Natural Compounds

2013 Edition
| Editors: Shakhnoza S. Azimova, Ashraf I. Saidkhodzhaev

15-(2′-Hydroxy-cinnamoyloxy)-dauca-4,8-diene (14-(O-Hydroxycinnamoyloxy)-dauc-4,8-diene)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_907

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Monoesters

Biological sources: Ferula communis L. [1]

C24H30O3: 366.2195

Mp: gum [1]

[α]D +19° (c 0.11, CHCl3) [1]

UV (MeOH): 215 (4.21), 270 (3.95), 315 (3.83) [1]; (MeOH + NaOH): 215 (4.26), 225 (4.05), 285 (3.86), 380 (2.95) [1]

IR (KBr): 3500, 2980, 1715, 1605, 1525, 1260, 760 [1]

EI-MS: 366 [M]+ (C24H30O3) (2), 221 (10), 178 (30), 146 (80), 118 (100) [1]

1H NMR (300 MHz): 0.93 (3H, d, J = 6.8, H-13), 0.93 (3H, s, H-14), 0.99 (3H, d, J = 6.8, H-12), 2.19, 2.08 (each 1H, m, H-10), 2.68 (1H, dq, J = 6.8, H-11), 4.63, 4.69 (each 1H, brd, J = 12.1, H-15), 5.85 (br t, J = 6.3, H-9); OCinn(2′-OH): 6.67 (1H, d, J = 16.3, H-8′), 6.87 (1H, dd, J = 1.0; 8.1, H-3′), 6.90 (1H, dt, J = 1.0; 7.5, H-5′), 7.24 (1H, dt, J = 1.5; 8.1, H-4′), 7.47 (1H, dd, J = 1.5; 7.5, H-6′), 8.01 (1H, d, J = 16.3, H-7′) [1]

13 C NMR (75 MHz) [ 1]:

Table...

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References

  1. 1.
    M.A. Al-Yahya, I. Muhammad, H.H. Mirza, F.S. El-Feraly, Phytother. Res. 12, 335 (1998)CrossRefGoogle Scholar

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