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3-EPI-ECDYSONE

Year of first isolation: 1974
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Serratula strangulata [Asteraceae] » Images of Serratula strangulata Wikipedia: Serratula strangulata [Asteraceae]
Occurence in animals:
Manduca sexta [Lepidoptera] » Images of Manduca sexta Wikipedia: Manduca sexta [Lepidoptera]
Pieris brassicae [Lepidoptera] » Images of Pieris brassicae Wikipedia: Pieris brassicae [Lepidoptera]
Spodoptera littoralis [Lepidoptera] » Images of Spodoptera littoralis Wikipedia: Spodoptera littoralis [Lepidoptera]
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
3-EPI-ECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)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)O)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,3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID23724769
InChiKey
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UPEZCKBFRMILAV-LVRQXCCVSA-N
InChIInChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22-,23-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)446 (M-18)+ (1), 431 (3), 428 (16), 413 (8), 410 (4), 395 (4), 348 (14), 330 (30), 315 (14), 301 (14), 300 (30), 285 (13), 279 (26), 250 (29), 249 (18), 173 (13), 161 (13), 145 10), 126 (16), 121 (14), 117 (14), 109 (17), 107 (10), 105 (13), 99 (100), 81 (77).
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 
CD3OD
01-Ha 
01-He 
02-Ha3.63 (m, w1/2=21)
03-He3.34 (m, w1/2=22)
04-Ha 
04-He 
05-H 
07-H5.82 (d, 2.4)
09-Ha3.17 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.725
19-Me0.949
21-Me0.944
22-H3.59 (brd, 10.6)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.185
27-Me1.193
D2O
01-Ha 
01-He 
02-Ha3.77
03-He3.51
04-Ha 
04-He 
05-H 
07-H5.99 (m)
09-Ha3.11 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.757
19-Me0.966
21-Me0.981
22-H3.71
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.244
27-Me1.250

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

TLC on silicaRf 0.35 (CHCl3-EtOH 4:1 v/v); Rf 0.41 (CHCl3-MeOH 4:1 v/v); Rf 0.33 (CHCl3-EtOH 9:2 v/v, continuous development fro 2.5 hours); Rf 0.52 (CHCl3-EtOH 65:35 v/v) (E : 0.47)); Rf 0.41 (CHCl3-MeOH 90:15 v/v, multiple development ) (E : 0.34)
NP-HPLCRetention volume 68 ml [column APS-Hypersil, 25 cm long, 4.6 mm i.d., solvent CH2Cl2-MeOH-iPrOH 95:2:3 v/v/v, flow-rate 3 ml.min-1] (E : 44 ml)
RP-HPLCRetention volume 35 ml [column Partisil-10 ODS, 25 cm long, 4.6 mm i.d., solvent linear gradient (40 min) of MeOH-H2O from 2:3 to 3:2, flow-rate 2 ml.min-1] (E : 35 ml)

BIOLOGICAL ACTIVITIES

Musca assay: 10-20% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationNIGG, H.N. et al. (1974) Lipids 9, 971-974 Search more
GeneralDINAN, L. et al. (1978) Steroids 32, 629-638 Search more
GeneralKAPLANIS, J.N. et al. (1979) Steroids 34, 333-345 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
GeneralLAFONT, R. et al. (1980) Steroids 36, 185-207 Search more
GeneralDINAN, L. et al. (1981) J. Chromatogr. 205, 139-145 Search more
GeneralMILNER, N.P. et al. (1985) Biochem. J. 231, 369-374 Search more
First isolationKAMBA, M. et al. (1995) J. Seric. Sci. Jpn. 64, 333-343 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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