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. 2021 Sep 17;26(18):5654. doi: 10.3390/molecules26185654

Table 1.

Complete compositions of the hemp essential oil extracted from all the samples.

Compounds l.r.i. 1 Relative Abundance (AVG ± SD)
CTRL [DMIM]DMP 100 [DMIM]DMP 100 R1 [DMIM]DMP 90 [DMIM]DMP 80 [DMIM]DMP 50
hexanal 805 - 2 - 0.1 ± 0.03 0.2 ± 0.02 - -
α-pinene 3 939 2.1 ± 0.71 BC 2.8 ± 0.03 B 5.4 ± 1.10 A 5.4 ± 0.89 A 0.9 ± 0.30 C 4.9 ± 0.90 A
camphene 954 - - 0.1 ± 0.03 0.1 ± 0.02 - 0.2 ± 0.05
β-pinene 980 0.8 ± 0.28 B 0.8 ± 0.00 B 2.1 ± 0.39 A 2.2 ± 0.34 A 0.7 ± 0.20 B 2.4 ± 0.38 A
myrcene 991 2.1 ± 0.58 B 2.2 ± 0.05 B 7.6 ± 1.08 A 6.7 ± 0.87 A 1.9 ± 0.60 B 7.5 ± 1.27 A
δ-3-carene 1012 - - 0.1 ± 0.02 0.2 ± 0.03 - 0.2 ± 0.03
p-cymene 1024 0.2 ± 0.04 0.2 ± 0.00 0.3 ± 0.04 0.4 ± 0.06 0.2 ± 0.06 0.5 ± 0.06
limonene 1031 2.2 ± 0.64 B 2.2 ± 0.03B 2.9 ± 0.37 A,B 2.7 ± 0.33 A,B 1.2 ± 0.35 C 3.0 ± 0.36 A
1,8-cineole 1035 0.6 ± 0.18 0.8 ± 0.02 0.5 ± 0.07 0.5 ± 0.06 0.3 ± 0.07 0.3 ± 0.06
(E)-β-ocimene 1050 0.2 ± 0.04 0.2 ± 0.01 0.4 ± 0.04 0.2 ± 0.03 - 0.3 ± 0.02
γ-terpinene 1062 0.1 ± 0.01 0.1 ± 0.08 - - - -
cis-sabinene hydrate 1070 0.1 ± 0.08 - - - - -
terpinolene 1089 1.2 ± 0.28 BC 1.0 ± 0.03C 2.0 ± 0.18 A 1.4 ± 0.14 B 0.5 ± 0.11 D 1.9 ± 0.13 A
methyl benzoate 1091 - 0.2 ± 0.01 - - - -
linalool 1100 0.3 ± 0.06 0.2 ± 0.03 0.3 ± 0.00 0.4 ± 0.06 0.4 ± 0.08 0.4 ± 0.03
perillene 1101 - - 0.1 ± 0.07 0.1 ± 0.01 0.1 ± 0.07 0.2 ± 0.03
nonanal 1103 - - 0.1 ± 0.01 0.1 ± 0.03 - 0.2 ± 0.02
fenchol 1115 0.3 ± 0.09 0.2 ± 0.01 0.3 ± 0.01 0.3 ± 0.04 0.3 ± 0.05 0.4 ± 0.02
cis-p-menth-2-en-1-ol 1123 0.2 ± 0.06 0.1 ± 0.11 0.2 ± 0.01 0.2 ± 0.04 0.2 ± 0.04 0.2 ± 0.00
trans-p-mentha-2,8-dien-1-ol 1125 - - - 0.2 ± 0.02 - -
cis-p-mentha-2,8-dien-1-ol 1138 - - 0.2 ± 0.00 0.4 ± 0.04 0.9 ± 0.18 0.4 ± 0.01
pinocarveol 1140 - - - - 0.1 ± 0.07 -
trans-verbenol 1145 - - 0.1 ± 0.08 - 0.1 ± 0.03 0.1 ± 0.01
(E)-tagetone 1146 0.1 ± 0.09 - - - - -
borneol 1167 0.1 ± 0.01 - - 0.1 ± 0.10 0.1 ± 0.01 0.1 ± 0.09
4-terpineol 1178 0.4 ± 0.07 0.4 ± 0.05 0.2 ± 0.01 0.5 ± 0.03 0.2 ± 0.04 0.3 ± 0.00
p-cymen-8-ol 1185 0.2 ± 0.01 - - 0.4 ± 0.01 0.3 ± 0.05 0.2 ± 0.02
α-terpineol 1190 0.4 ± 0.04 0.2 ± 0.02 0.3 ± 0.02 0.5 ± 0.03 0.4 ± 0.07 0.4 ± 0.00
carveol 1228 - - - 0.1 ± 0.01 - -
α-ylangene 1372 - - 0.1 ± 0.01 - - -
isocaryophyllene 1405 0.2 ± 0.01 0.3 ± 0.05 0.4 ± 0.06 0.3 ± 0.01 0.3 ± 0.00 0.1 ± 0.09
β-caryophyllene 1418 32.1 ± 0.68 B 40.3 ± 1.42 A 30.3 ± 1.00 B 22.5 ± 0.54 C 15.6 ± 1.27 D 10.2 ± 0.06 E
trans-α-bergamotene 1438 0.2 ± 0.06 0.5 ± 0.04 0.5 ± 0.03 0.3 ± 0.01 0.3 ± 0.00 -
α-guaiene 1440 0.3 ± 0.06 0.6 ± 0.02 0.4 ± 0.01 0.3 ± 0.01 0.2 ± 0.00 -
α-himachalene 1450 - 0.1 ± 0.13 - 0.1 ± 0.09 0.1 ± 0.00 -
α-humulene 1455 13.1 ± 0.13 B 15.3 ± 0.47 A 12.4 ± 0.43 C 10.0 ± 0.22 D 7.8 ± 0.45 E 5.3 ± 0.04 F
(E)-beta-farnesene 1459 - 0.2 ± 0.23 0.4 ± 0.06 0.3 ± 0.06 0.2 ± 0.02 -
alloaromadendrene 1461 0.7 ± 0.04 C 1.1 ± 0.05 A 0.9 ± 0.04 B 0.7 ± 0.01 C 0.6 ± 0.02 D 0.3 ± 0.00 E
γ-gurjunene 1469 - - 0.3 ± 0.01 0.2 ± 0.01 0.5 ± 0.02 0.2 ± 0.02
γ-muurolene 1476 - - 0.1 ± 0.08 0.1 ± 0.00 0.1 ± 0.00 -
β-chamigrene 1477 - - - 0.6 ± 0.01 - -
γ-selinene 1482 0.6 ± 0.06 0.9 ± 0.04 0.7 ± 0.08 - 0.5 ± 0.01 0.1 ± 0.19
β-selinene 1485 2.4 ± 0.13 B 3.8 ± 0.01 A 2.6 ± 0.17 B,C 2.1 ± 0.02 B 1.8 ± 0.02 B,C 1.0 ± 0.01C
valencene 1492 1.9 ± 0.02 C 3.4 ± 0.03 A 2.3 ± 0.06 B 1.7 ± 0.13 C 1.4 ± 0.01D 0.7 ± 0.07 E
α-bulnesene 1505 0.4 ± 0.04 0.8 ± 0.02 0.4 ± 0.02 0.3 ± 0.01 0.2 ± 0.04 0.1 ± 0.09
α-farnesene 1507 - - 0.5 ± 0.04 0.3 ± 0.03 - 0.1 ± 0.08
β-bisabolene 1509 - 0.3 ± 0.04 - - 0.1 ± 0.06 -
trans-γ-cadinene 1514 - - - 0.1 ± 0.07 0.1 ± 0.11 -
7-epi-α-selinene 1517 0.3 ± 0.01 0.5 ± 0.02 0.5 ± 0.13 0.4 ± 0.01 0.5 ± 0.04 0.1 ± 0.19
β-cadinene 1520 - 0.2 ± 0.00 - 0.2 ± 0.00 - -
δ-cadinene 1523 - 0.2 ± 0.00 0.2 ± 0.21 - 0.1 ± 0.16 -
selina-3,7(11)-diene 1542 1.8 ± 0.35 D,E 2.4 ± 0.04 D 2.1 ± 0.07C 1.8 ± 0.04 B 1.6 ± 0.11 A 1.2 ± 0.09 E
α-calacorene 1546 - 0.2 ± 0.04 - 0.1 ± 0.13 - -
elemol 1549 0.4 ± 0.04 0.3 ± 0.01 0.3 ± 0.03 0.6 ± 0.01 0.8 ± 0.07 0.8 ± 0.04
(E)-nerolidol 1565 0.3 ± 0.06 - 0.3 ± 0.08 0.7 ± 0.01 1.1 ± 0.09 1.0 ± 0.11
palustrol 1568 0.5 ± 0.09 - 0.4 ± 0.13 0.5 ± 0.01 - 0.8 ± 0.06
caryophyllene alcohol 1569 - - - - 0.9 ± 0.09 -
caryophyllene oxide 1582 12.8 ± 0.78 D 7.3 ± 0.44 F 10.2 ± 0.50 E 15.9 ± 0.37 C 23.6 ± 0.35 A 22.0 ± 0.25 B
viridiflorol 1590 - - - 0.2 ± 0.25 0.5 ± 0.13 0.2 ± 0.31
humulene oxide 1606 4.3 ± 0.16 D 2.5 ± 0.09 F 3.2 ± 0.16 E 4.9 ± 0.04 C 7.8 ± 0.10 A 7.2 ± 0.15 B
selin-6-en-4-ol 1618 1.7 ± 0.18 B 1.0 ± 0.14 D 0.9 ± 0.05 D 1.3 ± 0.02 C 1.8 ± 0.14 B 2.4 ± 0.18 A
1-epi-cubenol 1629 0.2 ± 0.22 - 0.2 ± 0.06 0.1 ± 0.11 0.7 ± 0.03 -
caryophylla-4(14),8(15)-dien-5-ol 1636 3.8 ± 0.37 B 1.9 ± 0.37 C 1.9 ± 0.21 D 2.9 ± 0.07 C 5.2 ± 0.25 A 4.9 ± 0.35 A
β-eudesmol 1649 - - - - - 0.2 ± 0.28
α-eudesmol 1653 0.4 ± 0.01 - - - - -
neointermedeol 1660 1.5 ± 0.09 A 0.8 ± 0.21 B 0.5 ± 0.05 B 0.9 ± 0.02 B 1.8 ± 0.16 A 1.9 ± 0.47 A
14-hydroxy-9-epi-(E)-caryophyllene 1665 1.7 ± 0.24 C 0.7 ± 0.14 D 0.8 ± 0.08 D 1.4 ± 0.03 C 3.0 ± 0.29 A 2.6 ± 0.29 B
α-bisabolol 1685 0.7 ± 0.08 0.5 ± 0.05 0.4 ± 0.01 0.5 ± 0.03 0.9 ± 0.13 0.8 ± 0.11
juniper camphor 1695 0.5 ± 0.07 0.3 ± 0.05 0.2 ± 0.01 0.4 ± 0.01 0.6 ± 0.04 0.6 ± 0.06
hexahydrofarnesyl acetone 1845 - - 0.8 ± 0.12 0.8 ± 0.05 0.9 ± 0.14 0.4 ± 0.00
cannabidiol 2431 3.4 ± 0.49 B 0.9 ± 0.13 C 0.6 ± 0.04 C 1.1 ± 0.01 C 6.0 ± 0.90 A 6.7 ± 0.39 A
Δ9-tetrahydro-cannabinol 2468 0.1 ± 0.04 B - B - B - B 0.1 ± 0.08 B 1.3 ± 0.66 A
Monoterpene hydrocarbons 8.8 ± 2.59 B 9.5 ± 0.16 B 21.0 ± 3.26 A 19.3 ± 2.70 A 5.5 ± 1.62 B 20.8 ± 3.18 A
Oxygenated monoterpenes 2.7 ± 0.67 A,B,C 1.9 ± 0.20 C 2.1 ± 0.06 B,C 3.7 ± 0.45 A 3.3 ± 0.76 A 2.9 ± 0.09 A,B
Sesquiterpene hydrocarbons 54.0 ± 0.11B 71.1 ± 1.55 A 55.1 ± 2.11 B 42.2 ± 1.16 C 32.0 ± 1.23 D 19.3 ± 0.81 E
Oxygenated sesquiterpenes 28.7 ± 2.39 C 15.4 ± 1.23 E 19.3 ± 1.27 D 30.1 ± 0.83 C 48.8 ± 1.16 A 45.3 ± 2.17 B
Apocarotenoids - D - D 0.8 ± 0.12 B 0.8 ± 0.05 A,B 0.9 ± 0.14 A 0.4 ± 0.00 C
Cannabinoids 3.5 ± 0.54 C 0.9 ± 0.13 D 0.6 ± 0.04 D 1.1 ± 0.01 D 6.1 ± 0.98 B 8.0 ± 0.27 A
Other non-terpene derivatives - C 0.2 ± 0.01 B 0.2 ± 0.02 B 0.3 ± 0.05 A - C 0.2 ± 0.02 B
Total identified (%) 97.8 ± 0.44 99.1 ± 0.18 99.0 ± 0.11 97.5 ± 1.26 96.6 ± 1.33 96.9 ± 0.58
Distillation yield (% w/w) 0.03 ± 0.01 B 0.06 ± 0.01 A 0.07 ± 0.01 A 0.06 ± 0.00 A 0.01 ± 0.00 C 0.01 ± 0.00 C

1 Linear retention index on a HP-5MS capillary column; 2 Not detected; 3 For all elements reported in bold (compounds > 1% in at least one sample, all the detected chemical classes, and distillation yields), uppercase superscript letters (A–F) indicate statistically significant differences (established according to Tukey’s HSD post-hoc test, with p ≤ 0.05) among the samples.