Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

doi:10.6023/cjoc201903069

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2139-2147.DOI: 10.6023/cjoc201903069 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Reviews

含硫香精香料的合成进展

王明^a, 王翠红^a, 姜雪峰^a,b

a 华东师范大学化学与分子工程学院上海市绿色化学与化工过程绿色化重点实验室上海 200062;
b 南开大学元素有机化学国家重点实验室天津 300071

收稿日期:2019-03-29 修回日期:2019-04-22 发布日期:2019-05-10
通讯作者: 王翠红, 姜雪峰 E-mail:xfjiang@chem.ecnu.edu.cn;chwang@chem.ecnu.edu.cn
基金资助:
国家重点研发计划（2017YFD0200500）、国家自然科学基金（Nos.21722202，21672069，21871089）资助项目.

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

Wang Ming^a, Wang Cuihong^a, Jiang Xuefeng^a,b

a Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received:2019-03-29 Revised:2019-04-22 Published:2019-05-10
Contact: 10.6023/cjoc201903069 E-mail:xfjiang@chem.ecnu.edu.cn;chwang@chem.ecnu.edu.cn
Supported by:
Project supported by the National Key Research and Development Program of China (No. 2017YFD0200500), and the National Natural Science Foundation of China (Nos. 21722202, 21672069, 21871089).

Scientists have found more and more sulfur compounds in food with the development of science and technology, high-precision analytical methods and equipment. In 2015, Flavor and Extract Manufactures Association of the United State published 2816 safe flavors, and there are more than 388 sulfur-containing compounds, accounting for more than 13%. The main smell of sulfur-containing flavors is food, especially the non-staple food and dishes. It is mainly used as food flavor, flower flavor and fruity flavor. Due to the increase of sulfur-containing perfume and flavors demand, its production scale is increasing, the research on synthesis methods is also deepening, and the green and efficient construction methods are also constantly reported. In this review, the recent progress in the construction of sulfide, thiol, thioester and polysulfide perfume & flavors is summarized.

Key words: sulfide, thiol, thioester, polysulfide, perfume, flavors

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Wang Ming, Wang Cuihong, Jiang Xuefeng. Recent Progress in the Sulfur-Containing Perfume & Flavors Construction[J]. Chin. J. Org. Chem., 2019, 39(8): 2139-2147.

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[1] Wei, W. Textbook of Organic Chemical Industry, Vol. 3, Chemical Industry Press, Beijing, 1990, p. 206(in Chinese). (魏文德,有机化工原料大全,第三卷,化学工业出版社,北京, 1990, p. 206.)
[2] Smith, R. L.; Doull, J.; Feron, V. J.; Goodman, J. I.; Munro, I. C.; Newberne, P. M.; Portoghese, P. S.; Waddell, W. J.; Wagner, B. M.; Adams, T. B.; Mcgowen, M. M. Food Technol. 2001, 55, 34.
[3] Cohen, S. M.; Fukushima, S.; Gooderham, N. J.; Hecht, S. S.; Marnett, L. J.; Rietjens, I. M. C. M.; Smith, R. L.; Bastaki, M.; McGowen, M. M.; Harman, C.; Taylor, S. V. Food Technol. 2015, 69, 40.
[4] Sun. B. G. Sulfur-Containing Fragrance Chemistry, Science Press, 2007 (in Chinese). (孙宝国,含硫香料化学,科学出版社, 2007.)
[5] Mosciano, G. Perfum. Flavor. 1998, 23, 33.
[6] Tehrani, K. A.; Boeykens, M.; Tyvorskii, V. I.; Kulinkovich, O.; Kimpe, N. D. Tetrahedron 2000, 56, 6541.
[7] (a) Seyedi, S. M.; Sadeghian, H.; Safari, Z. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 2297.
(b) Huang, M.; Tian, H.; Sun, B. Fine Chem. 2005, 22, 127(in Chinese). (黄明泉,田红玉,孙宝国,精细化工, 2005, 22, 127.)
[8] Wang, Y.-L.; Tian, H.; Sun, B.; Yu, J. China Surfactant Deterg. Cosmet. 2010, 40, 448(in Chinese). (王亚玲,田红玉,孙宝国,余洁菲,日用化学工业, 2010, 40, 448.)
[9] Lin, Y.; Yi, W.; Shen, W.; Lu, G. Org. Lett. 2016, 18, 592.
[10] Lin, Y.; Lu, G.; Wang, G.; Yi, W. Adv. Synth. Catal. 2016, 358, 4100.
[11] (a) Wang, S. CN 101607948, 2009.
(b) Sun, B.; Tian, H.; Huang, M.; Liu, Y.; Xie, J.; Zheng, F. CN 1709867, 2005.
[12] Singh, S.; Kumar, S.; Chimni, S. S. Tetrahedron:Asymmetry 2001, 12, 2457.
[13] Guo, A. China Condiment 2009, 10, 96(in Chinese). (郭安齐,中国调味品, 2009, 10, 96.)
[14] Brown, H.; Lynch, G. J. J. Org. Chem. 1981, 46, 930.
[15] Burk, M. J.; Gerlach, A.; Semmeril, D. J. Org. Chem. 2000, 65, 8933-8939.
[16] Sakai, N.; Moritaka, K.; Konakahara, T. Eur. J. Org. Chem. 2009, 4123-4127.
[17] Liu, X.; Long, S.; Mao, Y.; Diao, H.; Kong, Q.; Wang, Y.; Guo, F. CN 102127038, 2011.
[18] Schoenauer, S.; Schieberle, P. J. Agric. Food Chem. 2018, 66, 4189.
[19] (a) Russell, G. A.; Law, W. C.; Zaleta, M. J. Am. Chem. Soc. 1985, 107, 4175.
(b) Mussinan C. J.; Giacino, C.; WaIradt, J. P. DE 2426865, 1975.
[20] Schoenauer, S.; Schieberle, P. J. Agric. Food Chem. 2016, 64, 3849-3861.
[21] (a) He, K.; Xu, F.; Li, Q.; Wang, G.; Zhu, G. CN 108440457, 2018.
(b) Bom, D. C.; Christenson, P. A.; Lam, A. M.; Zhang, Y. WO 2012072631, 2011.
[22] Stefaniak, M.; Jasiński, M.; Romański, J. Synlett 2015, 26, 1045.
[23] Degl'Innocenti, A.; Capperucci, A.; Cerreti, A.; Pollicino, S.; Scapecchi, S.; Malesci, I.; Castagnoli, G. Synlett 2005, 3063.
[24] Ian, W. J.; Still, L.; Martyn, J. P. Synth. Commun. 1998, 28, 913.
[25] Vermeulen, C.; Christine, G. D.; Collin, S. J. Agric. Food Chem. 2003, 51, 3623.
[26] Polster, J.; Schieberle, P. J. Agric. Food Chem. 2017, 65, 4329.
[27] (a) Tamura, H.; Fujita, A.; Steinhaus, M.; Takahisa, E.; Watanabe, H.; Schieberle, P. J. Agric. Food Chem. 2010, 58, 7368.
(b) Tamura, H.; Fujita, A.; Steinhaus, M.; Takahisa, E.; Watanabe, H.; Schieberle, P. J. Agric. Food Chem. 2011, 59, 10211.
[28] Naef, R.; Velluz, A.; Jaquier, A. J. Agric. Food Chem. 2008, 56, 517.
[29] Wilson, R. A.; Giacino, C. US 3892878, 1975.
[30] Li, Q.; Zheng, L. Hebei Chem. Eng. Ind. 2006, (2), 24(in Chinese) (李庆奎,郑连义,河北化工, 2006, (2), 24).
[31] Hatanaka, T.; Yuki, R.; Saito, R.; Sasaki, K. Org. Biomol. Chem. 2016, 14, 10589.
[32] Qiao, Z.; Jiang, X. Org. Lett. 2016‚ 18‚ 1550.
[33] Khalili, D.; Iranpoor, N.; Firouzabadi, H. J. Sulfur Chem. 2015‚ 36‚ 544.
[34] Zhang, L.; Xiao, Y.; Liu, Y. CN 101824026, 2010.
[35] Soleiman-Beigi, M.; Yavari, I.; Sadeghizadeh, F. Phosphorus, Sulfur, Silicon Relat. Elem. 2018, 193, 41.
[36] Rys, A. Z.; Harpp, D. N. Tetrahedron Lett. 2000, 41, 7169.
[37] Evers, W. J. US 4020175, 1977.
[38] Xiao, X.; Feng, M.; Jiang, X. Chem. Commun. 2015, 51, 4208.
[39] Xiao, X.; Feng, M.; Jiang, X. Angew. Chem., Int. Ed. 2016, 55, 14121.
[40] Xiao, X.; Xue, J.; Jiang, X. Nat. Commun. 2018, 9, 2191.
[41] Wang, W.; Lin, Y.; Ma, Y.; Tung, C.-H.; Xu, Z. Org. Lett. 2018, 20, 3829.

含硫香精香料的合成进展

Recent Progress in the Sulfur-Containing Perfume & Flavors Construction

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