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. 2019 Nov 21;24(23):4244. doi: 10.3390/molecules24234244

Table 1.

Chemical compositions of Piper nigrum fruit volatile oils from the Aromatic Plant Research Center (APRC) collection.

RI a RI b Compound D170201A FO170518Y FO170518Z Re180525F DT162718
921 921 Tricyclene --- --- --- --- tr c
924 924 α-Thujene 0.1 0.1 0.2 0.9 0.6
932 932 α-Pinene 28.7 12.9 15.2 5.1 11.1
945 945 α-Fenchene --- --- --- --- tr
954 946 Camphene 1.0 0.6 0.6 0.1 0.3
969 969 Sabinene 0.2 0.4 0.7 6.9 13.9
974 974 β-Pinene 15.3 12.6 13.4 9.1 15.1
988 988 Myrcene 2.6 2.7 3.0 2.1 1.3
1002 1002 α-Phellandrene 2.2 2.5 3.4 2.3 0.6
1003 1003 p-Mentha-1(7),8-diene tr --- --- --- ---
1008 1008 δ-3-Carene 9.0 11.7 12.8 11.7 10.4
1017 1014 α-Terpinene 0.1 --- 0.1 0.2 0.1
1020 1020 p-Cymene 0.3 0.8 0.4 1.1 0.3
1022 1022 o-Cymene --- 0.1 --- 0.1 ---
1025 1025 β-Phellandrene 0.2 --- --- 1.4 0.9
1026 1026 1,8-Cineole 0.2 0.3 0.4 --- tr
1029 1024 Limonene 19.5 18.2 18.2 17.4 15.1
1032 1032 (Z)-β-Ocimene tr --- --- --- ---
1044 1044 (E)-β-Ocimene 0.4 0.2 0.3 0.1 0.1
1054 1054 γ-Terpinene 0.1 0.1 0.1 0.3 0.1
1069 1065 cis-Sabinene hydrate --- --- --- 0.1 0.1
1086 1086 Terpinolene 0.5 0.8 0.9 0.5 0.2
1095 1095 Linalool 0.6 0.4 0.3 0.5 0.3
1100 1098 trans-Sabinene hydrate --- --- --- --- 0.1
1135 1135 trans-Pinocarveol --- --- --- --- tr
1140 1140 cis-β-Terpineol --- 0.2 --- --- ---
1141 1141 Camphor 0.1 0.1 tr --- ---
1174 1174 Terpinen-4-ol 0.1 --- --- 0.3 0.2
1186 1186 α-Terpineol 0.3 --- 0.2 --- 0.1
1328 1330 Bicycloelemene 0.1 --- --- 0.1 tr
1335 1335 δ-Elemene 1.1 2.9 2.9 0.9 1.0
1348 1345 α-Cubebene tr 0.1 0.1 0.3 0.1
1369 1369 Cyclosativene d 0.2 --- --- 0.1 0.1
1373 1373 α-Ylangene --- 0.1 0.1 --- ---
1374 1374 Isoledene --- 0.2 0.2 --- ---
1376 1374 α-Copaene 0.1 0.2 0.2 3.1 2.0
1387 1387 β-Cubebene --- --- --- 0.2 0.2
1389 1389 β-Elemene 1.0 1.8 1.4 1.1 0.2
1408 1408 (Z)-β-Caryophyllene --- --- --- --- tr
1409 1408 α-Gurjunene 0.1 0.1 0.1 0.2 tr
1417 1417 (E)-β-Caryophyllene 8.7 18.3 15.2 25.6 21.6
1430 1430 β-Copaene --- 0.1 --- 0.1 0.1
1436 1434 γ-Elemene 0.1 0.1 0.1 --- ---
1437 1437 α-Guaiene 0.1 0.6 0.3 0.4 tr
1448 1448 cis-Murrola-3,5-diene --- --- --- --- tr
1452 1452 α-Humulene 0.9 1.8 1.3 1.6 0.7
1461 1461 cis-Cadina-1(6),4-diene --- --- --- --- tr
1475 1475 trans-Cadina-1(6),4-diene tr 0.1 0.4 --- tr
1484 1484 Germacrene D 2.0 2.5 3.0 0.2 0.1
1490 1489 β-Selinene 1.3 2.0 1.9 1.5 0.1
1493 1493 trans-Muurola-4(14),5-diene --- --- --- --- 0.1
1496 1496 Viridiflorene --- --- --- 0.1 ---
1498 1498 α-Selinene 1.0 1.5 1.5 1.3 ---
1500 1500 α-Muurolene --- 0.1 0.1 0.2 0.3
1500 1500 Bicyclogermacrene --- --- --- --- 0.3
1501 1501 epi-Zonarene 0.1 --- --- --- ---
1505 1505 β-Bisabolene tr 0.3 --- 0.1 0.7
1505 1505 (E,E)-α-Farnesene --- --- 0.1 --- ---
1514 1514 Cubebol tr --- --- 0.3 0.1
1518 1521 α-Panasinsen tr 0.1 0.1 --- ---
1521 1521 trans-Calamenene --- --- --- tr tr
1523 1522 δ-Cadinene 0.1 0.1 0.2 0.8 0.7
1533 1533 trans-Cadina-1,4-diene --- --- --- --- tr
1548 1548 α-Elemol tr --- --- --- ---
1561 1559 Germacrene B 0.1 0.2 0.1 --- ---
1561 1561 (E)-Nerolidol --- --- --- --- tr
1577 1577 Spathulenol tr --- --- 0.1 tr
1582 1582 Caryophyllene oxide 0.2 1.4 0.3 0.8 0.5
1608 1608 Humulene epoxide II --- 0.1 --- --- ---
1618 1618 1,10-di-epi-Cubenol 0.1 --- --- --- ---
1626 1629 iso-Spathulenol 0.3 --- --- 0.3 0.1
1639 1644 allo-Aromadendrene epoxide tr --- --- --- ---
1640 1640 τ-Muurolol --- --- --- 0.1 tr
1644 1644 α-Muurolol (=δ-Cadinol) --- --- --- 0.3 0.1
1651 1651 Pogostol 0.1 --- --- --- ---
1652 1652 α-Cadinol 0.1 --- 0.1 --- ---
1660 1660 Selin-11-en-4α-ol tr --- --- --- ---
1685 1685 Germacra-4(15),5,10(14)-trien-1α-ol 0.5 --- --- --- ---
Monoterpene hydrocarbons 80.1 63.5 69.2 59.2 69.9
Oxygenated monoterpenoids 1.2 1.0 0.9 0.8 0.7
Sesquiterpene hydrocarbons 17.0 33.3 29.2 37.7 28.2
Oxygenated sesquiterpenoids 1.3 1.5 0.4 1.9 0.8
Total identified 99.7 99.3 99.7 99.5 99.7

a RI = “Retention Index” determined in reference to a homologous series of n-alkanes. b Retention indices from the databases [22,23]. c tr = “trace” (<0.05%). d This compound may be cyclocopacamphene, an epimer of cyclosativene.