4736. Homoeriodictyol

Nomenclature

CAS number: 446-71-9
2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one; 4′,5,7-trihydroxy-3′-methoxyflavanone; eriodictyonone; cyanidanon-3-methyl ether 1625.
C16H14O6; mol wt 302.28.
C 63.57%, H 4.67%, O 31.76%.

Description and references

From Eriodictyon californicum (H. & A.) Torr., and E. angustifolium Nutt., Hydrophyllaceae: Geissman, J. Am. Chem. Soc. 62, 3258 (1940); Hadley, Gisvold, J. Am. Pharm. Assoc. 33, 275 (1944). Purification: Seka, Prosche, Monatsh. Chem. 69, 284 (1936). Structure: Shinoda, Sato, J. Pharm. Soc. Jpn. 49, 64 (1929), C.A. 23, 4210 (1929). Synthesis: Farooq et al., Naturwissenschaften 46, 76 (1959).

Chemical structure

Properties

Crystals from 70% acetic acid. Needles by sublimation in high vacuum (0.003-0.005 mm Hg) at 190-195°. Plates from dil alc, dec 225° (after drying in vacuo at 110°). [α]D20 28° (alc). uv max (alc): 290, 328 nm (log ε 2.26, 2.33). Moderately sol in alcohol, acetic acid. Nearly insol in water, ethyl acetate; practically insol in benzene, chloroform.

Derivative

Triacetate.

Properties

mp 115-116°.