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Predicentrine

Reference work entry

CAS Registry Number: 517-65-7 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids – Aporphine Alkaloids

Biological sources: Corydalis emanuelii, Dicentra peregrina, Glaucium corniculatum, Liriodendron tulipiferum

C20H23NO4: 341.1627

Mp: oil, 214°C (dec., hydrochloride) [1], 205°C (dec., hydrobromide) [2]

[α]D +97° (EtOH) [3]

UV: 282, 303(4.19, 4.20) [3]

MSm/z: 341(M+), 340(100), 326, 325, 310, 283, 266, 170.5(++) [3]

1H NMR: 2.49(3H, s, NCH3), 2.50–3.30(7H, m), 3.48(3H, s, 1-OCH3), 3.79, 3.82(each 3H, s, 2 × OCH3), 6.52(1H, s, H-3), 6.72(1H, s, H-8), 7.86(1H, s, H-11) [3]

13 C NMR: [ 4]

Table 1

C-1

142.3

C-5

53.3

C-11

110.0

1a

126.3

6a

62.5

11a

124.1

1b

125.9

7

34.2

NCH3

43.8

2

148.2

7a

129.2

1-OCH3

60.3

3

113.5

8

110.7

9-OCH3

55.8

3a

129.6

9

148.1

10-OCH3

56.0

4

28.7

 10

147.6

   

References

  1. 1.
    C.L. Chen, H.M. Chang, E.B. Cowling, C.H. Hsu, R.P. Gates, Phytochemistry 15, 1161 (1976)Google Scholar
  2. 2.
    S.R. Johns, J.A. Lamberton, A.A. Sioumis, H.J. Tweeddale, Aust. J. Chem. 22, 1277 (1969)Google Scholar
  3. 3.
    I.A. Israilov, F.M. Melikov, D.A. Murav’eva, Chem. Nat. Comp. 20, 74 (1984)Google Scholar
  4. 4.
    M. Shamma, J.L. Moniot, Isoquinoline Alkaloids Research (Plenum Press, New York/London, 1978)Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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