Solanidine
Title: Solanidine
CAS Registry Number: 80-78-4
CAS Name: (3b)-Solanid-5-en-3-ol
Additional Names: solatubine
Molecular Formula: C27H43NO
Molecular Weight: 397.64
Percent Composition: C 81.55%, H 10.90%, N 3.52%, O 4.02%
Literature References: From Solanum spp., Solanaceae. Potato sprouts contain about 0.008%. Obtained by hydrolysis of solanine. Extraction procedure: Soltys, Wallenfels, Ber. 69, 811 (1936). Review on structure: Reichstein, Reich, Annu. Rev. Biochem. 15, 155 (1946). Stereochemistry: Rosen, Rosen, Chem. Ind. (London) 1954, 1581. Revised stereochemistry: Höhne et al., Tetrahedron 22, 673 (1966). Synthesis: Schreiber, Roensch, Ber. 97, 2362 (1964); Tetrahedron 21, 645 (1965); Kessar et al., ibid. 27, 2153 (1971).
Properties: Long needles from chloroform-methanol, mp 218-219°. Sublimes near mp with slight decompn. [a]D21 -29° (c = 0.5 in chloroform). Freely sol in benzene, chloroform; slightly in alcohol, methanol; almost insol in ether, water.
Melting point: mp 218-219°
Optical Rotation: [a]D21 -29° (c = 0.5 in chloroform)
 
Derivative Type: Hydrochloride
Molecular Formula: C27H43NO.HCl
Molecular Weight: 434.10
Percent Composition: C 74.70%, H 10.22%, N 3.23%, O 3.69%, Cl 8.17%
Properties: Prisms from 80% alcohol, dec 345°.
 
Derivative Type: Methyliodide
Molecular Formula: C27H43NO.CH3I
Molecular Weight: 539.58
Percent Composition: C 62.33%, H 8.59%, N 2.60%, O 2.97%, I 23.52%
Properties: Crystals from 50% alcohol, dec 286°.
 
Derivative Type: Acetylsolanidine
Molecular Formula: C29H45NO2
Molecular Weight: 439.67
Percent Composition: C 79.22%, H 10.32%, N 3.19%, O 7.28%
Properties: Crystals from alc, mp 208°.
Melting point: mp 208°

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