Natural Compounds

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

6α-Isovaleroyloxy-4β-hydroxy-5α(H)-dauc-8-en-10-one (10-Oxo-jaeschkeanadiol Isovalerate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_913

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

Biological sources: Ferula communis L. subsp. communis L. [1]

C20H32O4: 336.2301

Mp: 79°C (hexane) (mix. with the 10-oxojaeschkeanadiol angelate, ca 1:4) [1]

[α]D25 (mix.): +97.5° (c 1.2, CHCl2) [1]

UV (EtOH) (mix.) 252 [1]

IR (KBr) (mix.): 3400, 1710, 1635, 1335, 1380, 1260, 1230, 1165, 1040 [1]

EI-MS (mix.): 336 [M]+ (1), 291 (25), 234 (50), 191 (82), 149 (90), 83 (100) [1]

1H NMR (250 MHz, CDCl3, TMS) (mix.): 0.94 and 0.86 ( 6H, d, J = 6.5, H-12, H-13), 1.39 (3H, s, H-14), 1.91 (3H, br s, H-15), 2.37 (1H, dd, J = 16.1; 2.7, H-7β), 2.44 (1H, d, J = 9.5, H-5), 3.00 (1H, dd, J = 16.1; 5.4, H-7α), 5.63 (1H, ddd, J = 9.5; 5.4; 2.7, H-6), 6.01 (1H, br s, H-9); OiVal: 0.94 (3H, d, H-4′), 0.98 (3H, d, H-5′), 2.10 (1H, m, H-3′), 2.20 (2H, m, H-2′) [1]

13 C NMR (62.89 MHz, CDCl 3, TMS) [ 1] (mix.):

Table 1

C-1

54.83 s

C-8

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References

  1. 1.
    G. Appendino, S. Tagliapietra, L. Paglino, G.M. Nano, D. Monti, V. Picci, Phytochemistry 29(5), 1481 (1990)CrossRefGoogle Scholar

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