Natural Compounds

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

2α-Acetoxy-6α-angeloyloxy-10β-cinnamoyloxy-5α(H)-dauc-8-en-4β-ol

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_973

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

Biological sources: Daucus carota L. ssp. carota [1]

C31H40O7: 524.2774

Mp: amorphous yellowish powder [1]

IR (KBr): 3500, 2980, 2960, 1730, 1260, 1164, 1032, 770 [1]

CI-MS: 507 [M + H – H2O]+, 377 [M – cinnamate]+ [1]

HR-CI-MS: 507.2769 [M + H – H2O]+ (calc. for C31H39O6, 507.2747) [1]

1H NMR (500 MHz, CDCl3): 0.88 (3H, H-13), 0.89 (3H, H-12), 1.28 (3H, H-14), 1.80 (1H, H-11), 1.84 (3H, H-15), 1.85 (1H, H-3β), 1.93 (3H, s, OAc), 2.09 (1H, H-3α), 2.21 (1H, H-7α), 2.58 (1H, H-5α), 2.67 (1H, H-7β), 5.06 (1H, H-2β), 5.21 (1H, H-6β), 5.29 (1H, H-9), 5.61 (1H, H-10α); OAng: 1.89 (3H, H-5′), 2.02 (3H, H-4′), 6.18 (1H, H-3′), OCinn: 7.45 7.60 [1]

13 C NMR (125 MHz, CDCl 3) [ 1]:

Table 1

C-1

51.0

C-10

75.3

C-2′

127.4

2

79.5

11

36.9

3′

140.1

3

39.3

12

17.4

4′

20.4

4

85.5

13

18.1

5′

15.9

5

54.5

14

15.3

OCinn: C=O

166.2

6

68.8

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References

  1. 1.
    A.A. Ahmed, M.M. Bishr, M.A. El-Shanawany, E.Z. Attia, S.A. Ross, P.W. Pare, Phytochemistry 66(14), 1680 (2005)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013