Isomerization Of Essential Oil Of (piper Hispidinervium) C. Dc To Obtain Isosafrole [isomerização Do óleo Essencial De Pimenta-longa (piper Hispidinervium C. Dc) Para A Obtenção De Isosafrol]

The Brazilian peppers present proprieties that can be used in fragrance and pharmaceutical industries, for example. One these pepper is long pepper (Piper hispidinervium C. DC.), who its essential oil is rich in safrole. Safrole is an important compound with application in several industries, such as pharmaceutics, cosmetics. After its chemical conversion, for example, it is possible to obtain heliotropin, a fixative agent for fragrances. The sequence to obtain the heliotropin is by safrole isomerization, that, initially, produce isosafrole. In this work, however, presents the synthesis of isosafrole directly from essential oil of Piper hispidinervium C. DC. In this case, the isomerization of essential oil was done getting 79,4 % of cis, trans-isosafrole mixture. The essential oil presented 86,4 % of safrole, resulting in 97,1 % yield to cis, trans-isosafrole.404737740Alécio, A.C., Bolzani, V.S., Young, M.C.M., Kato, M.J., Furlan, M., Antifungal amide from leaves of Piper hispidum (1998) Journal of Natural Products, 61, pp. 637-639Baldoqui, D.C., Kato, M.J., Cavalheiro, A.J., Bolzani, V.S., Young, M.C.M., Furlan, M., New chromene and prenylated benzoic acid from Piper aduncum (1999) Phytochemistry, 51, pp. 899-902Barreiro, E.J., Fraga, C.A.M., The utilization of safrole, principal chemical constituent of sassafras oil, in the synthesis of compounds actives in the arachidonic acid cascade: Antiinflammatory, analgesic and antithrombotic (1999) Química Nova, 22 (5), pp. 744-759Benevides, P.J.C., Sartorelli, P., Kato, M.J., Phenylpropanoids e neolignanas from Piper regnellii (1999) Phytochemistry, 52, pp. 339-343Bauer, K., Garbe, D., Surberg, H., (2002) Flavors and fragrances, Ullmann Encyclopedia of industrial Chemistry, , Electronic Release, 6th, EdCiccio, J.F., Ballestero, C.M., Volatile components of Piper aduncum (Piperaceae) leaves and spikes from Costa Rica (1997) Revista de Biologia Tropical, 45, pp. 783-790Costa, C.M.L., (1999) Influence of drying condition on yield and composition of long pepper (Piper hispidinervium C. DC.) essential oil, p. 214. , Dissertação de Mestrado, Departamento de Engenharia Química, Universidade Federal do Pará, Belém, Pará. (in Portuguese, with abstract in English)Lago, J.H.G., Ramos, C.S., Casanova, D.C.C., Morandim, A.A., Bergamo, D.C.B., Cavalheiro, A.J., Bolzani, V.S., Kato, M.J., Benzoic acid derivatives from Piperspecies and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum (2004) Journal of Natural Product, 67, pp. 1783-1788Maia, J.G.S., Silva, M.L., Luz, A.I.R., Zoghbi, M.G.B., Ramos, L.S., Pipper species from Amazon richies in safrole (1987) Química Nova, 10 (3), pp. 200-204Moreira, D.D., Guimarães, E.F., Kaplan, M.A.C., A chromene from Piper aduncum (1998) Phytochemistry, 48, pp. 1075-1077Navickiene, H.M.D., Alécio, A.C., Kato, M.J., Bolzani, V.S., Young, M.C.M., Cavalheiro, A.J., Furlan, M., Antifungal amides from Piper hispidum and Piper tuberculatum (2000) Phytochemistry, 55, pp. 621-626Santos, A.S., Pereira Jr., N., Silva, I.M., Sarquis, M.I.M., Antunes, O.A.C., Peroxidase catalyzed microbiological oxidation of isosafrol into piperonal (2004) Process Biochemistry, 39, pp. 2269-227

The effects of fixed-bed drying on the yield and composition of essential oil from long pepper (Piper hispidinervium C. DC) leaves

Piper hispidinervium C.DC (Piperaceae) is popularly known as long pepper. It grows in degraded areas of natural fields in the state of Acre, Brazil. Its leaves are 3 to 4 % essential oil rich in safrole, within the range of 90 to 94 %. In the chemical industry, safrole is an important raw material, mainly due to two of its derivatives: heliotropin, which is widely used as a fragrance and flavoring agent, and piperonyl butoxide (PBO), a vital ingredient of pyrethroid insecticides. Natural pyrethrum in particular would not be an economical insecticide without the synergistic effect of PBO; therefore, its industrial future is linked to the continued availability of PBO. As a fragrance, safrole has many applications in household products such as floor waxes, polishes, soaps, detergents and cleaning agents. In this work, leaves were dried in a fixed-bed dryer using different drying-air temperatures (35, 40, 45, 50, 55 and 60 ºC) and drying times (900, 2700 and 3600 seconds). Essential oil was extracted by cohobation (meaning that the condensed water that comes out of the flask is recycled) from both raw and dried leaves. The essential oil yield and safrole content are susceptible to rapid loss of moisture by Piper hispidinervium C. DC leaves. It was observed that the essential oil yield increased twice after the drying process. However, safrole content decreased about 20 percent when temperature was above 50 ºC and drying times were more than 2700 minutes