Abstract
For the search for a domestic natural source of allylpolyalkoxybenzenes and development of an effective process for their isolation, CO2 extracts of several varieties of parsley, dill, celery, caraway, and nutmeg were analyzed systematically for the first time by GC/MS and GLC techniques. The varieties with high contents of myristicin, elemicin, allyltetramethoxybenzene, apiol, and dillapiol were identified. The conditions of CO2 extraction for obtaining concentrates with minimum contents of the distillation residues were selected. Using high performance fractional distillation, polyalkoxyallylbenzenes with 98–99% purity were isolated from the concentrates on a pilot unit. By isomerization of some allylbenzenes followed by ozonolysis under specially selected conditions, apiol-and dillapiolaldehydes were obtained in 75–80% yields.
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O. N. Stas’eva, N. N. Latin, and G. I. Kas’yanov, CO 2-Ekstrakty Kompanii Karavan — novyi klass natural’nykh pishchevykh dobavok [CO 2-Extracts of the Karavan Company as a New Class of Natural Food Additives], KNIIKhP, Krasnodar, 2006 (in Russian).
B. Diaz-Reinoso, A. Moure, H. Dominguez, and J. C. Parajo, J. Agric. Food Chem., 2006, 54, 2441.
G. Singh, P. Marimuthu, C. S. Heluani, and C. A. N. Catalan, J. Agric. Food Chem., 2006, 54, 174.
B. N. Golovkin, R. N. Rudenskaya, I. A. Trofimova, and A. I. Shreter, Biologicheski aktivnye veshchestva rastitel’nogo proiskhozhdeniya [Biologically Active Compounds of Plant Origin], Nauka, Moscow, 2001–2002, Vols. I–III (in Russian).
US Pat. 4876277; Chem. Abstrs, 1990, 112, 216908f.
Canada Pat. 2198645; Chem. Abstrs, 1999, 131, 27947z.
E. Stahl and H. Jork, Archiv der Pharmazie, 1964, 297, 273.
J. E. Simon and J. Quinn, J. Agric. Food Chem., 1988, 38, 467.
B. Vinogradov, N. Vinogradova, L. Golan, Aromaterapiya, Fultus Publishing, Palo Alto, USA, 2006.
E. P. Lichtenstein, T. T. Liang, K. R. Schulz, H. R. Schnoes, and G. T. Carter, J. Agric. Food Chem., 1974, 22, 658.
S. S. Tomar, M. L. Maheshwari, and S. K. Mukerjee, J. Agric. Food Chem., 1979, 27, 548.
I. V. Krotova and A. A. Efremov, Khimiya rastitel’nogo syr’ya [The Chemistry of Plant Raw Materials], 2002, No. 3, 29 (in Russian).
R. Huopalahti and R. R. Linko, J. Agric. Food Chem., 1983, 31, 331.
M. G. Lopez, I. R. Sanchez-Mendoza, and Ochoa-Alejo, J. Agric. Food Chem., 1999, 47, 3292.
S. A. Alimukhamedov, N. A. Maksudov, M. I. Goryaev, and F. S. Sharipova, Khim. Farm. Zh., 1972, 9, 15 [Pharm. Chem. J., 1972, 9 (Engl. Transl.)].
H. O. Bernhard and K. Thiele, Helv. Chim. Acta, 1978, 61, 2273.
K. Yakushi**, T. Tohshima, R. Suzuki, H. Murata, S.-T. Lu, and H. Furukawa, Chem. Pharm. Bull., 1983, 31, 2879.
R. Mata, I. Moralez, O. Perez, I. Rivero-Cruz, L. Acevedo, I. Enriquez-Mendoza, R. Bye, S. Franzblau, and B. Timmermann, J. Nat. Prod., 2004, 67, 1961.
B. Bozin, N. Mimica-Dukic, N. Simin, and G. Anackov, J. Agric. Food Chem., 2006, 54, 1822.
I. Heilbronn and R. M. Banberry, Dictionary of Organic Compounds, Imperial Chemical Ltd, London, 1946.
Beilstein (4te Aufl.), Ed. F. Richter, Springer-Verlag, Berlin-Göttingen-Heidelberg, (a) Myristicine E (II), 1952, 19, H77, 84; (b) Elemicine E (II), 1944, 6, H 1131, 1093; (c) Allyltetramethoxybenzene E (II), 1944, 6, H 1161, 1124; (d) Apiol E (II), 1952, 19, H87–88, 98.
C. Devakumar, V. S. Saxena, and S. K. Mukerjee, Ind. Agric. Biol. Chem., 1985, 49, 725.
F. Dallacker, Chem. Ber., 1969, 102, 2663.
G. Ciamician and P. Silber, Chem. Ber., 1896, 29, 1799.
J. Ginsberg, Chem. Ber., 1888, 21, 1193.
US Pat. 3852305, Chem. Abstrs, 1972, 77, 61540n.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2364–2371, December, 2007.
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Semenov, V.V., Rusak, V.V., Chartov, E.M. et al. Polyalkoxybenzenes from plant raw materials 1. Isolation of polyalkoxybenzenes from CO2 extracts of Umbelliferae plant seeds. Russ Chem Bull 56, 2448–2455 (2007). https://doi.org/10.1007/s11172-007-0389-1
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DOI: https://doi.org/10.1007/s11172-007-0389-1