芦丁三水合物 , Rutin trihydrate

Capillary protectant; free radical scavenger; antioxidant.

Rutin analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Rutin is representative of vitamin P- related compounds. xanthon Extracted from aerial parts of Laganychim farctum

It has a wide spectrum of pharmacological activities, mainly anti-inflammmatory, anti-ulcerogenic, photo- and radioprotective.,It is a choleretic.

Rutin, also known as rutoside or phytomelin, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Rutin exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Rutin has been primarily detected in blood. Within the cell, rutin is primarily located in the cytoplasm. Outside of the human body, rutin can be found in a number of food items such as beer, eggplant, garlic, and lemon. This makes rutin a potential biomarker for the consumption of these food products.

Rutin is a rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. It has a role as a metabolite and an antioxidant. It is a disaccharide derivative, a quercetin O-glucoside, a tetrahydroxyflavone and a rutinoside.

A flavonol glycoside found in many plants, including buckwheat; tobacco; forsythia; hydrangea; viola, etc. It has been used therapeutically to decrease capillary fragility.

Title: Rutin

CAS Registry Number: 153-18-4

CAS Name: 3-[[6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one

Additional Names: rutoside; quercetin-3-rutinoside; 3,3',4',5,7-pentahydroxyflavone-3-rutinoside; melin; phytomelin; eldrin; ilixathin; sophorin; globularicitrin; paliuroside; osyritrin; osyritin; myrticolorin; violaquercitrin

Trademarks: Birutan (Merck KGaA)

Molecular Formula: C27H30O16

Molecular Weight: 610.52

Percent Composition: C 53.12%, H 4.95%, O 41.93%

Literature 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).

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). [a]D23 +13.82° (ethanol); [a]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).

Optical Rotation: [a]D23 +13.82° (ethanol); [a]D23 -39.43° (pyridine)

Toxicity data: LD50 i.v. in mice: 950 mg/kg (propylene glycol soln) (Harrison)

Therap-Cat: Capillary protectant.

Keywords: Vasoprotectant.