Arborinine

Reference work entry

CAS Registry Number: 5489-57-6 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Ruta graveolens

C16H15NO4: 285.1001

Mp: 175–176°C, 243°C (norarborinine) [1]

UV: 217, 265 sh, 274, 319 sh, 395(4.38, 4.63, 4.71, 3.77, 3.84) [2]

IR: 1637, 1587, 1550, 1493, 1460, 1316, 1282, 1143, 1105, 1053, 990, 855 [2]

MSm/z: 285(M+, 74), 284(23), 271(23), 270(100), 256(14), 243(13), 242(59), 226(7), 212(9), 200(8), 199(39), 184(6), 171(17), 170(18), 143(11), 142(8), 128(8), 115(13), 77(15) [3]

1H NMR: 3.65, 4.07, 4.12(each 3H, s, NCH3, 2 × OCH3), 6.07(1H, s, H-4), 6.98–7.80(3H, m, H–Ar), 8.23(1H, d, H-8) [2]

13 C NMR: [ 4]

Table 1

C-1

155.7

C-5

114.5

C-9a

105.3

 2

129.9

 6

133.7

2-OCH3

60.6

 3

159.1

 7

121.2

3-OCH3

55.8

 4

86.7

 8

126.0

NCH3

33.8

 4a

140.1

 8a

120.3

   

 5a

141.6

 9

180.4

   

References

  1. 1.
    S.K. Banerjee, D. Chakravarti, R.N. Chakravarti, H.M. Fales, D.L. Klayman, Tetrahedron 16, 251 (1961)Google Scholar
  2. 2.
    S.C. Pakrashi, S.K. Roy, L.F. Johnson, T. George, C. Djerassi, Chem. Ind. 464 (1961)Google Scholar
  3. 3.
    J.H. Bowie, R.G. Cooks, R.H. Prager, H.M. Thredgold, Austral. J. Chem. 20, 1179 (1967)Google Scholar
  4. 4.
    D. Bergenthal, I. Mester, Z. Rozsa, J. Reisch, Phytochemistry 18, 161 (1979)Google Scholar

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© Springer Science+Business Media New York 2013

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