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BIBLIOTECA DO INSTITUTO DE QUÍMICA
UNICAMP

 
DISSERTAÇÃO DE MESTRADO
 
Autora: Queiroga, Carmen Lucia
Título: Estudo Fitoquímico do Óleo Essencial de Baccharis dracunculifolia
Ano: 1989
Orientadora: Profa. Dra. Anita Jocelyne Marsaioli
Departamento: Química Orgânica
Palavras-chave: -
Resumo: Na análise do óleo essencial de Baccharis dracunculifolia conhecido como óleo de vassoura utilizamos vários métodos de separação de componentes, tais como: extração seletiva, Reagentes de Girard, cromatografia de adsorção em coluna de sílica gel de baixa e média eficiência, cromatografia de adsorção em coluna de sílica gel impregnada com nitrato de prata, cromatografia de camada espessa de sílica geI com ou sem nitrato de prata, e cromatografia gasosa. Para a identificação dos componentes utillzamos dados físicos (p.f.,[a]D), espectros de massas, I.V., RMNH, RMNC, CG-EM , e comparação com padrões isolados e sintéticos. Assim sendo, pudemos identificar 55 componentes no óleo de vassoura: limoneno 3, para-cimeno 4, b-elemeno 8, b-cariofileno 11, 3-tujeno 16 acetato de linalila 17, 1-metil-4-(1-metiletil)-cicloexanol 18, 3,3-dimetil-1,5-heptadieno (E) 19, a-cubebeno 20, a-copaeno 21, 1,2,3,4,4a,5,6,8a-octa- hidro -7- metil- 4-metileno-1-(1-metiletil)- (1a,4ab,8aa)- nafteno 22, q-cadineno 23, b-cubebeno 24, 1,2,4a,5,6,8a-hexa-hidro-4,7-dimetil-1-(1-metiletil)-(1a,4aa,8aa)-nafteno 25, sabineno 26 a-ionona 27, a-elemeno 28, aromadendreno 29, g-cadineno 30, humuleno 31, a-muuroleno 32, calameneno 33, farnesol 34, a-l-gurjuneno 35, alloaromadendreno 36, b-selineno 37, isolongifoleno 38, 2,6-dimetil-9-(2-propenil)-10-hidroxi-biciclo-[4.4.0]-dec-2-eno 39, citronelal 40, 1-para-menteno-9-al 41, safranal 42, palustrol 43, a-terpinen-4-ol 44,trans-citral 45, b-farneseno 46, b-terpineol 47, formiato de citronelila 48, nerol 49,geraniol 50, globulol 51, cadinol 52, 4-epi-globulol 53, viridiIforol 54, 4 b,7b-aromadendranodiol 55, 2- metoxi-4- (2- propenil)-fenol 58, ácido pentadecanóico 59, ácido eicosanóico 60, 9,12,15-octadecatrien-1-ol 61, 2,3-di-hidrobenzofurano 62, 2-metil-1,4-benzenodicarboxaldeído 63,4,11,11-triimetil-biciclo-[7.2.0]-undec-2-eno 64, e benzenopropionato de metila 65, e 3-metoxi-4-metil-benzoato de metiIa 66. Desses 55 componentes, 6 já haviam sido anteriormente identificados no óleo; portanto identificamos 48 produtos naturais novos no óleo essencial de vassoura e um componente, o (-)-4b,7b-aromadendranodiol 55, não isolado de fonte natural porém conhecido da literatura. Foram tambérn sintetizados seis padrões de aromadendranóis: (-)-globulol 51, (-)-4epi-globulol 53, (+)-viridiflorol 54, (-) -4b,7b-aromadendranodiol 55, e os compostos 1H- cicloprop[e]azuleno, 1a,2,3,4 ,4a,5, 7 a, 7b-octa-hidro-1,1,4, 7- tetrametil-(1aa,4b,4aa,7ab,7ba ) 56 e 1H-cicloprop[e]azuleno,1a,2,3,4, 4a, 5,7a,7b-octa-hidro-1,1,4, 7- tetrametil- (1aa,4a,4aa,7ab,7ba) 57 (inéditos na literatura).
Abstract: Isolation and analysis of Baccharis dracunculifolia essential oil, commonly known as: "Vassoura oil" was accomplished by using several techniques as: selective extraction, Girard's Reagent, column chromatography of low and medium pressure, argentation chromatography, which layer chromatography and gas chromatography. The identification of the components of this fragrant oil was achieved by the analysis of the corresponding physical and spectroscopic data (melting point, optical rotation, infrared, proton and carbon-13 nuclear magnetic ressonance and gas chromatography - mass spectroscopy) combined with their comparison with authentic samples, and terpene data reported in the literature. We have thus been able to identify 55 components in "Vassoura oil" 6 of which had been previously reported, and one of them is a new natural compound (4b,7b-aromadendranediol 55) although described in the literature as a synthetic product. The fragrant components of Baccharis dracunculifolia oil are: limonene 3, para-cimene 4, b-elemene 8, b- caryophylilene 11, 3-thujene 16, 1,6-octadien-3-ol,3,7-dimethyl acetat 17, cyclohexanol, 1-methyl- 4-(1-methyletheny) 18, 1,5-heptadiene, 3,3- dimethyl (E)19, a-cubebene 20, a-copaene 21, naphthalene, 1,2,34,4a,5,6, 8a-octa-hydro-7-methylene-1-(1-,methylethyl)-(1a,4ab,8aa) 22, q-cadinene 23, b-cubebene 24, naphythalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-(1a,4aa,8aa) 25, sabine 26, a-ionone 27, a-elemene 28, aromadendrene 29, g- cadinene 30, humulene 31, a-muurolene 32, calamenene 33, farnesol 34, a-L-gurjunene 35, alloaromadendrene 36, b- selinene 37, isolon gifolene 38, 2,6-dimethyl-9-(2-propenyl)-10-hydroxy-bicyclo-[4.4.0]-dec-2-ene 39, citronellal 40, 1-para-methene-9-al 41,safranal 42, palustrol 43, a-terpinen-4-ol 44, trans-citral 45, b-farnesene 46, a-terpineol 47, citronellyl formate 48, nerol 49, geraniol 50, globuol 51, cadinol 52, 4-epi-globulol 53, viridi florol 54, 4b,7b-aromadendranodiol 55, phenol,2-metoxy-4-(2-propenyl) 58, pentadecanoic acid 59, eicosanoic acid 60, 9,12,15-octadecatrien-1-ol 61, benzofuran,2,3-dihydro 62, 1-4-benzene dicarboxaldehyde,2-methyl 63, 4,11,11-trimethyl-bibyclo-[7.2.0]-undec-2- ene 64, e benzene propanoic, methyl ester 65, e benzoicacid 3-metoxy-4-methyl 66. We have also synthesized 6 aromadendranols which were used as model compounds: (-)-globulol 51, (-)-4-epi-globulol 53, (+)-viridiflorol 54, (-)-4b,7b-aromadendranediol 55, 1Hcycloprop[e] azulene, 1a,2,3,4,4a, 5,7,7a,7b-octahydro-1,1,4,7-tetramethyl-(1aa,4b,4aa,7ab,7ba ) 56 e 1H-cycloprop[e]azulene,1a,2,3,4,4a,5,7a,7b-octahydro-1,1,4,7-tetramenthyl- (1aa,4a,4aa,7ab,7ba) 57. It is worth mentioning that as far as we know compounds 56 e 57 were never referred to in the literature.
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