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Leptospermone information


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
CAS Number
  • 567-75-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2340805 checkY
PubChem CID
  • 3083632
UNII
  • 2F8XBE046L checkY
CompTox Dashboard (EPA)
  • DTXSID80205258 Edit this at Wikidata
InChI
  • 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
SMILES
  • O=C1C(C(=O)C(C(=O)C1(C)C)C(=O)CC(C)C)(C)C
Properties
Chemical formula
 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).
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Infobox references

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.

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Leptospermone

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Leptospermone is a chemical compound (a β-triketone) produced by some members of the myrtle family (Myrtaceae), such as Callistemon citrinus (Lemon Bottlebrush)...

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Mesotrione

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crops. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree Callistemon citrinus. It inhibits the...

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Manuka oil

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triketones (often as high as 33%), comprising flavesone, leptospermone and iso-leptospermone. Manuka that grows in the Marlborough Sounds region of New...

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Herbicide

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copper arsenate DSMA MSMA HPPD inhbitors flurochloridone isoxaflutole leptospermone mesotrione nitisinone sethoxydim sulcotrione Organophosphorus bensulide...

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Phloroglucinol

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synthesis of 1-(2,4,6-Trihydroxyphenyl)ethanone from phloroglucinol. Leptospermone can be synthesized from phloroglucinol by a reaction with isovaleroylnitrile...

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Melaleuca citrina

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The herbicide Mesotrione was developed as a synthetic analogue of leptospermone, a natural herbicide produced by the roots of Callistemon citrinus....

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C15H22O4

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mass: 266.333 g/mol, exact mass: 266.1518 u) may refer to: Agglomerin Leptospermone This set index page lists chemical structure articles associated with...

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Allelopathy

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available or in the process of large-scale manufacture. For example, leptospermone is an allelochemical in lemon bottlebrush (Callistemon citrinus). Although...

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Nitisinone

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herbicides, which are chemically derived from a natural phytotoxin, leptospermone, obtained from the Australian bottlebrush plant (Callistemon citrinus)...

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Tyrosinemia type I

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leptospermone – in the soil under the bottlebrush plant was shown to have bleaching activity on the emerging plants. The allelochemical leptospermone...

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