2880. Delphinidin

Nomenclature

CAS number: 528-53-0
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium chloride; 3,3′,4′,5,5′,7-hexahydroxyflavylium chloride; 3,3′,4′,5,5′,7-hexahydroxy-2-phenylbenzopyrylium chloride; delphinidol.
C15H11ClO7; mol wt 338.70.
C 53.19%, H 3.27%, Cl 10.47%, O 33.07%.

Description and references

The aglucone of delphinin: Willst"atter, Mieg, Ann. 408, 61 (1915); the aglucone of violanin: Willst"atter, 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.

Chemical structure

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.

Derivative

3-Glucoside.

Nomenclature

Myrtillin-a.
C21H21ClO12; mol wt 500.84.
C 50.36%, H 4.23%, Cl 7.08%, O 38.33%.

Description and references

From the whortleberry (Vaccinium myrtillus L., Ericaceae): Willst"atter, 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.

Derivative

3,5-Diglucoside.

Nomenclature

3,5-Bis(glucosyloxy)-3′,4′,5′,7-tetrahydroxyflavylium chloride; delphin; delphoside; hyacin.
C27H31ClO17; mol wt 662.98.
C 48.91%, H 4.71%, Cl 5.35%, O 41.03%.

Description and 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.

Derivative

Compound with glucose + hydroxybenzoic acid.

Nomenclature

Delphinin.
C41H39ClO21; mol wt 903.19.
C 54.52%, H 4.35%, Cl 3.93%, O 37.20%.

Description and references

From Delphinium consolida L., Ranunculaceae: Willst"atter, 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

Compound with glucose + rhamnose + p-hydroxycinnamic acid.

Nomenclature

Violanin.
C36H37ClO18; mol wt 793.12.
C 54.52%, H 4.70%, Cl 4.47%, O 36.31%.

Description and references

From flowers of Viola tricolor L., Violaceae: Willst"atter, 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.