Daphnin
Title: Daphnin
CAS Registry Number: 486-55-5
CAS Name: 7-b-D-Glucopyranosyloxy-8-hydroxy-2H-1-benzopyran-2-one
Additional Names: 7,8-dihydroxycoumarin 7-b-D-glucoside; daphnetin 7-b-D-glucoside; 7-glucosido-8-hydroxycoumarin
Molecular Formula: C15H16O9
Molecular Weight: 340.28
Percent Composition: C 52.94%, H 4.74%, O 42.32%
Literature References: In bark and flower of Daphne spp. Extraction from fresh bark of D. mezereum L., Thymelaeaceae: Beilstein XXXI, 248. Structure: Wessely, Sturm, Ber. 63, 1299 (1930); Hattori, Chem. Zentralbl. 1930 II, 2138. Synthesis: Gandini, Gazz. Chim. Ital. 70, 611 (1940), C.A. 35, 1394 (1941).
Properties: Monohydrate, prisms from water. Anhydr after drying at 80-90° at 2 mm Hg. When anhydrous, dec 215° (Wessely, Sturm); dec 224° (Hattori); dec 229° (older data). Optical rotations of monohydrate: [a]D22 -124° (15 mg in 4 ml MeOH); after 2 recrystns from water: [a]D22 -115° (abs MeOH) (Wessely, Sturm); [a]D15 -84.2° (MeOH) (Hattori). Sol in hot water, alcohol; sol in aq solns of alkalies and alkali carbonates with yellow color. Insol in ether. Hydrolyzed by dilute acid yielding 7,8-dihydroxycoumarin and D-glucose. Also split by emulsin.
Optical Rotation: [a]D22 -124° (15 mg in 4 ml MeOH); [a]D22 -115° (abs MeOH) (Wessely, Sturm); [a]D15 -84.2° (MeOH) (Hattori)

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