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2,22,25-TRIDEOXYECDYSONE

Year of first isolation: 1978
Formula:C27H44O3
Molecular weight:416
Occurence in plants:
 
Occurence in animals:
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: <br />
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2,22,25-TRIDEOXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCCC(C)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C)O
Isomeric SMILES
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C[C@H](CCCC(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(CC[C@@H](C4)O)C)C)O » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN39219-57-3
PubChem CID15942885
InChiKey
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FADCOUQPHXGWQS-ZCDXYYCTSA-N
InChIInChI=1S/C27H44O3/c1-17(2)7-6-8-18(3)20-11-14-27(30)22-16-24(29)23-15-19(28)9-12-25(23,4)21(22)10-13-26(20,27)5/h16-21,23,28,30H,6-15H2,1-5H3/t18-,19+,20-,21+,23+,25-,26-,27-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)416 (M)+ (30), 398 (12), 388 (100), 383 (15), 355 (20), 313 (6), 302 (3), 285 (7), 233 (68)
HR-MSM+ found 416.3285, calc. 416.3290

CARBON NMR

PROTON NMR

CD3OD
01 
02 
0366.4
04 
0553.2
06207.4
07122.6
08169.3
09 
10 
1123.0
12 
13 
1486.8
15 
16 
1752.8
1817.2
1925.3
20 
2120.3
22 
23 
24 
2530.0
2623.8
2724.4
CD3OD
01-Ha 
01-He 
02-Ha 
03-He4.01
04-Ha 
04-He 
05-H2.45
07-H5.83
09-Ha3.23
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.74
19-Me1.00
21-Me0.95
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.91
27-Me0.94
CDCl3
01-Ha 
01-He 
02-Ha 
03-He4.10 (m )
04-Ha 
04-He 
05-H 
07-H5.90
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.69
19-Me1.00
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.87 (d, 5)
27-Me0.87 (d, 5)

PHYSICAL PROPERTIES

M.P.172-173 °C
[α]D28+ 80.4 ° (c 5.6; MeOH)
IR (KBr) ν max (cm-1)3450 (OH), 1660 (cyclohexenone), 1450, 1380, 1035
UV (MeOH) λ max (log ε)245 (4.079)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC : column Spherisorb 5-ODS-2, solvent linear gradient (in 30 min) of 20% to 100% ACN-iPrOH (5:2) in 0.1% TFA in H2O, flow-rate 1 ml.min-1, Rt 35.9 min (2DE : 17.0 min)

BIOLOGICAL ACTIVITIES

Calliphora assay: 33% (20-hydroxyecdysone = 100%)

REFERENCES

GeneralHORN, D.H.S. et al. (1971) In: Marcel Dekker Inc., New York, pp. 333-459 Search more
GeneralBOLLENBACHER, W.E. et al. (1977) Steroids 29, 47-63 Search more
First isolationHETRU, C. et al. (1978) Life Sci. 22, 2141-2154 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
GeneralHAAG, T. et al. (1985) J. J. Labelled Compd. Radiopharm. 22, 547-557 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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