Tomatidine
Title: Tomatidine
CAS Registry Number: 77-59-8
CAS Name: (3b,5a,22b,25S)-Spirosolan-3-ol
Additional Names: 5a-tomatidan-3b-ol; 5a,20bF,22aF,25bF,27-azaspirostan-3b-ol
Molecular Formula: C27H45NO2
Molecular Weight: 415.65
Percent Composition: C 78.02%, H 10.91%, N 3.37%, O 7.70%
Literature References: By hydrolysis of tomatine: Kuhn et al., Ber. 83, 448 (1950). Isoln from the roots of Rutgers tomato plant [Lycopersicon esculentum Mill., cultivar. "Rutgers"]: Brink, Folkers, J. Am. Chem. Soc. 73, 4018 (1951); Fontaine et al., ibid. 878; Sato et al., ibid. 880; Kuhn, Low, US 2770618 (1956 to Amer. Home Prod.). Structure: Sato et al., J. Org. Chem. 25, 783 (1960); Schreiber, Adams, Experientia 17, 13 (1961). Synthesis: Uhle, Moore, J. Am. Chem. Soc. 76, 6412 (1954); Uhle, ibid. 83, 1460 (1961); Kessar et al., Tetrahedron 27, 2869 (1971).
Properties: Plates from ethyl acetate, mp 202-206°. [a]D25 +8° (chloroform).
Melting point: mp 202-206°
Optical Rotation: [a]D25 +8° (chloroform)
 
Derivative Type: Hydrochloride
Molecular Formula: C27H45NO2.HCl
Molecular Weight: 452.11
Percent Composition: C 71.73%, H 10.26%, N 3.10%, O 7.08%, Cl 7.84%
Properties: Crystals from abs ethanol, mp 265-270°. [a]D25 -5° (methanol).
Melting point: mp 265-270°
Optical Rotation: [a]D25 -5° (methanol)

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