Solanocapsine
Title: Solanocapsine
CAS Registry Number: 639-86-1
CAS Name: (3b,5a,16a,22a,23b,25b)-3-Amino-16,23-epoxy-16,28-secosolanidan-23-ol
Additional Names: solanocapsin; 3b-amino-22,26-imino-16b,23-oxido-5a,22a,23b,25a-cholestan-23-ol; 3b-amino-22,26-imino-16b,23-oxido-5a,22R,23S,25R-cholestan-23-ol
Molecular Formula: C27H46N2O2
Molecular Weight: 430.67
Percent Composition: C 75.30%, H 10.77%, N 6.50%, O 7.43%
Literature 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°. [a]D20 +26.3° (c = 1.80 in methanol); [a]D20 +24.9° (c = 2.13 in methanol).
Melting point: mp 213-215°
Optical Rotation: [a]D20 +26.3° (c = 1.80 in methanol); [a]D20 +24.9° (c = 2.13 in methanol)
 
Derivative Type: N¢-Acetylsolanocapsine
Molecular Formula: C29H48N2O3
Molecular Weight: 472.70
Percent Composition: C 73.69%, H 10.24%, N 5.93%, O 10.15%
Properties: Needles from ethanol, mp 233-234°. [a]D23 -33.7° (c = 1.59 in pyridine).
Melting point: mp 233-234°
Optical Rotation: [a]D23 -33.7° (c = 1.59 in pyridine)
 
Derivative Type: N,N¢-Diacetylsolanocapsine
Molecular Formula: C31H50N2O4
Molecular Weight: 514.74
Percent Composition: C 72.33%, H 9.79%, N 5.44%, O 12.43%
Properties: Crystals from chloroform + acetone, mp 281-283°. [a]D22 -38.6° (c = 1.31 in pyridine).
Melting point: mp 281-283°
Optical Rotation: [a]D22 -38.6° (c = 1.31 in pyridine)
 
Derivative Type: N,N,N¢-Trimethylsolanocapsine
Molecular Formula: C30H52N2O2
Molecular Weight: 472.75
Percent Composition: C 76.22%, H 11.09%, N 5.93%, O 6.77%
Properties: Needles from abs methanol, mp 222-224°. [a]D22 +53.2° (c = 1.09 in pyridine).
Melting point: mp 222-224°
Optical Rotation: [a]D22 +53.2° (c = 1.09 in pyridine)
 
Derivative Type: N-Benzylidenesolanocapsine
Molecular Formula: C34H50N2O2
Molecular Weight: 518.77
Percent Composition: C 78.72%, H 9.71%, N 5.40%, O 6.17%
Properties: Needles from pyridine + abs methanol, mp 249-251°. [a]D18 +31.4° (c = 0.78 in pyridine).
Melting point: mp 249-251°
Optical Rotation: [a]D18 +31.4° (c = 0.78 in pyridine)

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