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20-HYDROXYECDYSONE 22-PHOSPHATE

Year of first isolation: 1982
Formula:C27H45O10P
Molecular weight:560
Occurence in plants:
 
Occurence in animals:
Schistocerca gregaria [Orthoptera] » Images of Schistocerca gregaria Wikipedia: Schistocerca gregaria [Orthoptera]
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: Locusta migratoria [Orthoptera]
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
20-HYDROXYECDYSONE 22-PHOSPHATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)OP(=O)(O)O)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)OP(=O)([O-])[O-])O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R,3R)-2,6-dihydroxy-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] dihydrogen phosphate
CAS-RN86577-97-1
PubChem CID21122089
InChiKey
[ ChemIDPlus: search ]
VQMWDPXOYFYYKP-YPVLXUMRSA-N
InChIInChI=1S/C27H45O10P/c1-23(2,31)9-8-22(37-38(34,35)36)26(5,32)21-7-11-27(33)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-33H,6-11,13-14H2,1-5H3,(H2,34,35,36)/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

FAB-MS m/z581 (M-H+Na)-, 559 (M-H)-, 541 (M-H-18)-, 97, 79 EI m/z (direct introduction on gold support): 524 (M-2x18)+, (480), (462), 444, 416, 408
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
01 
0268.7 (d )
0368.6 (d )
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
1485.3 (s )
15 
16 
17 
18 
19 
2078.5 (s )
21 
2282.9 (d )
23 
24 
2571.4 (s )
26 
27 
CD3OD
01-Ha 
01-He 
02-Ha3.84 (m, w1/2=22)
03-He3.95 (m, w1/2=8)
04-Ha 
04-He 
05-H 
07-H5.80 (d, 2)
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.89 (s )
19-Me0.96 (s )
21-Me1.26 (s )
22-H4.07 (m, w1/2=22)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.18 (s )
D2O
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.92
19-Me0.98
21-Me1.32
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.21

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCIon-exchange HPLC : Retention volume 32 ml [column Whatman Partisil-SAX 25 cm long, 4.6 mm i.d., eluted with 0.1 M ammonium acetate, flow-rate 2 ml.min-1].Ion-suppression RP-HPLC, Retention volume 31 ml [column Whatman Partisil-ODS3 25 cm long, 4.6 mm i.d., eluted with MeOH in 20mM sodium citrate, pH 6.5, gradient 1:9 v/v to 7:3 v/v over 30 min, flow-rate 2 ml.min-1].

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTSOUPRAS, G. et al. (1982) Steroids 40, 551-560 Search more
GeneralISAAC, R.E. et al. (1983) Biochem. J. 213, 533-541 Search more
GeneralHETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 Search more
GeneralDIEHL, P.A. et al. (1985) Methods Enzymol. 111, 377-410 Search more
GeneralOHNISHI, E. et al. (1989) Insect Biochem. 19, 95-101 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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