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(-)-Phyllostine

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(-)-Phyllostine Basic information

Product Name:
(-)-Phyllostine
Synonyms:
  • (-)-Phyllostine
  • (1R,6S)-3-Hydroxymethyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
  • (1α,6α)-3-(Hydroxymethyl)-7-oxabicyclo[4.1.0]hepta-3-ene-2,5-dione
  • (5S,6R)-2-(Hydroxymethyl)-5,6-epoxy-2-cyclohexene-1,4-dione
  • Phyllostine
  • 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione, 3-(hydroxymethyl)-, (1R,6S)-
CAS:
27270-89-9
MF:
C7H6O4
MW:
154.12
Mol File:
27270-89-9.mol
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(-)-Phyllostine Chemical Properties

Melting point:
56 °C
Boiling point:
398.9±42.0 °C(Predicted)
Density 
1.555±0.06 g/cm3(Predicted)
pka
13.40±0.10(Predicted)
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(-)-Phyllostine Usage And Synthesis

Uses

Phyllostine ((-)-Phyllostine) can be isolated from D. miriciae. Phyllostine exhibits strong antifeedant, contact toxicity, and oviposition deterrent activities against P. xylostella[1].

Definition

ChEBI: Phyllostine is an epoxide resulting from epoxidation of the 5-6 double bond of 2-(hydroxymethyl)-1,4-benzoquinone (the 5S,6R enantiomer). It has a role as a Penicillium metabolite. It is an epoxide, a cyclic ketone and a primary allylic alcohol.

References

[1] Ratnaweera PB, et al. Antifeedant, contact toxicity and oviposition deterrent effects of phyllostine acetate and phyllostine isolated from the endophytic fungus Diaporthe miriciae against Plutella xylostella larvae. Pest Manag Sci. 2020 Apr;76(4):1541-1548. DOI:10.1002/ps.5673

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