Natural Compounds

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

8-Angeloyloxy-calamenen-2-ol

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_818

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

Biological sources: Heterotheca subaxillaris (Lam.) Britt. et Rusby [1]

C20H28O3: 316.2038

Mp: colorless oil [1]

[α]24 (λ, nm): +21.7° (589), +22.4° (578), +24.1° (546) (c 4.38, CHCl3) [1]

IR (CCl4): 3610, 1710, 1655, 1625 [1]

MS: 316.204 [M]+ (2) (calc. for C20H28O3: 316.204), 216 [M − C4H7COOH]+ (18), 173 [216 −⋅C3H7]+ (100), 83 [C4H7CO]+ (21) [1]

1H NMR (270 MHz, C6D6, TMS): 0.78 (3H, d, J = 7, H-13), 0.92 (3H, d, J = 7, H-12), 1.25 (3H, d, J = 7, H-14), 1.75 (1H, ddd, J = 3; 14; 6, H-7α), 2.05 (1H, ddd, J = 8.5; 14; 6, H-7β), 2.12 (1H, ddq, J = 6; 7; 7, H-11), 2.17 (3H, br s, H-15), 2.78 (1H, ddd, J = 6; 6; 6, H-6α), 2.90 (1H, dq, J = 4; 7, H-9), 5.55 (1H, ddd, J = 4; 3; 8.5, H-8β), 6.30 (1H, s, H-1), 6.86 (1H, br s, H-4); OAng: 1.83 (3H, dq, H-5′), 1.88 (3H, dq, H-4′), 5.70 (1H, qq, H-3′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, Phytochemistry 18(7), 1185 (1979)CrossRefGoogle Scholar

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