5715. Malvidin Chloride

Nomenclature

CAS number: 643-84-5
3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloride; 3,4′,5,7-tetrahydroxy-3′,5′-dimethoxyflavylium chloride; enidin; primulidin; syringidin; 3,4′,5,7-tetrahydroxy-3′,5′-dimethoxy-2-phenylbenzopyrylium chloride.
C17H15ClO7; mol wt 366.75.
C 55.67%, H 4.12%, Cl 9.67%, O 30.54%.

Description and references

Found as the diglucoside (malvin) in wild malve (Primula viscosa All., Primulaceae) and as the monoglucoside in blue grapes: Willst"atter, Mieg, Ann. 408, 122 (1915); Karrer, Widmer, Helv. Chim. Acta 10, 5 (1927). Structure: Anderson, Nabenhauer, J. Am. Chem. Soc. 48, 2997 (1926). Synthesis: Bradley, Robinson, J. Chem. Soc. 1928, 1541.

Chemical structure

Properties

Prisms or rhombic tablets, appearing red by transmitted light with a green luster when dry or with a steel-blue luster when in contact with solvent. Usually obtained as the mono- or dihydrate. The anhydr salt is very hygroscopic. Not melted at 300°. Sol in abs alc, giving a violet-red soln. Sparingly sol in water. Also sol in amyl alc. In methanol the substance is first sol with purple color, then begins to separate as red crystals which are violet by transmitted light.

Derivative

3-β-Glucoside tetrahydrate.

Nomenclature

3-(Glucosyloxy)-4′,5,7-trihydroxy-3′,5′-dimethoxyflavylium chloride; enin; cyclamin.
C23H25ClO12.4H2O; mol wt 600.95.
C 45.97%, H 5.53%, Cl 5.90%, O 42.60%.

Properties

Synthesis: Levy et al., J. Chem. Soc. 1931, 2701. Dark prisms with a green metallic shine, from alcohol + HCl. Sparingly sol in water, alcohol, glycerol. Practically insol in benzene, chloroform, ether.

Derivative

3,5-Diglucoside.

Nomenclature

3,5-Bis(glucosyloxy)-4′,7-dihydroxy-3′,5′-dimethoxyflavylium chloride; malvin; malvoside.
C29H35ClO17; mol wt 691.03.
C 50.40%, H 5.11%, Cl 5.13%, O 39.36%.

Properties

Synthesis: Robinson, Todd, ibid. 1932, 2299. Reddish-brown prisms or needles with a green shine from dil HCl, dec 165°.

Derivative

3-Galactoside hemihendecahydrate.

Nomenclature

Primulin.
C23H25ClO12.5 1/2 H2O; mol wt 627.97.
C 43.99%, H 5.78%, Cl 5.65%, O 44.59%.

Properties

Bronze metallic needles or prisms from methanol + HCl. Bluish-violet by transmitted light. Very sol in methanol, ethanol, cold water, forming deep red solns; slightly sol in acetone. Practically insol in ethyl acetate.