Title: Carthamin
CAS Registry Number: 36338-96-2
CAS Name: (2Z,6S)-6-b-D-Glucopyranosyl-2-[[(3S)-3-b-D-glucopyranosyl-2,3,4-trihydroxy-5-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-6-oxo-1,4-cyclohexadien-1-yl]methylene]-5,6-dihydroxy-4-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-4-cyclohexene-1,3-dione
Additional Names: carthamic acid; safflor carmine; safflor red; C.I. Natural Red 26; C.I. 75140
Molecular Formula: C43H42O22
Molecular Weight: 910.78
Percent Composition: C 56.71%, H 4.65%, O 38.65%
Literature References: Coloring principle from safflower, Carthamus tinctorius L., Compositae. Purification and review of early efforts: T. Kametaka, A. G. Perkin, J. Chem. Soc. 97, 1415 (1910). Structure: C. Kuroda, J. Chem. Soc. 1930, 752, 765. Revised structure: H. Obara, J. Onodera, Chem. Lett. 1979, 201. Absolute configuration: S. Sato et al., ibid. 1996, 833. Total synthesis as acetate: S. Sato et al., ibid. 2001, 1318. Biogenesis: M. Shimokoriyama, S. Hattori, Arch. Biochem. Biophys. 54, 93 (1955). Determn of levels in Carthamus Red: T. Morimoto et al., Nippon Shokuhin Kagaku Gakkaishi 5, 236 (1998). Color stability in aqueous soln: J.-B. Kim, Y.-S. Paik, Arch. Pharmacal Res. 20, 643 (1997); with polysaccharides: K. Saito, Acta. Bot. Croat. 57, 123 (1998). Review of prepn protocols: K. Saito, Y. Fukaya, Acta Alimentaria 26, 141-152 (1997). See also: Colour Index vol. 4 (3rd ed., 1971) p 4625.
Properties: Bright scarlet prismatic needles, mp 228-230° (dec). Hygroscopic. uv max (ethanol): 244, 373, 515 nm (log e 4.33, 4.48, 4.99). Absorption max (DMF): 530 nm; E1cm1% 992 (e 90370). Sparingly sol in water, ethanol and methanol; sol in dil alkali hydroxides, sodium carbonate and ammonia with an orange color. Insol in acetone.
Melting point: mp 228-230° (dec)
Absorption maximum: uv max (ethanol): 244, 373, 515 nm (log e 4.33, 4.48, 4.99); Absorption max (DMF): 530 nm; E1cm1% 992 (e 90370)
Use: Food color and dye in cosmetics. |