Natural Compounds

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

10α-Angeloyloxy-5β-hydroxy-4α(H)-dauc-8-en-2-one (Vaginatin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_862

CAS Registry Number: 11053-21-7 Open image in new window

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

Biological sources: Selinum vaginatum C.B. Clarke [1, 2]; Inula crithmoides L. [3]; Laserpitium halleri subsp. halleri Crantz [4]; Ferula jaeschkeana Vatke [5]

C20H30O4: 334.2144

Mp: 77–78°C (hexane) [1, 2]; oil [3, 6]; 68–69°C [4]

[α]D22 −266.7° (c 4.32, CHCl3) [1]; −212.8° [2]; [α]D25 −247° (c 1.5, CHCl3) [4]

UV: 217 (ε 12400) [1]; 217 (4.09) [2]; 218 (3.9) [4]

IR (nujol): 3531, 1730, 1637, 853 [1]; 3531, 1735, 1720, 1637, 1235, 1148, 853 [2]; 3420, 1720 [4]

MS: 334 [M]+ [1, 2]; 334.214298 [M]+ (1) (calc. for C20H30O4: 334.214396), 83 (100) [4]

Found: C, 72.28; H, 9.19. Calc. for C20H30O4: C, 71.82; H, 9.04% [2]

CD (MeOH): Δε305 −0.11, Δε215 −23.38 [4]

1H NMR: 1.00 (3H, s, H-14), 1.00 (6H, d, J = 7, H-12, H-13), 1.82 (3H, m, H-15), 2.53 (1H, disappeared on D2O exchange), 5.16...

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References

  1. 1.
    C.K. Mesta, S.K. Paknikar, S.C. Bhattacharyya, Chem. Commun. 584 (1968)Google Scholar
  2. 2.
    K. Rajendran, S.K. Paknikar, C.K. Trivedi, S.C. Bhettacharyya, Indian J. Chem. 16B, 4 (1978)Google Scholar
  3. 3.
    Z.F. Mahamoud, N.A.A. Salam, T.M. Sarg, F. Bohlmann, Phytochemistry 20(4), 735 (1981)CrossRefGoogle Scholar
  4. 4.
    G. Appendino, M.G. Valle, P. Gariboldi, J. Chem. Soc. Perkin Trans. 1 1363 (1986)CrossRefGoogle Scholar
  5. 5.
    S.N. Garg, L.N. Misra, S.K. Agarwal, V.P. Mahajan, S.N. Rastogi, Phytochemistry 26(2), 449 (1987)CrossRefGoogle Scholar
  6. 6.
    M. Miski, T.J. Mabry, Phytochemistry 25(7), 1673 (1986)CrossRefGoogle Scholar
  7. 7.
    L.H. Zalkov, M.G. Jr. Clower, M. Gordon, J. Smith, D. VanDerveer, J.A. Bertrand, J. Chem. Soc. Chem. Commun. 374 (1976)Google Scholar

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