Table 1.
Chemical composition of Brazilian orange terpenes’ fractions: F1, F2, F3, and F4.
| Compounds 1 | LRIc 2 | LRIL 3 | BOT 6,* | F1 6 | F2 6 | F3 6 | F4 6 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| NP 4 | P 5 | NP | P | NP | P | NP | P | NP | P | NP | P | NP | P | |
| α-Pinene | 936 | 1019 | - | 1025.4 | 0.06 | 0.13 | 0.06 | 0.11 | 0.03 | 0.05 | 0.01 | - | - | - |
| Sabinene | 975 | 1118 | 976 | 1122 | 0.04 | 0.08 | 0.06 | 0.10 | 0.04 | 0.06 | 0.02 | - | - | - |
| β-Pinene | 981 | 1105 | 980 | 1100 | 0.01 | 0.02 | 0.02 | 0.03 | 0.01 | - | - | - | - | - |
| Myrcene | 989 | 1158 | 991 | 1160.2 | 0.12 | 0.24 | 0.14 | 0.28 | 0.12 | 0.23 | 0.06 | 0.15 | - | - |
| Octanal | 1003 | - | 1002.8 | - | 0.03 | 0.002 | 0.01 | - | 0.01 | - | 0.01 | - | 0.09 | - |
| δ-3-Carene | 1015 | 1146 | 1011 | 1146.8 | 0.02 | 0.02 | 0.02 | 0.03 | 0.02 | 0.02 | 0.01 | - | 0.07 | - |
| β-Phellandrene | - | 1208 | - | 1209.3 | - | 0.02 | - | 0.02 | - | 0.02 | - | 0.01 | - | - |
| NI (1) | 1028 | - | - | - | 0.04 | - | 0.05 | - | 0.03 | - | 0.04 | - | - | - |
| Limonene | 1037 | 1201 | 1031 | 1198.2 | 10.96 | 13.73 | 11.06 | 16.41 | 10.86 | 15.80 | 11.81 | 15.66 | 0.13 | 0.08 |
| p-Cymenene | 1092 | 1430 | 1087.9 | 1437.5 | - | - | - | - | - | - | - | - | 0.11 | 0.08 |
| Linalool | 1099 | 1538 | 1098 | 1543.3 | 0.04 | 0.06 | 0.02 | 0.03 | 0.03 | 0.04 | 0.04 | 0.07 | 0.09 | 0.09 |
| 1,3,8-p-Menthatriene | 1116 | 1390 | 1111 | 1411 | - | - | - | - | - | - | - | - | 0.06 | 0.03 |
| trans-p-Mentha-2,8-dien-1-ol | 1125 | 1622 | 1123 | 1639 | 0.12 | 0.36 | 0.06 | 0.09 | 0.07 | 0.09 | 0.13 | 0.23 | 1.12 | 1.31 |
| 4-Acetyl-1-methylcyclohexene | 1133 | - | 1137 | - | 0.02 | - | - | - | 0.01 | - | - | - | 0.08 | - |
| cis-Limonene oxide | 1137 | 1446 | 1134 | 1450.5 | 0.27 | 0.33 | 0.19 | 0.23 | 0.22 | 0.26 | 0.44 | 0.50 | 0.48 | 0.53 |
| cis-p-Mentha-2,8-dien-1-ol | 1141 | 1664 | 1138 | 1652.1 | - | 0.24 | - | 0.07 | - | 0.06 | - | 0.15 | 1.41 | 1.15 |
| trans-Limonene oxide | 1141 | 1458 | 1139 | 1461.6 | 0.23 | 0.16 | 0.13 | 0.11 | 0.15 | 0.12 | 0.30 | 0.27 | - | 0.33 |
| β-Terpineol | 1153 | - | 1157 | - | - | - | - | - | 0.01 | - | 0.02 | - | 0.05 | - |
| Bicyclo [3.3.0]oct-2-en-7-one, 6-methyl- | 1172 | 1694 | - | - | - | 0.02 | - | - | - | - | - | - | 0.16 | 0.10 |
| Cryptone | - | 1673 | - | 1674.8 | - | 0.02 | - | - | - | - | - | - | - | 0.08 |
| 1,8-Menthadien-4-ol | 1183 | 1680 | 1189 | 1681 | 0.02 | 0.08 | 0.01 | - | 0.01 | - | 0.02 | 0.05 | 0.27 | 0.40 |
| p-Methylacetophenone | 1189 | 1765 | 1182.7 | 1765 | - | - | - | - | - | - | - | - | 0.07 | 0.05 |
| trans-p-Mentha-1(7),8-dien-2-ol | 1191 | 1789 | 1180.5 | 1791 | - | 0.05 | 0.01 | - | 0.01 | - | 0.02 | 0.04 | 0.28 | 0.28 |
| NI (2) | 1192 | 1732 | - | - | 0.03 | 0.48 | - | - | - | - | - | - | - | - |
| NI (3) | 1201 | - | - | - | 0.06 | - | 0.02 | - | 0.03 | - | 0.08 | - | 0.28 | - |
| NI (4) | 1204 | - | 1205.4 | - | 0.09 | - | 0.03 | - | 0.03 | - | 0.09 | - | 0.53 | - |
| trans-Carveol | 1222 | 1828 | 1217 | 1836.3 | 0.25 | 0.40 | 0.05 | 0.06 | 0.04 | 0.05 | 0.13 | 0.20 | 2.09 | 2.20 |
| cis-p-Mentha-1(7),8-dien-2-ol | 1233 | 1880 | 1233 | 1894.9 | 0.02 | 0.03 | - | - | - | - | - | - | 0.12 | 0.15 |
| cis-Carveol | 1236 | 1858 | 1229 | 1854.4 | 0.11 | 0.18 | 0.03 | 0.03 | 0.02 | 0.02 | 0.07 | 0.09 | 0.76 | 0.96 |
| Carvone | 1249 | 1731 | 1243 | 1733.6 | 0.23 | 0.11 | 0.04 | 0.06 | 0.03 | 0.04 | 0.13 | 0.22 | 1.77 | 2.12 |
| n-Decanol | 1274 | 1746 | 1272.1 | - | 0.02 | 0.07 | - | - | - | - | - | - | 0.21 | - |
| Perilla aldehyde | 1281 | 1781 | 1273.4 | 1793.9 | 0.03 | 0.04 | - | - | - | - | - | - | 0.17 | 0.17 |
| NI (5) | 1289 | 1947 | - | - | 0.06 | - | - | - | - | - | - | - | 0.49 | - |
| Limonen-10-ol | 1294 | 1985 | 1239 | 1979 | 0.02 | 0.03 | - | - | - | - | - | - | 0.17 | 0.23 |
| Perilla alcohol | 1303 | 1994 | 1296.3 | 2006.6 | 0.04 | 0.03 | - | - | - | - | - | - | 0.35 | 0.20 |
| Cyclohexene, 2-ethenyl-1,3,3-trimethyl- | 1308 | - | - | - | 0.21 | - | 0.01 | - | - | - | 0.03 | - | 0.30 | - |
| (1S,4R)-p-Mentha-2,8-diene, 1-hydroperoxide | 1322 | - | - | - | 0.20 | - | - | - | - | - | 0.02 | - | 0.27 | - |
| NI (6) | 1335 | - | - | - | 0.13 | - | - | - | - | - | 0.02 | - | 0.40 | - |
| NI (7) | 1344 | - | - | - | - | - | - | - | - | - | - | - | 0.12 | - |
| Citronellyl acetate | 1349 | - | 1352.4 | - | - | - | - | - | - | - | - | - | 0.25 | - |
| α-Terpinyl acetate | 1357 | - | 1347 | - | - | - | - | - | - | - | - | - | 0.14 | - |
| Neryl acetate | 1360 | - | 1362.9 | - | 0.21 | - | - | - | - | - | 0.02 | - | 0.21 | - |
| NI (8) | 1367 | - | - | - | 0.04 | - | - | - | - | - | - | - | 0.24 | - |
| Geranyl acetate | 1375 | - | 1381 | - | - | - | - | - | - | - | - | - | 0.24 | - |
| NI (9) | 1377 | - | - | - | 0.16 | - | - | - | - | - | 0.01 | - | - | - |
| α-Copaene | 1386 | - | 1377 | - | - | - | - | - | - | - | - | - | 0.13 | - |
| NI (10) | 1393 | - | - | - | - | - | - | - | - | - | - | - | 0.16 | - |
| β-elemene | 1396 | - | 1390.4 | - | - | - | - | - | - | - | - | - | 0.13 | - |
| Dodecanal | 1409 | - | 1408.1 | - | - | - | - | - | - | - | - | - | 0.19 | - |
| Decyl acetate | 1416 | - | 1407.1 | - | - | - | - | - | - | - | - | - | 0.11 | - |
| cis-α-Bergamotene | 1420 | 1552 | 1414.5 | 1559.1 | - | 0.11 | - | 0.03 | - | 0.05 | - | 0.13 | - | 0.34 |
| trans-α-Bergamotene | 1440 | 1559 | 1434.5 | 1575.7 | - | 0.06 | - | 0.06 | - | 0.03 | - | 0.09 | - | 0.26 |
| β-Copaene | 1447 | - | 1433.1 | - | - | - | - | - | - | - | - | - | 1.10 | - |
| NI (11) | 1701 | - | - | - | - | - | - | - | 0.02 | - | 0.03 | - | - | - |
| trans-Dihydrocarvone | - | 1609 | - | 1623.1 | - | - | - | - | - | - | - | 0.03 | - | 0.03 |
| NI (12) | - | 1633 | - | - | - | 0.03 | - | - | - | - | - | - | - | 0.04 |
| NI (13) | - | 1746 | - | - | - | - | - | - | - | - | - | 0.05 | - | 0.43 |
| NI (14) | - | 1839 | - | - | - | - | - | - | - | - | - | - | - | 0.34 |
| NI (15) | - | 1919 | - | - | - | - | - | - | - | - | - | - | - | 0.10 |
| (R)-4-methyl-3-(3′-oxobutyl)pent-4-enal | - | 1946 | - | - | - | 0.10 | - | - | - | - | - | - | - | 0.26 |
| NI (16) | - | 1978 | - | - | - | 0.01 | - | - | - | - | - | - | - | 0.05 |
1 Identification by GC/MS using non-polar and polar columns. 2 LRIC: Linear retention index (Calculated). 3 LRIL: Linear retention index (Literature). 4 NP: non-polar column DB-5MS. 5 P: polar column DB-WAX. 6 Relative amounts of the identified compounds on internal standardization using n-tetradecane as internal standard (0.002 v/v or 1.38 mg/mL). *Data published previously in [25]. NI: Not identified compound.