Issue in Honor of Prof. Marcial Moreno-Mañas ARKIVOC 2002 (v) 26-30
Synthesis of sterculic acid
Juan Hernando, M. Paz Matía, J. Luis Novella, and Julio Alvarez-Builla*
Planta Piloto de Química Fina, Universidad de Alcalá, 28871 Alcalá de Henares Madrid, Spain E-mail:
[email protected]
Dedicated to Professor Marcial Moreno-Manas on his 60th anniversary (received 27 Sep 01; accepted 28 Jan 02; published on the web 05 Feb 02)
Abstract
Sterculic acid, a cyclopropene fatty acid, present in the seed oil of several species, has been synthesized on 10 g scale, based on the addition of ethyl diazoacetate on an alkyne derivative.
Keywords: Sterculic acid, methylstearolate
Introduction
Naturally occurring three-membered ring compounds are endowed with a large spectrum of biological properties, ranging from insecticidal, antifungal, antibiotic, antiviral, herbicidal, hormonal, carcinogenic or antitumoral activities, enzyme and gluconeogenesis inhibitions to neurochemical activity.1,2 Among them, two cyclopropene fatty acids, sterculic and malvalic acids (Fig. 1), which are present in seed oil of various species, including Sterculia or the common cotton plant, Gossypium hirsutum, are potent inhibitors of the .9-desaturation of stearic to oleic acid.3,4 Additionally, both acids inhibit the .9-desaturation of different C-12 to C-20 aliphatic acids.5
O H3C
(CH2)nOH (CH2)7 n = 6 Malvalic acid n = 7 Sterculic acid 1
Figure 1
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