Imperialine
Structural Formula Vector Image
Title: Imperialine
CAS Registry Number: 18059-10-4
CAS Name: 3,20-Dihydroxycevan-6-one
Additional Names: raddeamine; sipeimine
Molecular Formula: C27H43NO3
Molecular Weight: 429.64
Percent Composition: C 75.48%, H 10.09%, N 3.26%, O 11.17%
Literature References: Isolation from bulb of Fritillaria imperialis L., Liliaceae: Fragner, Ber. 21, 3284 (1888); Boit, ibid. 87, 472 (1954); from Petilium eduardi: Shakirov et al., C.A. 60, 13280h (1964). Identity with sipeimine and raddeamine: Chu et al., C.A. 53, 7503e (1959); Nurridinov, Yunusov, C.A. 57, 15165h (1962). Structure: Nuriddinov et al., Khim. Prir. Soedin. 3, 316 (1967); C.A. 68, 69168g (1968). Prepn of the b-D-glucopyranoside: Shakirov et al., C.A. 63, 1858e (1965). Isolation and structure of the b-D-glucopyranoside: eidem, C.A. 63, 3007f (1965). Absolute configuration: S. Itô et al., Tetrahedron Lett. 1976, 3161.
Properties: Prisms from methanol, mp 267°. [a]D22 -38.5° (c = 1.5 in chloroform).
Melting point: mp 267°
Optical Rotation: [a]D22 -38.5° (c = 1.5 in chloroform)
 
Derivative Type: b-D-Glucopyranoside
Additional Names: Edpetiline
Molecular Formula: C33H53NO8
Molecular Weight: 591.78
Percent Composition: C 66.98%, H 9.03%, N 2.37%, O 21.63%
Properties: Crystals from methanol, mp 272-276°. [a]D -57.89° (c = 0.449 in methanol).
Melting point: mp 272-276°
Optical Rotation: [a]D -57.89° (c = 0.449 in methanol)

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