1063:
757:
960:
926:
979:
1017:
1524:
1040:
444:
493:
945:
318:
998:
20:
1440:
213:, usually oxygen-containing. The terms terpenes and terpenoids are often used interchangeably, however. Furthermore, terpenes are produced from terpenoids and many terpenoids are produced from terpenes. Both have strong and often pleasant odors, which may protect their hosts or attract pollinators. The number of terpenes and terpenoids is estimated at 55,000 chemical entities.
569:. These two pathways are mutually exclusive in most organisms, except for some bacteria and land plants. In general, most archaea and eukaryotes use the MVA pathway, while bacteria mostly have the MEP pathway. IPP and DMAPP are final products of both MVA and MEP pathways and the relative abundance of these two isoprene units is enzymatically regulated in host organisms.
459:
Terpenes are colorless, although impure samples are often yellow. Boiling points scale with molecular size: terpenes, sesquiterpenes, and diterpenes respectively at 110, 160, and 220 °C. Being highly non-polar, they are insoluble in water. Being hydrocarbons, they are highly flammable and have
1076:
Terpenes may be classified by the number of isoprene units in the molecule; a prefix in the name indicates the number of isoprene pairs needed to assemble the molecule. Commonly, terpenes contain 2, 3, 4 or 6 isoprene units; the tetraterpenes (8 isoprene units) form a separate class of compounds
663:
The mevalonate (MVA) pathway is distributed in all three domains of life; archaea, bacteria and eukaryotes. The MVA pathway is universally distributed in archaea and non-photosynthetic eukaryotes, while the pathway is sparse in bacteria. In photosynthetic eukaryotes, some species possess the MVA
193:
had been called "camphene", but many other hydrocarbons of the same composition had had different names. Kekulé coined the term "terpene" in order to reduce the confusion. The name "terpene" is a shortened form of "terpentine", an obsolete spelling of
898:
Most terpenes and terpenoids feature C=C groups, i.e. they exhibit unsaturation. Since they carry no functional groups aside from their unsaturation, terpenes are structurally distinctive. The unsaturation is associated with di- and trisubstituted
337:
has been investigated as an alternative to the use of petroleum-based feedstocks. However, few of these applications have been commercialized. Many other terpenes, however, have smaller scale commercial and industrial applications. For example,
2337:
Koziol, Agata; Stryjewska, Agnieszka; Librowski, Tadeusz; Salat, Kinga; Gawel, Magdalena; Moniczewski, Andrzej; Lochynski, Stanislaw (2014). "An
Overview of the Pharmacological Properties and Potential Applications of Natural Monoterpenes".
474:(mono-, sesqui-, di-, etc.) have similar physical properties but tend to be more polar and hence slightly more soluble in water and somewhat less volatile than their terpene analogues. Highly polar derivatives of terpenoids are the
95:, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.
1977:"Quantitative Analysis of Bioactive Compounds from Aromatic Plants by Means of Dynamic Headspace Extraction and Multiple Headspace Extraction-Gas Chromatography-Mass Spectrometry: Quantitative analysis of bioactive compounds…"
1397:
Norisoprenoids, characterized by the shortening of a chain or ring by the removal of a methylene group or substitution of one or more methyl side chains by hydrogen atoms. These include the C
2302:
Steenackers, B.; De Cooman, L.; De Vos, D. (2015). "Chemical transformations of characteristic hop secondary metabolites in relation to beer properties and the brewing process: A review".
2604:
Kumari, I.; Ahmed, M.; Akhter, Y. (2017). "Evolution of catalytic microenvironment governs substrate and product diversity in trichodiene synthase and other terpene fold enzymes".
1472:
While terpenes and terpenoids occur widely, their extraction from natural sources is often problematic. Consequently, they are produced by chemical synthesis, usually from
2510:
Eschenmoser, Albert; Arigoni, Duilio (December 2005). "Revisited after 50 Years: The 'Stereochemical
Interpretation of the Biogenetic Isoprene Rule for the Triterpenes'".
284:. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.
679:
Also, the archaeal MVA pathway is not completely homologous to the eukaryotic MVA pathway. Instead, the eukaryotic MVA pathway is closer to the bacterial MVA pathway.
4122:
959:
2970:
Zelena, K.; Hardebusch, B.; Hülsdau, B.; Berger, R. G.; Zorn, H. (2009). "Generation of
Norisoprenoid Flavors from Carotenoids by Fungal Peroxidases".
2857:
Carotenoid-Derived Aroma
Compounds; chapter 13: Norisoprenoid Aglycon Composition of Leaves and Grape Berries from Muscat of Alexandria and Shiraz Cultivars
149:
has been investigated. Many terpenes have been shown to have pharmacological effects. Terpenes are also components of some traditional medicines, such as
3005:
Cabaroğlu, T.; Selli, S.; Canbaş, A.; Lepoutre, J.-P.; Günata, Z. (2003). "Wine flavor enhancement through the use of exogenous fungal glycosidases".
842:) units "head to tail" to form chains and rings. A few terpenes are linked “tail to tail”, and larger branched terpenes may be linked “tail to mid”.
1746:
1275:
1016:
664:
pathway, while others have the MEP pathway or both MVA and MEP pathways. This is due to the acquisition of the MEP pathway by a common ancestor of
4214:
4174:
468:), with viscosity ranging from 1 cP (à la water) to 6 cP. Terpenes are local irritants and can cause gastrointestinal disturbances if ingested.
4179:
775:
In both MVA and MEP pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. IPP and DMAPP condense to give
4239:
4224:
818:
The genomes of many plant species contain genes that encode terpenoid synthase enzymes imparting terpenes with their basic structure, and
3058:
4234:
4164:
1039:
1590:
Davis, Edward M.; Croteau, Rodney (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes".
2277:
1335:. Sesquarterpenes are typically microbial in their origin. Examples of sesquarterpenoids are ferrugicadiol and tetraprenylcurcumene.
2537:
Hayakawa, Hajime; Motoyama, Kento; Sobue, Fumiaki; Ito, Tomokazu; Kawaide, Hiroshi; Yoshimura, Tohru; Hemmi, Hisashi (2018-10-02).
2171:
978:
2872:
1670:
1607:
3089:
2690:
Boutanaev, A. M.; Moses, T.; Zi, J.; Nelson, D. R.; Mugford, S. T.; Peters, R. J.; Osbourn, A. (2015).
2187:"Scientists discover cloud-thickening chemicals in trees that could offer a new weapon in the fight against global warming"
716:
DMAPP are the end-products in either pathway and are the precursors of terpenoids with various carbon numbers (typically C
390:
to improve their control of the baseball. Terpenes are widely used as fragrances and flavors in consumer products such as
358:, another by-product of conifer tree resin, is widely used as an ingredient in a variety of industrial products, such as
1975:
Omar, Jone; Olivares, Maitane; Alonso, Ibone; Vallejo, Asier; Aizpurua-Olaizola, Oier; Etxebarria, Nestor (April 2016).
4129:
4068:
2803:
1763:
1496:. Others are prepared from those terpenes and terpenoids that are readily isolated in quantity, say from the paper and
807:
425:
Many terpenes have been shown to have pharmacological effects, although most studies are from laboratory research, and
944:
676:
that possessed the MEP pathway. The MVA and MEP pathways were selectively lost in individual photosynthetic lineages.
287:
Higher amounts of terpenes are released by trees in warmer weather, where they may function as a natural mechanism of
79:
for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated
2839:
2260:
1565:
1062:
4265:
1527:
Summary of an industrial route to geranyl alcohol from simple reagents (wrong arrow. this is not a retrosynthesis)
2024:"Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce"
261:
2793:
2539:"Modified mevalonate pathway of the archaeon Aeropyrum pernix proceeds via trans -anhydromevalonate 5-phosphate"
1824:
Chen, Ke; Baran, Phil S. (June 2009). "Total synthesis of eudesmane terpenes by site-selective C–H oxidations".
2214:
1888:
1405:
leaves and 7,8-dihydroionone derivatives, such as megastigmane-3,9-diol and 3-oxo-7,8-dihydro-α-ionol found in
2210:, with Special Reference to the Soldier Frontal Gland Secretion, Its Chemical Composition, and Use in Defense"
256:
of many types of plants and flowers. In plants, terpenes and terpenoids are important mediators of ecological
2243:
Silvestre, Armando J.D.; Gandini, Alessandro (2008). "Terpenes: Major
Sources, Properties and Applications".
2186:
4270:
3545:
1228:
787:
745:
4095:
3067:
1880:
764:
546:
925:
874:
respectively. The structural diversity of mono-, sesqui-, and diterpenes is a consequence of isomerism.
702:
4089:
760:
550:
1810:
1702:(By the name "terpene" we designate in general the hydrocarbons composed according to the formula C
1629:
3082:
3039:
302:
265:
217:
2375:"The Effects of Essential Oils and Terpenes in Relation to Their Routes of Intake and Application"
1729:
1381:
3500:
1305:
783:
741:
688:
566:
257:
92:
1687:
997:
429:
in humans is preliminary. Terpenes are also components of some traditional medicines, such as
422:
quality. Some form hydroperoxides that are valued as catalysts in the production of polymers.
3347:
1976:
1797:
1485:
1082:
776:
768:
737:
2931:
Vinholes, J.; Coimbra, M. A.; Rocha, S. M. (2009). "Rapid tool for assessment of C
1920:
3373:
2703:
2550:
2433:
2128:
Roberts, Susan C (2007). "Production and engineering of terpenoids in plant cell culture".
2084:
1833:
1402:
538:
497:
482:
447:
321:
Structure of natural rubber, exhibiting the characteristic methyl group on the alkene group
221:
1643:
8:
3075:
904:
887:
277:
269:
3048:
2707:
2554:
2437:
2088:
1837:
333:). The possibility that other terpenes could be used as precursors to produce synthetic
145:). The possibility that other terpenes could be used as precursors to produce synthetic
2913:
2831:
2774:
2749:
Ružička, Leopold (1953). "The isoprene rule and the
Biogenesis of terpenic compounds".
2726:
2691:
2667:
2640:
2581:
2538:
2492:
2449:
2401:
2374:
2252:
2105:
2072:
2004:
1857:
1724:
Natural
Products of Woody Plants: Chemicals Extraneous to the Lignocellulosic Cell Wall
1696:] (in German). Vol. 2. Erlangen, (Germany): Ferdinand Enke. pp. 464–465.
1617:
886:. Chiral compounds can exist as non-superposable mirror images, which exhibit distinct
651:
562:
460:
low specific gravity (float on water). They are tactilely light oils considerably less
415:
229:
23:
Many terpenes are derived commercially from conifer resins, such as those made by this
3018:
2889:
2445:
2351:
2048:
2023:
1722:
Dev, Sukh (1989). "Chapter 8. Isoprenoids: 8.1. Terpenoids.". In Rowe, John W. (ed.).
436:
Reflecting their defensive role in plants, terpenes are used as active ingredients of
4115:
2987:
2952:
2917:
2868:
2835:
2799:
2766:
2731:
2672:
2621:
2586:
2568:
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2406:
2355:
2319:
2256:
2153:
2145:
2110:
2053:
1996:
1957:
1849:
1759:
1700:"Mit dem Namen Terpene bezeichnen wir … unter verschiedenen Namen aufgeführt werden."
1666:
1603:
1561:
1489:
756:
558:
554:
426:
233:
3035:
2778:
2641:"Multi-Substrate Terpene Synthases: Their Occurrence and Physiological Significance"
2496:
2453:
2008:
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1988:
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1751:
1595:
1553:
387:
299:
210:
37:
2692:"Investigation of terpene diversification across multiple sequenced plant genomes"
2467:
Ruzicka, L. (1953). "The isoprene rule and the biogenesis of terpenic compounds".
2424:
Isman, M. B. (2000). "Plant essential oils for pest and disease management".
170:
3806:
3721:
3679:
3187:
2948:
2894:-Norisoprenoid Compounds in Riesling Wine Are Generated From Multiple Precursors"
2617:
1455:
1301:
1090:
819:
509:
306:
64:
1779:
4159:
4072:
4026:
3939:
3934:
3924:
3901:
3863:
3853:
3434:
2909:
2864:
1893:
1411:
1406:
1362:
1358:
1251:). Diterpenes also form the basis for biologically important compounds such as
1174:
665:
411:
399:
326:
225:
138:
107:
806:(as well as sesequiterpenoids and diterpenoids). Biosynthesis is mediated by
4259:
4017:
3983:
3978:
3929:
3159:
3062:. Vol. 26 (11th ed.). Cambridge University Press. pp. 647–652.
3053:
2572:
2149:
1755:
1473:
1420:
1366:
1007:
799:
673:
407:
379:
354:
and as a chemical feedstock (mainly for the production of other terpenoids).
288:
253:
2716:
2657:
2563:
2141:
2096:
1992:
1788:
1599:
1523:
291:. The clouds reflect sunlight, allowing the forest temperature to regulate.
4031:
3949:
3868:
3858:
3801:
3784:
3769:
3738:
3698:
3668:
3594:
3273:
3253:
2991:
2956:
2770:
2735:
2676:
2625:
2590:
2523:
2488:
2410:
2359:
2323:
2157:
2114:
2057:
2000:
1961:
1853:
1501:
1391:
1338:
1313:
1096:
669:
501:
465:
430:
402:, as well as food and drink products. For example, the aroma and flavor of
330:
150:
142:
123:
99:
91:. In plants, terpenes and terpenoids are important mediators of ecological
80:
3097:
2822:
Ludwiczuk, A.; Skalicka-Woźniak, K.; Georgiev, M.I. (2017). "Terpenoids".
2039:
1557:
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4003:
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3645:
3640:
3508:
3472:
3449:
3388:
3337:
3327:
3277:
3197:
2391:
2228:
2205:
1505:
1432:
968:, a monoterpene which exists as two isomers, is a major consistituent of
935:
908:
725:
557:
to each other. This pair of building blocks are produced by two distinct
505:
375:
371:
281:
1952:
1935:
1845:
4219:
4199:
3988:
3906:
3832:
3791:
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3660:
3650:
3444:
3439:
3392:
2762:
2480:
1513:
1460:
1428:
1424:
1309:
1281:
1212:
1144:
1049:
984:
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657:
475:
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383:
339:
273:
206:
195:
131:
115:
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3615:
3524:
3477:
3408:
3248:
3103:
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1244:
1194:
1140:
1116:
1026:
1022:
988:
803:
461:
437:
395:
202:
185:
was one. Previously, many hydrocarbons having the empirical formula C
154:
88:
1726:. Berlin and Heidelberg, Germany: Springer-Verlag. pp. 691–807.
1504:, which is readily obtainable from natural sources, is converted to
492:
450:, a terpenoid, not a terpene, is the active ingredient in marijuana.
4209:
4204:
3959:
3944:
3916:
3845:
3811:
3610:
3482:
3383:
3357:
3342:
3293:
3283:
3243:
3168:
3107:
2888:
Winterhalter, P.; Sefton, M. A.; Williams, P. J. (1990).
2855:
Günata, Z.; Wirth, J. L.; Guo, W.; Baumes, R. L. (2001).
2073:"Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity"
1497:
1493:
1354:
1297:
1240:
1232:
1198:
1190:
1168:
1160:
1136:
1124:
1112:
1045:
1003:
931:
850:
Strictly speaking all monoterpenes have the same chemical formula C
831:
698:
583:
522:
367:
252:. Terpenes and terpenoids are also the primary constituents of the
249:
245:
182:
382:
on the soles of their shoes to maintain traction on the floor, by
294:
Some insects use some terpenes as a form of defense. For example,
4189:
4169:
4149:
3837:
3827:
3748:
3569:
3564:
3492:
3487:
3429:
3424:
3378:
3352:
3288:
3227:
3222:
3148:
3139:
2821:
2204:
Nutting, W. L.; Blum, M. S.; Fales, H. M. (1974).
1517:
1509:
1477:
1449:
1317:
1308:. Squalene is then processed biosynthetically to generate either
1274:
prefix means two and a half.) An example of a sesterterpenoid is
1256:
1252:
1236:
1202:
1164:
1148:
1128:
1068:
1053:
950:
900:
858:. Similarly all sesquiterpenes and diterpenes have formulas of C
733:
593:
391:
363:
351:
334:
317:
295:
146:
127:
478:, which are linked to sugars. These are water-soluble solids.
4244:
4229:
4154:
3998:
3540:
3398:
3332:
3298:
3269:
3182:
3047:
1589:
1444:
1377:
1260:
1152:
1086:
965:
883:
736:. Synthesis of all higher terpenoids proceeds via formation of
624:
343:
2336:
2022:
Martin, D. M.; Gershenzon, J.; Bohlmann, J. (July 2003).
52:
19:
2969:
1439:
1353:. Biologically important tetraterpenoids include the acyclic
1304:, is derived from the reductive coupling of two molecules of
1248:
1120:
1030:
903:. Di- and trisubstituted alkenes resist polymerization (low
634:
614:
604:
355:
347:
84:
3004:
46:
4107:
1416:
1156:
1132:
729:
697:-methyl-D-erythritol 4-phosphate (MEP) pathway starts with
419:
403:
370:. Rosin is also used by violinists (and players of similar
24:
2887:
2301:
2245:
Monomers, Polymers and
Composites from Renewable Resources
1189:. Examples of sesquiterpenes and sesquiterpenoids include
2859:. ACS Symposium Series. Vol. 802. pp. 255–261.
2278:"What the heck is rosin – and why do violinists need it?"
1974:
751:
359:
201:
Although sometimes used interchangeably with "terpenes",
173:
to denote all hydrocarbons having the empirical formula C
2536:
2021:
1663:
General, Organic, and
Biological Chemistry, 4th edition
1380:
consists of polyisoprene in which the double bonds are
1163:
derive from monoterpenes. Examples of iridoids include
2689:
1936:"Terpenes, hormones and life: Isoprene rule revisited"
1111:. Examples of monoterpenes and monoterpenoids include
1085:. It may form oxygen-containing derivatives such as
525:, the structures and formulas of terpenes follow the
55:
4067:
Terpene synthase enzymes (many), having in common a
2930:
2854:
830:
Terpenes can be visualized as the result of linking
779:, the precursor to monoterpenes and monoterpenoids.
305:
through the use of a specialized mechanism called a
49:
43:
2795:
Terpenes: Flavors, Fragrances, Pharmaca, Pheromones
1550:
Terpenes: Flavors, Fragrances, Pharmaca, Pheromones
1547:
454:
40:
2509:
1270:units, are rare relative to the other sizes. (The
98:Terpenes are classified by the number of carbons:
2603:
516:
248:, for example, are derivatives of the triterpene
244:Terpenes are major biosynthetic building blocks.
4257:
2638:
2372:
2242:
2203:
209:) are modified terpenes that contain additional
2696:Proceedings of the National Academy of Sciences
2543:Proceedings of the National Academy of Sciences
1266:Sesterterpenes, terpenes having 25 carbons and
464:than familiar vegetable oils like corn oil (28
346:), obtained from the distillation of pine tree
325:The one terpene that has major applications is
309:, which ejects a resinous mixture of terpenes.
137:The one terpene that has major applications is
16:Class of oily organic compounds found in plants
3145:Iridoid glycosides (iridoids bound to a sugar)
1875:Grandin, Karl, ed. (1966). "Leopold Ružička".
1747:Ullmann's Encyclopedia of Industrial Chemistry
1231:. Examples of diterpenes and diterpenoids are
4123:
3083:
386:to keep their grips while performing, and by
2373:Koyama, Sachiko; Heinbockel, Thomas (2020).
1934:Hillier, Stephen G.; Lathe, Richard (2019).
1933:
1743:
2898:American Journal of Enology and Viticulture
2817:
2815:
2683:
2379:International Journal of Molecular Sciences
2121:
953:is a monoterpenoid, a modified monoterpene.
782:Geranyl pyrophosphate is also converted to
771:, precursor to all terpenes and terpenoids.
656:This pathway conjugates three molecules of
545:isoprene units are provided in the form of
228:and higher terpenes", "including the first
67:consisting of compounds with the formula (C
4130:
4116:
3090:
3076:
2972:Journal of Agricultural and Food Chemistry
2791:
1744:Eggersdorfer, Manfred (2000). "Terpenes".
1386:. Some plants produce a polyisoprene with
160:
3038:at the U.S. National Library of Medicine
2725:
2715:
2666:
2656:
2580:
2562:
2460:
2400:
2390:
2227:
2206:"Behavior of the North American Termite,
2104:
2070:
2047:
1951:
1927:
1823:
1787:
1665:. Houghton Mifflin Company. p. 337.
1077:called carotenoids; the others are rare.
813:
682:
374:instruments) to increase friction on the
169:was coined in 1866 by the German chemist
2812:
2798:. John Wiley & Sons. pp. 1–13.
1522:
1438:
1401:-norisoprenoid 3-oxo-α-ionol present in
755:
491:
442:
316:
18:
2748:
2466:
2276:Roberts, Maddy Shaw (22 January 2019).
2275:
2127:
1874:
1467:
1372:Polyterpenes consist of long chains of
1316:, the structural precursors to all the
4258:
2197:
1685:
1660:
1585:
1583:
1581:
1579:
1577:
1543:
1541:
1345:units and have the molecular formula C
1327:units and have the molecular formula C
1288:units and have the molecular formula C
1219:units and have the molecular formula C
1181:units and have the molecular formula C
1103:units and have the molecular formula C
907:) but are susceptible to acid-induced
752:Geranyl pyrophosphate phase and beyond
239:
4111:
3071:
1868:
1739:
1737:
645:
3045:
2751:Cellular and Molecular Life Sciences
2295:
2184:
1877:Nobel Lectures, Chemistry: 1922-1941
1081:The basic unit isoprene itself is a
882:Terpenes and terpenoids are usually
693:The non-mevalonate pathway or the 2-
2639:Pazouki, L.; Niinemets, Ü. (2016).
2340:Mini-Reviews in Medicinal Chemistry
1921:"The Nobel Prize in Chemistry 1939"
1721:
1574:
1538:
1512:. Citronellal is also converted to
1409:leaves (both grapes in the species
1052:and universal precursor to natural
260:. For example, they play a role in
126:is a major component of the common
13:
4069:terpene synthase N terminal domain
2832:10.1016/B978-0-12-802104-0.00011-1
2253:10.1016/B978-0-08-045316-3.00002-8
2071:Pichersky, E. (10 February 2006).
1734:
822:that modify this basic structure.
668:(algae + land plants) through the
14:
4282:
3029:
2352:10.2174/1389557514666141127145820
1594:. Vol. 209. pp. 53–95.
914:
2185:Adam, David (October 31, 2008).
1323:Sesquarterpenes are composed of
1061:
1038:
1015:
996:
977:
958:
943:
924:
455:Physical and chemical properties
36:
3007:Enzyme and Microbial Technology
2998:
2963:
2924:
2881:
2848:
2785:
2742:
2632:
2597:
2530:
2503:
2417:
2366:
2330:
2269:
2236:
2178:
2164:
2064:
2015:
1968:
1913:
1689:Lehrbuch der organischen Chemie
1029:, precursor to the diterpenoid
893:
487:
342:, a mixture of terpenes (e.g.,
312:
280:. They appear to play roles as
276:, as well as potentially plant-
262:plant defense against herbivory
153:, and as active ingredients of
2316:10.1016/j.foodchem.2014.09.139
2208:Tenuirostritermes tenuirostris
1817:
1780:"IUPAC Gold Book - terpenoids"
1772:
1715:
1679:
1654:
1636:
517:Isoprene as the building block
83:are produced predominantly by
1:
3019:10.1016/S0141-0229(03)00179-0
2792:Breitmaier, Eberhard (2006).
2446:10.1016/S0261-2194(00)00079-X
2172:"An Introduction to Terpenes"
1694:Textbook of Organic Chemistry
1531:
1427:), can be produced by fungal
1419:(responsible for some of the
1209:prefix means one and a half.)
4137:
3546:Geranylgeranyl pyrophosphate
3064:Survey of terpene chemistry.
2949:10.1016/j.chroma.2009.09.061
2618:10.1016/j.biochi.2017.10.003
1548:Eberhard Breitmaier (2006).
1229:geranylgeranyl pyrophosphate
1127:(present in citrus fruits),
877:
825:
788:geranylgeranyl pyrophosphate
767:(DMAPP) condense to produce
746:geranylgeranyl pyrophosphate
724:), side chains of (bacterio)
705:(G3P) as the carbon source.
567:non-mevalonate (MEP) pathway
122:), as examples. The terpene
7:
4096:Dimethylallyl pyrophosphate
3046:Pope, Frank George (1911).
2937:Journal of Chromatography A
1889:"Leopold Ružička Biography"
1881:Elsevier Publishing Company
1661:Stoker, H. Stephen (2007).
1459:, emit terpenes from their
1300:, the major constituent of
765:dimethylallyl pyrophosphate
547:dimethylallyl pyrophosphate
496:Biosynthetic conversion of
10:
4287:
2935:norisoprenoids in wines".
2910:10.5344/ajev.1990.41.4.277
2865:10.1021/bk-2002-0802.ch018
2645:Frontiers in Plant Science
890:such as odor or toxicity.
845:
703:glyceraldehyde 3-phosphate
686:
649:
537:, as described in 1953 by
521:Conceptually derived from
480:
303:ward off predatory insects
4145:
4090:Isopentenyl pyrophosphate
4082:
4060:
4044:Norisoprenoids (modified)
4043:
4016:
3968:
3915:
3900:
3883:
3820:
3747:
3737:
3720:
3659:
3633:
3603:
3578:
3557:
3533:
3523:
3462:
3417:
3366:
3320:
3311:
3262:
3236:
3215:
3196:
3158:
3115:
1500:industries. For example,
1488:, which is extended with
761:Isopentenyl pyrophosphate
553:(IPP). DMAPP and IPP are
551:isopentenyl pyrophosphate
4083:Activated isoprene forms
3884:Sesquarterpenes/oids (7)
3133:Monocyclic (single ring)
3040:Medical Subject Headings
1940:Journal of Endocrinology
1756:10.1002/14356007.a26_205
1296:. The linear triterpene
1093:analogous to terpenoids.
563:mevalonate (MVA) pathway
527:biogenetic isoprene rule
350:, is used as an organic
218:Nobel Prize in Chemistry
4266:Terpenes and terpenoids
3706:Secodehydroabietic acid
3059:Encyclopædia Britannica
2717:10.1073/pnas.1419547112
2658:10.3389/fpls.2016.01019
2564:10.1073/pnas.1809154115
2142:10.1038/nchembio.2007.8
2130:Nature Chemical Biology
2097:10.1126/science.1118510
1993:10.1111/1750-3841.13257
1981:Journal of Food Science
1789:10.1351/goldbook.T06279
1750:. Weinheim: Wiley-VCH.
1686:Kekulé, August (1866).
1600:10.1007/3-540-48146-X_2
1453:butterflies, like this
1390:double bonds, known as
161:History and terminology
3501:Farnesyl pyrophosphate
2524:10.1002/hlca.200590245
2512:Helvetica Chimica Acta
2423:
1805:Cite journal requires
1528:
1484:are condensed to give
1464:
1447:caterpillars of Genus
1306:farnesyl pyrophosphate
1033:, an anticancer agent.
987:is a monoterpenoid, a
814:Terpenes to terpenoids
784:farnesyl pyrophosphate
772:
742:farnesyl pyrophosphate
689:Non-mevalonate pathway
683:Non-mevalonate pathway
513:
451:
322:
28:
3703:Sandaracopimaric acid
3348:Geranyl pyrophosphate
2040:10.1104/pp.103.021196
1558:10.1002/9783527609949
1526:
1486:2-Methylbut-3-yn-2-ol
1442:
1071:is a sesquiterpenoid.
777:geranyl pyrophosphate
769:geranyl pyrophosphate
759:
738:geranyl pyrophosphate
541:and colleagues. The C
508:and to the terpinoid
495:
446:
406:comes, in part, from
320:
22:
3893:Tetraprenylcurcumene
3374:Grapefruit mercaptan
2392:10.3390/ijms21051558
1468:Industrial syntheses
1403:Muscat of Alexandria
905:ceiling temperatures
498:geranylpyrophosphate
483:Triterpene glycoside
448:Tetrahydrocannabinol
4271:Plant communication
3676:Dehydroabietic acid
3142:(cyclopentane ring)
2708:2015PNAS..112E..81B
2555:2018PNAS..11510034H
2549:(40): 10034–10039.
2438:2000CrPro..19..603I
2089:2006Sci...311..808P
1953:10.1530/JOE-19-0084
1886:Now available from
1846:10.1038/nature08043
1838:2009Natur.459..824C
1644:"What are Terpenes"
1361:, and the bicyclic
1227:. They derive from
888:physical properties
278:plant communication
240:Biological function
3136:Bicyclic (2 rings)
2763:10.1007/BF02167631
2481:10.1007/BF02167631
2247:. pp. 17–38.
2229:10.1155/1974/13854
1698:From pp. 464–465:
1529:
1465:
773:
652:Mevalonate pathway
646:Mevalonate pathway
559:metabolic pathways
555:structural isomers
514:
452:
323:
266:disease resistance
230:chemical synthesis
29:
4253:
4252:
4105:
4104:
4053:7,8-dihydroionone
4012:
4011:
3879:
3878:
3716:
3715:
3684:Lambertianic acid
3458:
3457:
3307:
3306:
3122:Acyclic (linear,
2984:10.1021/jf901438m
2978:(21): 9951–9955.
2943:(47): 8398–8403.
2874:978-0-8412-3729-2
2518:(12): 3011–3050.
2432:(8–10): 603–608.
2346:(14): 1156–1168.
2083:(5762): 808–811.
1832:(7248): 824–828.
1672:978-0-618-73063-6
1609:978-3-540-66573-1
1490:acetoacetic ester
1443:Second- or third-
1357:, the monocyclic
920:Selected terpenes
643:
642:
427:clinical research
400:cleaning products
388:baseball pitchers
298:of the subfamily
234:male sex hormones
224:"for his work on
211:functional groups
157:in agriculture.
63:) are a class of
4278:
4132:
4125:
4118:
4109:
4108:
3913:
3912:
3745:
3744:
3722:Sesterterpenoids
3688:Levopimaric acid
3550:Geranyl-linalool
3531:
3530:
3464:Sesquiterpenoids
3404:Perillyl alcohol
3318:
3317:
3213:
3212:
3092:
3085:
3078:
3069:
3068:
3063:
3051:
3049:"Terpenes"
3023:
3022:
3002:
2996:
2995:
2967:
2961:
2960:
2928:
2922:
2921:
2885:
2879:
2878:
2852:
2846:
2845:
2819:
2810:
2809:
2789:
2783:
2782:
2746:
2740:
2739:
2729:
2719:
2687:
2681:
2680:
2670:
2660:
2636:
2630:
2629:
2601:
2595:
2594:
2584:
2566:
2534:
2528:
2527:
2507:
2501:
2500:
2464:
2458:
2457:
2421:
2415:
2414:
2404:
2394:
2370:
2364:
2363:
2334:
2328:
2327:
2299:
2293:
2292:
2290:
2288:
2273:
2267:
2266:
2240:
2234:
2233:
2231:
2201:
2195:
2194:
2182:
2176:
2175:
2168:
2162:
2161:
2125:
2119:
2118:
2108:
2068:
2062:
2061:
2051:
2034:(3): 1586–1599.
2028:Plant Physiology
2019:
2013:
2012:
1987:(4): C867–C873.
1972:
1966:
1965:
1955:
1931:
1925:
1924:
1917:
1911:
1910:
1908:
1906:
1899:Nobel Foundation
1884:
1872:
1866:
1865:
1821:
1815:
1814:
1808:
1803:
1801:
1793:
1791:
1776:
1770:
1769:
1741:
1732:
1727:
1719:
1713:
1712:
1683:
1677:
1676:
1658:
1652:
1651:
1650:. 13 April 2021.
1648:rareterpenes.com
1640:
1634:
1633:
1627:
1623:
1621:
1613:
1587:
1572:
1571:
1545:
1476:. In one route,
1215:are composed of
1065:
1042:
1019:
1000:
981:
962:
947:
928:
820:cytochrome P450s
808:terpene synthase
790:, respectively C
572:
571:
500:to the terpenes
440:in agriculture.
418:), which affect
300:Nasutitermitinae
268:, attraction of
65:natural products
62:
61:
58:
57:
54:
51:
48:
45:
42:
4286:
4285:
4281:
4280:
4279:
4277:
4276:
4275:
4256:
4255:
4254:
4249:
4141:
4136:
4106:
4101:
4078:
4056:
4039:
4008:
3964:
3904:
3902:Tetraterpenoids
3896:
3875:
3816:
3807:Cholecalciferol
3733:
3730:Geranylfarnesol
3712:
3695:Neoabietic acid
3680:Isopimaric acid
3655:
3629:
3599:
3574:
3553:
3519:
3454:
3413:
3362:
3313:
3312:Monoterpenoids
3303:
3258:
3232:
3208:
3204:
3200:
3192:
3188:Isovaleric acid
3178:
3174:
3154:
3111:
3096:
3032:
3027:
3026:
3003:
2999:
2968:
2964:
2934:
2929:
2925:
2893:
2886:
2882:
2875:
2853:
2849:
2842:
2820:
2813:
2806:
2790:
2786:
2757:(10): 357–367.
2747:
2743:
2688:
2684:
2637:
2633:
2602:
2598:
2535:
2531:
2508:
2504:
2475:(10): 357–367.
2465:
2461:
2426:Crop Protection
2422:
2418:
2371:
2367:
2335:
2331:
2300:
2296:
2286:
2284:
2274:
2270:
2263:
2241:
2237:
2202:
2198:
2183:
2179:
2170:
2169:
2165:
2126:
2122:
2069:
2065:
2020:
2016:
1973:
1969:
1932:
1928:
1919:
1918:
1914:
1904:
1902:
1887:
1885:
1873:
1869:
1822:
1818:
1806:
1804:
1795:
1794:
1778:
1777:
1773:
1766:
1742:
1735:
1720:
1716:
1709:
1705:
1684:
1680:
1673:
1659:
1655:
1642:
1641:
1637:
1625:
1624:
1615:
1614:
1610:
1588:
1575:
1568:
1546:
1539:
1534:
1494:geranyl alcohol
1470:
1456:Papilio glaucus
1400:
1376:units. Natural
1352:
1348:
1334:
1330:
1302:shark liver oil
1295:
1291:
1276:geranylfarnesol
1226:
1222:
1188:
1184:
1110:
1106:
1091:isovaleric acid
1072:
1066:
1057:
1043:
1034:
1020:
1011:
1001:
992:
982:
973:
963:
954:
948:
939:
929:
917:
896:
880:
873:
869:
865:
861:
857:
853:
848:
841:
837:
828:
816:
797:
793:
754:
723:
719:
715:
711:
691:
685:
654:
648:
544:
539:Leopold Ružička
534:
519:
490:
485:
457:
416:β-caryophyllene
315:
307:fontanellar gun
242:
222:Leopold Ružička
220:was awarded to
192:
188:
180:
176:
163:
121:
113:
105:
87:, particularly
78:
74:
70:
39:
35:
17:
12:
11:
5:
4284:
4274:
4273:
4268:
4251:
4250:
4248:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4167:
4162:
4160:Bornyl acetate
4157:
4152:
4146:
4143:
4142:
4135:
4134:
4127:
4120:
4112:
4103:
4102:
4100:
4099:
4093:
4086:
4084:
4080:
4079:
4077:
4076:
4073:protein domain
4064:
4062:
4058:
4057:
4055:
4054:
4051:
4047:
4045:
4041:
4040:
4038:
4037:
4034:
4029:
4027:Natural rubber
4023:
4021:
4018:Polyterpenoids
4014:
4013:
4010:
4009:
4007:
4006:
4001:
3996:
3991:
3986:
3981:
3975:
3973:
3966:
3965:
3963:
3962:
3957:
3952:
3947:
3942:
3940:Delta-Carotene
3937:
3935:Gamma-Carotene
3932:
3927:
3925:Alpha-Carotene
3921:
3919:
3910:
3898:
3897:
3895:
3894:
3891:
3887:
3885:
3881:
3880:
3877:
3876:
3874:
3873:
3872:
3871:
3866:
3864:Betulinic acid
3861:
3856:
3854:Oleanolic acid
3848:
3843:
3840:
3835:
3830:
3824:
3822:
3818:
3817:
3815:
3814:
3809:
3804:
3799:
3794:
3789:
3788:
3787:
3782:
3777:
3772:
3767:
3766:Citrostadienol
3764:
3753:
3751:
3742:
3735:
3734:
3732:
3731:
3727:
3725:
3718:
3717:
3714:
3713:
3711:
3710:
3709:Palustric acid
3707:
3704:
3701:
3696:
3693:
3690:
3685:
3682:
3677:
3674:
3671:
3665:
3663:
3657:
3656:
3654:
3653:
3648:
3643:
3637:
3635:
3631:
3630:
3628:
3627:
3624:
3621:
3618:
3613:
3607:
3605:
3601:
3600:
3598:
3597:
3592:
3589:
3582:
3580:
3576:
3575:
3573:
3572:
3567:
3561:
3559:
3555:
3554:
3552:
3551:
3548:
3543:
3537:
3535:
3528:
3521:
3520:
3518:
3517:
3514:
3511:
3506:
3503:
3498:
3495:
3490:
3485:
3480:
3475:
3469:
3467:
3460:
3459:
3456:
3455:
3453:
3452:
3447:
3442:
3437:
3435:Bornyl acetate
3432:
3427:
3421:
3419:
3415:
3414:
3412:
3411:
3406:
3401:
3396:
3386:
3381:
3376:
3370:
3368:
3364:
3363:
3361:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3324:
3322:
3315:
3309:
3308:
3305:
3304:
3302:
3301:
3296:
3291:
3286:
3281:
3266:
3264:
3260:
3259:
3257:
3256:
3251:
3246:
3240:
3238:
3234:
3233:
3231:
3230:
3225:
3219:
3217:
3210:
3206:
3202:
3194:
3193:
3191:
3190:
3185:
3180:
3176:
3172:
3165:
3163:
3160:Hemiterpenoids
3156:
3155:
3153:
3152:
3146:
3143:
3137:
3134:
3131:
3119:
3117:
3113:
3112:
3095:
3094:
3087:
3080:
3072:
3066:
3065:
3054:Chisholm, Hugh
3043:
3031:
3030:External links
3028:
3025:
3024:
3013:(5): 581–587.
2997:
2962:
2932:
2923:
2904:(4): 277–283.
2891:
2880:
2873:
2847:
2840:
2811:
2805:978-3527317868
2804:
2784:
2741:
2702:(1): E81–E88.
2682:
2631:
2596:
2529:
2502:
2459:
2416:
2365:
2329:
2304:Food Chemistry
2294:
2268:
2261:
2235:
2222:(1): 167–177.
2196:
2177:
2163:
2136:(7): 387–395.
2120:
2063:
2014:
1967:
1926:
1912:
1894:nobelprize.org
1867:
1816:
1807:|journal=
1771:
1765:978-3527306732
1764:
1733:
1714:
1707:
1703:
1678:
1671:
1653:
1635:
1626:|journal=
1608:
1573:
1566:
1536:
1535:
1533:
1530:
1474:petrochemicals
1469:
1466:
1437:
1436:
1412:Vitis vinifera
1398:
1395:
1370:
1367:beta-carotenes
1359:gamma-carotene
1350:
1346:
1343:eight isoprene
1336:
1332:
1328:
1325:seven isoprene
1321:
1293:
1289:
1279:
1264:
1247:(precursor of
1224:
1220:
1210:
1186:
1182:
1179:three isoprene
1175:Sesquiterpenes
1172:
1108:
1104:
1094:
1074:
1073:
1067:
1060:
1058:
1044:
1037:
1035:
1021:
1014:
1012:
1002:
995:
993:
983:
976:
974:
964:
957:
955:
949:
942:
940:
930:
923:
921:
916:
915:Classification
913:
895:
892:
879:
876:
871:
867:
863:
859:
855:
851:
847:
844:
839:
835:
827:
824:
815:
812:
800:sesquiterpenes
798:precursors to
795:
791:
753:
750:
721:
717:
713:
709:
687:Main article:
684:
681:
666:Archaeplastida
650:Main article:
647:
644:
641:
640:
637:
631:
630:
627:
621:
620:
617:
611:
610:
607:
600:
599:
596:
590:
589:
586:
580:
579:
576:
542:
532:
518:
515:
489:
486:
456:
453:
408:sesquiterpenes
380:ballet dancers
327:natural rubber
314:
311:
254:essential oils
241:
238:
226:polymethylenes
190:
186:
178:
174:
162:
159:
139:natural rubber
119:
111:
108:sesquiterpenes
103:
76:
72:
68:
15:
9:
6:
4:
3:
2:
4283:
4272:
4269:
4267:
4264:
4263:
4261:
4246:
4243:
4241:
4238:
4236:
4233:
4231:
4228:
4226:
4223:
4221:
4218:
4216:
4215:Neophytadiene
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4175:Aromadendrene
4173:
4171:
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4147:
4144:
4140:
4133:
4128:
4126:
4121:
4119:
4114:
4113:
4110:
4097:
4094:
4091:
4088:
4087:
4085:
4081:
4074:
4070:
4066:
4065:
4063:
4059:
4052:
4050:3-oxo-α-ionol
4049:
4048:
4046:
4042:
4035:
4033:
4030:
4028:
4025:
4024:
4022:
4019:
4015:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3984:Cryptoxanthin
3982:
3980:
3979:Canthaxanthin
3977:
3976:
3974:
3971:
3967:
3961:
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3933:
3931:
3930:Beta-Carotene
3928:
3926:
3923:
3922:
3920:
3918:
3914:
3911:
3908:
3903:
3899:
3892:
3890:Ferrugicadiol
3889:
3888:
3886:
3882:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3851:
3849:
3847:
3844:
3842:Serratenediol
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3825:
3823:
3819:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3786:
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3765:
3763:
3760:
3759:
3758:
3755:
3754:
3752:
3750:
3746:
3743:
3740:
3739:Triterpenoids
3736:
3729:
3728:
3726:
3723:
3719:
3708:
3705:
3702:
3700:
3697:
3694:
3692:Mercusic acid
3691:
3689:
3686:
3683:
3681:
3678:
3675:
3673:Communic acid
3672:
3670:
3667:
3666:
3664:
3662:
3658:
3652:
3649:
3647:
3644:
3642:
3639:
3638:
3636:
3632:
3625:
3622:
3619:
3617:
3614:
3612:
3609:
3608:
3606:
3602:
3596:
3593:
3590:
3587:
3584:
3583:
3581:
3577:
3571:
3568:
3566:
3563:
3562:
3560:
3556:
3549:
3547:
3544:
3542:
3539:
3538:
3536:
3532:
3529:
3526:
3522:
3515:
3512:
3510:
3507:
3504:
3502:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3470:
3468:
3465:
3461:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3422:
3420:
3416:
3410:
3407:
3405:
3402:
3400:
3397:
3394:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3371:
3369:
3365:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3325:
3323:
3319:
3316:
3310:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3279:
3275:
3271:
3268:
3267:
3265:
3261:
3255:
3252:
3250:
3247:
3245:
3242:
3241:
3239:
3235:
3229:
3226:
3224:
3221:
3220:
3218:
3214:
3211:
3199:
3195:
3189:
3186:
3184:
3181:
3170:
3167:
3166:
3164:
3161:
3157:
3150:
3147:
3144:
3141:
3138:
3135:
3132:
3129:
3125:
3121:
3120:
3118:
3114:
3109:
3105:
3101:
3093:
3088:
3086:
3081:
3079:
3074:
3073:
3070:
3061:
3060:
3055:
3050:
3044:
3041:
3037:
3034:
3033:
3020:
3016:
3012:
3008:
3001:
2993:
2989:
2985:
2981:
2977:
2973:
2966:
2958:
2954:
2950:
2946:
2942:
2938:
2927:
2919:
2915:
2911:
2907:
2903:
2899:
2895:
2884:
2876:
2870:
2866:
2862:
2858:
2851:
2843:
2841:9780128021040
2837:
2833:
2829:
2825:
2824:Pharmacognosy
2818:
2816:
2807:
2801:
2797:
2796:
2788:
2780:
2776:
2772:
2768:
2764:
2760:
2756:
2752:
2745:
2737:
2733:
2728:
2723:
2718:
2713:
2709:
2705:
2701:
2697:
2693:
2686:
2678:
2674:
2669:
2664:
2659:
2654:
2650:
2646:
2642:
2635:
2627:
2623:
2619:
2615:
2611:
2607:
2600:
2592:
2588:
2583:
2578:
2574:
2570:
2565:
2560:
2556:
2552:
2548:
2544:
2540:
2533:
2525:
2521:
2517:
2513:
2506:
2498:
2494:
2490:
2486:
2482:
2478:
2474:
2470:
2463:
2455:
2451:
2447:
2443:
2439:
2435:
2431:
2427:
2420:
2412:
2408:
2403:
2398:
2393:
2388:
2384:
2380:
2376:
2369:
2361:
2357:
2353:
2349:
2345:
2341:
2333:
2325:
2321:
2317:
2313:
2309:
2305:
2298:
2283:
2279:
2272:
2264:
2262:9780080453163
2258:
2254:
2250:
2246:
2239:
2230:
2225:
2221:
2217:
2216:
2211:
2209:
2200:
2192:
2188:
2181:
2173:
2167:
2159:
2155:
2151:
2147:
2143:
2139:
2135:
2131:
2124:
2116:
2112:
2107:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2067:
2059:
2055:
2050:
2045:
2041:
2037:
2033:
2029:
2025:
2018:
2010:
2006:
2002:
1998:
1994:
1990:
1986:
1982:
1978:
1971:
1963:
1959:
1954:
1949:
1946:(2): R9–R22.
1945:
1941:
1937:
1930:
1922:
1916:
1900:
1896:
1895:
1890:
1882:
1879:. Amsterdam:
1878:
1871:
1863:
1859:
1855:
1851:
1847:
1843:
1839:
1835:
1831:
1827:
1820:
1812:
1799:
1790:
1785:
1781:
1775:
1767:
1761:
1757:
1753:
1749:
1748:
1740:
1738:
1731:
1725:
1718:
1711:
1710:(see §. 1540)
1701:
1695:
1691:
1690:
1682:
1674:
1668:
1664:
1657:
1649:
1645:
1639:
1631:
1619:
1611:
1605:
1601:
1597:
1593:
1586:
1584:
1582:
1580:
1578:
1569:
1567:9783527609949
1563:
1559:
1555:
1552:. Wiley-VCH.
1551:
1544:
1542:
1537:
1525:
1521:
1519:
1515:
1511:
1507:
1503:
1499:
1495:
1491:
1487:
1483:
1479:
1475:
1462:
1458:
1457:
1452:
1451:
1446:
1441:
1434:
1430:
1426:
1422:
1418:
1414:
1413:
1408:
1404:
1396:
1393:
1389:
1385:
1384:
1379:
1375:
1374:many isoprene
1371:
1368:
1364:
1360:
1356:
1344:
1340:
1339:Tetraterpenes
1337:
1326:
1322:
1319:
1315:
1311:
1307:
1303:
1299:
1287:
1283:
1280:
1277:
1273:
1269:
1268:five isoprene
1265:
1262:
1258:
1254:
1250:
1246:
1242:
1238:
1234:
1230:
1218:
1217:four isoprene
1214:
1211:
1208:
1204:
1200:
1196:
1192:
1180:
1176:
1173:
1170:
1166:
1162:
1158:
1154:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1122:
1118:
1114:
1102:
1098:
1095:
1092:
1088:
1084:
1080:
1079:
1078:
1070:
1064:
1059:
1055:
1051:
1047:
1041:
1036:
1032:
1028:
1024:
1018:
1013:
1009:
1008:sesquiterpene
1005:
999:
994:
990:
986:
980:
975:
971:
967:
961:
956:
952:
946:
941:
937:
933:
927:
922:
919:
918:
912:
910:
906:
902:
891:
889:
885:
875:
843:
833:
823:
821:
811:
809:
805:
801:
789:
785:
780:
778:
770:
766:
762:
758:
749:
747:
743:
739:
735:
731:
727:
706:
704:
700:
696:
690:
680:
677:
675:
674:cyanobacteria
672:of ancestral
671:
670:endosymbiosis
667:
661:
659:
653:
638:
636:
633:
632:
628:
626:
623:
622:
618:
616:
613:
612:
608:
606:
602:
601:
597:
595:
592:
591:
587:
585:
582:
581:
577:
574:
573:
570:
568:
564:
560:
556:
552:
548:
540:
536:
528:
524:
511:
507:
503:
499:
494:
484:
479:
477:
473:
469:
467:
463:
449:
445:
441:
439:
434:
432:
428:
423:
421:
417:
413:
409:
405:
401:
397:
393:
389:
385:
381:
377:
373:
369:
365:
361:
357:
353:
349:
345:
341:
336:
332:
328:
319:
310:
308:
304:
301:
297:
292:
290:
289:cloud seeding
285:
283:
279:
275:
271:
267:
263:
259:
255:
251:
247:
237:
235:
231:
227:
223:
219:
214:
212:
208:
204:
199:
197:
184:
172:
171:August Kekulé
168:
158:
156:
152:
148:
144:
140:
135:
133:
129:
125:
117:
109:
101:
96:
94:
90:
86:
82:
66:
60:
33:
26:
21:
4200:β-Bisabolene
4180:Eremophilene
4155:Delta-carene
4150:Endo-Borneol
4138:
4036:Gutta-balatá
4032:Gutta percha
3970:Xanthophylls
3950:Neurosporene
3869:Moronic acid
3859:Ursolic acid
3802:Testosterone
3785:Stigmasterol
3770:Cycloartenol
3757:Phytosterols
3699:Pimaric acid
3669:Abietic acid
3620:Manoyl oxide
3595:Salvinorin A
3585:
3525:Diterpenoids
3389:Thujaplicins
3314:(2,modified)
3254:Phellandrene
3198:Monoterpenes
3127:
3123:
3116:Basic forms:
3099:
3057:
3010:
3006:
3000:
2975:
2971:
2965:
2940:
2936:
2926:
2901:
2897:
2883:
2856:
2850:
2823:
2794:
2787:
2754:
2750:
2744:
2699:
2695:
2685:
2648:
2644:
2634:
2609:
2605:
2599:
2546:
2542:
2532:
2515:
2511:
2505:
2472:
2468:
2462:
2429:
2425:
2419:
2382:
2378:
2368:
2343:
2339:
2332:
2307:
2303:
2297:
2285:. Retrieved
2281:
2271:
2244:
2238:
2219:
2213:
2207:
2199:
2191:The Guardian
2190:
2180:
2166:
2133:
2129:
2123:
2080:
2076:
2066:
2031:
2027:
2017:
1984:
1980:
1970:
1943:
1939:
1929:
1915:
1903:. Retrieved
1892:
1876:
1870:
1829:
1825:
1819:
1798:cite journal
1774:
1745:
1723:
1717:
1699:
1697:
1693:
1688:
1681:
1662:
1656:
1647:
1638:
1592:Biosynthesis
1591:
1549:
1471:
1454:
1448:
1433:glycosidases
1410:
1392:gutta-percha
1387:
1382:
1373:
1342:
1324:
1314:cycloartenol
1286:six isoprene
1285:
1271:
1267:
1216:
1206:
1178:
1155:(present in
1147:(present in
1139:(present in
1131:(present in
1119:(present in
1101:two isoprene
1100:
1097:Monoterpenes
1075:
897:
894:Unsaturation
881:
849:
829:
817:
781:
774:
726:chlorophylls
707:
694:
692:
678:
662:
655:
619:MVA and MEP
549:(DMAPP) and
530:
526:
520:
488:Biosynthesis
471:
470:
458:
435:
431:aromatherapy
424:
331:polyisoprene
324:
313:Applications
293:
286:
282:antifeedants
258:interactions
243:
215:
200:
166:
164:
151:aromatherapy
143:polyisoprene
136:
124:alpha-pinene
100:monoterpenes
97:
93:interactions
81:hydrocarbons
31:
30:
4185:Longifolene
4004:Rubixanthin
3994:Astaxanthin
3955:Phytofluene
3907:Carotenoids
3797:Cholesterol
3792:Tocopherols
3762:Campesterol
3661:Resin acids
3646:Gibberellin
3641:Aphidicolin
3634:Tetracyclic
3509:Longifolene
3473:Artemisinin
3450:Umbellulone
3338:Citronellol
3328:Citronellal
2890:"Volatile C
2826:: 233–266.
2469:Experientia
2385:(5): 1558.
2310:: 742–756.
1730:see p. 691.
1506:citronellal
1429:peroxidases
1421:spice notes
1284:consist of
1282:Triterpenes
1177:consist of
1099:consist of
1083:hemiterpene
991:derivative.
936:monoterpene
911:formation.
909:carbocation
744:(FPP), and
588:MVA or MEP
510:α-terpineol
274:pollinators
207:isoprenoids
181:, of which
4260:Categories
4240:Ketoursene
4225:Aristolone
4220:Ferruginol
4210:β-Selinene
4205:γ-Cadinene
4165:α-Ylangene
3989:Zeaxanthin
3833:Lanosterol
3780:Sitosterol
3775:Sitostanol
3651:Paclitaxel
3558:Monocyclic
3445:Ascaridole
3440:Eucalyptol
3393:Hinokitiol
3367:Monocyclic
3237:Monocyclic
3104:terpenoids
2282:Classic FM
1532:References
1514:rose oxide
1461:osmeterium
1425:Chardonnay
1310:lanosterol
1213:Diterpenes
1195:farnesenes
1151:trees) or
1145:hinokitiol
1050:triterpene
985:Hinokitiol
970:turpentine
804:diterpenes
763:(IPP) and
658:acetyl CoA
481:See also:
476:glycosides
472:Terpenoids
438:pesticides
412:α-humulene
340:turpentine
270:mutualists
203:terpenoids
196:turpentine
155:pesticides
132:turpentine
116:diterpenes
4195:Valencene
4190:β-Guaiene
4170:α-Copaene
4061:Synthesis
3917:Carotenes
3812:Ecdysones
3616:Forskolin
3604:Tricyclic
3591:Epimanool
3516:Nootkatin
3513:Muurolene
3505:Juniperol
3497:Chanootin
3478:Bisabolol
3409:Carvacrol
3249:Terpinene
3151:(4 rings)
3098:Types of
2918:101007887
2606:Biochimie
2573:0027-8424
2150:1552-4450
1628:ignored (
1618:cite book
1482:acetylene
1245:taxadiene
1117:terpineol
1027:diterpene
1023:Taxadiene
989:tropolone
878:Chirality
826:Structure
712:IPP and C
578:Pathways
575:Organism
523:isoprenes
396:cosmetics
378:hair, by
368:adhesives
364:varnishes
216:The 1939
165:The term
4245:α-Amyrin
4235:Oleanene
4230:β-Amyrin
4139:Terpenes
3960:Phytoene
3945:Lycopene
3846:Squalane
3838:Saponins
3749:Steroids
3611:Cembrene
3588:-Abienol
3579:Bicyclic
3483:Cadinene
3418:Bicyclic
3384:p-Cymene
3358:Linalool
3343:Geraniol
3294:Sabinene
3284:Camphene
3263:Bicyclic
3244:Limonene
3228:Myrcenes
3169:Isoprene
3149:Steroids
3140:Iridoids
3108:isoprene
3100:terpenes
3036:Terpenes
2992:19817422
2957:19828152
2779:44195550
2771:13116962
2736:25502595
2677:27462341
2651:: 1019.
2626:29017925
2612:: 9–20.
2591:30224495
2497:44195550
2489:13116962
2454:39469817
2411:32106479
2360:25429661
2324:25442616
2158:17576426
2115:16469917
2058:12857838
2009:21443154
2001:26925555
1962:31051473
1854:19440196
1728: ;
1502:α-pinene
1498:tall oil
1492:to give
1355:lycopene
1341:contain
1318:steroids
1298:squalene
1241:cembrene
1233:cafestol
1199:farnesol
1191:humulene
1169:catalpol
1161:Iridoids
1159:trees).
1141:lavender
1137:linalool
1125:limonene
1113:geraniol
1054:steroids
1046:Squalene
1004:Humulene
932:Limonene
832:isoprene
748:(GGPP).
734:quinones
699:pyruvate
584:Bacteria
565:and the
506:β-pinene
502:α-pinene
410:(mainly
392:perfumes
384:gymnasts
335:polymers
296:termites
272:such as
250:squalene
246:Steroids
183:camphene
147:polymers
89:conifers
32:Terpenes
4098:(DMAPP)
3828:Betulin
3626:Pimarol
3623:Pimaral
3570:Retinal
3565:Retinol
3534:Acyclic
3493:Cedrene
3488:Cadinol
3430:Borneol
3425:Camphor
3379:Menthol
3353:Halomon
3321:Acyclic
3289:Thujene
3223:Ocimene
3216:Acyclic
3056:(ed.).
2727:4291660
2704:Bibcode
2668:4940680
2582:6176645
2551:Bibcode
2434:Bibcode
2402:7084246
2287:22 July
2106:2861909
2085:Bibcode
2077:Science
1862:4312428
1834:Bibcode
1518:menthol
1510:camphor
1478:acetone
1450:Papilio
1272:sester-
1257:retinal
1253:retinol
1237:kahweol
1207:sesqui-
1205:. (The
1203:geosmin
1165:aucubin
1149:cypress
1129:myrcene
1069:Geosmin
951:Carvone
901:alkenes
846:Formula
740:(GPP),
625:Animals
594:Archaea
529:or the
462:viscous
352:solvent
329:(i.e.,
167:terpene
141:(i.e.,
128:solvent
4020:(many)
3999:Lutein
3850:Acids
3541:Phytol
3399:Thymol
3333:Citral
3299:Carene
3270:Pinene
3183:Prenol
3130:forms)
3110:units)
3106:(# of
3042:(MeSH)
2990:
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1762:
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1407:Shiraz
1378:rubber
1363:alpha-
1261:phytol
1259:, and
1153:pinene
1121:lilacs
1087:prenol
966:Pinene
884:chiral
615:Plants
603:Green
561:: the
344:pinene
85:plants
4092:(IPP)
3909:) (8)
3821:Other
3128:trans
3052:. In
2914:S2CID
2775:S2CID
2493:S2CID
2450:S2CID
2005:S2CID
1858:S2CID
1692:[
1415:) or
1388:trans
1249:taxol
1031:taxol
866:and C
794:and C
730:hemes
635:Fungi
605:Algae
372:bowed
356:Rosin
348:resin
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2988:PMID
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2941:1216
2869:ISBN
2836:ISBN
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2767:PMID
2732:PMID
2673:PMID
2622:PMID
2587:PMID
2569:ISSN
2485:PMID
2407:PMID
2356:PMID
2320:PMID
2289:2022
2257:ISBN
2154:PMID
2146:ISSN
2111:PMID
2054:PMID
1997:PMID
1958:PMID
1907:2017
1850:PMID
1811:help
1760:ISBN
1667:ISBN
1630:help
1604:ISBN
1562:ISBN
1516:and
1508:and
1480:and
1417:wine
1365:and
1243:and
1167:and
1157:pine
1133:hops
1089:and
1048:, a
1025:, a
1006:, a
934:, a
802:and
786:and
732:and
720:to C
701:and
639:MVA
629:MVA
609:MEP
598:MVA
535:rule
504:and
420:beer
414:and
404:hops
398:and
366:and
360:inks
205:(or
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3741:(6)
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3586:cis
3527:(4)
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3162:(1)
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3015:doi
2980:doi
2945:doi
2906:doi
2861:doi
2828:doi
2759:doi
2722:PMC
2712:doi
2700:112
2663:PMC
2653:doi
2614:doi
2610:144
2577:PMC
2559:doi
2547:115
2520:doi
2477:doi
2442:doi
2397:PMC
2387:doi
2348:doi
2312:doi
2308:172
2249:doi
2224:doi
2138:doi
2101:PMC
2093:doi
2081:311
2044:PMC
2036:doi
2032:132
1989:doi
1948:doi
1944:242
1842:doi
1830:459
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1752:doi
1596:doi
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