Molbank 2006 1 von 2 http://www.mdpi.org/molbank/molbank2006/m504.htm Molbank 2006, M504 http://www.mdpi.org/molbank/ 4α,14α,Dimethyl-5α-cholest-8-en-3-one thiosemicarbazone Noureddine Mazoir,*1 My Youssef Ait Itto,1 Matías Reina Artiles2 and Ahmed Benharref1 1 Laboratoire de Chimie des Substances Naturelles, Université Cadi Ayyad, Faculté des Sciences Semlalia, B.P: 2390. Marrakech. Maroc. 2 Instituto de Productos Naturales y Agrobiología, IPNA-CSIC, La Laguna, Tenerife, Spain E-mail: mazoir1@yahoo.fr *Author to whom correspondence should be addressed Received: 1 August 2005 / Accepted: 17 October 2006 / Published: 1 December 2006 Keywords: Euphorbia officinarum, latex, thiosemicarbazide The compound 2 was prepared from equimolecular quantity of 1 (1g, 2.43 mmol), derivative triterpene resulting from Euphorbia officinarum1, and thiosemicarbazide2,3 dissolved in ethanol with several drops of conc. H2SO4. The mixture was heated at reflux for 5h, and evaporated under reduced pressure. The residue was purified on silica gel column using hexane: ethyl acetate (90:10) as eluent yielded compound 2 (0.99g, 2.06mmol) in 85% yield. Melting point: 212-213 °C (Hexane) MS (EI, 70eV): 485 (M+.) 1 H NMR (300 MHz, CDCl3) d(ppm): 6.33 (NH); 7.25 (NH2); 8.74 (SH); 0.70 (3H-18, s); 0.96 (3H-19, s); 0.88 (3H-21, d, J = 6 Hz); 0.85 (3H-26, d, J = 2 Hz ); 0.86 (3H-27, d, J = 2 Hz ); 0.87 (3H-28, s); 1.20 (3H-29, d, J = 6 Hz ). 13 C NMR (75 MHz, CDCl3) d (ppm): 36.50 (C-1); 37.35 (C-2); 159.35 (C-3) ; 50.58 (C-4); 49.98 (C-5); 21.75 (C-6); 28.12 (C-7); 132.35 (C-8); 135.73 (C-9); 36.36 (C-10); 21.55 (C-11); 25.45 (C-12); 44.54 (C-13); 49.75 (C-14); 30.86 (C-15); 29.81 (C-16); 46.10 (C-17); 15.82 (C-18); 18.15 (C-19); 36.14 (C-20); 18.65 (C-21); 36.56 (C-22); 24.35 (C-23); 32.41 (C-24); 34.58 (C-25); 21.72 (C-26); 21.92 (C-27); 24.22 (C-28); 12.25 (C-29); 106.12 (C-30); 179.18 (C=S). MS (m/z): 485 (20%), 395 (42%), 282 (65%). Acknowledgments We would like to thank Pr. A. Idmessaaoud for helpful discussions. References 1. Benharref, A.; Lavergne, J.-P. Bull. Soc. Chim. Fr. 1985, 965-972. 27.11.2009 16:03 Molbank 2006 2 von 2 http://www.mdpi.org/molbank/molbank2006/m504.htm 2. Beatriz, N. B et al. Arkivok. 2002, 14-23. 3. Ourhriss, N.; Giorgi, M.; Mazoir, N and Benharref, A. Acta Cryst. 2005, C61, o699-o701. © 2006 MDPI. All rights reserved. 27.11.2009 16:03