Leptospermone

Leptospermone
Names
IUPAC name
2,2,4,4-Tetramethyl-6-(3-methylbutanoyl)cyclohexane-1,3,5-trione
Other names
Isovaleroylsyncarpic acid; 6-Isovaleroyl-2,2,4,4-tetramethyl-1,3,5-cyclohexanetrione
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C15H22O4/c1-8(2)7-9(16)10-11(17)14(3,4)13(19)15(5,6)12(10)18/h8,10H,7H2,1-6H3 checkY
    Key: YDWYMAHAWHBPPT-UHFFFAOYSA-N checkY
  • InChI=1/C15H22O4/c1-8(2)7-9(16)10-11(17)14(3,4)13(19)15(5,6)12(10)18/h8,10H,7H2,1-6H3
    Key: YDWYMAHAWHBPPT-UHFFFAOYAO
  • O=C1C(C(=O)C(C(=O)C1(C)C)C(=O)CC(C)C)(C)C
Properties
C15H22O4
Molar mass 266.337 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Leptospermone is a chemical compound (a β-triketone) produced by some members of the myrtle family (Myrtaceae), such as Callistemon citrinus (Lemon Bottlebrush), a shrub native to Australia, and Leptospermum scoparium (Manuka), a New Zealand tree from which it gets its name.[1] Modification of this allelopathic chemical to produce mesotrione led to the commercialization of derivative compounds as HPPD inhibitor herbicides.

  1. ^ van Klink JW, Brophy JJ, Perry NB, Weavers RT (1999). "β-Triketones from Myrtaceae: Isoleptospermone from Leptospermum scoparium and Papuanone from Corymbia dallachiana". J Nat Prod. 62 (3): 487–9. doi:10.1021/np980350n. PMID 10096865.