Title: Phloridzin
CAS Registry Number: 60-81-1
CAS Name: 1-[2-(b-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
Additional Names: phlorhizin; phlorizin; phlorrhizen; phloretin-2¢-b-glucoside; 4,6-dihydroxy-2-(b-D-glucosido)-b-(p-hydroxyphenyl)propiophenone
Molecular Formula: C21H24O10
Molecular Weight: 436.41
Percent Composition: C 57.80%, H 5.54%, O 36.66%
Literature References: A dihydrochalcone occurring in all parts of the apple tree except the mature fruit. Once thought to occur in pear, plum, cherry trees and other Rosaceae: A. H. Williams in Comparative Phytochemistry, T. Swain, Ed. (Academic Press, New York, 1966) pp 297-307. Isoln from root bark: De Koninck, Ann. 15, 75, 258 (1835); Stass, Ann. 30, 192 (1839); Bridel, Kramer, Bull. Soc. Chim. Biol. 15, 544 (1933). Hydrolysis by dil mineral acids yields phloretin and glucose. Procedure for acid hydrolysis: Wessely, Sturm, Monatsh. Chem. 53-54, 557 (1929); Müller, Robertson, J. Chem. Soc. 1933, 1170. The energy of activation required for the hydrolysis is much less than for other glucosides and approaches that for g-fructosides (sucrose, raffinose). Is hydrolyzed by saccharase at pH 4.45, by enzymes of Aspergillus niger and other enzymes found in invertebrates: Kobert, Pfluegers Arch. Gesamte Physiol. Menschen Tiere 99, 116 (1903); Moelwyn-Hughes, J. Gen. Physiol. 13, 807 (1930); cf. Trans. Faraday Soc. 25, 81 (1929). Synthesis: Zemplen, Bognár, Ber. 75B, 1040 (1942); cf. ibid. 645 and 76B, 386 (1943).
Derivative Type: Dihydrate
Properties: Long needles from water, mp 110°. Sweet, with bitter aftertaste. [a]D25 -52° (0.16 g in 5 ml of 96% alcohol). One gram dissolves in about one liter of water at 22°, in 64 ml at 60°, in 22 ml at 70°. Freely sol in boiling water; in about 4 parts alcohol, in methanol, amyl alcohol, acetone, ethyl acetate, pyridine, aniline, quinoline and other organic bases; in aq alkaline solns and in glacial acetic acid. Practically insol in ether, chloroform, benzene.
Melting point: mp 110°
Optical Rotation: [a]D25 -52° (0.16 g in 5 ml of 96% alcohol)
Use: Experimentally to produce glycosuria in animals. |