Natural Compounds

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

2β,8β-Diacetoxy-12-formyloyloxy-5α,9β,10α(H)-muurola-3,6(11)-diene (2β,8β-Diacetoxy-12-formyloxy-verboccidenten)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_823

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Cadinanes – Cadalenes – Triester

Biological sources: Verbesina occidentalis (L.) Walter [1]; V. cinerea Rusby [2]

C20H28O6: 364.1886

Mp: 127–128°C (Et2O – petrol) [1]

[α]24 (λ, nm): +87.6 (589), +98.0° (578), +111.8° (546), +194.8° (436) (c 1.15, CHCl3) [1]

IR: 1730, 1240, 1165 [1]

MS: 319 [M − ⋅OCHO]+ (0.5), 258.163 [M − HCOOH – AcOH]+ (12) [1]

1H NMR: (270 MHz, CDCl3, TMS): 0.87 (3H, d, J = 7, H-14), 1.50 (1H, br ddd, J = 3; 4.5; 10, H-10α), 1.70 (3H, br s, H-15), 1.78 (3H, d, H-13), 1.85 (1H, ddd, J = 15; 5; 4.5, H-1β), 1.95 (1H, br dd, J = 11; 13, H-7β), 2.07 (3H, s, OAc), 2.08 (3H, s, OAc), 2.16 (1H, ddq, J = 10; 11; 7, H-9), 2.27 (1H, ddd, J = 15; 3, H-1α), 4.31 (1H, ddd, J = 10; 11; 7, H-9), 2.86 (1H, ddd, J = 13, H-7α), 3.28 (1H, br s, H-5α), 4.67 (1H, d, J = 12, H-12a′), 4.77 (1H, d, J = 12; H-12b), 5.20 (1H, br d, J = 5, H-2α), 5.26...

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References

  1. 1.
    F. Bohlmann, M. Lonitz, Phytochemistry 17(3), 453 (1978)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, M. Grenz, R.K. Gupta, A.K. Dhar, M. Ahmed, R.M. King, H. Robinson, Phytochemistry 19(11), 2391 (1980)CrossRefGoogle Scholar

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