Veratramine
Title: Veratramine
CAS Registry Number: 60-70-8
CAS Name: (3b,23b)-14,15,16,17-Tetradehydroveratraman-3,23-diol
Molecular Formula: C27H39NO2
Molecular Weight: 409.60
Percent Composition: C 79.17%, H 9.60%, N 3.42%, O 7.81%
Literature References: Secondary base from Veratrum grandiflorum (Maxim.) Loes. f., and from V. viride Ait., Liliaceae. Isoln and structure: Saito, Bull. Chem. Soc. Jpn. 15, 22 (1940); Jacobs, Craig, J. Biol. Chem. 160, 555 (1945); Jacobs, Sato, ibid. 181, 55 (1949); 191, 71 (1951); Tamm, Wintersteiner, J. Am. Chem. Soc. 74, 3842 (1952); Wintersteiner, Festschrift Arthur Stoll (Birkhäuser-Verlag, Basel) pp 166-176. Total synthesis: Masamune et al., J. Am. Chem. Soc. 89, 4521 (1967); Johnson et al., ibid. 4523; Masamune et al., Tetrahedron 27, 3369 (1971); Kutney et al., Can. J. Chem. 53, 1796 (1975). Stereochemistry: Sicher, Tichy, Tetrahedron Lett. 1959(12), 6 (1959); Kataoka, Chem. Ind. (London) 1961, 512; Bailey et al., Tetrahedron Lett. 1963, 555. Revised stereochemistry: Scott et al., ibid. 1967, 2381; Kupchan, Suffness, J. Am. Chem. Soc. 90, 2730 (1968); Sprague et al., Tetrahedron 27, 4857 (1971). See also: Veratrum Viride.
Properties: Crystals, mp 206-207°. Slightly sol in water. Sol in methanol, alcohol. Precipitated by digitonin. [a]D25 -71.8° (c = 1.21); [a]D25 -70° (c = 1.56 in methanol). uv max: 268 nm.
Melting point: mp 206-207°
Optical Rotation: [a]D25 -71.8° (c = 1.21); [a]D25 -70° (c = 1.56 in methanol)
Absorption maximum: uv max: 268 nm
 
Derivative Type: Dihydroveratramine
Properties: Crystals, mp 192.5-194°. [a]D25 +26° (c = 1.26 in acetic acid).
Melting point: mp 192.5-194°
Optical Rotation: [a]D25 +26° (c = 1.26 in acetic acid)

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