C30H48O2, M 440
Taxonomy: Cycloartane Triterpenoids
Monocyclanthus vignei Keay (Annonaceae) [1].
Mp 166–168°C (from MeOH), [α] 21D +5° (c 0.80, CHCl3).
CAS Registry Number: 146257-58-1.
IR \({\rm \nu}_{\rm max}^{\rm CHCI_3} \), cm−1: 3629.
EIMS m/z (%): M+ 440.3654 (100), 425 (94), 422 (13), 407 (13), 300 (14), 285 (34), 175 (16), 125 (98).
1H NMR (CDCl3, δ): 0.27 and 0.48 (2H-19, d, J = 4.2 Hz), 0.73 (H-6β, dddd, J1 = J2 = J3 = 12.5 Hz, J4 = 2.5 Hz), 0.82, 0.84, 0.90, 0.92 (4 × CH3, s), 1.63 and 1.67 (CH3-26, CH3-27, d, J = 1.2 Hz), 3.33 (H-21B, dd, J1 = 9.5, J2 = 8 Hz), 3.42 (H-3, m), 3.89 (H-21A, dd, J = 8, J2 = 7.5 Hz), 4.48 (H-23, ddd, J = 10, J2 = 8.5, J3 = 5 Hz), 5.13 (H-24, dqq, J = 8.5, J2 = J3 = 1.2 Hz).
Table 1
δC(CDCl3) |
δC(CDCl3) |
δC(CDCl3) |
|||
---|---|---|---|---|---|
C-1 |
27.5 |
C-11 |
26.7 |
C-21 |
71.4 |
2 |
28.5 |
12 |
31.2 |
22 |
43.7 |
3 |
76.6 |
13 |
45.4 |
23 |
75.2 |
4 |
39.5 |
14 |
48.4 |
24 |
126.3 |
5 |
40.9 |
15 |
35.7 |
25 |
135.7 |
6 |
21.2a |
16 |
27.9 |
26 |
18.1 |
7 |
25.9b |
17 |
50.9 |
27 |
26.1b |
8 |
47.9 |
18 |
18.7 |
28 |
19.2 |
9 |
19.8a |
19 |
29.9 |
29 |
25.6 |
10 |
25.8b... |
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References
H. Achenbach, D. Frey, Phytochemistry 31(12), 4263–4274 (1992)
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(2013). (23S)-21,23-Epoxy -5α-cycloart-24-en-3α-ol. In: Azimova, S.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0537-5_93
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