Natural Compounds

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

13-Angeloyloxy-eremophil-9(10),7(11)-en-8-one (13-Angeloyloxy-3-desoxypetasol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1034

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

Biological sources: Petasites hybridus [1]

C20H28O3: 316.2038

UV (cyclohexane): 221, 244.5, 265 [1]

IR (CCl4): 1714, 1664, 1622 [1]

MS: 316.2046 [M]+ (calc. for C20H28O3: 316.2038) [1]

HPLC [1]

1H NMR (360 MHz, CDCl3, TMS): 0.95 (3H, d, J = 6.5), 1.00 (3H, s), 1.6–1.35 (4H, m), 1.85 (1H, m), 1.90 (3H, m), 1.99 (3H, qq, J = 7; 1.5), 2.11 (3H, d, J = 2.1), 2.23 (1H, br d, J = 13.5), 2.35–2.15 (3H, m), 2.95 (1H, d, J = 13.5), 4.77 (2H, s), 5.78 (1H, br s), 6.10 (1H, qq, J = 7; 1.3) [1]

13 C NMR (CDCl 3): [ 1]

Table 1

191.8 s

42.1 s

 

15.4 q

163.0 s

40.9 t

OAng

169.4 s

137.9 s

32.6 t

 

138.3 d

132.0 s

30.5 t

 

127.4 s

125.7 d

26.5 t

 

20.6 q

64.1 t

18.2 q

 

15.8 q

42.6 d

16.2 q

   
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References

  1. 1.
    M. Neuenschwander, A. Neuenschwander, E. Steinegger, P. Engel, Helv. Chim. Acta 62, 609 (1979)CrossRefGoogle Scholar

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