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25-EPI,28-EPI-CYASTERONE [cf. 28-EPI-ISOCYASTERONE]

Year of first isolation: 2005
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: Cyathula capitata [Amaranthaceae]
Occurence in animals:
 
25-EPI,28-EPI-CYASTERONE [cf. 28-EPI-ISOCYASTERONE]

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O
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](C[C@H]1[C@H](C(=O)O[C@H]1C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3R,4S,5S)-4-[(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]-3,5-dimethyloxolan-2-one
CAS-RN 
PubChem CID11455183
InChiKey
[ ChemIDPlus: search ]
NEFYSBQJYCICOG-LGVKSGJWSA-N
InChIInChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16+,17+,19+,21-,22+,23+,24-,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z
HR-FABMS m/z521.3109 [M+H]+, C29H45O8 requires 521.3114

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.1
0368.0
0432.4
0551.3
06203.4
07121.6
08165.8
0934.4
1038.6
1121.0
1231.9
1348.0
1484.0
1531.7
1621.6
1749.9
1817.7
1924.4
2076.6
2121.3
2274.9
2326.6
2439.8
2539.5
26180.0
2717.4
2878.6
2912.8
C5D5N
01-Ha1.94
01-He2.15 (dd, 13.1, 4.7)
02-Ha4.19 (brd, 11.5)
03-He4.23 (brs, w1/2=7.4)
04-Ha1.81
04-He2.03
05-H3.02 (dd, 13.2, 3.7)
07-H6.27 (d, 2.1)
09-H3.59 (brt, 9.9)
11-Ha1.74
11-He1.89
12-Ha2.57 (td, 13.0, 4.2)
12-He1.98
15-Ha1.89
15-Hb2.18
16-Ha2.49 (m)
16-Hb2.05
17-H2.89
18-Me1.22 (s)
19-Me1.08 (s)
21-Me1.59 (s)
22-H3.82 (brd, 11.5)
23-Ha1.69
23-Hb1.85
24-H3.14
25-H2.89 (m)
27-Me1.28 (d, 7.5)
28-H4.65 (qui, 6.7)
29-Me1.29 (d, 6.6)

PHYSICAL PROPERTIES

M.P.? °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)241.2 (4.11) ;

CHROMATOGRAPHY

HPLCRP-HPLC, column Shimadzu STR PREP-ODS, 6x15 mm i.d.), solvent MeOH-H2O (10:8), flow-rate 1 ml.min-1, ret. 17.2 min (cyasterone : 13.8 min)
GLC
HPTLC
TLCSilica plates, solvent CHCl3-MeOH (10:1), developed 3 times, Rf 0.35

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationOKUZUMI, K. et al. (2005) Org. Biomol. Chem. 3, 1227-1232 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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