8304. Rutin

Nomenclature

CAS number: 153-18-4
3-[[6-O-(6-Deoxy-α-l-mannopyranosyl)-β-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; rutoside; quercetin-3-rutinoside; 3,3′,4′,5,7-pentahydroxyflavone-3-rutinoside; melin; phytomelin; eldrin; ilixathin; sophorin; globularicitrin; paliuroside; osyritrin; osyritin; myrticolorin; violaquercitrin; Birutan (Merck KGaA).
C27H30O16; mol wt 610.52.
C 53.12%, H 4.95%, O 41.93%.

Description and references

Identity with ilixanthin: Schindler, Herb, Arch. Pharm. 288, 372 (1955). Found in many plants, especially the buckwheat plant (Fagopyrum esculentum Moench., Polygonaceae) which contains about 3% (dry basis): Couch et al., Science 103, 197 (1946). From tobacco (Nicotiana tabacum L., Solanaceae) Couch, Krewson, U.S. Dept. Agr., Eastern Regional Res. Lab. AIC-52 (1944). In forsythia [Forsythia suspensa (Thunb.) Vahl. var. fortunei (Lindl.) Rehd., Oleaceae], in hydrangea (Hydrangea paniculata Sieb., Saxifragaceae), in pansies (Viola sp., Violaceae). General extraction procedure: Beilstein XXXI, 376. From leaves of Eucalyptus macroryncha F. v. Muell., Myrtaceae: Attree, Perkin, J. Chem. Soc. 1927, 234. Industrial production from Eucalyptus spp.: Humphreys, Econ. Bot. 18, 195 (1964). Structure: Zemplén, Gerecs, Ber. 68B, 1318 (1935). Synthesis: Shakhova et al., Zh. Obshch. Khim. 32, 390 (1962), C.A. 58, 1426e (1963). Rutin is hydrolyzed by rhamnodiastase from the seed of Rhamnus utilis Decne, Rhamnaceae (Chinese buckthorn); emulsin is not effective: Bridel, Charaux, Compt. Rend. 181, 925 (1925). Toxicity data: Harrison et al., J. Am. Pharm. Assoc. 39, 557 (1950). Book: J. Q. Griffith, Jr., Rutin and Related Flavonoids (Mack, Easton, Pa., 1955). Comprehensive description: T. I. Khalifa et al., Anal. Profiles Drug Subs. 12, 623-681 (1983).

Chemical structure

Properties

Pale yellow needles from water, gradual darkening on exposure to light. The crystals contain 3 H2O and become anhydr after 12 hrs at 110° and 10 mm Hg. Anhydr rutin browns at 125°, becomes plastic at 195-197°, and dec 214-215° (with effervescence). [α]D23 +13.82° (ethanol); [α]D23 -39.43° (pyridine). Anhydr rutin is hygroscopic. One gram dissolves in about 8 liters water, about 200 ml boiling water, 7 ml boiling methanol. Sol in pyridine, formamide and alkaline solns; slightly sol in alcohol, acetone, ethyl acetate. Practically insol in chloroform, carbon bisulfide, ether, benzene, petr solvents. Dil solns give green color with ferric chloride. Rutin is colored brown by tobacco enzyme under experimental conditions: Neuberg, Kobel, Naturwissenschaften 23, 800 (1935). LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison).

Therapeutic Category

Capillary protectant.

Keywords

Vasoprotectant