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2-DEOXY-20-HYDROXYECDYSONE 3-CROTONATE

Year of first isolation: 1996
Formula:C31H48O7
Molecular weight:532
Occurence in plants:
Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: Silene otites [Caryophyllaceae]
Occurence in animals:
 
2-DEOXY-20-HYDROXYECDYSONE 3-CROTONATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC=CC(=O)OC1CCC2(C3CCC4(C(CCC4(C3=CC(=O)C2C1)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](C1)OC(=O)/C=C/C)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[(3S,5R,9R,10R,13R,14S,17S)-14-hydroxy-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-3-yl] (E)-but-2-enoate
CAS-RN 
PubChem CID102330432
InChiKey
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VIOAJLKYKXYAFR-HPGLHNLESA-N
InChIInChI=1S/C31H48O7/c1-7-8-26(34)38-19-9-14-28(4)20-10-15-29(5)24(30(6,36)25(33)12-13-27(2,3)35)11-16-31(29,37)21(20)18-23(32)22(28)17-19/h7-8,18-20,22,24-25,33,35-37H,9-17H2,1-6H3/b8-7+/t19-,20-,22-,24-,25+,28+,29+,30+,31+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z550(M+H+NH3)+, 533 (M+H)+, 447 (M+H-crotonic acid), 432 (M+H+NH3-C22-C27), 417 (M+H-C22-C27)
EI-MS m/z (relative intensity %) 
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 
CDCl3
01-Ha 
01-He 
02-Ha 
02-He 
03-He5.13 (sb, w1/2=12)
04-Ha 
04-He 
05-H2.39
07-H5.85 (d, 2.5)
09-Ha3.11 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.37
18-Me0.86 (s )
19-Me0.98 (s )
21-Me1.21 (s )
22-Hb3.44 (d, 10)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.24 (s )
27-Me1.25 (s )
CH3-CH=1.87 (d,d, 7.1, 1.6)
CHa=5.83 (dq, 16.1, 6)
CHb=6.95 (dq, 16, 7.1)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCNP-HPLC, Zorbax-SIL 25 cm x 4.6 mm i.d., solvent cyclohexane-iPrOH-H2O 100:30:1.5 v/v/v, flow-rate 1 ml.min-1, Ret. 10.3 min (2d20E 18.8 min); Zorbax-SIL 25 cm x 9.4 mm i.d., solvent CH2Cl2-PrOH-H2O 125:15:1 v/v/v, flow-rate 4 ml.min-1, Ret. 14.1 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationBATHORI, M. et al. (1997) J. Pharm. Biomed. Anal. 16, 327-336 Search more

see Important notice
© 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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