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Dubinine

Reference work entry

CAS Registry Number: 23092-72-0 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum dubium

C17H19NO5: 317.1263

Mp: 185–186°C (EtOH), 171°C (hydrochloride), 150°C (nitrate), 212°C (methiodide), 109°C (Ac) [1]

[α]D −59° (EtOH) [1]

Solubility: very sol. Me2CO, Py, MeOH; insol. H2O, pet. ether. [1]

UV: 225, 234 sh, 274, 283, 306 (5.26, 4.93, 4.32, 4.30, 4.16) [2]

IR: 3270, 1725, 1630, 1600, 1540, 1465, 1400, 1305, 1270, 1160, 1155, 910 [2]

MSm/z: 317(M+, 17), 245(4), 244(21), 226(6), 202(18), 201(35), 200(100), 199(8), 186(8), 185(9), 173(8), 172(7), 158(4), 156(2), 143(3), 142(3), 130(4), 129(3), 117(5), 115(5) [3]

1H NMR: 1.33(3H, s, CH3), 2.15(3H, s, OAc), 4.16(3H, s, OCH3), 4.56 (2H, s, CH2–OCO), 3.51, 3.93, 4.94(each 1H, q, J = 15.5, 9.5, 6.6, CH2–CH–O), 6.80–7.43(4H, m, H–Ar) [4, 5]

Pharm./Biol.: Weak estrogenic action [6]

References

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    I.A. Bessonova, G.P. Sidyakin, S.Yu. Yunusov, Zh. Obshch. Khim. 34, 347 (1964)Google Scholar
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    I.A. Bessonova, Z.Sh. Faizutdinova, Ya.V. Rashkes, S.Yu. Yunusov, Chem. Nat. Comp. 6, 455 (1970)Google Scholar
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    I.A. Bessonova, S.Yu. Yunusov, Chem. Nat. Comp. 5, 22 (1969)Google Scholar
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    K.P. Seitanidi, M.R. Yagudaev, Chem. Nat. Comp. 10, 774 (1974)Google Scholar
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    S.S. Nazrullaev, I.A. Bessonova, Kh.S. Akhmedkhodjaeva, Chem. Nat. Comp. 37, 551 (2001)Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

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