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20-HYDROXYECDYSONE 22-BENZOATE 25-GLUCOSIDE

Year of first isolation: 1990
Formula:C40H58O13
Molecular weight:746
Occurence in plants:
Silene otites [Caryophyllaceae] » Images of Silene otites Wikipedia: Silene otites [Caryophyllaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 22-BENZOATE 25-GLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C6=CC=CC=C6)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@](C)([C@@H](CCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)OC(=O)c1ccccc1)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R)-2-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-3-yl] benzoate
CAS-RN 
PubChem CID66869437
InChiKey
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ADATWESZSSNTDT-YEPBJDLISA-N
InChIInChI=1S/C40H58O13/c1-36(2,53-35-33(47)32(46)31(45)28(20-41)51-35)14-13-30(52-34(48)21-9-7-6-8-10-21)39(5,49)29-12-16-40(50)23-17-25(42)24-18-26(43)27(44)19-37(24,3)22(23)11-15-38(29,40)4/h6-10,17,22,24,26-33,35,41,43-47,49-50H,11-16,18-20H2,1-5H3/t22-,24-,26+,27-,28+,29-,30?,31+,32-,33+,35?,37+,38+,39+,40+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z747 (MH)+, 729, 643, 625, 607, 463, 445, 427, 363, 345
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 
CD3OD
01-Ha 
01-He 
02-Ha3.82 (m )
03-He3.94 (m, w1/2=8)
04-Ha 
04-He 
05-H2.37 (dd, 5, 12)
07-H5.81 (d, 2)
09-Ha~3.1-3.2
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.46 (m )
18-Me0.88 (s )
19-Me0.95 (s )
21-Me1.41 (s )
22-H5.14 (d br, 10)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.22 (s )
27-Me1.22 (s )
C6H5-CO- m7.49 (t, 7) (2H)
C6H5-CO- o8.08 (t, 7) (2H)
C6H5-CO- p7.61 (t, 7) (1H)
glu-1´4.41 (d, 7.6)
glu-2´3.12
glu-6´3.78 (dd, 12.3,2.2)
glu-6´´3.62

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC on silicaRf 0.48 (EtOAc-EtOH-H2O, 8:2:1) (20E 0.61); Rf 0.25 (CHCl3-MeOH-Me2CO 6:2:1) (20E 0.47)
GLC 
NP-HPLCRetention time 24.6 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O, 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 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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