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Terpenoid
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==Structure and classification== Terpenoids are modified [[terpene]]s,<ref>{{cite web |last1=Houghton |first1=Isaac |title=The Physiology of Cannabis Terpenes and Terpenoids โ A Brief Overview |url=https://cannabis-kings.net/the-physiology-of-cannabis-terpenes-and-terpenoids-a-brief-overview/ |publisher=Elliot Barker |access-date=3 May 2016}}</ref> wherein [[methyl group]]s have been moved or removed, or [[oxygen]] atoms added. Some authors use the term "terpene" more broadly, to include the terpenoids. Just like terpenes, the terpenoids can be classified according to the number of [[isoprene]] units that comprise the parent terpene: {| Class = "wikitable" ! Terpenoids ! Analogue [[terpene]]s ! Number of [[isoprene]] units ! Number of carbon atoms ! General formula ! Examples<ref name=Terpenoids>{{cite journal |last1=Ludwiczuk |first1=A. |last2=Skalicka-Woลบniak |first2=K. |last3=Georgiev |first3=M.I. |title=Terpenoids |journal=Pharmacognosy |date=2017 |pages=233โ266 |doi=10.1016/B978-0-12-802104-0.00011-1|isbn=9780128021040 }}</ref> |- | [[Hemiterpenoid]]s | [[Isoprene]] | 1 | 5 | C<sub>5</sub>H<sub>8</sub> | [[Dimethylallyl pyrophosphate|DMAPP]], [[isopentenyl pyrophosphate]], [[isoprenol]], [[isovaleramide]], [[isovaleric acid]], [[(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate|HMBPP]], [[prenol]] |- | [[Monoterpenoid]]s | [[Monoterpene]]s | 2 | 10 | C<sub>10</sub>H<sub>16</sub> | [[Bornyl acetate]], [[camphor]], [[carvone]], [[citral]], [[citronellal]], [[citronellol]], [[geraniol]], [[eucalyptol]], [[hinokitiol]], [[iridoid]]s, [[linalool]], [[menthol]], [[thymol]] |- | [[Sesquiterpenoid]]s | [[Sesquiterpene]]s | 3 | 15 | C<sub>15</sub>H<sub>24</sub> | [[Farnesol]], [[geosmin]], [[humulone]] |- | [[Diterpenoid]]s | [[Diterpene]]s | 4 | 20 | C<sub>20</sub>H<sub>32</sub> | [[Abietic acid]], [[ginkgolide]]s, [[paclitaxel]], [[retinol]], [[salvinorin A]], [[sclareol]], [[steviol]] |- | [[Sesterterpenoid]]s | [[Sesterterpene]]s | 5 | 25 | C<sub>25</sub>H<sub>40</sub> | [[Andrastin A]], [[manoalide]] |- | [[Triterpenoid]]s | [[Triterpene]]s | 6 | 30 | C<sub>30</sub>H<sub>48</sub> | [[Amyrin]], [[betulinic acid]], [[limonoid]]s, [[oleanolic acid]], [[sterol]]s, [[squalene]], [[ursolic acid]] |- | [[Tetraterpenoid]]s | [[Tetraterpene]]s | 8 | 40 | C<sub>40</sub>H<sub>64</sub> | [[Carotenoid]]s |- | [[Polyterpenoid]] | [[Terpene|Polyterpene]]s | >8 | >40 | (C<sub>5</sub>H<sub>8</sub>)<sub>n</sub> | [[Gutta-percha]], [[natural rubber]] |- |} Terpenoids can also be classified according to the type and number of cyclic structures they contain: linear, acyclic, monocyclic, bicyclic, tricyclic, tetracyclic, pentacyclic, or macrocyclic.<ref name=Terpenoids /> The [[Salkowski test]] can be used to identify the presence of terpenoids.<ref>{{cite journal| vauthors = Ayoola GA | title=Phytochemical Screening and Antioxidant Activities of Some Selected Medicinal Plants Used for Malaria Therapy in Southwestern Nigeria|journal=Tropical Journal of Pharmaceutical Research|date=2008|volume=7|issue=3|pages=1019โ1024|ref=2|doi=10.4314/tjpr.v7i3.14686|doi-access=free|hdl=1807/60332|hdl-access=free}}</ref> <gallery caption="Selected terpenoids"> File:Taxol.svg|[[Paclitaxel]] is a diterpenoid anticancer drug. File:Terpineol alpha.svg|[[Terpineol]]s are monoterpenoids. File:(S)-Humulone.svg|[[Humulone]]s are classified as sesquiterpenoids. File:All-trans-Retinol2.svg|[[Retinol]] is a diterpenoid. File:Beta-thujaplicin.png|[[Hinokitiol]] is a monoterpenoid, a [[tropolone]] derivative. File:Limonin.svg|[[Limonin]], a common [[limonoid]], is a triterpenoid. File:Geosmin_Structural_Formulae.svg|[[Geosmin]] is a [[sesquiterpenoid]]. </gallery>
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