Pelargonidin
Title: Pelargonidin
CAS Registry Number: 134-04-3
CAS Name: 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride
Additional Names: 3,4¢,5,7-tetrahydroxyflavylium chloride; 3,4¢,5,7-tetrahydroxy-2-phenylbenzopyrylium chloride
Molecular Formula: C15H11ClO5
Molecular Weight: 306.70
Percent Composition: C 58.74%, H 3.62%, Cl 11.56%, O 26.08%
Literature References: The aglucone of pelargonin: Willstätter, 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.
Properties: Reddish-brown prisms from 2% HCl or from alcoholic HCl. Not melted at 350°. Absorption max (ethanol + 0.01% HCl): 530 nm (e 32,000). Sol in alcohol, methanol; moderately sol in water; slightly sol in chloroform.
Absorption maximum: Absorption max (ethanol + 0.01% HCl): 530 nm (e 32,000)
 
Derivative Type: 3,5-Diglucoside
CAS Registry Number: 17334-58-6
CAS Name: 3,5-Bis(b-D-glucopyranosyloxy)-7-hydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride
Additional Names: pelargonin; monardin; salvinin; punicin
Molecular Formula: C27H31ClO15
Molecular Weight: 630.98
Percent Composition: C 51.39%, H 4.95%, Cl 5.62%, O 38.03%
Literature References: From flowers of Pelargonium zonale Ait. var. meteor, Geraniaceae: Willstätter, 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°. [a]D -291°. Absorption max (methanol + HCl): 269, 505 nm. Sol in water, alc.
Optical Rotation: [a]D -291°
Absorption maximum: Absorption max (methanol + HCl): 269, 505 nm
 
Derivative Type: 3-Glucoside
CAS Registry Number: 18466-51-8
CAS Name: 3-(b-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride
Additional Names: callistephin
Molecular Formula: C21H21ClO10
Molecular Weight: 468.84
Percent Composition: C 53.80%, H 4.51%, Cl 7.56%, O 34.13%
Literature References: From purple-red aster (Callistephus chinensis (L.) Nees, Compositae): Willstätter, 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 (e 13,000). Sol in water, methanol, ethanol, 0.5-7% aq HCl; moderately sol in 10% HCl.
Absorption maximum: Absorption max (ethanol + HCl): 515 nm (e 13,000)

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