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2,22-DIDEOXY-20-HYDROXYECDYSONE 3β-O-β-D-GLUCOPYRANOSIDE

Year of first isolation: 2001
Formula:C33H54O10
Molecular weight:610
Occurence in plants:
Cucubalus baccifer [Caryophyllaceae] » Images of Cucubalus baccifer Wikipedia: Cucubalus baccifer [Caryophyllaceae]
Occurence in animals:
 
2,22-DIDEOXY-20-HYDROXYECDYSONE 3β-O-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)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(3S,5R,9R,10R,13R,14S,17S)-17-((S)-2,6-dihydroxy-6-methylheptan-2-yl)-14-hydroxy-10,13-dimethyl-3-(((2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
WBZFDHVPSYROFE-VZSPAUEASA-N
InChIInChI=1S/C33H54O10/c1-29(2,39)10-6-11-32(5,40)24-9-14-33(41)20-16-22(35)21-15-18(7-12-30(21,3)19(20)8-13-31(24,33)4)42-28-27(38)26(37)25(36)23(17-34)43-28/h16,18-19,21,23-28,34,36-41H,6-15,17H2,1-5H3/t18-,19-,21-,23?,24-,25+,26?,27?,28+,30+,31+,32-,33+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
FAB-MS (negative)609 [M-H] - (100), 447 [M-163] -- (12)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CD3OD
0130.19
0227.93
0371.48
0431.49
0553.44
06206.30
07121.91
08168.97
09?
1037.49
1122.03
1232.57
1348.58
1485.71
1532.57
1620.08
17?
1818.12
1924.24
2075.99
2126.49
2245.70
2320.08
2445.88
2571.48
2629.34
2729.15
CD3OD
01-Ha 
01-He 
02-Ha 
02-He 
03-He3.85 (d)
04-Ha 
04-He 
05-H 
07-H5.80 (d)
09-H 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.94 (s)
19-Me0.84 (s)
21-Me1.24 (s)
22-Ha 
22-Hb 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.18 (s)
27-Me1.18 (s)
sugar (H-1')4.35 (d)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D28+ 49 ° (c 1.1 ; MeOH)
IR (KBr) ν max (cm-1)3348 (OH), 1653 (unsaturated ketone)
UV (EtOH) λ max (log ε)244 (-) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCHENG, Y.-X. et al. (2001) Zhiwu Xuebao 43(3), 316-318 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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