Quercetin
Title: Quercetin
CAS Registry Number: 117-39-5
CAS Name: 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
Additional Names: 3,3¢,4¢,5,7-pentahydroxyflavone; meletin; sophoretin; cyanidenolon 1522
Molecular Formula: C15H10O7
Molecular Weight: 302.24
Percent Composition: C 59.61%, H 3.33%, O 37.06%
Literature References: The aglucon of quercitrin, of rutin, and of other glycosides. Widely distributed in the plant kingdom, esp in rinds and barks, in clover blossoms and in ragweed pollen. Isoln from Rhododendron cinnabarinum Hook, Ericaceae: Rangaswami et al., Proc. Indian Acad. Sci. 56A, 239 (1962), C.A. 58, 9414a (1963). Structure: Underhill et al., Can. J. Biochem. Physiol. 35, 219 (1957). Biosynthesis: Watkin et al., ibid. 229; Grisebach, Biochem. J. 85, 3p (1962); Patschke et al., Z. Naturforsch. 21b, 201 (1966). Synthesis: Shakhova et al., Zh. Obshch. Khim. 32, 390 (1962), C.A. 58, 1426f (1963). Metabolism: Nakagawa et al., Biochim. Biophys. Acta 97, 233 (1965). Toxicity data: M. Sullivan et al., Proc. Soc. Exp. Biol. Med. 77, 269 (1951). See also Bioflavonoids.
 
Derivative Type: Dihydrate
CAS Registry Number: 6151-25-3
Properties: Yellow needles from dil alcohol. Becomes anhydr at 95-97°. When anhydr dec 314°. uv max (alc): 258, 375 nm (log e 2.75, 2.75). One gram dissolves in 290 ml abs alc, in 23 ml boiling alc. Soluble in glacial acetic acid; in aq alkaline solns with yellow color. Practically insol in water. Alcoholic solns taste very bitter. LD50 orally in mice: 160 mg/kg (Sullivan).
Absorption maximum: uv max (alc): 258, 375 nm (log e 2.75, 2.75)
Toxicity data: LD50 orally in mice: 160 mg/kg (Sullivan)
 
Derivative Type: Pentabenzyl ether
CAS Registry Number: 13157-90-9
Additional Names: 3,3¢,4¢,5,7-Pentakis(benzyloxy)flavone; penta-O-benzylquercetin
Trademarks: Parietrope (Marcofina)
Molecular Formula: C50H40O7
Molecular Weight: 752.85
Percent Composition: C 79.77%, H 5.36%, O 14.88%
Literature References: Prepn: Chopin, Chadenson, C.R. Seances Acad. Sci. Ser. C 263, 729 (1966); Binovic, DE 2122514 (1972 to Biosedra), C.A. 76, 113072n (1972).
Properties: Crystals, mp 123-125°. uv max (chloroform): 249, 343 nm (log e 4.43, 4.14).
Melting point: mp 123-125°
Absorption maximum: uv max (chloroform): 249, 343 nm (log e 4.43, 4.14)
 
Derivative Type: 3-b-D-Galactoside hemipentahydrate
Additional Names: Hyperin; hyperoside
Molecular Formula: C21H20O12.2½H2O
Molecular Weight: 509.41
Percent Composition: C 49.51%, H 4.95%, O 45.54%
Literature References: From Acacia melanoxylon R. Br., Leguminosae: Falco, de Vries, Naturwissenschaften 51, 462 (1964).
Properties: Yellow needles from ethanol, dec 227-230°. [a]D20 -83° (c = 0.2 in pyridine). uv max: 259, 364 nm (log e 4.31, 4.39).
Optical Rotation: [a]D20 -83° (c = 0.2 in pyridine)
Absorption maximum: uv max: 259, 364 nm (log e 4.31, 4.39)
 
Therap-Cat: Capillary protectant.
Keywords: Vasoprotectant.

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