7326. Phloretin

Nomenclature

CAS number: 60-82-2
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone; 2′,4′,6′-trihydroxy-3-(p-hydroxyphenyl)propiophenone; β-(p-hydroxyphenyl)phloropropiophenone; β-(p-hydroxyphenyl)-2,4,6-trihydroxypropiophenone.
C15H14O5; mol wt 274.27.
C 65.69%, H 5.14%, O 29.17%.

Description and references

The aglucon of phlorizin, q.v. From root bark of apple trees: Rochleder, J. Prakt. Chem. 98, 205 (1866). Structure: Seshadri, Annu. Rev. Biochem. 20, 495 (1951). Synthesis: Fischer, Nouri, Ber. 50, 611 (1917); Rosenmund, Rosenmund, ibid. 61B, 2608 (1928); Shinoda et al., J. Pharm. Soc. Jpn. 49, 797 (1929); Johnston, US 2789995 (1957 to Union Carbide).

Chemical structure

Properties

Needles from dil alcohol, dec 262°. Absorption spectrum: Lambrechts, Arch. Int. Physiol. 44, Suppl., 1-39 (1937). Freely sol in alc, methanol, acetone; sol in alkalies in hot glacial acetic acid; very sparingly sol in benzene, chloroform. Practically insol in water, ether, the soly being increased by addition of alcohol.