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CARTHAMOSTERONE

Year of first isolation: 1988
Formula:C29H42O8
Molecular weight:518
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
CARTHAMOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(C(=CC(=O)O1)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O)C
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@](O)(C)[C@@H](CC1=CC(=O)OC1(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-5,5-dimethylfuran-2-one
CAS-RN114805-00-4
PubChem CID101926945
InChiKey
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CCCCNNJVLKLLKV-UYQGPDJCSA-N
InChIInChI=1S/C29H42O8/c1-25(2)15(11-24(34)37-25)10-23(33)28(5,35)22-7-9-29(36)17-12-19(30)18-13-20(31)21(32)14-26(18,3)16(17)6-8-27(22,29)4/h11-12,16,18,20-23,31-33,35-36H,6-10,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z519 [MH]+, 501, 483, 393, 375, 363, 345
EI-MS m/z363, 345
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
CD3OD
0137.33
0238.70
0368.44
0432.82
0551.75
06206.35
07122.29
08167.56
0935.06
1039.26
1121.52
1232.46
13(49.0)
1485.28
1531.83
1621.63
1750.43
1818.02
1924.41
2077.41
2121.08
2275.49
2330.65
24174.91
2589.74
2625.02
2724.87
28115.46
29178.79
CD3OD
01-Ha1.43
01-Hb1.78
02-Ha3.82 (m, w1/2=22)
03-He3.94 (m, w1/2=8)
04-Ha1.65
04-He1.75
05-H2.40 (dd, 12, 5)
07-H5.81 (d, 2.5)
09-Ha3.15 (m, w1/2=22)
11-Ha1.67
11-He1.80
12-Ha2.13 (ddd )
12-He1.85
15-Ha 
15-Hb 
16-Ha2.05
16-Hb1.75
17-H2.38
18-Me0.91 (s )
19-Me0.97 (s )
21-Me1.27 (s )
22-H3.70 (dd, 10.5, 2)
23-Ha2.57 (ddd, 17.5, 2, 2)
23-Hb2.28
26-Me1.48 (s )
27-Me1.48 (s )
28-C=CH5.92 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)1745 (alpha,beta-ethylenic gama-lactone)
UV (MeOH) λ max (log ε)210 (?), 242 (?)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.39 (EtOAC-MeOH-NH4OH 85:10:5); Rf 0.47 (CH2Cl2-EtOH 85:15)
GLC 
HPLCNP-HPLC, (Zorbax-Sil) Ret. 20.4 min (CH2Cl2-iPrOH-H2O, 125:25:2); flow-rate 1 ml. min-1 (20E = 53.2 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.4 x 10-7M

REFERENCES

First isolationGIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 Search more
IdentificationVOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 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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