Populin

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
CAS Number	99-17-2  Y
3D model (JSmol)	Interactive image
ChemSpider	83713
ECHA InfoCard	100.002.488
KEGG	C10823
PubChem CID	92735
UNII	XC8BY5AX02  Y
CompTox Dashboard (EPA)	DTXSID90878492
InChI 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
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
Properties
Chemical formula	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

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]

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.