Natural Compounds

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

2β-Acetoxy-5β,6α(H)-cadina-3,9-dien-15-oic Acid Methyl Ester (Methyl-2β-acetoxy-δ-cadinene-15-oate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_804

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

Biological sources: Heterotheca latifolia Buckl. [1]

C18H26O4: 306.1831

Mp: oil [1]

[α]24 (λ, nm): −16° (589), −17° (578), −21° (546), −36° (436) (c 1.4, CHCl3) [1]

IR: 1730, 1720, 1645, 1245 [1]

MS: 306.183 [M]+ (0.7), 246 (21), 215 (7), 203 (42), 187 (61), 176 (100), 145 (38) [1]

1H NMR (270 MHz, CDCl3): 0.87 (3H, d, J = 7, H-13), 1.03 (3H, d, J = 11, H-12), 1.3 (1H, m, H-8a), 1.3 (1H, m, H-10), 1.62 (3H, br s, H-14), 1.74 (1H, br d, J = 12, H-8b), 1.99 (1H, br d, J = 15; 2, H-1b), 2.0 (2H, m, H-7), 2.01 (3H, s, OAc), 2.16 (1H, br qq, J = 11; 2, H-11), 2.72 (1H, br d, J = 2, H-5), 3.08 (1H, dd, J = 15; 2.5, H-1a), 3.74 (3H, s, OCH3), 5.79 (1H, br dd, J = 2.5; 2, H-2), 7.33 (1H, d, J = 2, H-4) [1]

References

  1. 1.
    F. Bohlmann, R.K. Gupta, R.M. King, H. Robinson, Phytochemistry 21(12), 2982 (1982)CrossRefGoogle Scholar

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