Populin

Populin is a glucoside occurring in the bark, buds and leaves of certain species of poplar.[1][2] The alkaline cleavage of populin produces benzoate and the glucoside salicin.[1]

Populin
Names
IUPAC name
2-(Hydroxymethyl)phenyl β-D-glucopyranoside 6-benzoate
Systematic IUPAC name
{(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl}methyl benzoate
Other names
Populoside; Populine; Salicin 6'-benzoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.488
KEGG
UNII
  • InChI=1S/C20H22O8/c21-10-13-8-4-5-9-14(13)27-20-18(24)17(23)16(22)15(28-

    20)11-26-19(25)12-6-2-1-3-7-12/h1-9,15-18,20-24H,10-11H2/t15-,16-,17+,

    18-,20-/m1/s1
    Key: HHSKNLJWHGXWPK-BFMVXSJESA-N
  • C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC=CC=C3CO)O)O)O
Properties
C20H22O8
Molar mass 390.388 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

References
  1. Richtmyer, Nelson K.; Yeakel, Eleanor H. (1934). "The Structure of Populin". Journal of the American Chemical Society. 56 (11): 2495–2497. doi:10.1021/ja01326a090. ISSN 0002-7863.
  2. Pearl, Irwin A.; Darling, Stephen F.; Justman, Oliver (1962). "Studies on the Leaves of the Family Salicaceae. I. Populin from the Leaves of Populus grandidentata and Populus tremuloides". The Journal of Organic Chemistry. 27 (7): 2685–2687. doi:10.1021/jo01054a538. ISSN 0022-3263.
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