Title: Jervine
CAS Registry Number: 469-59-0
CAS Name: (3b,23b)-17,23-Epoxy-3-hydroxyveratraman-11-one
Molecular Formula: C27H39NO3
Molecular Weight: 425.60
Percent Composition: C 76.20%, H 9.24%, N 3.29%, O 11.28%
Literature References: Steroidal alkaloid found in Veratrum grandiflorum (Maxim.) Loes F., V. album L., V. viride Sol., Liliaceae: Saito, Bull. Chem. Soc. Jpn. 9, 15 (1934), C.A. 28, 2463 (1934); Poethke, Arch. Pharm. 275, 357, 571 (1937); 276, 170 (1938); 282, 56 (1944); Seiferle et al., J. Econ. Entomol. 35, 35 (1942); Jacobs, Craig, J. Biol. Chem. 160, 555 (1945). Structure: Fried et al., J. Am. Chem. Soc. 73, 2970 (1951). Reviews: Wintersteiner in Graff, Essays in Biochemistry (Wiley, New York, 1956) pp 308-321; idem, Festschrift Arthur Stoll (Basel, 1957) pp 166-176; L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 870-877. Stereochemistry: Sicher, Tichy, Tetrahedron Lett. no. 12, 6 (1959); Augustine, Chem. Ind. (London) 196l, 1448; Mitsuhashi, Shimizu, Tetrahedron 19, 1027 (1963); Bailey et al., Tetrahedron Lett. 1963, 555; Masamune et al., ibid. 1965, 489. Revised stereochemistry: Scott et al., ibid. 1967, 2381; Kupchan, Suffness, J. Am. Chem. Soc. 90, 2730 (1968); Sprague et al., Tetrahedron 27, 4857 (1971). Total synthesis: Kutney et al., Can. J. Chem. 53, 1796 (1975). Comparative toxicity: O. Krayer et al., J. Pharmacol. Exp. Ther. 82, 167 (1944); K. Tanaka, ibid. 113, 89 (1955).
Properties: Needles from methanol + water, mp 243.5-244.5° (Saito). [a]D20 -150° (ethanol) (Saito); [a]D20 -167.6° (chloroform) (Poethke). uv max: 250, 360 nm (e 15000, 60). LD50 i.v. in mice: 9.3 mg/kg (Krayer). LD50 s.c. in male mice: 29 mg/kg (Tanaka).
Melting point: mp 243.5-244.5° (Saito)
Optical Rotation: [a]D20 -150° (ethanol) (Saito); [a]D20 -167.6° (chloroform) (Poethke)
Absorption maximum: uv max: 250, 360 nm (e 15000, 60)
Toxicity data: LD50 i.v. in mice: 9.3 mg/kg (Krayer); LD50 s.c. in male mice: 29 mg/kg (Tanaka)
Derivative Type: Diacetyljervine
Molecular Formula: C31H43NO5
Molecular Weight: 509.68
Percent Composition: C 73.05%, H 8.50%, N 2.75%, O 15.70%
Properties: mp 173-175°. [a]D -112°. uv max (ethanol): 250, 360 nm (e 16400, 80).
Melting point: mp 173-175°
Optical Rotation: [a]D -112°
Absorption maximum: uv max (ethanol): 250, 360 nm (e 16400, 80)
Derivative Type: Hydrochloride
Properties: mp 300-302°.
Melting point: mp 300-302°
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