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The terpenoids, also known as isoprenoids, are a class of naturally occurring organic compound derived from the 5-carbon compound isoprene and its derivatives called , , etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional , usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known Natural Products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists. (2025). 9781444320503 ISBN 9781444320503
Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in , and the red color in . Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant Salvia divinorum, ginkgolide and bilobalide found in Ginkgo biloba and the Cannabinoid found in cannabis. The provitamin beta carotene is a terpene derivative called a carotenoid.
The and in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to , e.g., to enhance their attachment to the cell membrane; this is known as isoprenylation. Terpenoids play a role in plant defense as prophylaxis against pathogens and for the predators of herbivores.
| Isoprene | 1 | 5 | C5H8 | DMAPP, isopentenyl pyrophosphate, isoprenol, isovaleramide, isovaleric acid, HMBPP, prenol | |
| 2 | 10 | C10H16 | Bornyl acetate, camphor, carvone, citral, citronellal, citronellol, geraniol, eucalyptol, hinokitiol, , linalool, menthol, thymol | ||
| 3 | 15 | C15H24 | Farnesol, geosmin, humulone | ||
| 4 | 20 | C20H32 | Abietic acid, , paclitaxel, retinol, salvinorin A, sclareol, steviol | ||
| 5 | 25 | C25H40 | Andrastin A, manoalide | ||
| 6 | 30 | C30H48 | Amyrin, betulinic acid, , oleanolic acid, , squalene, ursolic acid | ||
| 8 | 40 | C40H64 | |||
| Polyterpenoid | Terpene | >8 | >40 | (C5H8)n | 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. The Salkowski test can be used to identify the presence of terpenoids.
As an example the Blue Ridge Mountains in the U.S. and Blue Mountains of New South Wales in Australia are noted for having a bluish color when seen from a distance. Trees put the "blue" in Blue Ridge, from their terpenoids released into the atmosphere.
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