (EU) 2021/1902 OF 29 October 2021 amending Annexes II, III and V to Regulation (EC) No 1223/2009 of the European Parliament and of the Council as regards the use of cosmetic products of certain substances classified as carcinogenic, mutagenic or toxic for reproduction. Official Journal of the European Union. 2021-10-29 [2022-01-03].
CAS No. 80-54-6