Detail of "520-18-3"

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CAS Number:
520-18-3
Name:
4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-hydroxyphenyl)-
Superlist Name:
Kaempferol
Molecular Structure:
Formula:
C₁₅H₁₀O₆
Molecular Weight:
286.25
Synonyms:
Flavone,3,4',5,7-tetrahydroxy- (7CI,8CI);3,4',5,7-Tetrahydroxyflavone;3'-Deoxyquercetin;5,7,4'-Trihydroxyflavonol;C.I. 75640;Indigo Yellow;Kaempferol;Kaempherol;Kampcetin;Kempferol;NSC 407289;NSC 656277;Nimbecetin;Pelargidenolon;Pelargidenon;Populnetin;Rhamnolutein;Rhamnolutin;Robigenin;Swartziol;Trifolitin;
EINECS:
208-287-6
Density:
1.688 g/cm³
Melting Point:
276 °C
Boiling Point:
582.1 °C at 760 mmHg
Flash Point:
226.1 °C
Solubility:
ethanol: 20 mg/mL in water
Appearance:
Yellow solid
Hazard Symbols:
Xi
Risk Codes:
36/37/38
Safety:
26-36 Details

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Reference

Studies on flavonol degradation by peroxidase (donor:hydrogen peroxide-oxidoreductase, E: Studies on flavonol degradation by peroxidase (donor:hydrogen peroxide-oxidoreductase, E.C.1.11.1.7): Part 1. Kaempferol. Miller, Ernst; Schreier, Peter (Univ. Wuerzburg, Wuerzburg D-8700, Fed. Rep. Ger.). Food Chem., 17(2), 143-54 (English) 1985. CODEN: FOCHDJ. ISSN: 0308-8146. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) Section cross-reference(s): 7 The degrdn. of kaempferol [520-18-3] by peroxidase [9003-99-0] was studied at pH 5.5 under UV-spectrophotometric control. The reaction products obtained after incubation of kaempferol (dissolved in ethylene glycol monomethyl ether) with peroxidase/H2O2 were fractionated by liq. chromatog. on Sephadex LH-20. About 20 compds. were detected, of which 4 could be characterized by means of their spectroscopic data: 2,4,6-trihydroxybenzoic acid [83-30-7], 4-hydroxybenzoic acid [99-96-7], 2,2-dihydroxy-1-(2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-pro panedione [98119-98-3], and 2-(4-methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one (acacetin) [480-44-4].

Actions of flavonoids and the novel antiinflammatory flavone, hypoletin-8-glucoside, on prostaglandin biosynthesis and inactivation: Actions of flavonoids and the novel antiinflammatory flavone, hypoletin-8-glucoside, on prostaglandin biosynthesis and inactivation. Alcaraz, M. J.; Hoult, J. R. S. (Dep. Pharmacol., King's Coll., London WC2R 2LS, UK). Biochem. Pharmacol., 34(14), 2477-82 (English) 1985. CODEN: BCPCA6. ISSN: 0006-2952. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) The newly identified plant-derived flavone-glycoside hypoletin-8-glucoside (I) [27686-36-8] which has antiinflammatory and gastric ulcer protective properties, and its corresponding aglycon, hypolaetin [27696-41-9], were tested for effects on prostaglandin biosynthesis and degrdn. They were compared with 4 other flavonoids, viz. rutin [153-18-4] and its corresponding aglycon, quercetin [117-39-5], and the aglycons isocutellarein [41440-05-5] and kaempferol [520-18-3]. Over the range 10-1000 mM the glycosides rutin and hypoletin-8-glucoside stimulated prostaglandin formation by sheep seminal vesicle microsomes incubated with radiolabeled arachidonic acid; the other compds. were essentially inactive. Over 5-5000 mM rutin and hypoletin-8-glucoside enhanced the release of the prostacyclin (and other prostanoids) from fragments of rat cecum incubated in the absence of addnl. arachidonic acid; the 4 aglycons compds. did not stimulate prostacyclin release but some reduced it at 5000 mM. However, the glycosides did not affect the enzymic inactivation of radiolabeled prostaglandin F2a by semi-purified bovine lung prostaglandin 15-hydroxydehydrogenase (PGDH) [9030-87-9] or in 100,000 g supernatants prepd. from homogenized rat stomach. Three of the 4 aglycons (quercetin, kaempferol, isoscutellarein, in descending order of potency) were inhibitory to PGDH with ID50 values in the range 130-2100 mM. The results show that the capacity of flavonoids to enhance prostaglandin formation is assocd. with the presence of glycosidic substitution whereas PGDH-inhibition requires its absence. The relevance of this biochem. profile of hypoletin-8-glucoside to its anti-inflammatory gastroprotective effects in vivo is discussed.

Detail of "520-18-3"

4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-hydroxyphenyl)-

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Reference