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RAPISTERONE C

Year of first isolation: 1992
Formula:C29H48O7
Molecular weight:508
Occurence in plants:
Rhaponticum carthamoides [Compositae] » Images of Rhaponticum carthamoides Wikipedia: <br />
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Occurence in animals:
 
RAPISTERONE C

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C(CC(C)(C)O)CC)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)[C@@H](CC(C)(C)O)CC)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)[C@H](CC(C)(C)O)CC)O)O)C)C » JSMol: View in 3D
IUPAC Name 
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
FJBBFIDNOKNATE-BFSOYOPGSA-N
InChIInChI=1S/C29H48O7/c1-7-16(14-25(2,3)34)24(33)28(6,35)23-9-11-29(36)18-12-20(30)19-13-21(31)22(32)15-26(19,4)17(18)8-10-27(23,29)5/h12,16-17,19,21-24,31-36H,7-11,13-15H2,1-6H3/t16?,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)472 (M-2H2O)+ (4), 454 (28), 439 (19), 436 (4), 421 (4), 363 (16), 345 (40), 327 (24), 300 (32), 171 (20), 154 (16), 127 (100), 109 (40), 83 (16), 69 (9).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.01
0268.05
0368.10
0432.46
0551.40
06203.43
07121.63
08166.14
0934.48
1038.67
1121.59
1231.76
1348.11
1484.14
1532.02
1621.14
1749.98
1817.87
1924.46
2076.92
2121.53
2276.02
2350.67
2432.62
2572.57
2629.83 *
2725.72 *
2825.58
2913.82
C5D5N
01-Ha 
01-Hb 
02-Ha4.16 (m )
03-He4.22 (m )
04-Ha 
04-He 
05-H 
07-H6.26
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.22 (s )
19-Me1.08 (s )
21-Me1.56 (s )
22-H3.87 (d , 10)
23-H 
24-H 
26-Me1.25 (s )*
27-Me1.38 (s )*
28-Ha 
28-Hb 
29-Me1.01 (t )

PHYSICAL PROPERTIES

M.P.249-250 °C ;
[α]D20 
IR (KBr) ν max (cm-1)3340-3500 (OH), 1655 (cyclohexenone);
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 3.9 x 10-7M

REFERENCES

First isolationBALTAYEV, U.A. et al. (1992) Khim. Prir. Soedin., 231-233 Search more
BioactivitiesDINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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