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20-HYDROXYECDYSONE 22,25-DIBENZOATE

Year of first isolation: 1990
Formula:C41H52O9
Molecular weight:688
Occurence in plants:
Silene scabrifolia [Caryophyllaceae] » Images of Silene scabrifolia Wikipedia: Silene scabrifolia [Caryophyllaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 22,25-DIBENZOATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)OC(=O)C5=CC=CC=C5)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)OC(=O)c1ccccc1)OC(=O)c1ccccc1)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R,3R)-6-benzoyloxy-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]heptan-3-yl] benzoate
CAS-RN 
PubChem CID21626592
InChiKey
[ ChemIDPlus: search ]
JYQAIQIHWVPEBH-YGSULJDDSA-N
InChIInChI=1S/C41H52O9/c1-37(2,50-36(46)26-14-10-7-11-15-26)19-18-34(49-35(45)25-12-8-6-9-13-25)40(5,47)33-17-21-41(48)28-22-30(42)29-23-31(43)32(44)24-38(29,3)27(28)16-20-39(33,41)4/h6-15,22,27,29,31-34,43-44,47-48H,16-21,23-24H2,1-5H3/t27-,29-,31+,32-,33-,34+,38+,39+,40+,41+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)548 (M - C6H5COOH)+ (0.8), 530 (1), 515 (0.2), 512 (0.2), 479 (0.2), 467 (0.2), 462 (0.4), 450 (2.8), 444 (5), 426 (28), 408 (30), 393 (13), 375 (30), 363 (42), 357 (28), 345 (28), 329 (13), 301 (30), 250 (50), 163 (30), 122 (98), 105 (100), 99 (17), 81 (30), 77 (54), 51 (50).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0137.9
0268.0
0368.0
0432.2
0551.4
06202.2
07121.0
08165.5
0934.3
1038.7
1121.5
1231.8
1348.0
1483.8
1531.8
1622.2
1750.4
1817.5
1924.3
2076.5
2121.2
2280.9
2325.4
2439.1
2582.3
2625.6
2725.9
C6H5-1' 131.7, 131.7; 2', 6' 129.8; 130.1;
contin.3´,5´ 128.8, 128.8; 4´ 133.0, 133.1
O-C=O166.9
C5D5N
01-Ha 
01-He 
02-Ha4.0-4.3
03-He4.0-4.3
04-Ha 
04-He 
05-H 
07-H6.22
09-Ha3.52
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.18
19-Me1.06
21-Me1.73
22-H5.66
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.54
27-Me1.54
C6H5-CO-7.39 (6H), 8.25 (4H)

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 80.1 ? 2 ° (c 0.22 , MeOH)
IR (KBr) ν max (cm-1)3460-3520 (OH), 1670 (C=O), 1720, 1295, 1610, 1590, 730 (ben
UV (EtOH) λ max (log ε)235 (4.10) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Galleria mellonella in vivo assay: ED50 = 31.2 ug/g
Sarcophaga bullata in vivo assay: ED50 = 104.0 ug/g

REFERENCES

First isolationSAATOV, Z. et al. (1990) Khim. Prir. Soedin., 363-366 Search more
BioactivitiesSLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 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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