Natural Compounds

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

4α-Acetoxy-8α-benzoyloxy-2,15-epoxycaryophyllene

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_846

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Caryophyllanes – Diesters

Biological sources: Solidago nemoralis Aiton [1]

C24H30O5: 398.2093

Mp: colorless oil [1]

[α]24 (λ, nm): +0.4° (589), +1.2° (578), +3.7° (546), 15.9° (436) (c 4.3, CHCl3) [1]

IR (CCl4): 1735, 1715, 1610, 1590, 1270, 1240 [1]

MS: 399 [M + 1]+ (2.5) (C24H30O5), 339 (35), 277 (12), 217 (100) [1]

1H NMR (270 MHz, CDCl3, TMS): 1.00 (3H, s, H-13), 1.10 (3H, s, H-12), 1.21 (1H, dd, J = 10; 11, H-10b), 1.52 (1H, dd, J = 9; 11, H-10a), 1.70 (1H, dd, J = 10; 14, H-7α), 1.82 (3H, br s, H-14), 1.84 (1H, dd, J = 10; 10, H-9), 1.94 (1H, dd, J = 7; 13, H-3β), 2.04 (3H, s, OAc), 2.24 (1H, br dd, J = 10; 13, H-3α), 2.54 (1H, br ddd, J = 9; 10; 10; 1, H-1), 2.73 (1H, d, J = 4, H-15b), 2.77 (1H, dd, J = 1; 4, H-15a), 3.27 (1H, ddd, J = 1.5; 7; 14, H-7β), 5.37 (1H, ddd, J = 10; 10; 7, H-8), 5.40 (1H, br dq, J = 10; 1.5, H-5), 5.61 (1H,...

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References

  1. 1.
    F. Bohlmann, U. Fritz, R.M. King, H. Robinson, Phytochemistry 19(12), 2655 (1980)CrossRefGoogle Scholar

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