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ECDYSONE 22-PALMITATE

Year of first isolation: 1986
Formula:C43H74O7
Molecular weight:702
Occurence in plants:
 
Occurence in animals:
Boophilus microplus [Ixodidae] » Images of Boophilus microplus Wikipedia: Boophilus microplus [Ixodidae]
Heliothis virescens [Lepidoptera] » Images of Heliothis virescens Wikipedia: Heliothis virescens [Lepidoptera]
ECDYSONE 22-PALMITATE

STRUCTURE DESCRIPTORS

Canonical SMILESCCCCCCCCCCCCCCCC(=O)OC(CCC(C)(C)O)C(C)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)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@H](C)[C@@H](CCC(C)(C)O)OC(=O)CCCCCCCCCCCCCCC)O)C)C » JSMol: View in 3D
IUPAC Name[(2S)-6-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17R)-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] hexadecanoate
CAS-RN 
PubChem CID54300844
InChiKey
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SEAXTSQHMHXGKM-JMSLTBKCSA-N
InChIInChI=1S/C43H74O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-39(47)50-38(23-24-40(3,4)48)30(2)31-22-26-43(49)33-27-35(44)34-28-36(45)37(46)29-41(34,5)32(33)21-25-42(31,43)6/h27,30-32,34,36-38,45-46,48-49H,7-26,28-29H2,1-6H3/t30-,31+,32-,34-,36+,37-,38?,41+,42+,43+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z720 (M+H+NH3)+, 703, 685, 667, 447, 429, 413, 411.
EI-MS m/z (relative intensity %) 
FAB-MS (matrix tetraethyleneglycol TEG) m/z (relative intensity %)703 (M+H)+ (6), 685 (56), 667 (3), 447 (8), 429 (100), 411 (68), 393 (8).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.7
0268.2
0368.1
0432.5
0551.4
06203.4
07121.7
08165.3
0935.0
1038.0
1121.2
1231.5
1347.6
1483.9
1531.9
1626.4
1748.3
1815.8
1924.5
2039.9
2114.0
2277.7
2325.7
2441.6
2569.3
2630.0
2730.3
CH223.0, 29.5, 29.7, 29.8, 29.9,
CH2-29.95, 30.0, 32.2, 34.6
COOR173.6
Me14.3
CDCl3
01-Ha 
01-He 
02-Ha3.92 (m, w1/2=22)
03-He4.06 (m, w1/2=9)
04-Ha 
04-He 
05-H 
07-H5.855 (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-Me0.677 (s )
19-Me0.993 (s )
21-Me0.950 (d, 7)
22-H4.89 (m, w1/2=17)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.232 (s )
27-Me1.232 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLCRf 0.60 (silica gel Merck Si60, CHCl3-MeOH 4:1); Rf 0.14 (silica gel, CHCl3-MeOH 9:1); Rf 0.31 (C8 bonded silica gel, MeOH-H2O 19:1), other solvent systems also described for C18, C2 and CN bonded silica gel.
GLC(of fatty acid methyl ester)
HPLC1- Retention time 24.5 min [Partisil 5 (Whatman), 250 mm x 4.6 mm i.d., solvent dichloroethane-iPrOH-H2O 125:24:1 v/v/v, flow-rate 1 ml.min-1]. 2-Retention time 21.5 min [ Ultrasphere-ODS (Beckman) 250 mm x 4.6 mm i.d., solvent linear gradient (30 min) of MeOH in H2O from 9:1 to 1:0 v/v, flow-rate 1 ml.min-1]

BIOLOGICAL ACTIVITIES

 

REFERENCES

GeneralWIGGLESWORTH, K.P. et al. (1985) Arch. Insect Biochem. Physiol. 2, 39-54 Search more
GeneralHOFFMANN, K.H. et al. (1985) Life Sci. 37, 185-192 Search more
First isolationCROSBY, T. et al. (1986) Biochem. J. 240, 131-138 Search more
GeneralROBINSON, P.D. et al. (1987) Physiol. Entomol. 12, 321-330 Search more
GeneralDINAN, L. et al. (1987) J. Chromatogr. 411, 379-392 Search more
GeneralDINAN, L. et al. (1988) J. Steroid Biochem. 31, 237-245 Search more
GeneralDINAN, L. et al. (1988) J. Chromatogr. 436, 279-288 Search more

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