Natural Compounds

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

3α-(5′-Methyldodeca-2′E,4′E,6′E-trienoyloxy)-9β,12-dihydroxy-10βH-eremophil-7(11)-en-8-one (9β,12-Dihydroxy-8-oxo-isosenspeciosoltrienester)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1044

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

Biological sources: Senecio speciosus Willd. [1]; S. glanduloso-pilosus Volkens et Muschl. [2]

C28H42O5: 458.3032

C32H46O7: 542.3244 (9,12-diOAc)

Mp: colorless oil (diOAc) [1]

UV (Et2O) (9,12-diOAc) 303 [1]

IR (CCl4) (9,12-diOAc): 1745, 1705, 1640, 1610, 1230, 980 [1]

MS (9,12-diOAc): 542 [M]+ (5), 482.303 [M − AcOH]+ (54), 334 [M – C12H19COOH] (2), 292 (3), 275 (30), 232 (18), 191 [C12H19CO]+ (16), 163 (17), 43 [H3CCO]+ (100) [1]

1H NMR(270 MHz) (9,12-diOAc): 0.90 (3H, t, J = 6.5, H-12′), 0.96 (3H, d, J = 6.5, H-14), 1.01 (3H, s, H-15), 1.31 (4H, m, H-10′, H-11′), 1.43 (2H, tt, J = 7, H-9′), 1.89 (3H, br s, H-13), 1.99 (3H, br s, H-13′), 2.09 (3H, s, OAc-12), 2.17 (2H, dt, J = 7; 7, H-8′), 2.20 (3H, s, OAc-9), 3.02 (1H, d, J = 15, H-6β), 4.55 (1H, d, J = 12.5, H-12b), 4.70 (1H, d, J = 12.5, H-12a),...

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References

  1. 1.
    F. Bohlmann, A. Suwita, C. Zdero, Phytochemistry 17(10), 1763 (1978)CrossRefGoogle Scholar
  2. 2.
    F. Bohlmann, R.K. Gupta, Phytochemistry 21(10), 2595 (1982)CrossRefGoogle Scholar

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