Natural Compounds

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

3β,8β-Diangeloyloxy-dauc-4-en-9-one (Torosol Diangelate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_966

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Taxonomy: Physicochemical and Pharmacological Properties of Sesquiterpene Esters – The Bicyclic Sesquiterpene Esters – Daucanes (Carotanes) – Diesters

Biological sources: Ferula rigidula DC. [1]

C25H36O5: 416.2563

Mp: colorless gum [1]

IR (NaCl): 2965, 2870, 1720 (sh) (C=O), 1715 (C=O), 1708 (sh) (C=O), 1650, 1460, 1235, 1155, 1142, 1100, 1042, 940, 850 [1]

EI-MS: 416.25627 [M]+ (0.3) (calc. for C25H36O5: 416.25625), 334 [M − angelate acylium + H]+ (0.4), 316 [M − angelic acid]+ (9), 234 [M − angelic acid − angelate acylium + H]+ (10.5), 216 [M − 2 × angelic acid]+ (17.6), 173 [M − 2 × angelic acid − C3H7]+ (13.4), 83 [angelate acylium]+ (100) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.95 (3H, d, J = 7, H-12), 0.98 (3H, d, J = 7, H-13), 1.17 (3H, s, H-14), 1.47 (3H, s, H-15), 2.10 (1H, d, J = 12, H-10α), 2.68 (1H, d, J = 12, H-10β), 2.58 (1H, qq, J = 7, H-11), 2.24 (1H, m, H-7β), 1.25 (1H, m, H-7α), 2.46 (1H, m, H-6α), 2.24 (1H, m, H-6β), 5.67 (1H, br d, J = 7,...

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References

  1. 1.
    M. Miski, J. Jakupovic, Phytochemistry 29(1), 173 (1990)CrossRefGoogle Scholar

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