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(−)-Canadine [(−)-Tetrahydroberberine]

Reference work entry

CAS Registry Number: 2086-96-6 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Diisoquinoline Alkaloids

Biological sources: Berberis heteropoda, Papaver somniferum

C20H21NO4: 339.1471

Mp: 134–135°C

[α]D −298° (CHCl3) [1, 2]

UV: 230, 284 [3]

IR: 2800-2700, 940 [3]

MSm/z: 339(M+, 66), 176(5), 174(26), 164(100), 149(72) [2]

1H NMR: 2.60(1H, m, H-5e), 2.64(1H, m, H-6a), 2.81(1H, dd, J = 15.7; 7.12, H-13a), 3.15(1H, m, H-5a), 3.20(1H, m, H-6e), 3.23(1H, dd, J = 15; 7.4, H-13e), 3.40(1H, dd, J = 12; 4, H-14), 3.49(1H, d, J = 15.5, H-8a), 4.22(1H, d, J = 15.5, H-8e), 5.88(2H, s, CH2O2), 6.59(1H, s, H-4), 6.73(1H, s, H-1), 6.83(1H, d, J = 8.2, H-11), 6.87(1H, d, J = 8.2, H-12) [4]

13 C NMR: [ 4]

Table 1

C-1

105.5

C-8

53.9

C-13

36.0

2

146.4

8a

127.4

14

59.8

3

146.3

9

150.4

14a

130.4

4

108.5

10

145.0

CH2O2

101.0

4a

127.5

11

111.3

9-OCH3

60.2

5

29.1

12

124.2

10-OCH3

55.9

6

51.5

12a

128.0

   

References

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    I.A. Bessonova, Z.Sh. Faizutdinova, S.Yu. Yunusov, Chem. Nat. Comp. 6, 721 (1970)Google Scholar
  2. 2.
    A. Karimov, A.V. Butayarov, M.M. Yusupov, R.T. Mirzamatov, R. Shakirov, Chem. Nat. Comp. 28, 523 (1992)Google Scholar
  3. 3.
    R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Akhmedzhanova, V.I. Vinogradova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. comp. 32, 386 (1996)Google Scholar
  4. 4.
    R.A. Hussain, J. Kim, C.W. Beecher, A.D. Kinghorn, Heterocycles29, 2257 (1989)Google Scholar
  5. 5.
    G. Snatzke, J. Hrbek, J. Hruban, A. Horeau, F. Santavy, Tetrahedron 26, 5013 (1970)Google Scholar

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