Title: Diosmetin
CAS Registry Number: 520-34-3
CAS Name: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Additional Names: 3¢,5,7-trihydroxy-4¢-methoxyflavone; cyanidenon-4¢-methyl ether 1479; luteolin-4¢-methyl ether
Molecular Formula: C16H12O6
Molecular Weight: 300.26
Percent Composition: C 64.00%, H 4.03%, O 31.97%
Literature References: Aglycone of diosmin, q.v. Prepn from diosmin isolated from various plant sources: O. A. Oesterle, G. Wander, Helv. Chim. Acta 8, 519 (1925); isoln from lemons (Citrus limon Linn., Rutaceae): R. M. Horowitz, J. Org. Chem. 21, 1184 (1956). Synthesis and structural elucidation: G. Zemplén, R. Bognár, Ber. 76, 452 (1943). Synthesis: A. Lovecy et al., J. Chem. Soc. 1930, 817; N. B. Lorette et al., J. Org. Chem. 16, 930 (1951); J. H. Looker, M. J. Holm, ibid. 24, 1019 (1959). HPLC determn in biological fluids: D. Baylocq et al., Ann. Pharm. Fr. 41, 115 (1983).
Derivative Type: Hemimethanolate
Molecular Formula: C16H12O6.½CH3OH
Molecular Weight: 316.28
Percent Composition: C 62.66%, H 4.46%, O 32.88%
Properties: Yellow needles from alcohol/ethyl acetate, sinters at 248°. mp 253-254°. Also reported as small yellow needles from methanol, mp 258-259° (Horowitz). uv max: 345, 268, 253 nm (log e 4.32, 4.25, 4.28).
Melting point: mp 253-254°; mp 258-259° (Horowitz)
Absorption maximum: uv max: 345, 268, 253 nm (log e 4.32, 4.25, 4.28)
Derivative Type: Triacetate
Molecular Formula: C22H18O9
Molecular Weight: 426.37
Percent Composition: C 61.97%, H 4.26%, O 33.77%
Properties: Colorless needles from methanol, mp 195-196°.
Melting point: mp 195-196°
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