7071. Pelargonidin

Nomenclature

CAS number: 134-04-3
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride; 3,4′,5,7-tetrahydroxyflavylium chloride; 3,4′,5,7-tetrahydroxy-2-phenylbenzopyrylium chloride.
C15H11ClO5; mol wt 306.70.
C 58.74%, H 3.62%, Cl 11.56%, O 26.08%.

Description and references

The aglucone of pelargonin: Willst"atter, Bolton, Ann. 408, 42 (1914). Synthesis: Malkin, Robinson, J. Chem. Soc. 127, 1190 (1925); Robertson et al., 1928, 1533. Prepn from kaempferol: Mirza, Robinson, Nature 166, 997 (1950); King, White, J. Chem. Soc. 1957, 3901.

Chemical structure

Properties

Reddish-brown prisms from 2% HCl or from alcoholic HCl. Not melted at 350°. Absorption max (ethanol + 0.01% HCl): 530 nm (ε 32,000). Sol in alcohol, methanol; moderately sol in water; slightly sol in chloroform.

Derivative

3,5-Diglucoside.

Nomenclature

CAS number: 17334-58-6
3,5-Bis(β-d-glucopyranosyloxy)-7-hydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride; pelargonin; monardin; salvinin; punicin.
C27H31ClO15; mol wt 630.98.
C 51.39%, H 4.95%, Cl 5.62%, O 38.03%.

Description and references

From flowers of Pelargonium zonale Ait. var. meteor, Geraniaceae: Willst"atter, Bolton, loc. cit.; from scarlet roses: Harborne, Experientia 17, 72 (1961). Identity with monardin and salvinin: Robinson, Todd, J. Chem. Soc. 1932, 2488. Identity with punicin: Karrer, Widmer, Helv. Chim. Acta 10, 67 (1927). Structure: Leon et al., J. Chem. Soc. 1931, 2672.

Properties

Red needles with green luster from methanol + HCl, dec 175-180°. [α]D -291°. Absorption max (methanol + HCl): 269, 505 nm. Sol in water, alc.

Derivative

3-Glucoside.

Nomenclature

CAS number: 18466-51-8
3-(β-d-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride; callistephin.
C21H21ClO10; mol wt 468.84.
C 53.80%, H 4.51%, Cl 7.56%, O 34.13%.

Description and references

From purple-red aster (Callistephus chinensis (L.) Nees, Compositae): Willst"atter, Burdick, Ann. 412, 149 (1916); from strawberries: Sondheimer, Kertesz, J. Am. Chem. Soc. 70, 3476 (1948). Structure and synthesis: Robertson, Robinson, J. Chem. Soc. 1928, 1460.

Properties

Dark brownish-red needles with bronze luster. Absorption max (ethanol + HCl): 515 nm (ε 13,000). Sol in water, methanol, ethanol, 0.5-7% aq HCl; moderately sol in 10% HCl.