Hesperidin, 二氢黄酮苷, 橙皮苷

Hesperidin is a flavonoid that is found in citrus fruits. Hesperidin has been shown to have pro-apoptotic properties and can be used to prevent neuronal death. It also has been shown to have biological properties that include anion radical scavenging, which may be due to its ability to form bound forms with iron ions. Hesperidin has been shown to have anti-infectious properties as well as cardioprotective effects such as the prevention of myocardial infarcts.

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)