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20-HYDROXYECDYSONE 2-ACETATE

Year of first isolation: 1978
Formula:C29H46O8
Molecular weight:522
Occurence in plants:
Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: Lychnis flos-culculi [Caryophyllaceae]
Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: Ajuga reptans [Lamiaceae (alt. Labiatae)]
Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: Cyanotis arachnoidea [Commelinaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 2-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC1CC2(C3CCC4(C(CCC4(C3=CC(=O)C2CC1O)O)C(C)(C(CCC(C)(C)O)O)O)C)C
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] acetate
CAS-RN 
PubChem CID11060408
InChiKey
[ ChemIDPlus: search ]
TXLUXHSVMYTTCI-FORVDKSSSA-N
InChIInChI=1S/C29H46O8/c1-16(30)37-22-15-26(4)17-7-11-27(5)23(28(6,35)24(33)9-10-25(2,3)34)8-12-29(27,36)18(17)13-20(31)19(26)14-21(22)32/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z540, 523 (MH)+, 505, 487, 469, 405 (MH - C22-C27)+, 387, 345, 329
EI-MS m/z (relative intensity %)522, 486, 468, 405 (58), 388 (100), 387 (86), 373, 345, 343 (13), 329, 311, 291, 285, 269, 258, 231, 199, 183, 161, 143, 119, 99, 81

CARBON NMR

PROTON NMR

C5D5N
0133.63 $
0272.50
0365.09
0432.55 $
0551.09
06202.81
07121.55
08166.20
0934.25
1038.70
1121.06 &
1231.89 *
1347.94
1484.09
1531.64 *
1621.35&
1749.94
1817.78
1924.19
2076.75
2121.58 &
2277.43
2327.40
2442.58
2569.51
2629.84
2730.16
CH3COO20.10; 170.40,
CDCl3
01-Ha1.55
01-He1.82
02-Ha5.01 (m, w1/2=22)
03-He4.11 (m, w1/2=8)
04-Ha1.6
04-He1.85
05-H2.51 (dd, 13, 4)
07-H5.84 (d, 2.5)
09-Ha3.09 (m, w1/2=21)
11-Ha1.70
11-He1.80
12-Ha 
12-He 
14-H--
15-Ha 
15-Hb 
16-Ha2.0
16-Hb1.75
17-H2.34 (m )
18-Me0.86 (s )
19-Me0.99 (s )
21-Me1.21 (s )
22-H3.44 (d br, 10)
23-Ha1.35
23-Hb1.65
24-Ha 
24-Hb 
25-H--
26-Me1.24 (s )
27-Me1.25 (s )
O-Ac2.08 (s )
C5D5N
01-Ha 
01-He 
02-Ha5.25 (w1/2=22.5)
03-He4.29 (w1/2=7.0)
04-Ha 
04-He 
05-H3.04
07-H6.25
09-Ha3.65 (w1/2=20)
11-Ha 
11-He 
12-Ha2.50
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb3.02
17-H 
18-Me1.20
19-Me1.07
21-Me1.57
22-H3.86 (w1/2=15.0)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.38
27-Me1.38
O-Ac1.98

PHYSICAL PROPERTIES

M.P.219-220 °C ;
[α]D20 
IR (KBr) ν max (cm-1)3410 (OH), 1658 (cyclohexenone), 1715, 1260.
UV (EtOH) λ max (log ε)243 (4.043) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC1- Retention time 8.7 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); 2-Retention time 13.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min); 3-Retention time 15.0 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min).

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-7M

REFERENCES

GeneralGALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1045-1046 Search more
First isolationNIEN, S.-L. et al. (1978) Acta Chim. Sinica 36, 137-141 Search more
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
GeneralCALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 Search more
GeneralDANIELI, B. et al. (1997) Tetrahedron 53, 5855-5862 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 Search more

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