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2,22-DIDEOXY-20-HYDROXYECDYSONE

Year of first isolation: 1981
Formula:C27H44O5
Molecular weight:448
Occurence in plants:
 
Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
2,22-DIDEOXY-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(CCCC(C)(C)O)O)O)C)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3R,5R,10R,13R,14S,17R)-17-(2,6-dihydroxy-6-methylheptan-2-yl)-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID129637605
InChiKey
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NGORFCHZENUGIY-UOMGQMBVSA-N
InChIInChI=1S/C27H44O5/c1-23(2,30)10-6-11-26(5,31)22-9-14-27(32)19-16-21(29)20-15-17(28)7-12-24(20,3)18(19)8-13-25(22,27)4/h16-18,20,22,28,30-32H,6-15H2,1-5H3/t17-,18?,20+,22-,24-,25-,26?,27-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)448 (M)+, 430 (M - 18)+, 415 (M - 18 - 15)+, 412, 397, 394, 379, 361, 347 (M - C22-C27)+, 329, 311, 304 (M - C20-C27)+, 286, 271, 253, 234, 145 (C20-C27)+, 127, 109, 59, 41
HR-MS448.3198 (M)+

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 
CDCl3
01-Ha 
01-He 
02-Ha 
03-He5.14 (m )
04-Ha 
04-He 
05-H 
07-H5.90 (s br )
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.86 (s )
19-Me1.00 (s )
21-Me1,24 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1,26 (s )
27-Me1,26 (s )
Me-CO-2.08 (s,3H)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)245 (4.079)

CHROMATOGRAPHY

HPTLC 
TLCsilica Rf 0.46 (solvent CHCl3-96% EtOH) (2DE 0.54; E 0.32)
GLC 
HPLC1- Retention time 9.2 min [ Zorbax-Sil 150 mm x 4.6 mm i.d., solvent CH2Cl2-MeOH 93:7 v/v, flow-rate 1 ml.min-1 ] (2DE : 8.5 min; E : 14.6 min) 2-Retention time 21.0 min [ Wakogel ODS-10K 500 mm x 4.6 mm i.d., solvent MeOH-H2O 3:2 v/v, flow-rate 1 ml.min-1 ] (2DE : 19.1 min; E : 9.9 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = ca. 5.0 x 10-5M

REFERENCES

First isolationIKEKAWA, N. et al. (1980) Chem. Commun., 448-449 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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