1074:
768:
971:
937:
990:
1028:
1535:
1051:
455:
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329:
224:, 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.
1009:
580:. 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.
31:
1451:
470:
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
1087:
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
674:
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
204:
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
909:
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
348:
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,
2348:
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".
485:(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
106:, 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.
1988:"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…"
1408:
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
2313:
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".
2615:
Kumari, I.; Ahmed, M.; Akhter, Y. (2017). "Evolution of catalytic microenvironment governs substrate and product diversity in trichodiene synthase and other terpene fold enzymes".
1483:
While terpenes and terpenoids occur widely, their extraction from natural sources is often problematic. Consequently, they are produced by chemical synthesis, usually from
2521:
Eschenmoser, Albert; Arigoni, Duilio (December 2005). "Revisited after 50 Years: The 'Stereochemical
Interpretation of the Biogenetic Isoprene Rule for the Triterpenes'".
970:
295:. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.
1757:
690:
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.
1027:
2981:
Zelena, K.; Hardebusch, B.; Hülsdau, B.; Berger, R. G.; Zorn, H. (2009). "Generation of
Norisoprenoid Flavors from Carotenoids by Fungal Peroxidases".
2868:
Carotenoid-Derived Aroma
Compounds; chapter 13: Norisoprenoid Aglycon Composition of Leaves and Grape Berries from Muscat of Alexandria and Shiraz Cultivars
3069:
160:
has been investigated. Many terpenes have been shown to have pharmacological effects. Terpenes are also components of some traditional medicines, such as
3016:
Cabaroğlu, T.; Selli, S.; Canbaş, A.; Lepoutre, J.-P.; Günata, Z. (2003). "Wine flavor enhancement through the use of exogenous fungal glycosidases".
853:) 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”.
675:
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
1050:
479:), with viscosity ranging from 1 cP (à la water) to 6 cP. Terpenes are local irritants and can cause gastrointestinal disturbances if ingested.
989:
2883:
1681:
1618:
786:
In both MVA and MEP pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. IPP and DMAPP condense to give
3100:
829:
The genomes of many plant species contain genes that encode terpenoid synthase enzymes imparting terpenes with their basic structure, and
4140:
4079:
2814:
1774:
818:
1601:
Davis, Edward M.; Croteau, Rodney (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes".
2850:
2288:
2271:
1576:
1346:. Sesquarterpenes are typically microbial in their origin. Examples of sesquarterpenoids are ferrugicadiol and tetraprenylcurcumene.
1073:
2548:
Hayakawa, Hajime; Motoyama, Kento; Sobue, Fumiaki; Ito, Tomokazu; Kawaide, Hiroshi; Yoshimura, Tohru; Hemmi, Hisashi (2018-10-02).
2182:
4276:
955:
272:
2225:
2701:
Boutanaev, A. M.; Moses, T.; Zi, J.; Nelson, D. R.; Mugford, S. T.; Peters, R. J.; Osbourn, A. (2015).
2198:"Scientists discover cloud-thickening chemicals in trees that could offer a new weapon in the fight against global warming"
727:
DMAPP are the end-products in either pathway and are the precursors of terpenoids with various carbon numbers (typically C
401:
to improve their control of the baseball. Terpenes are widely used as fragrances and flavors in consumer products such as
369:, another by-product of conifer tree resin, is widely used as an ingredient in a variety of industrial products, such as
4281:
3556:
1986:
Omar, Jone; Olivares, Maitane; Alonso, Ibone; Vallejo, Asier; Aizpurua-Olaizola, Oier; Etxebarria, Nestor (April 2016).
1239:
798:
756:
1507:. Others are prepared from those terpenes and terpenoids that are readily isolated in quantity, say from the paper and
436:
Many terpenes have been shown to have pharmacological effects, although most studies are from laboratory research, and
4106:
1891:
775:
687:
that possessed the MEP pathway. The MVA and MEP pathways were selectively lost in individual photosynthetic lineages.
557:
298:
Higher amounts of terpenes are released by trees in warmer weather, where they may function as a natural mechanism of
90:
for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated
936:
713:
1538:
Summary of an industrial route to geranyl alcohol from simple reagents (wrong arrow. this is not a retrosynthesis)
4100:
2035:"Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce"
771:
561:
2804:
2550:"Modified mevalonate pathway of the archaeon Aeropyrum pernix proceeds via trans -anhydromevalonate 5-phosphate"
1835:
Chen, Ke; Baran, Phil S. (June 2009). "Total synthesis of eudesmane terpenes by site-selective C–H oxidations".
3093:
3050:
1899:
1416:
leaves and 7,8-dihydroionone derivatives, such as megastigmane-3,9-diol and 3-oxo-7,8-dihydro-α-ionol found in
313:
276:
228:
2221:, with Special Reference to the Soldier Frontal Gland Secretion, Its Chemical Composition, and Use in Defense"
1392:
267:
of many types of plants and flowers. In plants, terpenes and terpenoids are important mediators of ecological
2254:
Silvestre, Armando J.D.; Gandini, Alessandro (2008). "Terpenes: Major
Sources, Properties and Applications".
4133:
2197:
3511:
1316:
794:
752:
699:
577:
268:
103:
3078:
3358:
1808:
1496:
885:
respectively. The structural diversity of mono-, sesqui-, and diterpenes is a consequence of isomerism.
787:
779:
748:
1008:
767:
549:
232:
3384:
2714:
2561:
2444:
2095:
1844:
1413:
1286:
508:
493:
458:
1713:(By the name "terpene" we designate in general the hydrocarbons composed according to the formula C
4225:
4185:
3086:
915:
898:
288:
280:
4190:
2386:"The Effects of Essential Oils and Terpenes in Relation to Their Routes of Intake and Application"
2924:
2785:
2503:
2460:
2015:
1868:
1740:
1628:
662:
573:
426:
240:
4250:
4235:
4245:
4175:
4126:
2998:
2963:
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2846:
2810:
2777:
2742:
2683:
2632:
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2579:
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2417:
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2007:
1968:
1860:
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1500:
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in humans is preliminary. Terpenes are also components of some traditional medicines, such as
437:
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quality. Some form hydroperoxides that are valued as catalysts in the production of polymers.
244:
1987:
1093:
3698:
3474:
3414:
3025:
2990:
2955:
2942:
Vinholes, J.; Coimbra, M. A.; Rocha, S. M. (2009). "Rapid tool for assessment of C
2916:
2871:
2838:
2769:
2732:
2722:
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2624:
2587:
2569:
2530:
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2054:
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1958:
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1909:
1852:
1794:
1762:
1606:
1564:
398:
310:
221:
181:
48:
2139:
Roberts, Susan C (2007). "Production and engineering of terpenoids in plant cell culture".
1534:
332:
Structure of natural rubber, exhibiting the characteristic methyl group on the alkene group
3817:
3732:
3690:
3198:
1821:
1654:
1640:
1466:
1312:
1101:
830:
520:
317:
75:
3059:
2718:
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2448:
2099:
1848:
344:). The possibility that other terpenes could be used as precursors to produce synthetic
156:). The possibility that other terpenes could be used as precursors to produce synthetic
4170:
4083:
4037:
3950:
3945:
3935:
3912:
3874:
3864:
3445:
2842:
2760:
Ružička, Leopold (1953). "The isoprene rule and the
Biogenesis of terpenic compounds".
2737:
2702:
2678:
2651:
2592:
2549:
2412:
2385:
2263:
2116:
2083:
1904:
1735:
Natural
Products of Woody Plants: Chemicals Extraneous to the Lignocellulosic Cell Wall
1707:] (in German). Vol. 2. Erlangen, (Germany): Ferdinand Enke. pp. 464–465.
1422:
1417:
1373:
1369:
1185:
897:. Chiral compounds can exist as non-superposable mirror images, which exhibit distinct
676:
471:
low specific gravity (float on water). They are tactilely light oils considerably less
422:
410:
337:
236:
149:
118:
34:
Many terpenes are derived commercially from conifer resins, such as those made by this
3029:
2900:
2456:
2362:
2059:
2034:
1733:
Dev, Sukh (1989). "Chapter 8. Isoprenoids: 8.1. Terpenoids.". In Rowe, John W. (ed.).
447:
Reflecting their defensive role in plants, terpenes are used as active ingredients of
4270:
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3994:
3989:
3940:
3170:
3064:
2928:
1711:"Mit dem Namen Terpene bezeichnen wir … unter verschiedenen Namen aufgeführt werden."
1484:
1431:
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1018:
810:
684:
418:
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264:
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2789:
2652:"Multi-Substrate Terpene Synthases: Their Occurrence and Physiological Significance"
2507:
2464:
2019:
454:
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161:
153:
134:
110:
91:
2703:"Investigation of terpene diversification across multiple sequenced plant genomes"
2478:
Ruzicka, L. (1953). "The isoprene rule and the biogenesis of terpenic compounds".
2435:
Isman, M. B. (2000). "Plant essential oils for pest and disease management".
2959:
2905:-Norisoprenoid Compounds in Riesling Wine Are Generated From Multiple Precursors"
2628:
4195:
4014:
4004:
3980:
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3772:
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3656:
3651:
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3483:
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3348:
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1790:
1516:
1443:
946:
919:
736:
516:
503:
386:
382:
292:
2920:
2875:
1262:). Diterpenes also form the basis for biologically important compounds such as
4230:
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3785:
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3661:
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1471:
1439:
1435:
1320:
1292:
1223:
1155:
1060:
995:
980:
817:(as well as sesequiterpenoids and diterpenoids). Biosynthesis is mediated by
668:
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350:
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217:
206:
142:
126:
3073:. Vol. 26 (11th ed.). Cambridge University Press. pp. 647–652.
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and as a chemical feedstock (mainly for the production of other terpenoids).
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3626:
3535:
3488:
3419:
3259:
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2727:
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2574:
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2107:
2003:
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1255:
1205:
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1037:
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328:
302:. The clouds reflect sunlight, allowing the forest temperature to regulate.
213:
165:
99:
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2601:
2534:
2499:
2421:
2370:
2334:
2168:
2125:
2068:
2011:
1972:
1864:
413:, as well as food and drink products. For example, the aroma and flavor of
102:. In plants, terpenes and terpenoids are important mediators of ecological
2833:
Ludwiczuk, A.; Skalicka-Woźniak, K.; Georgiev, M.I. (2017). "Terpenoids".
2050:
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1243:
1209:
1201:
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1147:
1135:
1123:
1056:
1014:
979:, a monoterpene which exists as two isomers, is a major consistituent of
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842:
709:
594:
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to each other. This pair of building blocks are produced by two distinct
533:
378:
260:
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193:
1963:
1946:
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30:
17:
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was one. Previously, many hydrocarbons having the empirical formula C
1737:. Berlin and Heidelberg, Germany: Springer-Verlag. pp. 691–807.
1515:, which is readily obtainable from natural sources, is converted to
461:, a terpenoid, not a terpene, is the active ingredient in marijuana.
2899:
Winterhalter, P.; Sefton, M. A.; Williams, P. J. (1990).
2866:
Günata, Z.; Wirth, J. L.; Guo, W.; Baumes, R. L. (2001).
2084:"Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity"
861:
Strictly speaking all monoterpenes have the same chemical formula C
263:. Terpenes and terpenoids are also the primary constituents of the
1533:
1449:
1259:
1131:
1041:
766:
645:
625:
615:
502:
393:
on the soles of their shoes to maintain traction on the floor, by
366:
358:
327:
305:
Some insects use some terpenes as a form of defense. For example,
95:
29:
2215:
Nutting, W. L.; Blum, M. S.; Fales, H. M. (1974).
1319:. Squalene is then processed biosynthetically to generate either
1285:
prefix means two and a half.) An example of a sesterterpenoid is
869:. Similarly all sesquiterpenes and diterpenes have formulas of C
1427:
1167:
1143:
740:
489:, which are linked to sugars. These are water-soluble solids.
430:
414:
35:
4122:
3082:
3058:
747:. Synthesis of all higher terpenoids proceeds via formation of
2033:
Martin, D. M.; Gershenzon, J.; Bohlmann, J. (July 2003).
370:
63:
1364:. Biologically important tetraterpenoids include the acyclic
1315:, is derived from the reductive coupling of two molecules of
914:. Di- and trisubstituted alkenes resist polymerization (low
57:
4118:
708:-methyl-D-erythritol 4-phosphate (MEP) pathway starts with
381:. Rosin is also used by violinists (and players of similar
2256:
Monomers, Polymers and
Composites from Renewable Resources
1200:. Examples of sesquiterpenes and sesquiterpenoids include
2870:. ACS Symposium Series. Vol. 802. pp. 255–261.
2289:"What the heck is rosin – and why do violinists need it?"
212:
Although sometimes used interchangeably with "terpenes",
184:
to denote all hydrocarbons having the empirical formula C
1674:
General, Organic, and
Biological Chemistry, 4th edition
1391:
consists of polyisoprene in which the double bonds are
1174:
derive from monoterpenes. Examples of iridoids include
1947:"Terpenes, hormones and life: Isoprene rule revisited"
1122:. Examples of monoterpenes and monoterpenoids include
1096:. It may form oxygen-containing derivatives such as
536:, the structures and formulas of terpenes follow the
66:
4078:
Terpene synthase enzymes (many), having in common a
841:
Terpenes can be visualized as the result of linking
790:, the precursor to monoterpenes and monoterpenoids.
316:
through the use of a specialized mechanism called a
60:
54:
4093:
4071:
4054:
4027:
3979:
3926:
3911:
3894:
3831:
3758:
3748:
3731:
3670:
3644:
3614:
3589:
3568:
3544:
3534:
3473:
3428:
3377:
3331:
3322:
3273:
3247:
3226:
3207:
3169:
3126:
2806:
Terpenes: Flavors, Fragrances, Pharmaca, Pheromones
1561:
Terpenes: Flavors, Fragrances, Pharmaca, Pheromones
51:
1281:units, are rare relative to the other sizes. (The
109:Terpenes are classified by the number of carbons:
259:, for example, are derivatives of the triterpene
255:Terpenes are major biosynthetic building blocks.
220:) are modified terpenes that contain additional
2707:Proceedings of the National Academy of Sciences
2554:Proceedings of the National Academy of Sciences
1277:Sesterterpenes, terpenes having 25 carbons and
475:than familiar vegetable oils like corn oil (28
357:), obtained from the distillation of pine tree
336:The one terpene that has major applications is
320:, which ejects a resinous mixture of terpenes.
148:The one terpene that has major applications is
27:Class of oily organic compounds found in plants
3156:Iridoid glycosides (iridoids bound to a sugar)
1886:Grandin, Karl, ed. (1966). "Leopold Ružička".
1758:Ullmann's Encyclopedia of Industrial Chemistry
1242:. Examples of diterpenes and diterpenoids are
4134:
3094:
397:to keep their grips while performing, and by
8:
2384:Koyama, Sachiko; Heinbockel, Thomas (2020).
1945:Hillier, Stephen G.; Lathe, Richard (2019).
2909:American Journal of Enology and Viticulture
2828:
2826:
2390:International Journal of Molecular Sciences
964:is a monoterpenoid, a modified monoterpene.
793:Geranyl pyrophosphate is also converted to
782:, precursor to all terpenes and terpenoids.
667:This pathway conjugates three molecules of
556:isoprene units are provided in the form of
239:and higher terpenes", "including the first
78:consisting of compounds with the formula (C
4141:
4127:
4119:
3923:
3755:
3541:
3328:
3223:
3101:
3087:
3079:
2983:Journal of Agricultural and Food Chemistry
1755:Eggersdorfer, Manfred (2000). "Terpenes".
1397:. Some plants produce a polyisoprene with
3049:at the U.S. National Library of Medicine
2736:
2726:
2677:
2667:
2591:
2573:
2411:
2401:
2238:
2217:"Behavior of the North American Termite,
2115:
2058:
1962:
1798:
1676:. Houghton Mifflin Company. p. 337.
1088:called carotenoids; the others are rare.
385:instruments) to increase friction on the
180:was coined in 1866 by the German chemist
2809:. John Wiley & Sons. pp. 1–13.
1412:-norisoprenoid 3-oxo-α-ionol present in
582:
453:
2287:Roberts, Maddy Shaw (22 January 2019).
1548:
1383:Polyterpenes consist of long chains of
1327:, the structural precursors to all the
929:
1817:
1806:
1636:
1626:
1596:
1594:
1592:
1590:
1588:
1554:
1552:
1356:units and have the molecular formula C
1338:units and have the molecular formula C
1299:units and have the molecular formula C
1230:units and have the molecular formula C
1192:units and have the molecular formula C
1114:units and have the molecular formula C
918:) but are susceptible to acid-induced
763:Geranyl pyrophosphate phase and beyond
1750:
1748:
7:
2762:Cellular and Molecular Life Sciences
1888:Nobel Lectures, Chemistry: 1922-1941
1092:The basic unit isoprene itself is a
893:Terpenes and terpenoids are usually
704:The non-mevalonate pathway or the 2-
2650:Pazouki, L.; Niinemets, Ü. (2016).
2351:Mini-Reviews in Medicinal Chemistry
1932:"The Nobel Prize in Chemistry 1939"
1523:. Citronellal is also converted to
1420:leaves (both grapes in the species
1063:and universal precursor to natural
271:. For example, they play a role in
137:is a major component of the common
4080:terpene synthase N terminal domain
2843:10.1016/B978-0-12-802104-0.00011-1
2264:10.1016/B978-0-08-045316-3.00002-8
2082:Pichersky, E. (10 February 2006).
833:that modify this basic structure.
679:(algae + land plants) through the
25:
2363:10.2174/1389557514666141127145820
1605:. Vol. 209. pp. 53–95.
2196:Adam, David (October 31, 2008).
1334:Sesquarterpenes are composed of
1072:
1049:
1026:
1007:
988:
969:
954:
935:
466:Physical and chemical properties
47:
3018:Enzyme and Microbial Technology
1700:Lehrbuch der organischen Chemie
1040:, precursor to the diterpenoid
353:, a mixture of terpenes (e.g.,
291:. They appear to play roles as
287:, as well as potentially plant-
273:plant defense against herbivory
164:, and as active ingredients of
2327:10.1016/j.foodchem.2014.09.139
2219:Tenuirostritermes tenuirostris
1791:"IUPAC Gold Book - terpenoids"
528:Isoprene as the building block
94:are produced predominantly by
1:
3030:10.1016/S0141-0229(03)00179-0
2803:Breitmaier, Eberhard (2006).
2457:10.1016/S0261-2194(00)00079-X
2183:"An Introduction to Terpenes"
1705:Textbook of Organic Chemistry
1438:), can be produced by fungal
1430:(responsible for some of the
1220:prefix means one and a half.)
3557:Geranylgeranyl pyrophosphate
3075:Survey of terpene chemistry.
2960:10.1016/j.chroma.2009.09.061
2629:10.1016/j.biochi.2017.10.003
1559:Eberhard Breitmaier (2006).
1240:geranylgeranyl pyrophosphate
1138:(present in citrus fruits),
799:geranylgeranyl pyrophosphate
778:(DMAPP) condense to produce
757:geranylgeranyl pyrophosphate
735:), side chains of (bacterio)
716:(G3P) as the carbon source.
578:non-mevalonate (MEP) pathway
133:), as examples. The terpene
4107:Dimethylallyl pyrophosphate
3057:Pope, Frank George (1911).
2948:Journal of Chromatography A
1900:"Leopold Ružička Biography"
1892:Elsevier Publishing Company
1672:Stoker, H. Stephen (2007).
1470:, emit terpenes from their
1311:, the major constituent of
776:dimethylallyl pyrophosphate
558:dimethylallyl pyrophosphate
507:Biosynthetic conversion of
4298:
2946:norisoprenoids in wines".
2921:10.5344/ajev.1990.41.4.277
2876:10.1021/bk-2002-0802.ch018
2656:Frontiers in Plant Science
901:such as odor or toxicity.
714:glyceraldehyde 3-phosphate
697:
660:
548:, as described in 1953 by
532:Conceptually derived from
491:
314:ward off predatory insects
4156:
4101:Isopentenyl pyrophosphate
4055:Norisoprenoids (modified)
1511:industries. For example,
1499:, which is extended with
772:Isopentenyl pyrophosphate
564:(IPP). DMAPP and IPP are
562:isopentenyl pyrophosphate
4094:Activated isoprene forms
3895:Sesquarterpenes/oids (7)
3144:Monocyclic (single ring)
3051:Medical Subject Headings
1951:Journal of Endocrinology
1767:10.1002/14356007.a26_205
1307:. The linear triterpene
1104:analogous to terpenoids.
574:mevalonate (MVA) pathway
538:biogenetic isoprene rule
361:, is used as an organic
229:Nobel Prize in Chemistry
4277:Terpenes and terpenoids
3717:Secodehydroabietic acid
3070:Encyclopædia Britannica
2728:10.1073/pnas.1419547112
2669:10.3389/fpls.2016.01019
2575:10.1073/pnas.1809154115
2153:10.1038/nchembio.2007.8
2141:Nature Chemical Biology
2108:10.1126/science.1118510
2004:10.1111/1750-3841.13257
1992:Journal of Food Science
1800:10.1351/goldbook.T06279
1761:. Weinheim: Wiley-VCH.
1697:Kekulé, August (1866).
1611:10.1007/3-540-48146-X_2
1464:butterflies, like this
1401:double bonds, known as
172:History and terminology
3512:Farnesyl pyrophosphate
2535:10.1002/hlca.200590245
2523:Helvetica Chimica Acta
1816:Cite journal requires
1539:
1495:are condensed to give
1475:
1458:caterpillars of Genus
1317:farnesyl pyrophosphate
1044:, an anticancer agent.
998:is a monoterpenoid, a
825:Terpenes to terpenoids
795:farnesyl pyrophosphate
783:
753:farnesyl pyrophosphate
700:Non-mevalonate pathway
694:Non-mevalonate pathway
524:
462:
333:
39:
3714:Sandaracopimaric acid
3359:Geranyl pyrophosphate
2051:10.1104/pp.103.021196
1569:10.1002/9783527609949
1537:
1497:2-Methylbut-3-yn-2-ol
1453:
1082:is a sesquiterpenoid.
788:geranyl pyrophosphate
780:geranyl pyrophosphate
770:
749:geranyl pyrophosphate
552:and colleagues. The C
519:and to the terpinoid
506:
457:
417:comes, in part, from
331:
33:
3904:Tetraprenylcurcumene
3385:Grapefruit mercaptan
2403:10.3390/ijms21051558
1479:Industrial syntheses
1414:Muscat of Alexandria
916:ceiling temperatures
509:geranylpyrophosphate
494:Triterpene glycoside
459:Tetrahydrocannabinol
4282:Plant communication
3687:Dehydroabietic acid
3153:(cyclopentane ring)
2719:2015PNAS..112E..81B
2566:2018PNAS..11510034H
2560:(40): 10034–10039.
2449:2000CrPro..19..603I
2100:2006Sci...311..808P
1964:10.1530/JOE-19-0084
1897:Now available from
1857:10.1038/nature08043
1849:2009Natur.459..824C
1655:"What are Terpenes"
1372:, and the bicyclic
1238:. They derive from
899:physical properties
289:plant communication
251:Biological function
3147:Bicyclic (2 rings)
2774:10.1007/BF02167631
2492:10.1007/BF02167631
2258:. pp. 17–38.
2240:10.1155/1974/13854
1709:From pp. 464–465:
1540:
1476:
784:
663:Mevalonate pathway
657:Mevalonate pathway
570:metabolic pathways
566:structural isomers
525:
463:
334:
277:disease resistance
241:chemical synthesis
40:
4264:
4263:
4116:
4115:
4064:7,8-dihydroionone
4023:
4022:
3890:
3889:
3727:
3726:
3695:Lambertianic acid
3469:
3468:
3318:
3317:
3133:Acyclic (linear,
2995:10.1021/jf901438m
2989:(21): 9951–9955.
2954:(47): 8398–8403.
2885:978-0-8412-3729-2
2529:(12): 3011–3050.
2443:(8–10): 603–608.
2357:(14): 1156–1168.
2094:(5762): 808–811.
1843:(7248): 824–828.
1683:978-0-618-73063-6
1620:978-3-540-66573-1
1501:acetoacetic ester
1454:Second- or third-
1368:, the monocyclic
931:Selected terpenes
654:
653:
438:clinical research
411:cleaning products
399:baseball pitchers
309:of the subfamily
245:male sex hormones
235:"for his work on
222:functional groups
168:in agriculture.
74:) are a class of
16:(Redirected from
4289:
4143:
4136:
4129:
4120:
3924:
3756:
3733:Sesterterpenoids
3699:Levopimaric acid
3561:Geranyl-linalool
3542:
3475:Sesquiterpenoids
3415:Perillyl alcohol
3329:
3224:
3103:
3096:
3089:
3080:
3074:
3062:
3060:"Terpenes"
3034:
3033:
3013:
3007:
3006:
2978:
2972:
2971:
2939:
2933:
2932:
2896:
2890:
2889:
2863:
2857:
2856:
2830:
2821:
2820:
2800:
2794:
2793:
2757:
2751:
2750:
2740:
2730:
2698:
2692:
2691:
2681:
2671:
2647:
2641:
2640:
2612:
2606:
2605:
2595:
2577:
2545:
2539:
2538:
2518:
2512:
2511:
2475:
2469:
2468:
2432:
2426:
2425:
2415:
2405:
2381:
2375:
2374:
2345:
2339:
2338:
2310:
2304:
2303:
2301:
2299:
2284:
2278:
2277:
2251:
2245:
2244:
2242:
2212:
2206:
2205:
2193:
2187:
2186:
2179:
2173:
2172:
2136:
2130:
2129:
2119:
2079:
2073:
2072:
2062:
2045:(3): 1586–1599.
2039:Plant Physiology
2030:
2024:
2023:
1998:(4): C867–C873.
1983:
1977:
1976:
1966:
1942:
1936:
1935:
1928:
1922:
1921:
1919:
1917:
1910:Nobel Foundation
1895:
1883:
1877:
1876:
1832:
1826:
1825:
1819:
1814:
1812:
1804:
1802:
1787:
1781:
1780:
1752:
1743:
1738:
1730:
1724:
1723:
1694:
1688:
1687:
1669:
1663:
1662:
1661:. 13 April 2021.
1659:rareterpenes.com
1651:
1645:
1644:
1638:
1634:
1632:
1624:
1598:
1583:
1582:
1556:
1487:. In one route,
1226:are composed of
1076:
1053:
1030:
1011:
992:
973:
958:
939:
831:cytochrome P450s
819:terpene synthase
801:, respectively C
583:
511:to the terpenes
451:in agriculture.
429:), which affect
311:Nasutitermitinae
279:, attraction of
76:natural products
73:
72:
69:
68:
65:
62:
59:
56:
53:
21:
4297:
4296:
4292:
4291:
4290:
4288:
4287:
4286:
4267:
4266:
4265:
4260:
4152:
4147:
4117:
4112:
4089:
4067:
4050:
4019:
3975:
3915:
3913:Tetraterpenoids
3907:
3886:
3827:
3818:Cholecalciferol
3744:
3741:Geranylfarnesol
3723:
3706:Neoabietic acid
3691:Isopimaric acid
3666:
3640:
3610:
3585:
3564:
3530:
3465:
3424:
3373:
3324:
3323:Monoterpenoids
3314:
3269:
3243:
3219:
3215:
3211:
3203:
3199:Isovaleric acid
3189:
3185:
3165:
3122:
3107:
3056:
3043:
3038:
3037:
3015:
3014:
3010:
2980:
2979:
2975:
2945:
2941:
2940:
2936:
2904:
2898:
2897:
2893:
2886:
2865:
2864:
2860:
2853:
2832:
2831:
2824:
2817:
2802:
2801:
2797:
2768:(10): 357–367.
2759:
2758:
2754:
2700:
2699:
2695:
2649:
2648:
2644:
2614:
2613:
2609:
2547:
2546:
2542:
2520:
2519:
2515:
2486:(10): 357–367.
2477:
2476:
2472:
2437:Crop Protection
2434:
2433:
2429:
2383:
2382:
2378:
2347:
2346:
2342:
2312:
2311:
2307:
2297:
2295:
2286:
2285:
2281:
2274:
2253:
2252:
2248:
2214:
2213:
2209:
2195:
2194:
2190:
2181:
2180:
2176:
2138:
2137:
2133:
2081:
2080:
2076:
2032:
2031:
2027:
1985:
1984:
1980:
1944:
1943:
1939:
1930:
1929:
1925:
1915:
1913:
1898:
1896:
1885:
1884:
1880:
1834:
1833:
1829:
1815:
1805:
1789:
1788:
1784:
1777:
1754:
1753:
1746:
1732:
1731:
1727:
1720:
1716:
1696:
1695:
1691:
1684:
1671:
1670:
1666:
1653:
1652:
1648:
1635:
1625:
1621:
1600:
1599:
1586:
1579:
1558:
1557:
1550:
1545:
1505:geranyl alcohol
1481:
1467:Papilio glaucus
1411:
1387:units. Natural
1363:
1359:
1345:
1341:
1313:shark liver oil
1306:
1302:
1287:geranylfarnesol
1237:
1233:
1199:
1195:
1121:
1117:
1102:isovaleric acid
1083:
1077:
1068:
1054:
1045:
1031:
1022:
1012:
1003:
993:
984:
974:
965:
959:
950:
940:
928:
907:
891:
884:
880:
876:
872:
868:
864:
859:
852:
848:
839:
827:
808:
804:
765:
734:
730:
726:
722:
702:
696:
665:
659:
555:
550:Leopold Ružička
545:
530:
501:
496:
468:
427:β-caryophyllene
326:
318:fontanellar gun
253:
233:Leopold Ružička
231:was awarded to
203:
199:
191:
187:
174:
132:
124:
116:
98:, particularly
89:
85:
81:
50:
46:
28:
23:
22:
15:
12:
11:
5:
4295:
4293:
4285:
4284:
4279:
4269:
4268:
4262:
4261:
4259:
4258:
4253:
4248:
4243:
4238:
4233:
4228:
4223:
4218:
4213:
4208:
4203:
4198:
4193:
4188:
4183:
4178:
4173:
4171:Bornyl acetate
4168:
4163:
4157:
4154:
4153:
4148:
4146:
4145:
4138:
4131:
4123:
4114:
4113:
4111:
4110:
4104:
4097:
4095:
4091:
4090:
4088:
4087:
4084:protein domain
4075:
4073:
4069:
4068:
4066:
4065:
4062:
4058:
4056:
4052:
4051:
4049:
4048:
4045:
4040:
4038:Natural rubber
4034:
4032:
4029:Polyterpenoids
4025:
4024:
4021:
4020:
4018:
4017:
4012:
4007:
4002:
3997:
3992:
3986:
3984:
3977:
3976:
3974:
3973:
3968:
3963:
3958:
3953:
3951:Delta-Carotene
3948:
3946:Gamma-Carotene
3943:
3938:
3936:Alpha-Carotene
3932:
3930:
3921:
3909:
3908:
3906:
3905:
3902:
3898:
3896:
3892:
3891:
3888:
3887:
3885:
3884:
3883:
3882:
3877:
3875:Betulinic acid
3872:
3867:
3865:Oleanolic acid
3859:
3854:
3851:
3846:
3841:
3835:
3833:
3829:
3828:
3826:
3825:
3820:
3815:
3810:
3805:
3800:
3799:
3798:
3793:
3788:
3783:
3778:
3777:Citrostadienol
3775:
3764:
3762:
3753:
3746:
3745:
3743:
3742:
3738:
3736:
3729:
3728:
3725:
3724:
3722:
3721:
3720:Palustric acid
3718:
3715:
3712:
3707:
3704:
3701:
3696:
3693:
3688:
3685:
3682:
3676:
3674:
3668:
3667:
3665:
3664:
3659:
3654:
3648:
3646:
3642:
3641:
3639:
3638:
3635:
3632:
3629:
3624:
3618:
3616:
3612:
3611:
3609:
3608:
3603:
3600:
3593:
3591:
3587:
3586:
3584:
3583:
3578:
3572:
3570:
3566:
3565:
3563:
3562:
3559:
3554:
3548:
3546:
3539:
3532:
3531:
3529:
3528:
3525:
3522:
3517:
3514:
3509:
3506:
3501:
3496:
3491:
3486:
3480:
3478:
3471:
3470:
3467:
3466:
3464:
3463:
3458:
3453:
3448:
3446:Bornyl acetate
3443:
3438:
3432:
3430:
3426:
3425:
3423:
3422:
3417:
3412:
3407:
3397:
3392:
3387:
3381:
3379:
3375:
3374:
3372:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3335:
3333:
3326:
3320:
3319:
3316:
3315:
3313:
3312:
3307:
3302:
3297:
3292:
3277:
3275:
3271:
3270:
3268:
3267:
3262:
3257:
3251:
3249:
3245:
3244:
3242:
3241:
3236:
3230:
3228:
3221:
3217:
3213:
3205:
3204:
3202:
3201:
3196:
3191:
3187:
3183:
3176:
3174:
3171:Hemiterpenoids
3167:
3166:
3164:
3163:
3157:
3154:
3148:
3145:
3142:
3130:
3128:
3124:
3123:
3108:
3106:
3105:
3098:
3091:
3083:
3077:
3076:
3065:Chisholm, Hugh
3054:
3042:
3041:External links
3039:
3036:
3035:
3024:(5): 581–587.
3008:
2973:
2943:
2934:
2915:(4): 277–283.
2902:
2891:
2884:
2858:
2851:
2822:
2816:978-3527317868
2815:
2795:
2752:
2713:(1): E81–E88.
2693:
2642:
2607:
2540:
2513:
2470:
2427:
2376:
2340:
2315:Food Chemistry
2305:
2279:
2272:
2246:
2233:(1): 167–177.
2207:
2188:
2174:
2147:(7): 387–395.
2131:
2074:
2025:
1978:
1937:
1923:
1905:nobelprize.org
1878:
1827:
1818:|journal=
1782:
1776:978-3527306732
1775:
1744:
1725:
1718:
1714:
1689:
1682:
1664:
1646:
1637:|journal=
1619:
1584:
1577:
1547:
1546:
1544:
1541:
1485:petrochemicals
1480:
1477:
1448:
1447:
1423:Vitis vinifera
1409:
1406:
1381:
1378:beta-carotenes
1370:gamma-carotene
1361:
1357:
1354:eight isoprene
1347:
1343:
1339:
1336:seven isoprene
1332:
1304:
1300:
1290:
1275:
1258:(precursor of
1235:
1231:
1221:
1197:
1193:
1190:three isoprene
1186:Sesquiterpenes
1183:
1119:
1115:
1105:
1085:
1084:
1078:
1071:
1069:
1055:
1048:
1046:
1032:
1025:
1023:
1013:
1006:
1004:
994:
987:
985:
975:
968:
966:
960:
953:
951:
941:
934:
932:
927:
926:Classification
924:
906:
903:
890:
887:
882:
878:
874:
870:
866:
862:
858:
855:
850:
846:
838:
835:
826:
823:
811:sesquiterpenes
809:precursors to
806:
802:
764:
761:
732:
728:
724:
720:
698:Main article:
695:
692:
677:Archaeplastida
661:Main article:
658:
655:
652:
651:
648:
642:
641:
638:
632:
631:
628:
622:
621:
618:
611:
610:
607:
601:
600:
597:
591:
590:
587:
553:
543:
529:
526:
500:
497:
467:
464:
419:sesquiterpenes
391:ballet dancers
338:natural rubber
325:
322:
265:essential oils
252:
249:
237:polymethylenes
201:
197:
189:
185:
173:
170:
150:natural rubber
130:
122:
119:sesquiterpenes
114:
87:
83:
79:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4294:
4283:
4280:
4278:
4275:
4274:
4272:
4257:
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4229:
4227:
4226:Neophytadiene
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4187:
4186:Aromadendrene
4184:
4182:
4179:
4177:
4174:
4172:
4169:
4167:
4164:
4162:
4159:
4158:
4155:
4151:
4144:
4139:
4137:
4132:
4130:
4125:
4124:
4121:
4108:
4105:
4102:
4099:
4098:
4096:
4092:
4085:
4081:
4077:
4076:
4074:
4070:
4063:
4061:3-oxo-α-ionol
4060:
4059:
4057:
4053:
4046:
4044:
4041:
4039:
4036:
4035:
4033:
4030:
4026:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3995:Cryptoxanthin
3993:
3991:
3990:Canthaxanthin
3988:
3987:
3985:
3982:
3978:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3952:
3949:
3947:
3944:
3942:
3941:Beta-Carotene
3939:
3937:
3934:
3933:
3931:
3929:
3925:
3922:
3919:
3914:
3910:
3903:
3901:Ferrugicadiol
3900:
3899:
3897:
3893:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3862:
3860:
3858:
3855:
3853:Serratenediol
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3836:
3834:
3830:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3797:
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3776:
3774:
3771:
3770:
3769:
3766:
3765:
3763:
3761:
3757:
3754:
3751:
3750:Triterpenoids
3747:
3740:
3739:
3737:
3734:
3730:
3719:
3716:
3713:
3711:
3708:
3705:
3703:Mercusic acid
3702:
3700:
3697:
3694:
3692:
3689:
3686:
3684:Communic acid
3683:
3681:
3678:
3677:
3675:
3673:
3669:
3663:
3660:
3658:
3655:
3653:
3650:
3649:
3647:
3643:
3636:
3633:
3630:
3628:
3625:
3623:
3620:
3619:
3617:
3613:
3607:
3604:
3601:
3598:
3595:
3594:
3592:
3588:
3582:
3579:
3577:
3574:
3573:
3571:
3567:
3560:
3558:
3555:
3553:
3550:
3549:
3547:
3543:
3540:
3537:
3533:
3526:
3523:
3521:
3518:
3515:
3513:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3481:
3479:
3476:
3472:
3462:
3459:
3457:
3454:
3452:
3449:
3447:
3444:
3442:
3439:
3437:
3434:
3433:
3431:
3427:
3421:
3418:
3416:
3413:
3411:
3408:
3405:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3382:
3380:
3376:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3336:
3334:
3330:
3327:
3321:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3290:
3286:
3282:
3279:
3278:
3276:
3272:
3266:
3263:
3261:
3258:
3256:
3253:
3252:
3250:
3246:
3240:
3237:
3235:
3232:
3231:
3229:
3225:
3222:
3210:
3206:
3200:
3197:
3195:
3192:
3181:
3178:
3177:
3175:
3172:
3168:
3161:
3158:
3155:
3152:
3149:
3146:
3143:
3140:
3136:
3132:
3131:
3129:
3125:
3120:
3116:
3112:
3104:
3099:
3097:
3092:
3090:
3085:
3084:
3081:
3072:
3071:
3066:
3061:
3055:
3052:
3048:
3045:
3044:
3040:
3031:
3027:
3023:
3019:
3012:
3009:
3004:
3000:
2996:
2992:
2988:
2984:
2977:
2974:
2969:
2965:
2961:
2957:
2953:
2949:
2938:
2935:
2930:
2926:
2922:
2918:
2914:
2910:
2906:
2895:
2892:
2887:
2881:
2877:
2873:
2869:
2862:
2859:
2854:
2852:9780128021040
2848:
2844:
2840:
2836:
2835:Pharmacognosy
2829:
2827:
2823:
2818:
2812:
2808:
2807:
2799:
2796:
2791:
2787:
2783:
2779:
2775:
2771:
2767:
2763:
2756:
2753:
2748:
2744:
2739:
2734:
2729:
2724:
2720:
2716:
2712:
2708:
2704:
2697:
2694:
2689:
2685:
2680:
2675:
2670:
2665:
2661:
2657:
2653:
2646:
2643:
2638:
2634:
2630:
2626:
2622:
2618:
2611:
2608:
2603:
2599:
2594:
2589:
2585:
2581:
2576:
2571:
2567:
2563:
2559:
2555:
2551:
2544:
2541:
2536:
2532:
2528:
2524:
2517:
2514:
2509:
2505:
2501:
2497:
2493:
2489:
2485:
2481:
2474:
2471:
2466:
2462:
2458:
2454:
2450:
2446:
2442:
2438:
2431:
2428:
2423:
2419:
2414:
2409:
2404:
2399:
2395:
2391:
2387:
2380:
2377:
2372:
2368:
2364:
2360:
2356:
2352:
2344:
2341:
2336:
2332:
2328:
2324:
2320:
2316:
2309:
2306:
2294:
2290:
2283:
2280:
2275:
2273:9780080453163
2269:
2265:
2261:
2257:
2250:
2247:
2241:
2236:
2232:
2228:
2227:
2222:
2220:
2211:
2208:
2203:
2199:
2192:
2189:
2184:
2178:
2175:
2170:
2166:
2162:
2158:
2154:
2150:
2146:
2142:
2135:
2132:
2127:
2123:
2118:
2113:
2109:
2105:
2101:
2097:
2093:
2089:
2085:
2078:
2075:
2070:
2066:
2061:
2056:
2052:
2048:
2044:
2040:
2036:
2029:
2026:
2021:
2017:
2013:
2009:
2005:
2001:
1997:
1993:
1989:
1982:
1979:
1974:
1970:
1965:
1960:
1957:(2): R9–R22.
1956:
1952:
1948:
1941:
1938:
1933:
1927:
1924:
1911:
1907:
1906:
1901:
1893:
1890:. Amsterdam:
1889:
1882:
1879:
1874:
1870:
1866:
1862:
1858:
1854:
1850:
1846:
1842:
1838:
1831:
1828:
1823:
1810:
1801:
1796:
1792:
1786:
1783:
1778:
1772:
1768:
1764:
1760:
1759:
1751:
1749:
1745:
1742:
1736:
1729:
1726:
1722:
1721:(see §. 1540)
1712:
1706:
1702:
1701:
1693:
1690:
1685:
1679:
1675:
1668:
1665:
1660:
1656:
1650:
1647:
1642:
1630:
1622:
1616:
1612:
1608:
1604:
1597:
1595:
1593:
1591:
1589:
1585:
1580:
1578:9783527609949
1574:
1570:
1566:
1563:. Wiley-VCH.
1562:
1555:
1553:
1549:
1542:
1536:
1532:
1530:
1526:
1522:
1518:
1514:
1510:
1506:
1502:
1498:
1494:
1490:
1486:
1478:
1473:
1469:
1468:
1463:
1462:
1457:
1452:
1445:
1441:
1437:
1433:
1429:
1425:
1424:
1419:
1415:
1407:
1404:
1400:
1396:
1395:
1390:
1386:
1385:many isoprene
1382:
1379:
1375:
1371:
1367:
1355:
1351:
1350:Tetraterpenes
1348:
1337:
1333:
1330:
1326:
1322:
1318:
1314:
1310:
1298:
1294:
1291:
1288:
1284:
1280:
1279:five isoprene
1276:
1273:
1269:
1265:
1261:
1257:
1253:
1249:
1245:
1241:
1229:
1228:four isoprene
1225:
1222:
1219:
1215:
1211:
1207:
1203:
1191:
1187:
1184:
1181:
1177:
1173:
1169:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1137:
1133:
1129:
1125:
1113:
1109:
1106:
1103:
1099:
1095:
1091:
1090:
1089:
1081:
1075:
1070:
1066:
1062:
1058:
1052:
1047:
1043:
1039:
1035:
1029:
1024:
1020:
1019:sesquiterpene
1016:
1010:
1005:
1001:
997:
991:
986:
982:
978:
972:
967:
963:
957:
952:
948:
944:
938:
933:
930:
925:
923:
921:
917:
913:
904:
902:
900:
896:
888:
886:
856:
854:
844:
836:
834:
832:
824:
822:
820:
816:
812:
800:
796:
791:
789:
781:
777:
773:
769:
762:
760:
758:
754:
750:
746:
742:
738:
717:
715:
711:
707:
701:
693:
691:
688:
686:
685:cyanobacteria
683:of ancestral
682:
681:endosymbiosis
678:
672:
670:
664:
656:
649:
647:
644:
643:
639:
637:
634:
633:
629:
627:
624:
623:
619:
617:
613:
612:
608:
606:
603:
602:
598:
596:
593:
592:
588:
585:
584:
581:
579:
575:
571:
567:
563:
559:
551:
547:
539:
535:
527:
522:
518:
514:
510:
505:
498:
495:
490:
488:
484:
480:
478:
474:
465:
460:
456:
452:
450:
445:
443:
439:
434:
432:
428:
424:
420:
416:
412:
408:
404:
400:
396:
392:
388:
384:
380:
376:
372:
368:
364:
360:
356:
352:
347:
343:
339:
330:
323:
321:
319:
315:
312:
308:
303:
301:
300:cloud seeding
296:
294:
290:
286:
282:
278:
274:
270:
266:
262:
258:
250:
248:
246:
242:
238:
234:
230:
225:
223:
219:
215:
210:
208:
195:
183:
182:August Kekulé
179:
171:
169:
167:
163:
159:
155:
151:
146:
144:
140:
136:
128:
120:
112:
107:
105:
101:
97:
93:
77:
71:
44:
37:
32:
19:
4211:β-Bisabolene
4191:Eremophilene
4166:Delta-carene
4161:Endo-Borneol
4149:
4047:Gutta-balatá
4043:Gutta percha
3981:Xanthophylls
3961:Neurosporene
3880:Moronic acid
3870:Ursolic acid
3813:Testosterone
3796:Stigmasterol
3781:Cycloartenol
3768:Phytosterols
3710:Pimaric acid
3680:Abietic acid
3631:Manoyl oxide
3606:Salvinorin A
3596:
3536:Diterpenoids
3400:Thujaplicins
3325:(2,modified)
3265:Phellandrene
3209:Monoterpenes
3138:
3134:
3127:Basic forms:
3110:
3068:
3021:
3017:
3011:
2986:
2982:
2976:
2951:
2947:
2937:
2912:
2908:
2894:
2867:
2861:
2834:
2805:
2798:
2765:
2761:
2755:
2710:
2706:
2696:
2659:
2655:
2645:
2620:
2616:
2610:
2557:
2553:
2543:
2526:
2522:
2516:
2483:
2479:
2473:
2440:
2436:
2430:
2393:
2389:
2379:
2354:
2350:
2343:
2318:
2314:
2308:
2296:. Retrieved
2292:
2282:
2255:
2249:
2230:
2224:
2218:
2210:
2202:The Guardian
2201:
2191:
2177:
2144:
2140:
2134:
2091:
2087:
2077:
2042:
2038:
2028:
1995:
1991:
1981:
1954:
1950:
1940:
1926:
1914:. Retrieved
1903:
1887:
1881:
1840:
1836:
1830:
1809:cite journal
1785:
1756:
1734:
1728:
1710:
1708:
1704:
1699:
1692:
1673:
1667:
1658:
1649:
1603:Biosynthesis
1602:
1560:
1482:
1465:
1459:
1444:glycosidases
1421:
1403:gutta-percha
1398:
1393:
1384:
1353:
1335:
1325:cycloartenol
1297:six isoprene
1296:
1282:
1278:
1227:
1217:
1189:
1166:(present in
1158:(present in
1150:(present in
1142:(present in
1130:(present in
1112:two isoprene
1111:
1108:Monoterpenes
1086:
908:
905:Unsaturation
892:
860:
840:
828:
792:
785:
737:chlorophylls
718:
705:
703:
689:
673:
666:
630:MVA and MEP
560:(DMAPP) and
541:
537:
531:
499:Biosynthesis
482:
481:
469:
446:
442:aromatherapy
435:
342:polyisoprene
335:
324:Applications
304:
297:
293:antifeedants
269:interactions
254:
226:
211:
177:
175:
162:aromatherapy
154:polyisoprene
147:
135:alpha-pinene
111:monoterpenes
108:
104:interactions
92:hydrocarbons
42:
41:
4196:Longifolene
4015:Rubixanthin
4005:Astaxanthin
3966:Phytofluene
3918:Carotenoids
3808:Cholesterol
3803:Tocopherols
3773:Campesterol
3672:Resin acids
3657:Gibberellin
3652:Aphidicolin
3645:Tetracyclic
3520:Longifolene
3484:Artemisinin
3461:Umbellulone
3349:Citronellol
3339:Citronellal
2901:"Volatile C
2837:: 233–266.
2480:Experientia
2396:(5): 1558.
2321:: 742–756.
1741:see p. 691.
1517:citronellal
1440:peroxidases
1432:spice notes
1295:consist of
1293:Triterpenes
1188:consist of
1110:consist of
1094:hemiterpene
1002:derivative.
947:monoterpene
922:formation.
920:carbocation
755:(FPP), and
599:MVA or MEP
521:α-terpineol
285:pollinators
218:isoprenoids
192:, of which
4271:Categories
4251:Ketoursene
4236:Aristolone
4231:Ferruginol
4221:β-Selinene
4216:γ-Cadinene
4176:α-Ylangene
4000:Zeaxanthin
3844:Lanosterol
3791:Sitosterol
3786:Sitostanol
3662:Paclitaxel
3569:Monocyclic
3456:Ascaridole
3451:Eucalyptol
3404:Hinokitiol
3378:Monocyclic
3248:Monocyclic
3115:terpenoids
2293:Classic FM
1543:References
1525:rose oxide
1472:osmeterium
1436:Chardonnay
1321:lanosterol
1224:Diterpenes
1206:farnesenes
1162:trees) or
1156:hinokitiol
1061:triterpene
996:Hinokitiol
981:turpentine
815:diterpenes
774:(IPP) and
669:acetyl CoA
492:See also:
487:glycosides
483:Terpenoids
449:pesticides
423:α-humulene
351:turpentine
281:mutualists
214:terpenoids
207:turpentine
166:pesticides
143:turpentine
127:diterpenes
4206:Valencene
4201:β-Guaiene
4181:α-Copaene
4072:Synthesis
3928:Carotenes
3823:Ecdysones
3627:Forskolin
3615:Tricyclic
3602:Epimanool
3527:Nootkatin
3524:Muurolene
3516:Juniperol
3508:Chanootin
3489:Bisabolol
3420:Carvacrol
3260:Terpinene
3162:(4 rings)
3109:Types of
2929:101007887
2617:Biochimie
2584:0027-8424
2161:1552-4450
1639:ignored (
1629:cite book
1493:acetylene
1256:taxadiene
1128:terpineol
1038:diterpene
1034:Taxadiene
1000:tropolone
889:Chirality
837:Structure
723:IPP and C
589:Pathways
586:Organism
534:isoprenes
407:cosmetics
389:hair, by
379:adhesives
375:varnishes
227:The 1939
176:The term
4256:α-Amyrin
4246:Oleanene
4241:β-Amyrin
4150:Terpenes
3971:Phytoene
3956:Lycopene
3857:Squalane
3849:Saponins
3760:Steroids
3622:Cembrene
3599:-Abienol
3590:Bicyclic
3494:Cadinene
3429:Bicyclic
3395:p-Cymene
3369:Linalool
3354:Geraniol
3305:Sabinene
3295:Camphene
3274:Bicyclic
3255:Limonene
3239:Myrcenes
3180:Isoprene
3160:Steroids
3151:Iridoids
3119:isoprene
3111:terpenes
3047:Terpenes
3003:19817422
2968:19828152
2790:44195550
2782:13116962
2747:25502595
2688:27462341
2662:: 1019.
2637:29017925
2623:: 9–20.
2602:30224495
2508:44195550
2500:13116962
2465:39469817
2422:32106479
2371:25429661
2335:25442616
2169:17576426
2126:16469917
2069:12857838
2020:21443154
2012:26925555
1973:31051473
1865:19440196
1739: ;
1513:α-pinene
1509:tall oil
1503:to give
1366:lycopene
1352:contain
1329:steroids
1309:squalene
1252:cembrene
1244:cafestol
1210:farnesol
1202:humulene
1180:catalpol
1172:Iridoids
1170:trees).
1152:lavender
1148:linalool
1136:limonene
1124:geraniol
1065:steroids
1057:Squalene
1015:Humulene
943:Limonene
843:isoprene
759:(GGPP).
745:quinones
710:pyruvate
595:Bacteria
576:and the
517:β-pinene
513:α-pinene
421:(mainly
403:perfumes
395:gymnasts
346:polymers
307:termites
283:such as
261:squalene
257:Steroids
194:camphene
158:polymers
100:conifers
43:Terpenes
18:Terpenes
4109:(DMAPP)
3839:Betulin
3637:Pimarol
3634:Pimaral
3581:Retinal
3576:Retinol
3545:Acyclic
3504:Cedrene
3499:Cadinol
3441:Borneol
3436:Camphor
3390:Menthol
3364:Halomon
3332:Acyclic
3300:Thujene
3234:Ocimene
3227:Acyclic
3067:(ed.).
2738:4291660
2715:Bibcode
2679:4940680
2593:6176645
2562:Bibcode
2445:Bibcode
2413:7084246
2298:22 July
2117:2861909
2096:Bibcode
2088:Science
1873:4312428
1845:Bibcode
1529:menthol
1521:camphor
1489:acetone
1461:Papilio
1283:sester-
1268:retinal
1264:retinol
1248:kahweol
1218:sesqui-
1216:. (The
1214:geosmin
1176:aucubin
1160:cypress
1140:myrcene
1080:Geosmin
962:Carvone
912:alkenes
857:Formula
751:(GPP),
636:Animals
605:Archaea
540:or the
473:viscous
363:solvent
340:(i.e.,
178:terpene
152:(i.e.,
139:solvent
4031:(many)
4010:Lutein
3861:Acids
3552:Phytol
3410:Thymol
3344:Citral
3310:Carene
3281:Pinene
3194:Prenol
3141:forms)
3121:units)
3117:(# of
3053:(MeSH)
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1389:rubber
1374:alpha-
1272:phytol
1270:, and
1164:pinene
1132:lilacs
1098:prenol
977:Pinene
895:chiral
626:Plants
614:Green
572:: the
355:pinene
96:plants
4103:(IPP)
3920:) (8)
3832:Other
3139:trans
3063:. In
2925:S2CID
2786:S2CID
2504:S2CID
2461:S2CID
2016:S2CID
1869:S2CID
1703:[
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1399:trans
1260:taxol
1042:taxol
877:and C
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741:hemes
646:Fungi
616:Algae
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2598:PMID
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2300:2022
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2165:PMID
2157:ISSN
2122:PMID
2065:PMID
2008:PMID
1969:PMID
1918:2017
1861:PMID
1822:help
1771:ISBN
1678:ISBN
1641:help
1615:ISBN
1573:ISBN
1527:and
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1491:and
1428:wine
1376:and
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1168:pine
1144:hops
1100:and
1059:, a
1036:, a
1017:, a
945:, a
813:and
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743:and
731:to C
712:and
650:MVA
640:MVA
620:MEP
609:MVA
546:rule
515:and
431:beer
425:and
415:hops
409:and
377:and
371:inks
216:(or
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2711:112
2674:PMC
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2625:doi
2621:144
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2558:115
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1955:242
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