Natural Compounds

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

14-Acetoxy-5,6-dihydro-6,7-dehydrocaryophyllen-5-one

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_835

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

Biological sources: Fleischmannia pycnocephaloides (B.L. Rob.) R.M. King et H. Rob. [1]

C17H24O3: 276.1725

Mp: colorless oil [1]

[α]D24 (λ, nm): −11° (589), −12° (578), −15° (546), −23° (436) (c 0.11, CHCl3) [1]

IR (CCl4): 1740, 1695, 1230 [1]

MS: 276.3630.173 [M]+ (14), 216 (74), 201 (37), 173 (44), 91 (100) [1]

1H NMR (270 MHz, CDCl3, TMS): 0.99 (3H, s, H-12), 1.02 (3H, s, H-13), 1.64 (1H, ddd, J = 10; 10; 2, H-9), 1.68 (1H, dd, J = 10; 10.5, H-10b), 1.80 (1H, dd, J = 8; 10.5, H-10a), 2.05 (3H, s, OAc), 2.10 (1H, ddd, J = 8; 15; 2, H-8b), 2.40 (1H, ddd, J = 8; 15; 10, H-8a), 2.50 (1H, ddd, J = 10; 8; 10, H-1), 2.6−2.4 (2H, m, (400 MHz: J = ∼4; 10; 13), H-4), 2.60 (2H, m, (400 MHz: J = 13; ∼4; 10), H-3), 4.56 (1H, d, J = 12.5, H-14b), 4.71 (1H, br s, H-15b), 4.82 (1H, br d, J = 12.5, H-14a), 4.86 (1H, br s, H-15a),...

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References

  1. 1.
    F. Bohlmann, A.K. Dhar, J. Jakupovic, R.M. King, H. Robinson, Phytochemistry 20(6), 1425 (1981)CrossRefGoogle Scholar

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