铃兰醛

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。 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。 在实验室中，它可由2-甲基烯丙醇（維基數據所列：Q72488865）和4-叔丁基碘苯（維基數據所列：Q72503448）在碳酸钠存在下、氯化钯催化下反应制得。 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。 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。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。 欧盟消费者安全科学委员会（英语：Scientific Committee on Consumer Safety）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。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。 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