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ECDYSONE 3-ACETATE

Year of first isolation: 1981
Formula:C29H46O7
Molecular weight:506
Occurence in plants:
 
Occurence in animals:
Schistocerca gregaria [Orthoptera] » Images of Schistocerca gregaria Wikipedia: <br />
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Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: <br />
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ECDYSONE 3-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC(=O)C)O)C)C)O)C(CCC(C)(C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S)-3,6-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
CAS-RN 
PubChem CID53893325
InChiKey
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HSADMKYEQWKERB-NIVYSHQQSA-N
InChIInChI=1S/C29H46O7/c1-16(22(31)9-10-26(3,4)34)18-8-12-29(35)20-13-23(32)21-14-25(36-17(2)30)24(33)15-27(21,5)19(20)7-11-28(18,29)6/h13,16,18-19,21-22,24-25,31,33-35H,7-12,14-15H2,1-6H3/t16-,18+,19-,21-,22?,24-,25+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z (relative intensity %)524 (M+H+NH3)+ (0.1), 506 (0.3), 489 (10), 488 (10), 447 (2), 446 (2), 429 (12), 99 (100).
EI-MS m/z (relative intensity %)470 (M-2x18)+ (2), 428 (M-18-60)+ (1), 410 (2), 395 (8), 390 (M-C22--C27)+ (3), 342 (10), 99 (100).
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 
CDCl3
01-Ha 
01-He 
02-Ha4.05 (m, w1/2=20)
03-He5.23 (m, w1/2=7)
04-Ha 
04-He 
05-H 
07-H5.87 (d )
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.71 (s )
19-Me1.03 (s )
21-Me0.97 (d, 7)
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.27 (s )
27-Me1.27 (s )
O-Ac2.14 (s, 3H)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCRf on silica gel 0.62 (CHCl3-MeOH 4:1) (E : 0.37; 20E : 0.30)
GLC 
HPLC1-Retention volume 128 ml [Whatman Magnum 9 Partisil ODS-3, 50 cm x 9.4 mm i.d., eluted with a linear gradient (40 min) of 40 --> 80% MeOH-H2O] (20E 82 ml, E 110 ml, E2Ac 145 ml); 2-Retention time 9.1 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 31.5 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationISAAC, R.E. et al. (1981) Chem. Commun., 594-595 Search more
GeneralMODDE, J.-F. et al. (1984) Int. J. Invertebr. Reprod. Develop. 7, 181-183 Search more

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