Natural Compounds

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

6α-Anisoyloxy-4β-hydroxy-5α(H)-dauc-8-en-10-one (10-Oxo-jaeschkeanadiol Anisate)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_872

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

Biological sources: Ferula communis L. subsp. communis L. [1]; Ferula linkii Webb et Berthel. [2]

C23H30O5: 386.2093

Mp: 161°C (hexane) [1]

[α]D +91° (c 0.88, CH2Cl2) [1]

UV 252 [1]

IR: 3500, 1690, 1660, 1610, 1280, 1180, 850, 780 [1]

MS: 355 [M − 31]+ (10), 234 (42), 149 (78), 135 (100), 96 (84) [1]

1H NMR (250 MHz, CDCl3): 0.87 and 0.85 (6H, d, J = 6.7, H-12, H-13), 1.37 (3H, s, H-14), 2.00 (3H, br s, H-15), 2.46 (1H, dd, J = 16.2; 2.7, H-7β), 2.55 (1H, d, J = 9.6, H-5), 3.03 (1H, dd, J = 16.2; 2.5, H-7α), 5.85 (1H, ddd, J = 9.6; 5.3; 2.7, H-6), 6.02 (1H, br s, H-9); OAnis: 3.90 (3H, s, OCH3), 7.98 and 6.95 (AA′ BB′system) [1]

13 C NMR (62.89 MHz, CDCl 3, TMS) [ 1]:

Table 1

C-1

55.33 s

C-9

128.70 d

OAnis

166.24 s

2

36.92 ta

10

208.78 s

 

165.76 d

3

31.25 ta

11

36.45 d

 

131.69 d

4

84.55 s

12

18.35 qb

 

122.28 d

5

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References

  1. 1.
    G. Appendino, S. Tagliapietra, L. Paglino, G.M. Nano, D. Monti, V. Picci, Phytochemistry 29(5), 1481 (1990)CrossRefGoogle Scholar
  2. 2.
    J.C. Diaz, B.M. Fraga, A.G. Gonzalez, M.G. Hernandez, A. Perales, Phytochemistry 25(5), 1161 (1986)CrossRefGoogle Scholar

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