6- -esculetin

Other Names Coumarin, 6,7-dihydroxy- Esculetin 6,7-Dihydroxy-2-benzopyrone 6,7-Dihy-droxycoumarin Aesculetin Asculetine Cichorigenin Cichoriin aglycon Esculetol Esculin aglycon NSC 26428 Esculetin CA Index Name 2H-l-Benzopyran-2-one, 6,7-dihydroxy-CAS R istry Number 305-01-1 Merck Index Number 3697 Chemical Structure 

Chemical/Dye Class Fluorescent, Coumarin Molecular Formula C9H5O4 Molecular Weight 178.14 pH Range 1.5-2.0 

Color Change at pH Weak blue fluorescence (1.5) to strong blue fluorescence (2.0) pKa 1.71 

Solubility Almost insoluble in boiling water, ether solnble in hot ethanol, glacial acetic add Melting Point 272-274°C 

Boiling Point (Calcd.) 469.7 45.0 °C Pressure 760 Torr Synthesis Synthetic methods - o 

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Goumanns. By treatment of flax with escuUn, a glucoside of esculetin [305-01-1] (10), a brightening effect is achieved however, this effect is not fast to washing and light. The use of P-methylumbeUiferone [90-33-5] (11) and similar compounds as brighteners for textiles and soap has been patented. 

NMR, 4, 575 Erythritol, 1,4-anhydro-structure, 4, 546 Erythromycin antibacterial veterinary use, 1, 206 as pharmaceutical, 1, 153 synthesis, 1, 480 Erythropterin biosynthesis, 3, 321 occurence, 3, 323 structure, 3, 276 synthesis, 3, 289 Erythropterin, 3,5-dimethyl-methyl ester synthesis, 3, 303 Erythrosine application, 3, 879 Esculetin... 

Methylene Iodide, 1, 57 7, 90 0-Methyl Esculetin, 4, 45 df-METHYL Ethyl Acetic Acid, 5,75 Methyl formate, 3, 67 a-M ETHYL d-GLUCOSIDE, 6, 64... 

Compounds 1 = 4-hydroxycoumarin 2 = umbelliferon 3 = 4-methyl-esculetin 4 = isopimpinellin 5 = esculin 6 = flavone 7 = a-naphtoflavone 8 = kaempferol 9 = quercetin 10 = isoquercitrin 11 = robinetin 12 = robinin 13 = myricetin 14 = luteolin 7-O-glucoside 15 = rutin 16 = hes-peretin 17 = hespiridin 18 = naringin 19 = pelargonin chloride 20 = polargonin chloride 21 = malvin chloride. 

Euphorbia lathyrus L. E. lucorum Rupr. E. resinfera Berger E. thymifolia L. Xu Sui Zi Da Ji Ru Zi Shu Xiao Fei Yang Cao (Caper spurge, petroleum plant) (seed) Euphorbiasteroid, betulin, 7-hydroxylathyrol, lathyrol diacetate benzoate, lathyrol diacetate nicotinate, euphol, euphorbol, euphorbetin, esculetin, daphnetin.33-53-144 This herb is very toxic. Diuretic to remove edema, eliminate blood stasis and resolve masses, antitumor. 

Zanthoxylum schinifolium Sieb. et Zucc. Hua Jiao (Pepper) (pericarp) Estragol, citronellol, phellandrene, xanthoxylene, skimmianine, magnoflorine, xanthoplanine, dictamnine, bergapten, berberine, esculetin dimethyl ether.33 48-53 Treat ascaris, relieve abdominal pain caused by ascariar obstruction. 

Euphorbia lathyrus L. China Euphorbiasteroid, betulin, 7-hydroxylathyrol, lathyrol diacetate benzoate, lathyrol diacetate nicotinate, euphol, euphorbol, euphorbetin, esculetin, daphnetin.33-53 Diuretic to remove edema, eliminate blood stasis and resolve masses, antitumor. 

N.A. Campanula rotundifolia L. C. palustris L. Lutein-7-primveroside, luteolin-7-0-beta-D-glucopyranosil, rhamnetin-3-0-beta-D-galactoside, esculetin, caffeic, n-coumaric, ferulic acids.302 For faintness or a weak heart, stop bleeding, reduce swelling.274... 

Dihydroxycoumarin (esculetin) [305-01-1 ] M 178.2, m 268-270 (dec). Crystd from glacial acetic acid. See also esculetin. 

Both direct and heavy-atom methods have been used to determine structures of substituted coumarins. Examples include 4-hydroxycoumarin and its 3-bromo derivative (65AX927, 66AX646) and the 7,8- and 6,7-dihydroxycoumarins, daphnetin and esculetin, respectively <76AX(B)946, 77AX(B)283). In the last compounds, hydrogen bonds link the molecules in the crystal. The stacking distances are comparable to those for other substituted coumarins <75AX(B)1287). A study of the structure of 7-hydroxy-4-methylcoumarin contains... 

A pure product may be obtained by dissolving with the aid of heat and stirring ioo g. of /3-methyl esculetin in a solution of 200 g. of borax in 700 cc. of water. The solution obtained is filtered while hot and then cooled, whereupon the esculetin borate separates (Note 3). This is filtered off and dissolved in 1800 cc. of water, and the solution thus obtained added to 50 g. of concentrated sulfuric acid in 500 cc. of water. /3-Methyl esculetin separates and, after the mixture has been cooled, is filtered, washed, and dried. From 100 g. of the crude material, 85 g. of pure product melting at 272-2740 (uncor.) is obtained. This is generally nearly colorless but occasionally possesses a slight grayish tinge. 

Hecht SS, Kenney PM, Wang M, Trushin N, Agarwal S, Rao AV, Upadhyaya P. 1999. Evaluation of butylated hydroxyanisole, myo-inositol, curcumin, esculetin, resveratrol and lycopene as inhibitors of benzo[a]pyrene plus 4-(methylnitrosamino)-l-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice. Cancer Lett 137 123-130. 

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