Natural Compounds

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

8β-Acetoxy-caryophyll-2(15)-en-7-one (Dihydrobuddledin A)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_828

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

Biological sources: Buddleja globosa C. Hope [1]

C17H26O3: 278.1882

[α]D20 −64.7° (c 0.51, CHCl3) [1]

IR (КBr): 2955, 2935, 1738, 1716, 1455, 1371, 1244, 1020, 890 [1]

FAB-MS: 279 [M + 1]+ [1]

HR-FAB-MS: 279.1945 (calc. for C17H27O3 279.1960) [1]

1H NMR (CDCl3, 400 MHz): 5.12 (H, d, J = 11.4, H-8), 4.75 (1H, s, H-15a), 4.62 (1H, t, J = 1.8, H-15b), 3.03 (1H, m, H-1), 2.96 (1H, m, H-6), 2.08 (3H, s, OAc), 2.07 (1H, dd, J = 11.4, J = 10.0, H-9), 2.01–1.53 (8H, m, H-5, H-4, H-3, H-10), 1.14 (3H, s, H-13), 1.12 (3H, s, H-12), 1.11 (3H, d, J = 6.8, H-14) [1]

13 C NMR (400 MHz, CDCl 3) [ 1]:

Table 1

C-1

50.5

C-7

32.9

C-13

23.0

2

79.6

8

153.2

14

15.8

3

213.4

9

38.2

15

111.4

4

44.4

10

39.4

OAc

 

5

30.7

11

34.5

1′

171.0

6

26.4

12

31.6

2′

21.0

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References

  1. 1.
    Y.-H. Liao, P.J. Houghton, R.S. Hoult, J. Nat. Prod. 62, 1241 (1999)CrossRefGoogle Scholar

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