5090. Irigenin

Nomenclature

CAS number: 548-76-5
5,7-Dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 3′,5,7-trihydroxy-4′,5′,6-trimethoxyisoflavone.
C18H16O8; mol wt 360.31.
C 60.00%, H 4.48%, O 35.52%.

Description and references

From rhizome of Iris florentina L., Iridaceae: de Laire, Tiemann, Ber. 26, 2010 (1893). Structure: Baker, J. Chem. Soc. 1928, 1022. Synthesis: Baker et al., Tetrahedron Lett. no. 5, 6 (1960); Farkas, Várady, Ber. 93, 2685 (1960); Baker et al., J. Chem. Soc. C 1970, 1219.

Chemical structure

Properties

Yellow plates or needles from dil alc, mp 185°. uv max (abs ethanol): 267 nm. Sol in warm alcohol, benzene, chloroform; practically insol in water, ether, petr ether.

Derivative

Triacetate.
C24H22O11; mol wt 486.42.
C 59.26%, H 4.56%, O 36.18%.

Properties

Prisms from dil acetic acid, mp 127-128°.

Derivative

7-Glucoside.

Nomenclature

Iridin; 7-(glucosyloxy)-3′,5-dihydroxy-4′,5′,6-trimethoxyisoflavone.
C24H26O13; mol wt 522.46.
C 55.17%, H 5.02%, O 39.81%.

Properties

Monohydrate, needles from dil alc, mp 208°. When anhydrous, mp 217°. One gram of anhydrous iridin dissolves in 500 ml water, 43 ml acetone. Sol in hot alcohol; practically insol in ether, ethyl acetate, benzene, chloroform.

Note

There also is an oleoresin called iridin (Extractum Iridis) from Iris versicolor (blue flag) by extraction with 60% alc. Another substance named iridine is a protamine from the sperm of rainbow trout: Felix, Mager, Z. Physiol. Chem. 249, 124 (1937).