Natural Compounds

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

10α-Angeloyloxy-5β,15-dihydroxy-4α(H)-dauc-2-one (15-Hydroxy-vaginatin)

Reference work entry
DOI: https://doi.org/10.1007/978-1-4614-0539-9_861

CAS Registry Number: 128397-55-7 Open image in new window

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

Biological sources: Ferula sinaica Boiss. [1]

C20H30O5: 350.2093

IR: 3560, 3400, 2940, 2360, 1700, 1680, 1160 [1]

MS: 350 [M]+ (5), 332 [M − H2O]+ (2), 307 [M − C3H7]+ (3), 267 [M − C5H7O]+ (38), 83 [C4H7CO]+ (100) [1]

1H NMR (400 MHz,CDCl3): 1.00 (3H, d, J = 7, H-13), 1.06 (3H, d, J = 7, H-12), 1.07 (3H, s, H-15), 4.03 (2H, br s, H-14), 5.34 (1H, J = 9, H-10), 5.94 (1H, br d, J = 9, H-9); OAng: 1.83 (3H, q, H-5′), 1.97 (3H, dq. J = 7; 1.5, H-4′), 6.06 (1H, qq, J = 7.0; 1.5, H-3′) [1]

13 C NMR (CDCl 3) [ 1]:

Table 1

C-1

59.9 s

C-8

148.4 s

C-15

67.7 t

2

220 s

9

119.7 d

OAng

 

3

37.0 t

10

75.2 d

1′

166.0 s

4

50.5 d

11

26.3 d

2′

126.6 s

5

82.4 s

12

21.2 q

3′

140.0 d

6

38.5 t

13

24.6 q

4′

20.7 q

7

24.2 t

14

18.0 q

5′

15.8 q

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References

  1. 1.
    A.A. Ahmed, J. Nat. Prod. 53, 483 (1990)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013