3-Oxo-cycloart-24-en-21-oic Acid

Reference work entry

C30H46O3, M 454 Open image in new window

Taxonomy: Cycloartane Triterpenoids

Lansium domesticum (Meliaceae) [1].

Mp 185–186°C, [α]D12 +18.7° (c 1.16, CHCl3).

IR νmax, cm−1: 3200, 1710.

1H NMR (CDCl3, δ, 0-TMS): 0.50 and 0.79 (2H-19, d, J = 4.3 Hz), 0.90, 1.06, 1.08, 1.08, 1.57, 1.67 (6 × CH3, s), 5.81 (H-24, t, J = 7.3 Hz).

The correct structure was finally derived by a single crystal x-ray diffraction study.

Table 1

δC(CDCl3)

       

C-1

33.3

C-7

32.6

C-13

48.6

C-19

29.4

C-25

132.9

2

37.4

8

47.5

14

45.2

20

48.2

26

25.7

3

218.5

9

21.0

15

34.9

21

182.6

27

17.7

4

50.2

10

26.1

16

26.0

22

25.7

28

19.3

5

47.7

11

26.6

17

49.1

23

27.2

29

22.2

6

21.3

12

29.9

18

17.8

24

123.6

30

20.8

References

  1. 1.
    M. Nishizawa, M. Emura, H. Yamada, M.S. Chairul, Y. Hayashi, H. Tokuda, Tetrahedron Lett. 30(41), 5615–5618 (1989)CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2013

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