Natural Compounds

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

6α-Vanilloyloxy-4β-hydroxy-5α(H)-dauc-8-en-10-one (Vanillate of Lapidol)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_932

CAS Registry Number: 119425-94-4 Open image in new window

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

Biological sources: Ferula latipinna A. Santos [1], F. kuhistanica Korov. [2]

C23H30O6: 402.2042

Mp: 176–178°C (hexane–EtOAc) [1]

IR (CHCl3): 3510, 3000, 2955, 1685, 1640, 1600, 1590, 1512, 1460, 1420, 1355, 1275, 1100, 1030, 930 [1]

EI-MS: 359 [M - C3H7]+ (7), 235 (26), 217 (9), 191 (23), 168 (36), 163 (10) [1]

1H NMR (200 MHz): 0.86 (6H, d, J = 6.7, H-12, H-13), 1.39 (3H, s, H-14), 2.00 (3H, br s, H-15), 2.46 (1H, dd, J = 16; 2.5, H-7β), 2.57 (1H, d, J = 9.6, H-5), 3.02 (1H, dd, J = 16; 5, H-7α), 5.83 (1H, m, H-6), 6.01 (1H, br s, H-9); OVan: 6.95 (1H, d, J = 8.2, H-5′), 7.52 (1H, d, J = 1.8, H-2′), 7.58 (1H, dd, J = 8.2; 1.8, H-6′) [1]

13 C NMR (67.9 MHz) [ 1]:

Table 1

C-1

55.3

C-9

128.6

C-1′

121.8

2

31.2

10

208.3

2′

150.8

3

36.9

11

36.4

3′

140.5

4

84.7

12

18.2

4′

146.6

5

50.3

13...

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References

  1. 1.
    A.G. Gonzalez, J. Bermejo, J.G. Diaz, L. Arancibia, J. Nat. Prod. 51, 1140 (1988)CrossRefGoogle Scholar
  2. 2.
    B. Chen, R. Teranishi, K. Kawazoe, Y. Takaishi, G. Honda, M. Itoh, Y. Takeda, O.K. Kodzhimatov, Phytochemistry 54(7), 717 (2000)CrossRefGoogle Scholar

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