Populin

{{Chembox

| ImageFile = Populin.png

| ImageSize = 200px

| IUPACName = 2-(Hydroxymethyl)phenyl β-D-glucopyranoside 6-benzoate

| SystematicName = {(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl}methyl benzoate

| OtherNames = Populoside; Populine; Salicin 6'-benzoate

|Section1={{Chembox Identifiers

| CASNo = 99-17-2

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XC8BY5AX02

| PubChem = 92735

| ChemSpiderID = 83713

| KEGG = C10823

| SMILES = 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

| 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

| InChIKey = HHSKNLJWHGXWPK-BFMVXSJESA-N

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|Section2={{Chembox Properties

| C=20 | H=22 | O=8

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|Section3={{Chembox Hazards

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Populin is a glucoside occurring in the bark, buds and leaves of certain species of poplar.{{cite journal|last1=Richtmyer|first1=Nelson K.|last2=Yeakel|first2=Eleanor H.|journal=Journal of the American Chemical Society|title=The Structure of Populin|volume=56|issue=11|year=1934|pages=2495–2497|issn=0002-7863|doi=10.1021/ja01326a090}}{{cite journal|last1=Pearl|first1=Irwin A.|last2=Darling|first2=Stephen F.|last3=Justman|first3=Oliver|title=Studies on the Leaves of the Family Salicaceae. I. Populin from the Leaves of Populus grandidentata and Populus tremuloides|journal=The Journal of Organic Chemistry|volume=27|issue=7|year=1962|pages=2685–2687|issn=0022-3263|doi=10.1021/jo01054a538}} The alkaline cleavage of populin produces benzoate and the glucoside salicin.

References