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20-HYDROXYECDYSONE 3,22-DIACETATE

Year of first isolation: 1992
Formula:C31H48O9
Molecular weight:564
Occurence in plants:
Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: Serratula tinctoria [Asteraceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 3,22-DIACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC1CC2C(=O)C=C3C(C2(CC1O)C)CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)OC(=O)C)O)O)C
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@](C)([C@@H](CCC(C)(C)O)OC(=O)C)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-3-acetyloxy-2,6-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 CID101642418
InChiKey
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SWWDJZZNTORSLE-VIEKNRERSA-N
InChIInChI=1S/C31H48O9/c1-17(32)39-24-15-21-22(34)14-20-19(28(21,5)16-23(24)35)8-12-29(6)25(9-13-31(20,29)38)30(7,37)26(40-18(2)33)10-11-27(3,4)36/h14,19,21,23-26,35-38H,8-13,15-16H2,1-7H3/t19-,21-,23-,24+,25-,26+,28+,29+,30+,31+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z582 (M+H+NH3)+, 565 (M+H)+, 547, 529, 504, 487, 469, 453, 422, 387, 362, 345, 327
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 
28 
29 
CDCl3
01-Ha 
01-Hb 
02-Ha4.0 (m, w1/2=22)
03-He5.20 (m, w1/2=8)
04-Ha 
04-He 
05-H2.50 (dd, 14,4.5)
07-H5.84
09-Ha3.04 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.34 (m )
18-Me0.84 (s )
19-Me1.01 (s )
21-Me1.24 (s )
22-H4.85 (dd, 10,2)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.21 (s )
27-Me1.23 (s )
CH3CO-(03)2,11 (s, 3H)
CH3CO-(22)2.10 (s, 3H)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCNP-HPLC, Rt 15.3 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent isoC8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml.min-1) (20E 22.6 min); RP-HPLC, Rt 19.5 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent linear gradient 20 to 70% ACN in 1? TFA in H2O, flow-rate 1ml.min-1) (20E 12.3 min).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationRUDEL, D. et al. (1992) Planta Med. 58, 358-364 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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