Natural Compounds

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

3α-(4′-Angeloyloxy-hex-2′-trans-enoyloxy)-9β-hydroxy-eremophil-11(12)-en-8-one (4′-Angeloyloxy-senspeciosone)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1013

CAS Registry Number: 85966-31-0 Open image in new window

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

Biological sources: Senecio glanduloso-pilosus Volkens et Muschl. [1]

C26H38O6: 446.2668

Mp: colorless gum [1]

[α]24 (λ, nm): −40° (589), − 44° (578), −53° (546), −90° (436) (c 0.2, CHCl3) [1]

IR (CCl4): 3500, 1740, 1235 [1]

MS: 446.267 [M]+ (5) (C26H38O6), 346 (1), 235 (27), 234 (26), 195 (2), 113 (59), 83 (100) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.94 (3H, d, J = 6.5, H-15), 1.00 (3H, t, H-6′), 1.17 (3H, s, H-14), 1.5 (2H, m, H-5′), 1.80 (3H, br s, H-13), 3.25 (1H, dd, J = 5; 13, H-7α), 3.51 (1H, d, J = 1.5, OH), 3.98 (1H, dd, J = 11.5; 2.5, H-9α), 4.80 (1H, br s, H-12b), 4.89 (1H, dd, J = 10; 5, H-3β), 5.01 (1H, dq, J = 1.5, H-12a), 5.83 (1H, dd, H-2′), 6.14 (1H, dd, H-3′), 6.22 (1H, ddd, H-4′); OAng: 1.90 (3H, dq, H-5″), 1.99 (3H, dq, H-4″), 6.08 (1H, qq, H-3″) [1]

References

  1. 1.
    F. Bohlmann, R.K. Gupta, Phytochemistry 21(10), 2595 (1982)CrossRefGoogle Scholar

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