Chemistry:Pungenin

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
CAS Number	55483-00-6;
3D model (JSmol)	Interactive image;
ChemSpider	24669457;
PubChem CID	12314759;
UNII	SC67H2S7NM ;
	InChI 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;
	SMILES CC(=O)c1ccc(c(c1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O;
Properties
Chemical formula	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]

↑ 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.
↑ 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.

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Names
Chemical structure of Pungenin
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
CAS Number	55483-00-6
3D model (JSmol)	Interactive image
ChemSpider	24669457
PubChem CID	12314759
UNII	SC67H2S7NM^Y
InChI 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
SMILES CC(=O)c1ccc(c(c1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
Properties
Chemical formula	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