Natural Compounds

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

14-(2′-Methylbutyroyloxy)-calomen-2-ol (2,14-Dihydroxycalomen-14-O-2-methylbutyrate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_822

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

Biological sources: Heterotheca grandiflora Nutt. [1]

C20H28O3: 316.2038

Mp: oil [1]

[α]D +6° (c 0.7, CHCl3) [1]

IR: 3600, 1740, 1710 [1]

MS: 316.203 [M]+ (1.0), 216 (28), 173 (100), 158 (12), 145 (10), 83 (14), 55 (18) [1]

1H NMR (400 MHz, CDCl3): 0.70 (3H, d, J = 7, H-13), 0.99 (3H, d, J = 11, H-12), 1.65 (3H, m, H-8b, H-9a, H-9b), 2.19 (3H, br s, H-15), 2.24 (1H, m, H-11), 2.24 (1H, m, H-8a), 2.58 (1H, m, H-6), 3.02 (1H, dddd, J = 5; 6; 11, H-9), 4.11 (1H, dd, J = 11; 12, H-14b), 4.24 (1H, dd, J = 5; 12, H-14a), 6.61 (1H, s, H-1), 6.98 (1H, s, H-4); OMeBu: 0.90 (3H, t, H-4′), 1.15 (3H, d, H-5′), 1.49 (1H, ddq, H-3′b), 1.75 (1H, ddq, H-3′a), 2.39 (1H, tq, H-2′) [1]

References

  1. 1.
    S. El-Damy, T. Sarg, N.M. Farrag, A.M. Ateya, J. Jakupovic, F. Bohlmann, R.M. King, Phytochemistry 25(6), 1474 (1986)CrossRefGoogle Scholar

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