8706. Solanocapsine
Nomenclature
CAS number: 639-86-1
(3β,5α,16α,22α,23β,25β)-3-Amino-16,23-epoxy-16,28-secosolanidan-23-ol; solanocapsin; 3β-amino-22,26-imino-16β,23-oxido-5α,22α,23β,25α-cholestan-23-ol; 3β-amino-22,26-imino-16β,23-oxido-5α,22R,23S,25R-cholestan-23-ol. C27H46N2O2; mol wt 430.67.
C 75.30%, H 10.77%, N 6.50%, O 7.43%.
Description and references
From Solanum pseudocapsicum L., S. capsicastrum Link, S. hendersonii hort., Solanaceae. Isolation: Barger, Fraenkel-Conrat, J. Chem. Soc. 1936, 1537; K. Schreiber, H. Ripperger, Z. Naturforsch. 17B, 217 (1962). Structure: eidem, Experientia 16, 536 (1960). Revised structure and synthesis: eidem, Ann. 723, 159 (1969). Stereochemistry: eidem, Tetrahedron Letters no. 27, 9 (1960); Ann. 655, 114 (1962). Synthesis: Ripperger et al., Tetrahedron Lett. 1970, 5251; eidem, Tetrahedron 28, 1629 (1972).
Properties
Monohydrate, needles from methanol, mp 213-215°. [α]D20 +26.3° (c = 1.80 in methanol); [α]D20 +24.9° (c = 2.13 in methanol).Derivative
N′-Acetylsolanocapsine.C29H48N2O3; mol wt 472.70.
C 73.69%, H 10.24%, N 5.93%, O 10.15%.
Properties
Needles from ethanol, mp 233-234°. [α]D23 33.7° (c = 1.59 in pyridine).Derivative
N,N′-Diacetylsolanocapsine.C31H50N2O4; mol wt 514.74.
C 72.33%, H 9.79%, N 5.44%, O 12.43%.
Properties
Crystals from chloroform + acetone, mp 281-283°. [α]D22 38.6° (c = 1.31 in pyridine).Derivative
N,N,N′-Trimethylsolanocapsine.C30H52N2O2; mol wt 472.75.
C 76.22%, H 11.09%, N 5.93%, O 6.77%.
Properties
Needles from abs methanol, mp 222-224°. [α]D22 +53.2° (c = 1.09 in pyridine).Derivative
N-Benzylidenesolanocapsine.C34H50N2O2; mol wt 518.77.
C 78.72%, H 9.71%, N 5.40%, O 6.17%.