7594. Populin

Nomenclature

CAS number: 99-17-2
2-(Hydroxymethyl)phenyl-β-d-glucopyranoside 6-benzoate; populoside; salicin benzoate.
C20H22O8; mol wt 390.38.
C 61.53%, H 5.68%, O 32.79%.

Description and references

In bark and leaves of Populus tremula L., P. nigra L., P. nigra L. var. italica Duroi, P. canadensis Moench., P. grandidentate Michx., and P. tremuloides Michx., Salicaceae, perhaps also in Salix helix, Salix purpureae L. var helix (L.) Koch. Isoln: Pearl et al., J. Org. Chem. 27, 2685 (1962). May be made from salicin by melting with benzoic anhydride, or from salicin and benzoyl chloride in presence of potassium hydroxide: Richtmyer, Yeakel, J. Am. Chem. Soc. 56, 2495 (1934). Alkaline cleavage produces benzoic acid and salicin. Enzymatic hydrolysis using taka-diastase, q.v., gives salicyl alcohol and benzoyl glucose: Kitasato, Biochem. Z. 190, 109 (1927).

Chemical structure

Derivative

Dihydrate.

Properties

Needles from water, sweet taste, like licorice. Becomes anhydr at 100°. mp 179°. [α]D20 -2.0° (c = 5 in pyridine); [α]D25 -29.7° (c = 5 in acetone). One gram dissolves in about 2 liters water, in 42 ml boiling water, in about 100 ml alcohol. Practically insol in ether.