## 3 Results
### Isolation of \(\alpha\)-copaene
#### 3.2.1 Open Column  
1. DCO. A practically pure fraction in \(\alpha\)-copaene was obtained eluting with hexane the initial DCO. This fraction had a richness of 99% (GC) and a yield of 85% of the DCO\({}_{\alpha\text{-copaene}}\), corresponding to 1.8% of the total oil. In Figure 1, the analytical HPLC chromatogram is shown. This DCO\({}_{\alpha\text{-copaene}}\) was used in attraction tests. In the following fractions, \(\alpha\)-cubebene, \(\beta\)-caryophyllene, and \(\alpha\)-humulene were separated. The \(\beta\)-caryophyllene fraction had a richness of 98% and contained 85% of the total DCO\({}_{\beta\text{-caryophyllene}}\).  
Characterization of \(\alpha\)-copaene was performed by IR spectra, \({}^{1}\)H NMR, \({}^{13}\)C NMR, and MS according to the following parameters: \([\alpha]^{25}\)p = -2.36\({}^{\circ}\) (\(c\) 0.89, CHCl\({}_{3}\)); IR: \(\
u_{\text{max}}\) 3029, 1665 y 786 cm\({}^{-1}\); \({}^{1}\)H NMR: \(\delta_{\text{H}}\) 5.2 (sa, 1H, C=CH), 2.2-2.0 (m, 3H, H-2 + H-5), 1.7 (sa, 3H, C=CCH\({}_{3}\)), 0.8 [dd, \(J\) = 7, 5 Hz, 6H, CH(CH\({}_{3}\))\({}_{2}\)] y 0.7 (s, 3H, CCH\({}_{3}\)) ppm; \({}^{13}\)C NMR: \(\delta_{\text{L}}\) 143.9  
\begin{table}
\begin{tabular}{c c c c c c c} \hline \hline \multirow{2}{*}{**Fraction**} & **Vol** & **\%** & **T\({}^{\bullet}\)** & **\(\alpha\)-cubebene** & **\(\alpha\)-copaene** & **\(\beta\)-caryophyllene** & **\(\alpha\)-humulene** \\  & **(mL)** & & (\({}^{\circ}\)C) & **(\%)** & **(\%)** & **(\%)** & **(\%)** & **(\%)** \\ \hline
**Total** & 500 & & & 2.46 & 4.62 & 86.27 & 6.02 \\
**IF1** & 16 & 3.2 & 68–109 & 10.02 & 9.75 & 65.63 & 1.78 \\
**IF2** & 50 & 17.6 & 109 & 5.12 & 7.50 & 82.00 & 2.63 \\
**IF3** & 396 & 79.2 & – & 1.93 & 4.10 & 86.68 & 6.23 \\ \hline \hline \end{tabular}
\end{table}
Table 2: Distilled fraction composition of the industrial oil (IF).  
Figure 1: Analytical HPLC chromatogram of \(\alpha\)-copaene. Column Spherisorb, 5 \(\upmu\)m (25 \(\times\) 0.7 cm\({}^{2}\)); Hexane, 1.5 mL min\({}^{-1}\). Detector UV Varian 9065 PolyChrom 229 nm.  
(C\({}_{6}\)), 116.0 (C\({}_{5}\)), 54.2 (C\({}_{4}\)), 44.7 (C\({}_{1}\)), 44.3 (C\({}_{9}\)), 39.4 (C\({}_{2}\)), 36.9 (C\({}_{10}\)), 36.2 (C\({}_{11}\)), 32.2 (C\({}_{7}\)), 30.0 (C\({}_{3}\)), 23.1 (C\({}_{8}\)), 21.8 (CH=CCH3), 19.9, 19.6 y 19.3 (3 xCH3) ppm; MS: \(m/z\) 204 (M\({}^{+}\),20), 161 (96), 133 (11), 119 (100), 105 (93), 93 (48), 77 (20) y 55 (21).  
Also, a practically pure fraction in \(\alpha\)-copaene was obtained with the same solvent from DCO1- to DCO4-gathered fractions. This fraction had a richness in \(\alpha\)-copaene of 99% (GC) and a yield of 89%, corresponding to 2.9% of the total of the four fractions collected. DCO1- to DCO4-gathered fractions had a \(\beta\)-caryophyllene yield of 90%, containing 97% of the total DCO\({}_{\beta\text{-caryophyllene}}\).  
2. IF industrial fraction. A practically pure fraction in \(\alpha\)-copaene was obtained with a richness of 99% (GC) and a 90% yield of the IF\({}_{\alpha\text{-copaene}}\), corresponding to 3.7% of the total IF. The \(\beta\)-caryophyllene fraction contained 98% of total IF\({}_{\beta\text{-caryophyllene}}\), with a 92% yield.