Natural Compounds

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

7α-Angeloyloxy-5α,6α,7β(H)-cadina-3,9-dien-2-one (7α-Angeloyloxy-δ-cadinen-2-one)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_815

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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: colorless oil [1]

[α]24 (λ, nm): +51.4° (589), +53.6° (578), +62.9° (546), +131.2° (436) (c 0.58, CHCl3) [1]

IR (CCl4): 1712, 1678, 1650 [1]

MS: 216.151 [M − C4H7COOH]+ (24) (calc. for C15H20O: 216.151), 201 (10), 173 (100), 145 (85) [1]

1H NMR (270 MHz, CDCl3): 1.02 (3H, d, J = 7, H-13), 1.11 (3H, d, J = 7, H-12), 1.65 (3H, br s, H-14), 1.75 (3H, br s, H-15), 1.8 (1H, m, H-11), 2.37 (1H, br d, J = 16; 4, H-8β), 2.86 (1H, br d, J = 16.5, H-1α), 3.03 (1H, m, H-5), 3.56 (1H, d, J = 16.5, H-1β), 5.19 (1H, ddd, J = 4; 9; 8, H-7β), 6.67 (1H, dq, J = 1.5; 1.5, H-4); OAng: 1.81 (3H, dq, J = 1.3; 1.3, H-5′), 1.96 (3H, dq, J = 7; 1.3, H-4′), 6.05 (1H, qq, J = 7; 1.3, H-3′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, H. Robinson, R.M. King, Phytochemistry 18(10), 1675 (1979)CrossRefGoogle Scholar

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