Title: Delphinidin
CAS Registry Number: 528-53-0
CAS Name: 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium chloride
Additional Names: 3,3¢,4¢,5,5¢,7-hexahydroxyflavylium chloride; 3,3¢,4¢,5,5¢,7-hexahydroxy-2-phenylbenzopyrylium chloride; delphinidol
Molecular Formula: C15H11ClO7
Molecular Weight: 338.70
Percent Composition: C 53.19%, H 3.27%, Cl 10.47%, O 33.07%
Literature References: The aglucone of delphinin: Willstätter, Mieg, Ann. 408, 61 (1915); the aglucone of violanin: Willstätter, Weil, ibid. 412, 178 (1917). Occurrence in plants: Acheson, Can. J. Biochem. Physiol. 37, 1 (1959). Synthesis: Pratt, Robinson, J. Chem. Soc. 127, 166 (1925); Bradley et al., ibid. 1930, 793.
Properties: Chocolate-brown prisms or needles with metallic luster from 5% HCl. Crystallizes from water with 1, 2 or 4 mols H2O. When anhydr does not melt below 350°. Absorption max (methanolic HCl): 544 nm. Sol in methanol, ethanol, ethyl acetate.
Absorption maximum: Absorption max (methanolic HCl): 544 nm
Derivative Type: 3-Glucoside
Additional Names: Myrtillin-a
Molecular Formula: C21H21ClO12
Molecular Weight: 500.84
Percent Composition: C 50.36%, H 4.23%, Cl 7.08%, O 38.33%
Literature References: From the whortleberry (Vaccinium myrtillus L., Ericaceae): Willstätter, Zollinger, Ann. 408, 83 (1915); 412, 195 (1916); from the pansy (Viola tricolor L., Violaceae): Karrer, de Meuron, Helv. Chim. Acta 16, 292 (1933). Structure and synthesis: Reynolds, Robinson, J. Chem. Soc. 1934, 1039.
Properties: Deep purple crystals from dil HCl. Absorption max (methanolic HCl): 535 nm.
Absorption maximum: Absorption max (methanolic HCl): 535 nm
Derivative Type: 3,5-Diglucoside
Additional Names: 3,5-Bis(glucosyloxy)-3¢,4¢,5¢,7-tetrahydroxyflavylium chloride; delphin; delphoside; hyacin
Molecular Formula: C27H31ClO17
Molecular Weight: 662.98
Percent Composition: C 48.91%, H 4.71%, Cl 5.35%, O 41.03%
Literature References: From flowers of Salvia patens Cav., Labiatae, structure and synthesis: Reynolds et al., J. Chem. Soc. 1934, 1235; from flowers of Verbena hybrida Hart., Verbenaceae: Scott-Moncrieff, Sturgess, Biochem. J. 34, 268 (1940); from grape skins: Bockian et al., J. Agric. Food Chem. 3, 695 (1955). Identity with hyacin: Saito et al., Proc. Jpn. Acad. 36, 340 (1960).
Properties: Leaflets with bronze luster from dil HCl. Absorption max (methanolic HCl): 534 nm. Practically insol in cold water, alcohol, dil acids; sol in hot dil HCl.
Absorption maximum: Absorption max (methanolic HCl): 534 nm
Derivative Type: Compound with glucose + hydroxybenzoic acid
Additional Names: Delphinin
Molecular Formula: C41H39ClO21
Molecular Weight: 903.19
Percent Composition: C 54.52%, H 4.35%, Cl 3.93%, O 37.20%
Literature References: From Delphinium consolida L., Ranunculaceae: Willstätter, Mieg, loc. cit.
Properties: Dark red-brown plates or prisms from 3% HCl. dec 200-203°. Sol in water with decompn, dil alcohol, acetone, boiling alcohol.
Derivative Type: Compound with glucose + rhamnose + p-hydroxycinnamic acid
Additional Names: Violanin
Molecular Formula: C36H37ClO18
Molecular Weight: 793.12
Percent Composition: C 54.52%, H 4.70%, Cl 4.47%, O 36.31%
Literature References: From flowers of Viola tricolor L., Violaceae: Willstätter, Weil, loc. cit. Structure: Karrer, de Meuron, loc. cit.
Properties: Bluish-violet plates with green metallic luster from methanolic HCl + ether. Sol in amyl alcohol, in 0.15-0.5% HCl; less sol in 1% HCl; slightly sol in water; practically insol in 5-12% HCl.
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