Nootkatin
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| IUPAC name
2-hydroxy-5-(3-methylbut-2-enyl)-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
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Other names
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C15H20O2 | |
| Molar mass | 232.323 g·mol−1 |
| Density | g/cm3 |
| Melting point | 95 °C (203 °F; 368 K) |
| Hazards | |
| Flash point | 206 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Nootkatin is a naturally occurring organic compound classified as a sesquiterpenoid with the molecular formula C15H20O2.[1] The compound belongs to the nootkatone family of natural products derived from grapefruit and other citrus sources, distinguished by its special structure featuring multiple double bonds, cycloheptatriene ring, and a ketone functional group. Nootkatin was initially isolated in 1952 from the steam-volative oil of the heartwood of yellow cedar by Carlsson et al.[2]
Natural occurrence
Nootkatin occurs as a minor component in the essential oils of grapefruit (Citrus paradisi) and Alaskan yellow cedar (Callitropsis nootkatensis), formed via oxidative degradation of nootkatone. Biosynthetically, the compound is formed from farnesyl pyrophosphate through cyclization pathways typical of sesquiterpenes, with enzymatic oxidation yielding the ketone functionality.[3][4]
The compound is also found in such taxons as Juniperus communis, Juniperus thurifera, Juniperus osteosperma, Juniperus taiwaniana, Cupressus torulosa, among others.[5]
Biological activities
Nootkatin displays diverse bioactivities, including potential antimicrobial, antiinflammatory, and insect-repellent properties akin to nootkatone, which is a biopesticide against ticks and mosquitoes.[6]
See also
References
- ^ "Nootkatin". NIST. Retrieved 26 February 2026.
- ^ Hillis, W. E. (12 May 2014). Wood Extractives and Their Significance to the Pulp and Paper Industries. Academic Press. p. 322. ISBN 978-1-4832-5861-4. Retrieved 26 February 2026.
- ^ Paech, K.; Tracey, M. V. (6 December 2012). Moderne Methoden der Pflanzenanalyse / Modern Methods of Plant Analysis. Springer Science & Business Media. p. 357. ISBN 978-3-642-64958-5. Retrieved 26 February 2026.
- ^ Zavarin, Eugene; Smith, Leslie V.; Bicho, Joseph G. (1 October 1967). "Tropolones of cupressaceae—III". Phytochemistry. 6 (10): 1387–1394. doi:10.1016/S0031-9422(00)82881-2. ISSN 0031-9422. Retrieved 27 February 2026.
- ^ Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès Dans La Chimie Des Substances Organiques Naturelles. Springer Science & Business Media. 6 December 2012. p. 254. ISBN 978-3-7091-8143-0. Retrieved 26 February 2026.
- ^ Harrington, Constance (June 2011). Tale of Two Cedars: International Symposium on Western Redcedar and Yellow-Cedar. DIANE Publishing. p. 147. ISBN 978-1-4379-4228-6. Retrieved 26 February 2026.