Title: Hesperidin
CAS Registry Number: 520-26-3
CAS Name: (2S)-7-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Additional Names: hesperetin 7-rhamnoglucoside; cirantin; hesperetin-7-rutinoside
Molecular Formula: C28H34O15
Molecular Weight: 610.56
Percent Composition: C 55.08%, H 5.61%, O 39.31%
Literature References: Predominant flavonoid in lemons and sweet oranges (Citrus sinensis). Extraction procedures: Higby, J. Am. Pharm. Assoc. Sci. Ed. 30, 629 (1941); US 2421061 (1947); Baier, US 2442110 (1948 to Calif. Fruit Growers Exchange). Structure: King, Robertson, J. Chem. Soc. 1931, 1704; Arthur et al., ibid. 1956, 632; Horowitz, Gentili, Tetrahedron 19, 773 (1963). Synthesis: Zemplen, Bognar, Ber. 75, 1043 (1943); 76, 773 (1943). Identity with cirantin: Manwaring et al., Phytochemistry 7, 1881 (1968). See also Bioflavonoids, Rutinose.
Properties: Fine, dendritic needles by precipitation at pH 6-7, mp 258-262° (softens at 250°). [a]D20 -76° (c = 2 in pyridine). One gram dissolves in 50 l water. Sol in formamide, DMF at 60°. Slightly sol in methanol, hot glacial acetic acid. Almost insol in acetone, benzene, chloroform. Freely sol in dil alkalies, pyridine.
Melting point: mp 258-262° (softens at 250°)
Optical Rotation: [a]D20 -76° (c = 2 in pyridine) |