Tylophorine

Title: Tylophorine
CAS Registry Number: 482-20-2
CAS Name: (13aS)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline
Additional Names: 2,3,6,7-tetramethoxyphenanthro[9,10:6¢,7¢]indolizidine
Molecular Formula: C24H27NO4
Molecular Weight: 393.48
Percent Composition: C 73.26%, H 6.92%, N 3.56%, O 16.26%
Literature References: Major alkaloid from Tylophora asthmatica Wight et Arn., Asclepiadaceae. Also found in other Asclepiadaceae, Moraceae, Urticaceae and Lauraceae. Naturally occurring form originally isolated and reported to be levorotatory; later corrected to dextrorotatory. Isoln: A. N. Ratnagiriswaran, K. Venkatachalam, Indian J. Med. Res. 22, 433 (1935); R. N. Chopra et al., Arch. Pharm. 275, 236 (1937); T. R. Govindachari et al., J. Chem. Soc. 1954, 2801. Structure: eidem, Tetrahedron 9, 53 (1960). Absolute configuration: eidem, J. Chem. Soc. Perkin Trans. 1 1974, 1161. Synthesis of the dl-form: eidem, Chem. Ind. (London) 1960, 664; N. A. Khatri et al., J. Am. Chem. Soc. 103, 6387 (1981). Synthesis and verification of dextrorotation of naturally occurring form: T. F. Buckley 3rd, H. Rapoport, J. Org. Chem. 48, 4222 (1983); J. E. Nordlander, F. G. Njoroge, ibid. 52, 1627 (1987). Stereoselective synthesis of l-form: M. Ihara et al., Tetrahedron Lett. 29, 4135 (1988). Biosynthesis: Mulchandani et al., Phytochemistry 8, 1931 (1969); ibid. 10, 1047 (1971); D. S. Bhakuni, V. K. Mangla, Tetrahedron 37, 401 (1981). Pharmacology: C. Gopalakrishnan et al., Indian J. Med. Res. 69, 513 (1979); 71, 940 (1980).
Properties: Crystals, dec 282-284°. [a]D23 +15° (c = 0.7 in chloroform); [a]D21 +73° (c = 0.7 in chloroform). uv max in ethanol: 257, 286, 339, 356 nm (log e 4.7, 4.42, 3.28, 3.19). Unstable in solutions, decomposition with yellowing sets in promptly accompanied by decreasing rotatory strength.
Optical Rotation: [a]D23 +15° (c = 0.7 in chloroform); [a]D21 +73° (c = 0.7 in chloroform)
Absorption maximum: uv max in ethanol: 257, 286, 339, 356 nm (log e 4.7, 4.42, 3.28, 3.19)
Derivative Type: l-Form
Properties: Colorless crystals, dec 286-287°. [a]D27 -11.6° (c = 1.07 in chloroform). uv max 255, 290, 340, 352 nm (log e 4.74, 4.49, 3.30, 2.93). Sol in chloroform; slightly sol in abs alc, ether, cold benzene. Practically insol in water.
Optical Rotation: [a]D27 -11.6° (c = 1.07 in chloroform)
Absorption maximum: uv max 255, 290, 340, 352 nm (log e 4.74, 4.49, 3.30, 2.93)
Derivative Type: dl-Form
Properties: Crystals from chloroform + ethanol, mp 292°.
Melting point: mp 292°
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