Pungenin

Chemical structure of Pungenin
Names
IUPAC name
1-[3-(β-D-Glucopyranosyloxy)-4-hydroxyphenyl]ethan-1-one
Systematic IUPAC name
1-(4-Hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethan-1-one
Other names
Pungenin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C14H18O8/c1-6(16)7-2-3-8(17)9(4-7)21-14-13(20)12(19)11(18)10(5-15)22-14/h2-4,10-15,17-20H,5H2,1H3/t10-,11-,12+,13-,14-/m1/s1
    Key: AOXMCWFZPZRDPE-RKQHYHRCSA-N
  • InChI=1/C14H18O8/c1-6(16)7-2-3-8(17)9(4-7)21-14-13(20)12(19)11(18)10(5-15)22-14/h2-4,10-15,17-20H,5H2,1H3/t10-,11-,12+,13-,14-/m1/s1
    Key: AOXMCWFZPZRDPE-RKQHYHRCBY
  • CC(=O)c1ccc(c(c1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
Properties
C14H18O8
Molar mass 314.290 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pungenin is a phenolic compound found in the needles of Blue Spruce (Picea pungens).[1] It is the glucoside of 3,4-dihydroxyacetophenone.

Chemical Ecology

The compound serves a feeding deterrent against Spruce Budworm larvae.[2]

See also

References

  1. ↑ Neish, A. C. (1957). "Pungenin: a Glucoside found in the leaves of Picea Pungens (Colorado Spruce)". Canadian Journal of Biochemistry and Physiology. 35 (2): 161–167. doi:10.1139/o57-020. PMID 13404533.
  2. ↑ Strunz, George M.; Giguère, Pierre; Thomas, Anthony W. (1986). "Synthesis of pungenin, a foliar constituent of some spruce species, and investigation of its efficacy as a feeding deterrent for spruce budworm [Choristoneura fumiferana (Clem.)]". Journal of Chemical Ecology. 12 (1): 251–260. doi:10.1007/BF01045608. PMID 24306414. S2CID 28774331.
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