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(5α)-20-HYDROXYECDYSONE 22-BENZOATE

Year of first isolation: 1987
Formula:C34H48O8
Molecular weight:584
Occurence in plants:
Silene scabrifolia [Caryophyllaceae] » Images of Silene scabrifolia Wikipedia: Silene scabrifolia [Caryophyllaceae]
Occurence in animals:
 
(5α)-20-HYDROXYECDYSONE 22-BENZOATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)OC(=O)C5=CC=CC=C5)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)OC(=O)c1ccccc1)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R,3R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,5S,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 CID13889282
InChiKey
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GHZYCHXISZLQFT-PJTODFGVSA-N
InChIInChI=1S/C34H48O8/c1-30(2,39)14-13-28(42-29(38)20-9-7-6-8-10-20)33(5,40)27-12-16-34(41)22-17-24(35)23-18-25(36)26(37)19-31(23,3)21(22)11-15-32(27,34)4/h6-10,17,21,23,25-28,36-37,39-41H,11-16,18-19H2,1-5H3/t21-,23+,25+,26-,27-,28+,31+,32+,33+,34+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)566 (M-18)+(0.1), 548 (0.2), 530 (0.3), 515 (0.2), 462 (0.7), 444 (1), 426 (6), 411 (2), 408 (6), 393 (2), 363 (2), 345 (6), 329 (2), 301 (8), 300 (9), 250 (7), 122 (benzoic acid) (44), 105 (100), 99 (22), 81 (23), 77 (50), 69 (24), 55 (24),

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 
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-Ha3.60
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.21 (s )
19-Me1.10 (s )
21-Me1.78 (s )
22-H5.76
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.32 (s )
27-Me1.32 (s )

PHYSICAL PROPERTIES

M.P.262-264 °C
[α]D2045.8 ? 2 ° (c ; MeOH)
IR (KBr) ν max (cm-1)3420-3470 (OH), 1660 (cyclohexenone), 1720, 1710, 1200 (benz
UV (EtOH) λ max (log ε)234 (4.09)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSAATOV, Z. et al. (1987) Khim. Prir. Soedin., 678-681 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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