Natural Compounds

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

2β-Senecioyloxy-10βH-furanoeremophilane (2β-[3-Methyl-2-butenoyl]-furanoeremophilane)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_1268

CAS Registry Number: 87339-52-4 Open image in new window

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

Biological sources: Petasites niveus Baumg. [1]

C20H28O3: 316.2038

Mp: colorless oil [1]

[α]D22 −51.3° (c 0.85, CHCl3) [1]

UV (cyclohexane) 218 (4.01) [1]

IR (film): 1709, 1650, 1570 [1]

MS: 316 [M]+ (3), 233 (3), 216 (13), 108 (100) [1]

HPLC [1]

1H NMR (CDCl3, C6D6): 0.93, 0.81 (3H, d, J = 7.0, H-15), 1.00, 0.80 (3H, s, H-14), 1.89, 1.47 (3H, d, J = 1.2, Me trans to −C(O)O−), 1.90, 1.78 (3H, d, J = 1.1, H-13), 2.17, 2.16 (3H, d, J = 1.2, Me cis to −C(O)O−), 2.7−1.2, 2.6−1.1 (10H, m), 5.16, 5.18 (1H, m, H-2), 5.66, 5.76 (1H, m, =CHC(O)O−), 7.03, 7.01 (1H, m, H-12) [1]

13 C NMR (C 6D 6): [ 1]

Table 1

C-2

69.08 d

C-2′

117.20 d

26.41 q

7

119.56 s

3′

155.62 s

26.99 q

8

148.68 s

 

8.16 q

32.71 q

11

115.58 s

 

16.90 q

30.00 q

12

137.65 d

 

20.02 q

34.60 q

1′

165.63 s

 

22.76...

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References

  1. 1.
    A. Guerriero, F. Pietra, Phytochemistry 21(12), 2887 (1982)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013