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鈴蘭醛

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鈴蘭醛
IUPAC名
3-(4-tert-Butylphenyl)-2-methylpropanal
別名 4-叔丁基-α-甲基苯丙醛
4-叔丁基-α-甲基氫化肉桂醛
百合醛
2-(4-叔丁苄基)丙醛
α-甲基對叔丁基苯丙醛
4-(1,1-二甲基乙基)-α-甲基苯丙醛
識別
CAS號 80-54-6(外消旋體)  checkY
75166-31-3(2R checkY
75166-30-2(2S checkY
PubChem 1549660(2R
1715213(2S
228987
ChemSpider 1266494 (2R), 1363748 (2S), 199342
SMILES
 
  • CC(CC1=CC=C(C=C1)C(C)(C)C)C=O
InChI
 
  • 1S/C14H20O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-8,10-11H,9H2,1-4H3
InChIKey SDQFDHOLCGWZPU-UHFFFAOYSA-N
UN編號 3082
EINECS 201-289-8
RTECS MW4895000
性質
化學式 C14H20O
摩爾質量 204.31 g·mol−1
外觀 澄清的粘稠液體
密度 0.94 g/cm3
熔點 −20 °C(253 K)
沸點 275 °C(548 K)[1]
溶解性 0.045 g/L(20 °C)
log P 4.36 [1]
藥理學
給藥途徑 局部
相關物質
相關化合物 4-叔丁基苯並醛英語Bourgeonal
異丁醛
2-亞苄基辛醛英語Hexyl cinnamaldehyde
2-甲基十一醛
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

鈴蘭醛又名百合醛,是一種醛類有機化合物,化學式為C14H20O,常用作化妝品或洗衣粉中的香料。

合成

[編輯]

BASF公司通過對4-叔丁基甲苯進行雙陽極氧化來生產鈴蘭醛,年產量超過1萬噸。[2]

在實驗室中,它可由2-甲基烯丙醇維基數據所列Q724888654-叔丁基碘苯維基數據所列Q72503448碳酸鈉存在下、氯化鈀催化下反應製得。[3]

性質

[編輯]

鈴蘭醛以外消旋混合物的形式生成並銷售,但它的不同對映異構體對其氣味的貢獻並不相同。(R)-異構體具有仙客來鈴蘭的強烈的花香,而(S)-異構體的氣味則比較淡。[4]

(R)-鈴蘭醛(上圖)和(S)-鈴蘭醛(下圖)的結構式

它和乙二醇二氧化硅負載的硫酸氫銨催化下反應,可以得到相應的縮醛。[5]它和三苯基膦四溴化碳二氯甲烷中反應,可以得到4-(4,4-二溴-2-甲基-3-丁烯-1-基)叔丁苯。[6]

安全性

[編輯]

歐盟消費者安全科學委員會英語Scientific Committee on Consumer Safety在2019年認定將鈴蘭醛應用於沖洗型和免洗型化妝品中是不安全的。[7]由於鈴蘭醛在動物研究中被發現有生殖毒性,歐盟將其重新劃分為禁用物質,並於2022年3月起禁止其在化妝品中使用。[8]

參考文獻

[編輯]
  1. ^ 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. 
  2. ^ 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. 
  3. ^ Richard F. Heck. Palladium-Catalyzed Vinylation of Organic Halides. Organic Reactions. 2005. doi:10.1002/0471264180.or027.02. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ Scientific Committee on Consumer Safety. OPINION ON the safety of Butylphenyl methylpropional (p-BMHCA) in cosmetic products (PDF). 2019-05-10 [2020-05-28] (英語). 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. 
  8. ^ 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