Esculin
Title: Esculin
CAS Registry Number: 531-75-9
CAS Name: 6-(b-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one
Additional Names: 6,7-dihydroxycoumarin 6-glucoside; esculoside; bicolorin; enallachrome; polychrome
Trademarks: Escosyl
Molecular Formula: C15H16O9
Molecular Weight: 340.28
Percent Composition: C 52.94%, H 4.74%, O 42.32%
Literature References: In leaves and bark of horse chestnut tree Aesculus hippocastanum L., Hippocastanaceae. Extraction procedure: Tumann, Chem. Zentralbl. 1916, I, 1277. Synthesis: Merz, Hagemann, Naturwissenschaften 29, 650 (1941); eidem, Arch. Pharm. 282, 79 (1944); Amiard, Nominé, Bull. Soc. Chim. Fr. 1948, 476. Use in bile-esculin test for identification of group D streptococci: C. Chuard, L. B. Reller, J. Clin. Microbiol. 36, 1135 (1998).
 
Derivative Type: Sesquihydrate
Properties: Needles from hot water, mp 204-206°. One gram dissolves in 580 ml water, 13 ml boiling water. Sol in hot alcohol, methanol, pyridine, ethyl acetate, acetic acid. Aq solns show blue fluorescence above pH 5.8. [a]D18 -78.4° (c = 2.5 in 50% dioxane). Absorption spectrum: Merz, Arch. Pharm. 270, 482 (1932); Goodwin, Pollock, Arch. Biochem. Biophys. 49, 1 (1954). Has vitamin P activity.
Melting point: mp 204-206°
Optical Rotation: [a]D18 -78.4° (c = 2.5 in 50% dioxane)
 
Derivative Type: Pentaacetate dihydrate
Properties: Needles from methanol, mp 163-164°.
Melting point: mp 163-164°
 
Derivative Type: 4-Methylesculin
Molecular Formula: C16H18O9
Molecular Weight: 354.31
Percent Composition: C 54.24%, H 5.12%, O 40.64%
Literature References: Prepn: Velluz, Amiard, Bull. Soc. Chim. Fr. 1948, 1109.
 
Use: Reagent for microbiological identification test.

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