Two long chain alkyl alcohols from the leaves of acroton tonkinensis gagnep, euphorbiaceae

Journal of Chemistry, Vol. 42 (1), P. 132, 2004<br /> <br /> <br /> short communication<br /> <br /> TWO LONG CHAIN ALKYL ALCOHOLS FROM THE LEAVES OF<br /> aCROTON TONKINENSIS GAGNEP., EUPHORBIACEAE<br /> Received 18-9-2003<br /> Phan Minh Giang, Phan Tong Son<br /> Faculty of Chemistry, College of Natural Science, Vietnam National University<br /> <br /> <br /> In continuation of our reports on the n-Nonacosan-2-ol (1). White powder. EIMS (70<br /> chemical constituents of Croton tonkinensis eV) m/z 406 ([M-H2O]+.); 1H-NMR (300 MHz,<br /> Gagnep. (Euphorbiaceae) [1] this paper deals CDCl3): 0.88 (3H, t, J = 6.6 Hz, CH3-29), 1.19<br /> with the isolation and structure elucidation of (3H, d, J = 6.3 Hz, CH3-1), 1.25 (m) and 1.60<br /> two long chain alkyl alcohols. Two compounds 1 (m) (26 CH2), 3.8 (1H, sextet, J = 6.3 Hz, CH-2);<br /> and 2 were isolated by repeated silica gel 13<br /> C-NMR (300 MHz, CDCl3): 14.1 (q, C-29),<br /> column chromatography of the n-hexane soluble 23.5 (q, C-1), 22.7, 25.8, 29.4, 29.7, 31.9 (all t,<br /> fraction obtained from the methanol extract of 25 CH2), 39.4 (t, C-3), 68.2 (d, C-2).<br /> the dried leaves of C. tonkinensis by liquid - liquid<br /> fractionation [2]. The long aliphatic chains of n-Triacontan-1-ol (2). White powder. EIMS (70<br /> both compounds 1 and 2 were characterized by eV) m/z 420 ([M-H2O]+.); 1H-NMR (300 MHz,<br /> the 1H and 13C NMR spectra: H 0.88 (3H, t, J = CDCl3): 0.88 (3H, t, J = 6.6 Hz, CH3-30), 1.25<br /> (m) and 1.56 (m) (29 CH2), 3.6 (2H, t, J = 6.6<br /> 6.6 Hz), C 14.1 (q) for the terminal methyl groups;<br /> Hz, CH2-1); 13C-NMR (300 MHz, CDCl3):<br /> H 1.25 (m) and 1.56 - 1.6 (m), C 22.7 - 32.8 (all t)<br /> for the chain methylene groups. 14.1 (q, C-30), 22.7, 25.7, 29.4, 29.6, 31.9, 32.8<br /> (all t, 28 CH2), 63.1 (t, C-1).<br /> In the 1H and 13C NMR spectra of compound<br /> 1 the signals for the second methyl group at H Acknowledgements: This research was supported<br /> 1.19 (3H, d, J = 6.3 Hz), C 23.5 (q) and for the by the International Foundation for Science,<br /> neighbouring carbinol methine at H 3.8 (1H, Stockholm, Sweden, through a grant to Phan<br /> sextet, J = 6.3 Hz), C 68.2 (d) were indicative for Minh Giang, and the National Basic Research<br /> a secondary alcohol. The molecular ion peak was Program in Natural Sciences.<br /> not visible in the EIMS spectrum of 1, but the<br /> peak at m/z 406 ([M-H2O]+.) allowed us to References<br /> calculate the molecular formula of 1 as C29H60O.<br /> Thus the structure of 1 was elucidated as 1. Phan Tong Son, Van Ngoc Huong, Phan Minh<br /> n-nonacosan-2-ol. Differing from alcohol 1 Giang, C. Taylor Walter. Vietnam J. Chem.,<br /> which possesses a secondary structure, the Vol. 37, No. 1-2 (1999).<br /> primary structure of alcohol 2 was deduced from 2. Phan Tong Son, Phan Minh Giang, C. Taylor<br /> the NMR signals at H 3.6 (2H, t, J = 6.6 Hz), Walter. Austr. J. Chem., Vol. 53, P. 1003 - 1005<br /> (2000).<br /> C 63.1 (t). Compound 2 was determined as n-<br /> triacontan-1-ol on the basis of the EIMS peak at 3. Phan Minh Giang, Jung Joon Lee, Phan Tong<br /> m/z 420 ([M-H2O]+.), C30H62O. Son. Vietnam J. Chem., Vol. 41, No. 1 (2003).<br /> <br /> <br /> 132<br />