Natural Compounds

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

2β-Angeloyloxy-9α(H)-furanocadin-3-en-8-one (2β-Angeloyloxy-1,2,5,6-tetrahydrochromolaenin-8-one)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_825

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

Biological sources: Acritopappus prunifolius R. M. King & H. Rob. [1]

C20H24O4: 328.1675

Mp: colorless gum [1]

[α]D +9.4° (c 0.77, CHCl3) [1]

IR (CCl4): 1725, 1683, 1640 [1]

MS: 328.167 [M]+ (0.5) (C20H24O4), 228 [M − AngOH]+ (100), 213 [228 − CH3]+ (64), 185 [213 − CO]+ (27), 83 [C4H7CO]+ (74), 55 [83 − CO]+ (95) [1]

1H NMR (400 MHz, CDCl3, TMS): 0.95 (6H, s, H-12, H-13), 1.43 (4H, m, H-7, H-8), 2.04 (2H, m, H-9), 2.30 (2H, m, H-3), 2.38 (2H, m, H-2), 4.53 (2H, br s, H-14), 4.88 (1H, br s, H-15b), 4.92 (1H, br s, H-15a), 5.45 (1H, d, J = 16, H-6), 5.52 (1H, br dd, J = 8, H-1), 5.85 (1H, d, J = 16, H-5); OAng: 1.87 (3H, dq, J = 1.5; 1.5, H-5′), 1.97 (3H, dq, J = 7; 1.5, H-4′), 6.03 (1H, qq, J = 7; 1.5, H-3′) [1]

References

  1. 1.
    F. Bohlmann, C. Zdero, R.M. King, H. Robinson, Phytochemistry 21(1), 147 (1982)CrossRefGoogle Scholar

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