Irigenin
Title: Irigenin
CAS Registry Number: 548-76-5
CAS Name: 5,7-Dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
Additional Names: 3¢,5,7-trihydroxy-4¢,5¢,6-trimethoxyisoflavone
Molecular Formula: C18H16O8
Molecular Weight: 360.31
Percent Composition: C 60.00%, H 4.48%, O 35.52%
Literature 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.
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.
Melting point: mp 185°
Absorption maximum: uv max (abs ethanol): 267 nm
 
Derivative Type: Triacetate
Molecular Formula: C24H22O11
Molecular Weight: 486.42
Percent Composition: C 59.26%, H 4.56%, O 36.18%
Properties: Prisms from dil acetic acid, mp 127-128°.
Melting point: mp 127-128°
 
Derivative Type: 7-Glucoside
Additional Names: Iridin; 7-(glucosyloxy)-3¢,5-dihydroxy-4¢,5¢,6-trimethoxyisoflavone
Molecular Formula: C24H26O13
Molecular Weight: 522.46
Percent Composition: 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.
Melting point: mp 208°; mp 217°
 
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).

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