895. Azafrin
Nomenclature
CAS number: 507-61-9
(5R,6R)-5,6-Dihydro-5,6-dihydroxy-10′-apo-β,ψ-carotenoic acid; escobedin. C27H38O4; mol wt 426.59.
C 76.02%, H 8.98%, O 15.00%.
Description and references
Carotenoid-carboxylic acid from roots of the South American plant “Azafranillo,” Escobedia scabrifolia Ruiz & Pav., and Escobedia laevis Cham. & Schlecht., Scrophulariaceae. Isoln: R. Kuhn et al., Ber. 64, 333 (1931); ibid. 65, 1873 (1932). Structure: R. Kuhn, A. Deutsch, ibid. 66, 883 (1933); R. Kuhn, H. Brockmann, ibid. 67, 885 (1934); Ann. 516, 104 (1935). Absolute configuration (5R:6R): W. Eschenmoser, C. H. Eugster, Helv. Chim. Acta 58, 1722 (1975).
Properties
Orange-colored prisms from toluene, mp 213°. [α]206438 75° (c = 0.28 in alcohol). Absorption max (chloroform): 458, 428 nm. Practically insol in water. Sol in dil NaOH or Na2CO3 solns, in chloroform, alc, acetic acid and benzene; sparingly sol in ether.Derivative
Methyl ester.C28H40O4; mol wt 440.61.
C 76.33%, H 9.15%, O 14.52%.