Síntese do piperonal a partir do óleo essencial de pimenta longa (Piper hispidinervium C. DC.)

Abstract

RESUMOO óleo essencial de pimenta longa (Piper hispidinervum C. DC) é rico em safrol, tornando-o suscetível à reação de isomerização para a obtenção de cis, trans-isosafrol. O presente artigo apresenta a etapa de eletroxidação dos isômeros cis, trans-isosafrol advindos da isomerização direta do óleo essencial de pimenta longa, apresentando 99,7% de conversão em isosafrol glicol, o qual é sujeito à oxidação com conversão de 99% em piperonal, este apresentando 84,9% de pureza. PALAVRAS-CHAVE: Isomerização, eletroxidação, isosafrol, isosafrol glicol Synthesis of piperonal from essential oil of long-pepper (Piper hispidinervium C. DC.) ABSTRACTThe essential oil of long-pepper (Piper hispidinervum C. DC) is rich in safrole, then susceptible to isomerization reaction to obtain cis, trans-isosafrole. In this paper it is presented the eletroxidation of cis, trans-isosafrole from direct isomerization of essential oil of long-pepper, with 99,7% of convertion to isosafrole glicol, that it is react by oxidation to convert 99% into piperonal with 84,9% purity.

A química fina que poderia ter sido: a extração de óleo de sassafrás e de safrol no alto e médio vale do Itajaí

“…Mencionamos como exemplo a síntese do piperonal a partir do óleo essencial de pimenta longa, desenvolvida recentemente (cf. Cremasco & Braga, 2012).…”

Equilibrium and mass transfer parameters estimation of the products of synthesis of piperonal by high performance liquid chromatography

“…Piperonal [3,4-(methylenedioxy)benzaldehyde] is applied to obtain various products in the pharmaceutical industry (Torri et al, 1984;Santos et al, 2004). Its synthesis from Piper hispidinervum presents 84.9% purity, and other compounds such as terpinolene, safrole, cis-trans-isosafrole (Cremasco and Braga, 2012). One of separation technique possible to employ in its separation from organic compounds is high performance liquid chromatography (HPLC).…”

Safrole and the Versatility of a Natural Biophore

“…4,5 Historically, the demand for sassafras oil depends mainly on the international market for piperonyl butoxide (PBO, 2), a semisynthetic derivative of safrole, that is a crucial component in the natural pyrethroid insecticides, due its synergist activity, and for heliotropin (3), used in flagrances and as flavoring agent (Figure 1). 4,5 The finding that heliotropin or piperonal (3), easily synthesized from safrole [6][7][8] (Figure 2), was a key intermediate in the synthesis of complex organic molecules expanded its value and its industrial application. In fact, 3 can be used as starting material from the synthesis of several biological active compounds, including the drugs cinoxacin (5), tadalafil (6) and levodopa (7) (Figure 2).…”

“…4,5 The finding that heliotropin or piperonal (3), easily synthesized from safrole [6][7][8] (Figure 2), was a key intermediate in the synthesis of complex organic molecules expanded its value and its industrial application. In fact, 3 can be used as starting material from the synthesis of several biological active compounds, including the drugs cinoxacin (5), tadalafil (6) and levodopa (7) (Figure 2). It is also used in the synthesis of illicit drug 3,4methylenedioxy-N-methylamphetamine (MDMA, ecstasy, 8).…”