LI Shi-tou, LI Shan, WANG Ying-ying, et al. Synthesis of 3-hydroxy-β-damascone and its pyrolysis analysis[J]. Journal of Light Industry, 2013, 28(2): 64-68. doi: 10.3969/j.issn.2095-476X.2013.02.015
Citation:
LI Shi-tou, LI Shan, WANG Ying-ying, et al. Synthesis of 3-hydroxy-β-damascone and its pyrolysis analysis[J]. Journal of Light Industry, 2013, 28(2): 64-68.
doi:
10.3969/j.issn.2095-476X.2013.02.015
Synthesis of 3-hydroxy-β-damascone and its pyrolysis analysis
-
College of Tobacco Science and Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001, China
-
Received Date:
2013-02-24
Available Online:
2013-03-15
-
Abstract
The synthetic technology of 3-hydroxy-β-damascone and its pyrolysis analysis were performed.Firstly ethyl 2,6,6-trimethyl-4-oxo-2cyclohexene-1-carboxylate was obtained by reactions of Michael addition and Robinson cyclation with mesityl oxide and ethyl acetoacetate as starting materials,then it was ketalized with ethylene glycol,and was hydrolated and reduced by sodium borohydride to afford ethyl 2,6,6-trimethyl4-hydroxyl-cyclohexene-lcarboxylate,finally the obtained compound was coupled with allyllithium to give the title compound 3-hydroxyβ-damascone.The structure of 3-hydroxyβ-damascone was charactered by GC-MS,IR,LC-ESI-MS,1H NMR,and 13C NMR.The pyrolysis results of 3-hydroxy-β-damascone showed that it could hardly be pyrolyzed at 300℃,but could be pyrolyzed at 600℃,750℃,900℃ to produce β-damascenone,isophorone,etc,which are important flavoring comopositions in tobacco.
-
-
References
-
[1]
Anthony J N Bolt,Stephen W Purkis,John S Sadd.A damascone derivative from nicotiana tabacum[J].Phytochrmrsfry,1983,22(2):613.
-
[2]
Kaneko H,Arada M.4-Hydroxy-β-damaseone and 4-H ydroxy-dihydro-β-damascene from cigar tobacco[J].Agric Biol Chem,1972,36(1):168.
-
[3]
Lloyd R A,Miller C W,Roberts D L,et al.Flue-cured tobacco flavor I Essence and essential oil components[J].Tobacco Sci,1976,20(10):40.
-
[4]
Mani Naiker.β-damascenone-yielding precursor(s) from Cabernet Sauvignon grapes[J].The South Pacific Journal of Natural Science,2001,19(1):11.
-
[5]
Sanja Radeka,Igor Lukic,Dordano Peršuric.Influence of different maceration treatments on the aroma profile of rosé and red wines from croatian aromatic cv.muškat ruža porecki[J].Food Technol Biotechnol,2012,50(4):442.
-
[6]
Yasuko T,Makoto S,Hajime M,et al.A new convenient synthesis of 3-hydroxy-beta-damascone[J].Agric Biol Chem,1981,45(7):1731.
-
[7]
杨君,高宏建,张献忠,等.烟草香味物质及其精油应用研究进展[J].香精香料化妆品,2012,28(3):45.
-
[8]
黄致喜,黄惠成.萜类香料化学[M].北京:中国轻工业出版社,1999:178-224.
-
[9]
Surmatis J D,Walser A,Gibas J,et al.A study on the condensation of mesityl oxide with acetoacetic ester[J].Organic Chemistry,1970,35(4):1053.
-
[10]
Tohn J E,Alan M J.A convenient preparation of allyllithiurn[J].Organic Chemistry,1963,28(8):2145.
-
[11]
Mariappan P,Muniappan T.Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis[J].Journal of Organometallic Chemistry,2000,65:137.
-
Proportional views
-
-