7327. Phloridzin

Nomenclature

CAS number: 60-81-1
1-[2-(β-d-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone; phlorhizin; phlorizin; phlorrhizen; phloretin-2′-β-glucoside; 4,6-dihydroxy-2-(β-d-glucosido)-β-(p-hydroxyphenyl)propiophenone.
C21H24O10; mol wt 436.41.
C 57.80%, H 5.54%, O 36.66%.

Description and 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 γ-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).

Chemical structure

Derivative

Dihydrate.

Properties

Long needles from water, mp 110°. Sweet, with bitter aftertaste. [α]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.

Use

Experimentally to produce glycosuria in animals.