Nootkatin

Last updated
Nootkatin
Nootkatin.png
Names
IUPAC name
2-hydroxy-5-(3-methylbut-2-enyl)-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
Other names
  • NSC 43339
  • NSC 403527
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C15H20O2/c1-10(2)5-6-12-7-8-14(16)15(17)9-13(12)11(3)4/h5,7-9,11H,6H2,1-4H3,(H,16,17) X mark.svgN
    Key: MNMNTZYOZZLKSV-UHFFFAOYSA-N
  • CC(C)C1=CC(=O)C(=CC=C1CC=C(C)C)O
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).

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 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]

Contents

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]

The compound is also found in such taxons as Juniperus communis , Juniperus thurifera , Juniperus osteosperma , Juniperus taiwaniana, Cupressus torulosa , among others. [4]

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. [5]

See also

References

  1. ↑ "Nootkatin". NIST . Retrieved 26 February 2026.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
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