Abstract
Diethyl [(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]phosphonate (9) was synthesized via a condensation between tetraethyl methylenebis(phosphonate) (7) and 6,10-dimethyl-3,5,9-undecatrien-2-one(8) by Wittig-Horner reaction, (3E,5E,7E)-3,8-dimethyldeca-3,5,7-trienedial (5) was prepared from (E)-tetraethyl but-2-ene-1,4-diylbis-(phosphonate)(2) and 4,4-dimethoxy-2-butanone (3) by Wittig-Horner reaction followed by hydrogenation. Lycopene was synthesized from diethyl [(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]phosphonate(9)and(3E,5E,7E)-3,8-dimethyldeca-3,5,7-trienedial(5) by Wittig-Horner reaction，the structure of products was confirmed by NMR, HRMS/GC-MS and IR techniques. The total yield was 16.7%.
Publication Date
3-28-2021
First Page
162
Last Page
167
DOI
10.13652/j.issn.1003-5788.2021.03.030
Recommended Citation
Guo, CHEN; Ri-an, YAN; Hai-mei, LI; Hua, ZHOU; and Chun-zhi, LI
(2021)
"Total synthesis of lycopene based on dodecatrienal,"
Food and Machinery: Vol. 37:
Iss.
3, Article 30.
DOI: 10.13652/j.issn.1003-5788.2021.03.030
Available at:
https://www.ifoodmm.cn/journal/vol37/iss3/30
References
[1] 李睿. 番茄中番茄红素提取工艺的比较研究[J]. 应用化工, 2020, 49(12): 2 994-2 997.
[10] 陈瑶. 番茄红素生产工艺研究进展[J]. 化工设计通讯, 2016, 42(12): 58-62.
[11] FUKUMOTO T H K O K. Process for the preparation of phosphonium salts: US 5481040[P]. 1996-01-02.
[12] 李卓才, 鲁波, 尹红, 等. 番茄红素化学合成的研究进展[J]. 合成化学, 2006(2): 118-121.
[13] MEYER K. Method for the manufacture of carotinoids and the novel intermediates: US 5166445[P]. 1992-11-24.
[14] 李昆明. β-胡萝卜素的合成工艺研究[D]. 杭州: 浙江大学, 2016: 8-10.
[15] BABLER J H P H W. C-15 phosphonate reagent compositions for the manufacture of compounds such as lycopene and methods of synthesizing the same: US 5973179[P]. 1999-10-26.
[16] GUHA S K, KOO S. Sulfone coupling and double-elimination strategy for carotenoid synthesis[J]. The Journal of Organic Chemistry, 2005, 70(23): 9 662-9 665.
[17] 穆小青, 晏日安, 谭奇坤, 等. 新型高倍二肽甜味剂的制备与表征[J]. 食品与机械, 2019, 35(12): 36-41.
[18] JI M, CHOI H, JEONG Y C, et al. Allylic sulfones containing triene moieties as key synthons for carotenoid synthesis[J]. Helvetica Chimica Acta, 2003, 86(7): 2 620-2 628.
[19] 张希波, 刘洪海, 张晓丽, 等. 番茄红素化学合成的研究进展[J]. 西北药学杂志, 2009, 24(1): 78-80.
[20] SHEN Run-pu, JIANG Xiao-yue, YE Wei-dong, et al. A novel and practical synthetic route for the total synthesis of lycopene[J]. Tetrahedron, 2011, 67(31): 5 610-5 614.
[21] 马文鑫, 梁智平, 王渭军, 等. 番茄红素的全合成[J]. 中国药科大学学报, 2013, 44(5): 390-393.
[22] SONG Xiao-hua, XU Hui-ting, YE Wei-dong, et al. Practical synthesis of lycopene[J]. Organic Preparations and Procedures International, 2016, 48(4): 350-354.
[23] 谭奇坤, 陈果, 彭青霞, 等. 基于α-叔碳-β,γ-不饱和醛的制备全合成番茄红素[J]. 精细化工, 2020, 37(3): 561-566.
[24] VAN WIJK A, LUGTENBURG J. Synthetic scheme for the preparation of C-13-labeled 2,7-dimethylocta-2,4,6-triene-1,8-dial, the central part of carotenoids[J]. European Journal of Organic Chemistry, 2002, 2 002(24): 4 217-4 221.
[25] 杨泽慧, 闫海英, 李茂林, 等. 2,7-二甲基-2,4,6-辛三烯-1,8-二醛合成新工艺研究[J]. 浙江大学学报(理学版), 2005(6): 668-673.
[26] SUN Pei-dong, WANG Jian-xin, FANG Zhi-kai, et al. Synthesis of crocetin dimethyl ester with wittig and wittig-horner reaction[J]. Chemical World, 2012(6): 353-357.
[27] 汤丹丹, 方志凯, 孙培冬, 等. 2,7-二甲基-2,4,6-辛三烯二醛的合成研究[J]. 化学研究与应用, 2010, 22(9): 1 217-1 219.