646:. Another study suggests monoterpenes substantially affect ambient organic aerosol with uncertainties regarding environmental impacts. In a review, scientists concluded that they hope that these "substances will be extensively studied and used in more and more in medicine". A 2013 study found that "Based on adverse effects and risk assessments, d-limonene may be regarded as a safe ingredient. However, the potential occurrence of skin irritation necessitates regulation of this chemical as an ingredient in cosmetics." According to a review, several studies showed "that some monoterpenes (e.g., pulegone, menthofuran, camphor, and limonene) and sesquiterpenes (e.g., zederone, germacrone) exhibited liver toxicity" and that i.a. intensive research on terpenes toxicity is needed.
175:
224:
205:
160:
139:
190:
1416:
Weiwei; Day, Douglas A.; Campuzano-Jost, Pedro; Jimenez, Jose L.; Guo, Hongyu; Weber, Rodney J.; de Gouw, Joost; Koss, Abigail R.; Edgerton, Eric S.; Brune, William; Mohr, Claudia; Lopez-Hilfiker, Felipe D.; Lutz, Anna; Kreisberg, Nathan M.; Spielman, Steve R.; Hering, Susanne V.; Wilson, Kevin R.; Thornton, Joel A.; Goldstein, Allen H. (12 February 2018).
1415:
Zhang, Haofei; Yee, Lindsay D.; Lee, Ben H.; Curtis, Michael P.; Worton, David R.; Isaacman-VanWertz, Gabriel; Offenberg, John H.; Lewandowski, Michael; Kleindienst, Tadeusz E.; Beaver, Melinda R.; Holder, Amara L.; Lonneman, William A.; Docherty, Kenneth S.; Jaoui, Mohammed; Pye, Havala O. T.; Hu,
1534:
Kim, Young Woo; Kim, Min Ji; Chung, Bu Young; Bang, Du Yeon; Lim, Seong Kwang; Choi, Seul Min; Lim, Duck Soo; Cho, Myung Chan; Yoon, Kyungsil; Kim, Hyung Sik; Kim, Kyu Bong; Kim, You Sun; Kwack, Seung Jun; Lee, Byung-Mu (1 January 2013). "Safety
Evaluation And Risk Assessment Of d-Limonene".
1349:
Rosales, Colleen
Marciel F.; Jiang, Jinglin; Lahib, Ahmad; Bottorff, Brandon P.; Reidy, Emily K.; Kumar, Vinay; Tasoglou, Antonios; Huber, Heinz; Dusanter, Sebastien; Tomas, Alexandre; Boor, Brandon E.; Stevens, Philip S. (25 February 2022).
87:
Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids). Elimination of the pyrophosphate group from geranyl pyrophosphate leads to the formation of acyclic monoterpenes such as
38:. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called
917:
869:
1483:
Wojtunik-Kulesza, Karolina A.; Kasprzak, Kamila; Oniszczuk, Tomasz; Oniszczuk, Anna (8 November 2019). "Natural
Monoterpenes: Much More than Only a Scent".
1324:
72:. An alternative, unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP-(2-methyl-
1308:
1240:
1127:
1057:
1021:
989:
853:
744:
204:
1671:
1594:
Zárybnický, Tomáš; Boušová, Iva; Ambrož, Martin; Skálová, Lenka (1 January 2018). "Hepatotoxicity of monoterpenes and sesquiterpenes".
42:. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.
2650:
723:
Davis, Edward M.; Croteau, Rodney (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes".
1178:
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777:
707:
138:
2704:
174:
631:
223:
159:
2127:
1194:
Caputi, Lorenzo; Aprea, Eugenio (1 January 2011). "Use of
Terpenoids as Natural Flavouring Compounds in Food Industry".
1151:
795:"Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions"
2677:
1352:"Chemistry and human exposure implications of secondary organic aerosol production from indoor terpene ozonolysis"
2671:
643:
345:
69:
57:
1664:
329:
activities and participate in wound healing. Some of these compounds are produced to protect the trees from
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2082:
415:
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1296:
1256:
969:
2699:
1929:
1037:
189:
1955:
1603:
1544:
1429:
1418:"Monoterpenes are the largest source of summertime organic aerosol in the southeastern United States"
1363:
926:
568:
Volatile monoterpenes produced by plants can attract or repel insects, thus some of them are used in
443:
1657:
909:
16:
Any unsaturated hydrocarbon with structure that is a result of the assembling of two isoprene units
84:. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase.
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1433:
1367:
930:
793:
Vil’, Vera; Yaremenko, Ivan; Ilovaisky, Alexey; Terent’ev, Alexander (2 November 2017).
269:
are examples of bicyclic monoterpenoids containing ketone, alcohol, ether, and bridging
2654:
2608:
2521:
2516:
2506:
2483:
2445:
2435:
2016:
1460:
1417:
1392:
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981:
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510:
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65:
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999:
954:
769:
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627:
506:
423:
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326:
306:
286:
96:. Hydrolysis of the phosphate groups leads to the prototypical acyclic monoterpenoid
1639:
1580:
2613:
2531:
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2440:
2383:
2366:
2351:
2320:
2280:
2250:
2176:
1855:
1835:
562:
550:
360:
1556:
348:(CCN). Such aerosols can increase the brightness of clouds and cool the climate.
2585:
2575:
2551:
2536:
2378:
2343:
2338:
2227:
2222:
2090:
2054:
2031:
1970:
1919:
1909:
1859:
1207:
1119:
1114:. Advances in Experimental Medicine and Biology. Vol. 464. pp. 49–62.
573:
435:
403:
274:
151:
109:
105:
309:
are very rich in monoterpenes. Several monoterpenes produced by trees, such as
2570:
2488:
2414:
2373:
2361:
2356:
2242:
2232:
2026:
2021:
1974:
1615:
811:
699:
635:
630:
equivalent or exceeding the harm to respiratory tracts when the time is spent
611:
603:
589:
577:
558:
542:
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447:
314:
266:
262:
210:
61:
1623:
1564:
1504:
1451:
1383:
2197:
2106:
2059:
1990:
1830:
1685:
1442:
1073:
Saeidnia, Soodabeh; Gohari, Ahmad Reza (2012). "Trypanocidal
Monoterpenes".
736:
665:
660:
502:
483:
384:
322:
294:
290:
214:
1631:
1572:
1512:
1496:
1469:
1401:
1375:
1215:
1137:
946:
938:
830:
375:
has a lemon-like pleasant odor and contributes to the distinctive smell of
970:"14 - Toxicological Aspects of Ingredients Used in Nonalcoholic Beverages"
2541:
2526:
2498:
2427:
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2192:
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388:
368:
364:
352:
310:
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246:
242:
229:
180:
113:
97:
27:
1325:"Cleaning products cause indoor pollution levels similar to a busy road"
2419:
2409:
2330:
2151:
2146:
2074:
2069:
2011:
2006:
1960:
1934:
1870:
1809:
1804:
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1721:
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318:
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195:
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144:
121:
117:
93:
89:
77:
51:
23:
762:
Supplements to the 2nd
Edition of Rodd's Chemistry of Carbon Compounds
2580:
2122:
1980:
1914:
1880:
1851:
1764:
1044:(2nd ed.). Amsterdam: Academic Press. 2003. pp. 3082–3090.
597:
554:
546:
514:
475:
431:
376:
372:
337:
330:
238:
148:
101:
100:. Additional rearrangements and oxidations provide compounds such as
116:, and many others. Many monoterpenes found in marine organisms are
976:. Duxford, United Kingdom: Woodhead Publishing. pp. 441–481.
356:
298:
285:
Monoterpenes are found in many parts of different plants, such as
1301:
Essential oil safety : a guide for health care professionals
1110:
Loza-Tavera, Herminia (1999). "Monoterpenes in
Essential Oils".
910:"Boreal forests, aerosols and the impacts on clouds and climate"
302:
1653:
351:
Many monoterpenes have unique smell and flavor. For example,
844:
Sjöström, Eero (22 October 2013). "Chapter 5: Extractives".
974:
Non-alcoholic beverages. Volume 6: The
Science of Beverages
968:
Tamer, Canan Ece; Suna, Senem; Özcan-Sinir, Gülşah (2019).
1016:(4th ed.). Montvale, NJ: Thomson. 2007. p. 802.
883:
Rowell, Roger M. (2013). "Chater 3: Cell Wall
Chemistry".
76:-erythritol-4-phosphate) pathway, which is initiated from
1235:(1st ed.). Amsterdam: Elsevier. 1999. p. 306.
56:
Monoterpenes are derived biosynthetically from units of
1537:
Journal of
Toxicology and Environmental Health, Part B
690:
Eberhard Breitmaier (2006). "Hemi- and Monoterpenes".
1303:(Second ed.). Edinburgh: Churchill Livingstone.
2649:
Terpene synthase enzymes (many), having in common a
2664:
2642:
2625:
2598:
2550:
2497:
2482:
2465:
2402:
2329:
2319:
2302:
2241:
2215:
2185:
2160:
2139:
2115:
2105:
2044:
1999:
1948:
1902:
1893:
1844:
1818:
1797:
1778:
1740:
1697:
1196:
Recent Patents on Food, Nutrition & Agriculture
692:
Terpenes: Flavors, Fragrances, Pharmaca, Pheromones
277:is another example of bicyclic monoterpene ketone.
887:(2nd ed.). Boca Raton: Taylor & Francis.
918:Philosophical Transactions of the Royal Society A
908:D. V. Spracklen; B. Bonn; K. S. Carslaw (2008).
1422:Proceedings of the National Academy of Sciences
760:Brown, R.T. (1975). "Bicyclic Monoterpenoids".
614:are monoterpenes that have pharmaceutical use.
1727:Iridoid glycosides (iridoids bound to a sugar)
885:Handbook of Wood Chemistry and Wood Composites
1665:
1264:United States Environmental Protection Agency
846:Wood Chemistry: Fundamentals and Applications
8:
1042:Encyclopedia of food sciences and nutrition
626:with certain monoterpenes may cause indoor
2494:
2326:
2112:
1899:
1794:
1672:
1658:
1650:
868:: CS1 maint: location missing publisher (
418:compounds and some of them are well-known
293:, bark and leaves of coniferous trees, in
1459:
1441:
1391:
1112:Chemicals via Higher Plant Bioengineering
820:
810:
642:leading to the production of atmospheric
1278:"Camphor Cream and Ointment Information"
1233:Comprehensive natural products chemistry
1173:. Chicago: University of Chicago Press.
133:Selected Monoterpenes and Monoterpenoids
682:
131:
861:
30:units and have the molecular formula C
1227:
1225:
1075:Studies in Natural Products Chemistry
7:
1297:"Chapter 13: Essential oil profiles"
501:Many monoterpenes are used as food
2651:terpene synthase N terminal domain
1087:10.1016/B978-0-444-59514-0.00006-7
982:10.1016/B978-0-12-815270-6.00014-1
14:
622:A study suggests that a range of
273:functional groups, respectively.
770:10.1016/B978-044453346-3.50098-6
222:
203:
188:
173:
158:
137:
1050:10.1016/B0-12-227055-X/00593-9
848:(Second ed.). San Diego.
344:that are proposed to serve as
237:Bicyclic monoterpenes include
147:is an acyclic monoterpene, an
1:
426:of many plants. For example,
168:is a monocyclic monoterpenoid
2128:Geranylgeranyl pyrophosphate
1557:10.1080/10937404.2013.769418
1485:Chemistry & Biodiversity
402:Monoterpenes are considered
336:Monoterpenes are emitted by
2678:Dimethylallyl pyrophosphate
1208:10.2174/2212798411103010009
1120:10.1007/978-1-4615-4729-7_5
725:Topics in Current Chemistry
371:an earthy taste and smell,
232:is an acyclic monoterpenoid
183:is a monocyclic monoterpene
52:Terpene § Biosynthesis
2726:
1295:Tisserand, Robert (2014).
49:
2672:Isopentenyl pyrophosphate
2626:Norisoprenoids (modified)
1616:10.1007/s00204-017-2062-2
812:10.3390/molecules22111881
700:10.1002/9783527609949.ch2
346:cloud condensation nuclei
70:HMG-CoA reductase pathway
58:isopentenyl pyrophosphate
2665:Activated isoprene forms
2466:Sesquarterpenes/oids (7)
1715:Monocyclic (single ring)
1156:pubchem.ncbi.nlm.nih.gov
1014:PDR for herbal medicines
387:are responsible for the
64:via the intermediacy of
2705:Terpenes and terpenoids
2288:Secodehydroabietic acid
1443:10.1073/pnas.1717513115
1169:Laszlo, Pierre (2007).
1038:"Herbs of the Labiatae"
737:10.1007/3-540-48146-X_2
60:, which is formed from
2083:Farnesyl pyrophosphate
1596:Archives of Toxicology
1497:10.1002/cbdv.201900434
1376:10.1126/sciadv.abj9156
1257:"R.E.D. FACTS: Thymol"
939:10.1098/rsta.2008.0201
414:Many monoterpenes are
213:is a monoterpenoid, a
2285:Sandaracopimaric acid
1930:Geranyl pyrophosphate
638:of monoterpenes like
2475:Tetraprenylcurcumene
1956:Grapefruit mercaptan
444:grapefruit mercaptan
26:that consist of two
2258:Dehydroabietic acid
1724:(cyclopentane ring)
1608:2018ArTox..92....1Z
1549:2013JTEHB..16...17K
1434:2018PNAS..115.2038Z
1368:2022SciA....8J9156R
931:2008RSPTA.366.4613S
355:contributes to the
1718:Bicyclic (2 rings)
694:. pp. 10–23.
198:is a monoterpenoid
2687:
2686:
2635:7,8-dihydroionone
2594:
2593:
2461:
2460:
2298:
2297:
2266:Lambertianic acid
2040:
2039:
1889:
1888:
1704:Acyclic (linear,
1310:978-0-443-06241-4
1242:978-0-08-091283-7
1171:Citrus: A history
1129:978-1-4613-7143-4
1059:978-0-12-227055-0
1023:978-1-56363-512-0
991:978-0-12-815270-6
925:(1885): 4613–26.
855:978-0-08-092589-9
746:978-3-540-66573-1
634:. This is due to
570:insect repellents
549:are also used in
75:
2717:
2495:
2327:
2304:Sesterterpenoids
2270:Levopimaric acid
2132:Geranyl-linalool
2113:
2046:Sesquiterpenoids
1986:Perillyl alcohol
1900:
1795:
1674:
1667:
1660:
1651:
1644:
1643:
1591:
1585:
1584:
1531:
1525:
1524:
1491:(12): e1900434.
1480:
1474:
1473:
1463:
1445:
1428:(9): 2038–2043.
1412:
1406:
1405:
1395:
1356:Science Advances
1346:
1340:
1339:
1337:
1335:
1321:
1315:
1314:
1292:
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1285:
1274:
1268:
1267:
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1253:
1247:
1246:
1229:
1220:
1219:
1191:
1185:
1184:
1166:
1160:
1159:
1148:
1142:
1141:
1107:
1101:
1100:
1070:
1064:
1063:
1034:
1028:
1027:
1010:
1004:
1003:
965:
959:
958:
914:
905:
899:
898:
880:
874:
873:
867:
859:
841:
835:
834:
824:
814:
790:
784:
783:
757:
751:
750:
720:
714:
713:
687:
632:near a busy road
492:perillyl alcohol
399:, respectively.
226:
207:
192:
177:
162:
141:
73:
2725:
2724:
2720:
2719:
2718:
2716:
2715:
2714:
2690:
2689:
2688:
2683:
2660:
2638:
2621:
2590:
2546:
2486:
2484:Tetraterpenoids
2478:
2457:
2398:
2389:Cholecalciferol
2315:
2312:Geranylfarnesol
2294:
2277:Neoabietic acid
2262:Isopimaric acid
2237:
2211:
2181:
2156:
2135:
2101:
2036:
1995:
1944:
1895:
1894:Monoterpenoids
1885:
1840:
1814:
1790:
1786:
1782:
1774:
1770:Isovaleric acid
1760:
1756:
1736:
1693:
1678:
1648:
1647:
1593:
1592:
1588:
1533:
1532:
1528:
1482:
1481:
1477:
1414:
1413:
1409:
1362:(8): eabj9156.
1348:
1347:
1343:
1333:
1331:
1323:
1322:
1318:
1311:
1294:
1293:
1289:
1276:
1275:
1271:
1259:
1255:
1254:
1250:
1243:
1231:
1230:
1223:
1193:
1192:
1188:
1181:
1168:
1167:
1163:
1150:
1149:
1145:
1130:
1109:
1108:
1104:
1097:
1072:
1071:
1067:
1060:
1036:
1035:
1031:
1024:
1012:
1011:
1007:
992:
967:
966:
962:
912:
907:
906:
902:
895:
882:
881:
877:
860:
856:
843:
842:
838:
792:
791:
787:
780:
759:
758:
754:
747:
722:
721:
717:
710:
689:
688:
684:
679:
652:
620:
412:
404:allelochemicals
283:
233:
227:
218:
208:
199:
193:
184:
178:
169:
163:
154:
142:
130:
81:
54:
48:
37:
33:
22:are a class of
17:
12:
11:
5:
2723:
2721:
2713:
2712:
2707:
2702:
2692:
2691:
2685:
2684:
2682:
2681:
2675:
2668:
2666:
2662:
2661:
2659:
2658:
2655:protein domain
2646:
2644:
2640:
2639:
2637:
2636:
2633:
2629:
2627:
2623:
2622:
2620:
2619:
2616:
2611:
2609:Natural rubber
2605:
2603:
2600:Polyterpenoids
2596:
2595:
2592:
2591:
2589:
2588:
2583:
2578:
2573:
2568:
2563:
2557:
2555:
2548:
2547:
2545:
2544:
2539:
2534:
2529:
2524:
2522:Delta-Carotene
2519:
2517:Gamma-Carotene
2514:
2509:
2507:Alpha-Carotene
2503:
2501:
2492:
2480:
2479:
2477:
2476:
2473:
2469:
2467:
2463:
2462:
2459:
2458:
2456:
2455:
2454:
2453:
2448:
2446:Betulinic acid
2443:
2438:
2436:Oleanolic acid
2430:
2425:
2422:
2417:
2412:
2406:
2404:
2400:
2399:
2397:
2396:
2391:
2386:
2381:
2376:
2371:
2370:
2369:
2364:
2359:
2354:
2349:
2348:Citrostadienol
2346:
2335:
2333:
2324:
2317:
2316:
2314:
2313:
2309:
2307:
2300:
2299:
2296:
2295:
2293:
2292:
2291:Palustric acid
2289:
2286:
2283:
2278:
2275:
2272:
2267:
2264:
2259:
2256:
2253:
2247:
2245:
2239:
2238:
2236:
2235:
2230:
2225:
2219:
2217:
2213:
2212:
2210:
2209:
2206:
2203:
2200:
2195:
2189:
2187:
2183:
2182:
2180:
2179:
2174:
2171:
2164:
2162:
2158:
2157:
2155:
2154:
2149:
2143:
2141:
2137:
2136:
2134:
2133:
2130:
2125:
2119:
2117:
2110:
2103:
2102:
2100:
2099:
2096:
2093:
2088:
2085:
2080:
2077:
2072:
2067:
2062:
2057:
2051:
2049:
2042:
2041:
2038:
2037:
2035:
2034:
2029:
2024:
2019:
2017:Bornyl acetate
2014:
2009:
2003:
2001:
1997:
1996:
1994:
1993:
1988:
1983:
1978:
1968:
1963:
1958:
1952:
1950:
1946:
1945:
1943:
1942:
1937:
1932:
1927:
1922:
1917:
1912:
1906:
1904:
1897:
1891:
1890:
1887:
1886:
1884:
1883:
1878:
1873:
1868:
1863:
1848:
1846:
1842:
1841:
1839:
1838:
1833:
1828:
1822:
1820:
1816:
1815:
1813:
1812:
1807:
1801:
1799:
1792:
1788:
1784:
1776:
1775:
1773:
1772:
1767:
1762:
1758:
1754:
1747:
1745:
1742:Hemiterpenoids
1738:
1737:
1735:
1734:
1728:
1725:
1719:
1716:
1713:
1701:
1699:
1695:
1694:
1679:
1677:
1676:
1669:
1662:
1654:
1646:
1645:
1586:
1526:
1475:
1407:
1341:
1316:
1309:
1287:
1269:
1248:
1241:
1221:
1186:
1179:
1161:
1143:
1128:
1102:
1095:
1065:
1058:
1029:
1022:
1005:
990:
960:
900:
893:
875:
854:
836:
785:
778:
752:
745:
715:
708:
681:
680:
678:
675:
674:
673:
668:
663:
658:
651:
648:
624:floor cleaners
619:
618:Health effects
616:
511:bornyl acetate
507:food additives
424:essential oils
411:
408:
307:Essential oils
282:
279:
235:
234:
228:
221:
219:
209:
202:
200:
194:
187:
185:
179:
172:
170:
164:
157:
155:
143:
136:
134:
129:
126:
79:
66:mevalonic acid
50:Main article:
47:
44:
40:monoterpenoids
35:
31:
15:
13:
10:
9:
6:
4:
3:
2:
2722:
2711:
2710:Wood extracts
2708:
2706:
2703:
2701:
2698:
2697:
2695:
2679:
2676:
2673:
2670:
2669:
2667:
2663:
2656:
2652:
2648:
2647:
2645:
2641:
2634:
2632:3-oxo-α-ionol
2631:
2630:
2628:
2624:
2617:
2615:
2612:
2610:
2607:
2606:
2604:
2601:
2597:
2587:
2584:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2566:Cryptoxanthin
2564:
2562:
2561:Canthaxanthin
2559:
2558:
2556:
2553:
2549:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2512:Beta-Carotene
2510:
2508:
2505:
2504:
2502:
2500:
2496:
2493:
2490:
2485:
2481:
2474:
2472:Ferrugicadiol
2471:
2470:
2468:
2464:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2433:
2431:
2429:
2426:
2424:Serratenediol
2423:
2421:
2418:
2416:
2413:
2411:
2408:
2407:
2405:
2401:
2395:
2392:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2368:
2365:
2363:
2360:
2358:
2355:
2353:
2350:
2347:
2345:
2342:
2341:
2340:
2337:
2336:
2334:
2332:
2328:
2325:
2322:
2321:Triterpenoids
2318:
2311:
2310:
2308:
2305:
2301:
2290:
2287:
2284:
2282:
2279:
2276:
2274:Mercusic acid
2273:
2271:
2268:
2265:
2263:
2260:
2257:
2255:Communic acid
2254:
2252:
2249:
2248:
2246:
2244:
2240:
2234:
2231:
2229:
2226:
2224:
2221:
2220:
2218:
2214:
2207:
2204:
2201:
2199:
2196:
2194:
2191:
2190:
2188:
2184:
2178:
2175:
2172:
2169:
2166:
2165:
2163:
2159:
2153:
2150:
2148:
2145:
2144:
2142:
2138:
2131:
2129:
2126:
2124:
2121:
2120:
2118:
2114:
2111:
2108:
2104:
2097:
2094:
2092:
2089:
2086:
2084:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2052:
2050:
2047:
2043:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2004:
2002:
1998:
1992:
1989:
1987:
1984:
1982:
1979:
1976:
1972:
1969:
1967:
1964:
1962:
1959:
1957:
1954:
1953:
1951:
1947:
1941:
1938:
1936:
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1907:
1905:
1901:
1898:
1892:
1882:
1879:
1877:
1874:
1872:
1869:
1867:
1864:
1861:
1857:
1853:
1850:
1849:
1847:
1843:
1837:
1834:
1832:
1829:
1827:
1824:
1823:
1821:
1817:
1811:
1808:
1806:
1803:
1802:
1800:
1796:
1793:
1781:
1777:
1771:
1768:
1766:
1763:
1752:
1749:
1748:
1746:
1743:
1739:
1732:
1729:
1726:
1723:
1720:
1717:
1714:
1711:
1707:
1703:
1702:
1700:
1696:
1691:
1687:
1683:
1675:
1670:
1668:
1663:
1661:
1656:
1655:
1652:
1641:
1637:
1633:
1629:
1625:
1621:
1617:
1613:
1609:
1605:
1601:
1597:
1590:
1587:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1554:
1550:
1546:
1542:
1538:
1530:
1527:
1522:
1518:
1514:
1510:
1506:
1502:
1498:
1494:
1490:
1486:
1479:
1476:
1471:
1467:
1462:
1457:
1453:
1449:
1444:
1439:
1435:
1431:
1427:
1423:
1419:
1411:
1408:
1403:
1399:
1394:
1389:
1385:
1381:
1377:
1373:
1369:
1365:
1361:
1357:
1353:
1345:
1342:
1330:
1329:New Scientist
1326:
1320:
1317:
1312:
1306:
1302:
1298:
1291:
1288:
1283:
1279:
1273:
1270:
1265:
1258:
1252:
1249:
1244:
1238:
1234:
1228:
1226:
1222:
1217:
1213:
1209:
1205:
1201:
1197:
1190:
1187:
1182:
1180:9780226470283
1176:
1172:
1165:
1162:
1157:
1153:
1147:
1144:
1139:
1135:
1131:
1125:
1121:
1117:
1113:
1106:
1103:
1098:
1096:9780444595140
1092:
1088:
1084:
1080:
1076:
1069:
1066:
1061:
1055:
1051:
1047:
1043:
1039:
1033:
1030:
1025:
1019:
1015:
1009:
1006:
1001:
997:
993:
987:
983:
979:
975:
971:
964:
961:
956:
952:
948:
944:
940:
936:
932:
928:
924:
920:
919:
911:
904:
901:
896:
894:9781439853801
890:
886:
879:
876:
871:
865:
857:
851:
847:
840:
837:
832:
828:
823:
818:
813:
808:
804:
800:
796:
789:
786:
781:
779:9780444533463
775:
771:
767:
763:
756:
753:
748:
742:
738:
734:
730:
726:
719:
716:
711:
709:9783527609949
705:
701:
697:
693:
686:
683:
676:
672:
671:Sesquiterpene
669:
667:
664:
662:
659:
657:
654:
653:
649:
647:
645:
641:
637:
633:
629:
628:air pollution
625:
617:
615:
613:
609:
605:
601:
599:
595:
591:
587:
583:
579:
575:
571:
566:
564:
560:
556:
552:
548:
544:
540:
536:
532:
528:
524:
520:
516:
512:
508:
504:
499:
497:
493:
489:
485:
481:
477:
473:
469:
465:
461:
457:
453:
449:
445:
441:
437:
433:
429:
425:
422:found in the
421:
417:
409:
407:
405:
400:
398:
394:
393:summer savory
390:
386:
382:
378:
374:
370:
366:
362:
358:
354:
349:
347:
343:
339:
334:
332:
328:
327:antibacterial
324:
320:
316:
312:
308:
304:
300:
296:
292:
288:
281:Natural roles
280:
278:
276:
272:
268:
264:
260:
256:
252:
248:
244:
240:
231:
225:
220:
216:
212:
206:
201:
197:
191:
186:
182:
176:
171:
167:
161:
156:
153:
150:
146:
140:
135:
132:
128:Main examples
127:
125:
123:
119:
115:
111:
107:
103:
99:
95:
91:
85:
83:
71:
67:
63:
59:
53:
45:
43:
41:
29:
25:
21:
2700:Monoterpenes
2618:Gutta-balatá
2614:Gutta percha
2552:Xanthophylls
2532:Neurosporene
2451:Moronic acid
2441:Ursolic acid
2384:Testosterone
2367:Stigmasterol
2352:Cycloartenol
2339:Phytosterols
2281:Pimaric acid
2251:Abietic acid
2202:Manoyl oxide
2177:Salvinorin A
2167:
2107:Diterpenoids
1971:Thujaplicins
1896:(2,modified)
1836:Phellandrene
1780:Monoterpenes
1779:
1709:
1705:
1698:Basic forms:
1599:
1595:
1589:
1543:(1): 17–38.
1540:
1536:
1529:
1488:
1484:
1478:
1425:
1421:
1410:
1359:
1355:
1344:
1332:. Retrieved
1328:
1319:
1300:
1290:
1281:
1272:
1263:
1251:
1232:
1199:
1195:
1189:
1170:
1164:
1155:
1146:
1111:
1105:
1078:
1074:
1068:
1041:
1032:
1013:
1008:
973:
963:
922:
916:
903:
884:
878:
845:
839:
805:(11): 1881.
802:
798:
788:
761:
755:
728:
724:
718:
691:
685:
621:
602:
567:
565:properties.
563:disinfectant
551:oral hygiene
500:
494:are used in
478:are used in
413:
401:
379:fruits, and
361:black pepper
350:
335:
284:
236:
86:
55:
46:Biosynthesis
39:
20:Monoterpenes
19:
18:
2586:Rubixanthin
2576:Astaxanthin
2537:Phytofluene
2489:Carotenoids
2379:Cholesterol
2374:Tocopherols
2344:Campesterol
2243:Resin acids
2228:Gibberellin
2223:Aphidicolin
2216:Tetracyclic
2091:Longifolene
2055:Artemisinin
2032:Umbellulone
1920:Citronellol
1910:Citronellal
1602:(1): 1–13.
1202:(1): 9–16.
1081:: 173–190.
574:citronellol
436:citronellol
391:flavors of
275:Umbellulone
152:hydrocarbon
118:halogenated
110:citronellol
106:citronellal
2694:Categories
2571:Zeaxanthin
2415:Lanosterol
2362:Sitosterol
2357:Sitostanol
2233:Paclitaxel
2140:Monocyclic
2027:Ascaridole
2022:Eucalyptol
1975:Hinokitiol
1949:Monocyclic
1819:Monocyclic
1686:terpenoids
1152:"Limonene"
677:References
636:ozonolysis
612:eucalyptol
604:Ascaridole
590:hinokitiol
578:eucalyptol
572:, such as
559:antiseptic
553:products.
543:hinokitiol
527:hinokitiol
519:eucalyptol
509:, such as
498:products.
486:products.
448:eucalyptol
323:fungicidal
315:hinokitiol
295:vegetables
267:ascaridole
263:eucalyptol
217:derivative
211:Hinokitiol
120:, such as
62:acetyl-CoA
2643:Synthesis
2499:Carotenes
2394:Ecdysones
2198:Forskolin
2186:Tricyclic
2173:Epimanool
2098:Nootkatin
2095:Muurolene
2087:Juniperol
2079:Chanootin
2060:Bisabolol
1991:Carvacrol
1831:Terpinene
1733:(4 rings)
1680:Types of
1624:1432-0738
1565:1093-7404
1521:203850556
1505:1612-1872
1452:0027-8424
1384:2375-2548
1282:Drugs.com
1000:187341441
955:206156442
864:cite book
799:Molecules
764:: 53–93.
731:: 53–95.
666:Diterpene
661:Terpenoid
557:also has
420:fragrants
385:carvacrol
359:taste of
340:and form
333:attacks.
291:heartwood
215:tropolone
2542:Phytoene
2527:Lycopene
2428:Squalane
2420:Saponins
2331:Steroids
2193:Cembrene
2170:-Abienol
2161:Bicyclic
2065:Cadinene
2000:Bicyclic
1966:p-Cymene
1940:Linalool
1925:Geraniol
1876:Sabinene
1866:Camphene
1845:Bicyclic
1826:Limonene
1810:Myrcenes
1751:Isoprene
1731:Steroids
1722:Iridoids
1690:isoprene
1682:terpenes
1640:22483285
1632:28905185
1581:40274650
1573:23573938
1513:31587473
1470:29440409
1402:35213219
1334:10 March
1216:21114471
1138:10335385
947:18826917
831:29099089
650:See also
640:Limonene
586:linalool
582:limonene
535:limonene
531:camphene
496:cleaning
488:Limonene
484:cosmetic
480:perfumes
472:camphene
464:linalool
460:limonene
440:geraniol
416:volatile
369:cannabis
365:3-carene
353:sabinene
342:aerosols
311:linalool
271:peroxide
247:camphene
243:sabinene
230:Linalool
181:Limonene
114:linalool
98:geraniol
94:myrcenes
92:and the
28:isoprene
24:terpenes
2680:(DMAPP)
2410:Betulin
2208:Pimarol
2205:Pimaral
2152:Retinal
2147:Retinol
2116:Acyclic
2075:Cedrene
2070:Cadinol
2012:Borneol
2007:Camphor
1961:Menthol
1935:Halomon
1903:Acyclic
1871:Thujene
1805:Ocimene
1798:Acyclic
1604:Bibcode
1545:Bibcode
1461:5834703
1430:Bibcode
1393:8880786
1364:Bibcode
927:Bibcode
822:6150334
656:Terpene
608:camphor
594:menthol
539:Menthol
523:menthol
503:flavors
476:pinenes
468:menthol
456:myrcene
452:ocimene
428:camphor
397:oregano
389:pungent
381:thujene
338:forests
319:ocimene
259:borneol
255:Camphor
251:thujene
196:Carvone
166:Menthol
145:Myrcene
122:halomon
90:ocimene
68:in the
2602:(many)
2581:Lutein
2432:Acids
2123:Phytol
1981:Thymol
1915:Citral
1881:Carene
1852:Pinene
1765:Prenol
1712:forms)
1692:units)
1688:(# of
1638:
1630:
1622:
1579:
1571:
1563:
1519:
1511:
1503:
1468:
1458:
1450:
1400:
1390:
1382:
1307:
1239:
1214:
1177:
1136:
1126:
1093:
1056:
1020:
998:
988:
953:
945:
891:
852:
829:
819:
776:
743:
706:
598:thymol
555:Thymol
547:thymol
515:citral
432:citral
377:citrus
373:citral
367:gives
331:insect
317:, and
299:fruits
249:, and
239:carene
149:alkene
102:citral
82:sugars
2674:(IPP)
2491:) (8)
2403:Other
1710:trans
1636:S2CID
1577:S2CID
1517:S2CID
1260:(PDF)
996:S2CID
951:S2CID
913:(PDF)
357:spicy
321:have
303:herbs
287:barks
1858:and
1791:)(2)
1708:and
1684:and
1628:PMID
1620:ISSN
1569:PMID
1561:ISSN
1509:PMID
1501:ISSN
1466:PMID
1448:ISSN
1398:PMID
1380:ISSN
1336:2022
1305:ISBN
1237:ISBN
1212:PMID
1175:ISBN
1134:PMID
1124:ISBN
1091:ISBN
1054:ISBN
1018:ISBN
986:ISBN
943:PMID
889:ISBN
870:link
850:ISBN
827:PMID
774:ISBN
741:ISBN
704:ISBN
610:and
596:and
561:and
545:and
533:and
505:and
490:and
482:and
474:and
410:Uses
395:and
383:and
325:and
301:and
265:and
2323:(6)
2306:(5)
2168:cis
2109:(4)
2048:(3)
1744:(1)
1706:cis
1612:doi
1553:doi
1493:doi
1456:PMC
1438:doi
1426:115
1388:PMC
1372:doi
1204:doi
1116:doi
1083:doi
1046:doi
978:doi
935:doi
923:366
817:PMC
807:doi
766:doi
733:doi
729:209
696:doi
644:SOA
2696::
1789:16
1785:10
1783:(C
1753:(C
1634:.
1626:.
1618:.
1610:.
1600:92
1598:.
1575:.
1567:.
1559:.
1551:.
1541:16
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1464:.
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1436:.
1424:.
1420:.
1396:.
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1378:.
1370:.
1358:.
1354:.
1327:.
1299:.
1280:.
1262:.
1224:^
1210:.
1198:.
1154:.
1132:.
1122:.
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1079:37
1077:.
1052:.
1040:.
994:.
984:.
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866:}}
862:{{
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