Natural Compounds

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

10-Acetoxy-5β-hydroxy-4α(H)-dauc-8-en-2-one (Siol Acetate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_851

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

Biological sources: Sium latijugum C.B. Clarke [1]; S. latifolium L. [2]

C17H26O4: 294.1831

Mp: 130–131°C [2]

[α]D20 −252° (c 0.28, CHCl3) [2]

IR: 3500, 1740, 1720 [2]

MS: 276.1722 [M − H2O]+ (calc. for C17H24O3: 276.1725) [2]

1H NMR (100 MHz, CDCl3, TMS): 1.02 and 1.12 (each 3H, both d, J = 6.5, H-12, H-13), 1.15 (3H, s, H-14), 1.65 (3H, s, H-15), 1.95 (3H, s, OAc), 5.17 (1H, d, J = 7.5, H-10), 5.63 (1H, J = 7.5, H-9) [2]

13 C NMR (CDCl 3, TMS) [ 2]:

Table 1

18.1 q

29.2 t

82.3 s

21.1 q

37.3 t

119.3 d

21.3 q

38.9 t

146.5 s

24.8 q

51.7 d

169.2 s

26.1 q

60.3 s

220.3 s

26.6 d

76.0 d

 
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References

  1. 1.
    K. Pandita, S.G. Agarwal, R.K. Thappa, K.L. Dhar, Indian J. Chem. 23B, 956 (1984)Google Scholar
  2. 2.
    C.G. Casinovi, S. Cerrini, O. Motl, G. Fardella, W. Fedeli, E. Gavuzzo, D. Lamba, Collect. Czech. Chem. Commun. 48, 2411 (1983)CrossRefGoogle Scholar

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