Title: Populin
CAS Registry Number: 99-17-2
CAS Name: 2-(Hydroxymethyl)phenyl-b-D-glucopyranoside 6-benzoate
Synonyms: populoside; salicin benzoate
Molecular Formula: C20H22O8
Molecular Weight: 390.38
Percent Composition: C 61.53%, H 5.68%, O 32.79%
Literature 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).
Derivative Type: Dihydrate
Properties: Needles from water, sweet taste, like licorice. Becomes anhydr at 100°. mp 179°. [a]D20 -2.0° (c = 5 in pyridine); [a]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.
Melting point: mp 179°
Optical Rotation: [a]D20 -2.0° (c = 5 in pyridine); [a]D25 -29.7° (c = 5 in acetone)
