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7-Oxoglaucine (O-Methylateroline)

Reference work entry

CAS Registry Number: 5574-24-3 Open image in new window

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

Biological sources: Glaucium elegans, G. flavum, G. grandiflorum, G. serpieri, Liriodendron tulipiferum, Thalictrum foetidum

C20H17NO5: 351.1107

Mp: 219–221°C (dec.) [1]

UV: 243, 272, 290 sh, 355, 433 [1]

UV(H+): 254, 285, 383, 495 [1]

IR: 1655 [2]

MSm/z: 351(M+, 100), 353, 352, 350, 336, 321, 320, 308, 306, 293, 292, 175.5(++) [3]

1H NMR: 3.89, 3.97(3H, 9H, s, 4 × OCH3), 6.96, 7.82, 8.54(each 1H, s, H-3, H-8, H-11), 7.57, 8.67(each 1H, d, J = 5.5, H-4, H-5) [1]

13 C NMR: [ 4]

Table 1

C-1

155.9

C-5

133.1

C-11

111.3

1a

120.1

6a

141.7

11a

130.4

1b

123.4

7

174.8

1-OCH3

61.6

2

162.9

7a

133.1

OCH3

57.3

3

106.5

8

110.1

OCH3

56.3

3a

135.3

9

150.2

OCH3

56.3

4

126.2

10

156.7

   

References

  1. 1.
    S. Mukhamedova, S.Kh. Maekh, S.Yu. Yunusov, Chem. Nat. Comp. 19, 376 (1983)Google Scholar
  2. 2.
    K.G. Kiryakov, P. Panov, Dokl. Bolg. Akad. Nauk 22, 1019 (1970)Google Scholar
  3. 3.
    I.R.C. Bick, J.H. Bowie, G.K. Douglas, Aust. J. Chem. 20, 1403 (1967)Google Scholar
  4. 4.
    A.J. Marsaioli, A.F. Magalhaes, E.A. Ruveda, F.A.M. Ries, Phytochemistry 19, 995 (1980)Google Scholar
  5. 5.
    C.D. Hufford, A.S. Sharma, B.O. Oguntimein, J. Pharm. Sci. 69, 1180 (1980)Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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