6424. Naringenin

Nomenclature

CAS number: 480-41-1
2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4′,5,7-trihydroxyflavanone; naringetol; salipurpol; pelargidanon 1602.
C15H12O5; mol wt 272.25.
C 66.17%, H 4.44%, O 29.38%.

Description and references

The aglucon of naringin. Prepn by hydrolysis of naringin: Asahina, Inubuse, Ber. 61, 1514 (1928); Haley, Bassin, J. Am. Pharm. Assoc. 40, 111 (1951). From kino of Eucalyptus maculata Hook, Myrtaceae: Gell et al., Aust. J. Chem. 11, 372 (1958). Synthesis: Rosenmund, Rosenmund, Ber. 61, 2608 (1928); Zemplén, Bognár, Ber. 75, 648 (1942). Absolute configuration: Gaffield, Waiss, Chem. Commun. 1968, 29.

Chemical structure

Properties

Needles from dilute alc, mp 251°. uv max: 226, 292 nm. Sol in alcohol, ether, benzene; almost insol in water.

Derivative

Triacetylnaringenin.
C15H9(CH3CO)3O5; mol wt 398.36.
C 63.32%, H 4.55%, O 32.13%.

Properties

Crystals, mp 55°.