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20-HYDROXYECDYSONE 22-PALMITATE

Year of first isolation: 1985
Formula:C43H74O8
Molecular weight:718
Occurence in plants:
 
Occurence in animals:
Ornithodoros moubata [Argasidae] » Images of Ornithodoros moubata Wikipedia: Ornithodoros moubata [Argasidae]
20-HYDROXYECDYSONE 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)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)CCCCCCCCCCCCCCC)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R)-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] hexadecanoate
CAS-RN 
PubChem CID66868929
InChiKey
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OZOKSHXSPFULSG-SKLMLGQNSA-N
InChIInChI=1S/C43H74O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(47)51-37(23-24-39(2,3)48)42(6,49)36-22-26-43(50)31-27-33(44)32-28-34(45)35(46)29-40(32,4)30(31)21-25-41(36,43)5/h27,30,32,34-37,45-46,48-50H,7-26,28-29H2,1-6H3/t30-,32-,34+,35-,36-,37?,40+,41+,42+,43+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z719 (M+H)+, 701, 683, 665, 463 (M-fatty acid)+, 445, 427, 411, 409, 363, 345
EI-MS m/z (relative intensity %) 
SI-MS m/z719 (M+H)+, 701, 683, 665, 463 (M-fatty acid)+, 445, 427, 353, 301

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 
CDCl3
01-Ha 
01-He 
02-Ha3.89 (m, w1/2=22) 3.88 (m )
03-He4.04 (m, w1/2=8) 4.04 (m )
04-Ha 
04-He 
05-H2.42 (q, 13.5, 4.5) 2.43 (m )
07-H5.83 (d, 2.6) 5.85 (d, 1.7)
09-Ha2.99 (m, w1/2=21) 3.00 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.84 0.86 (s )
19-Me0.97 0.98 (s )
21-Me1.19-1.23 1.21 (s )
22-H4.85 (d ) 4.89 (d, 9.4)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.19-1.23 1.24 (s )
27-Me1.19-1.23 1.25 (s )
O-CO-CH22.36 (t, 7) 2.37 (t, 7.1)
termin CH3 0.88 (t, 7)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 1715 (CO), 1654 (cyclohexenone)
UV (EtOH) λ max (log ε)242 (?) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC(of fatty acid methyl esters)
HPLCRP-HPLC, Retention time 27 min [YMC pack ODS column, 15 cm long, 6 mm i.d., eluted with MeOH-H2O 9:1 v/v at 1.25 ml.min-1]; Retention volume 28.8 ml [Lichrospher-Si 25 cm long, 4 mm i.d., eluted with CH2Cl2-iPrOH-H2O 125:20.5:1 v/v/v ; flow-rate 1.2 ml.min-1] (2dE : 15.6 ml)

BIOLOGICAL ACTIVITIES

Musca assay: 52% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationDIEHL, P.A. et al. (1985) Int. J. Invertebr. Reprod. Develop. 8, 1-13 Search more
GeneralKUBO, I. et al. (1987) J. Chem. Ecol. 13, 785-794 Search more
BioactivitiesSUKSAMRARN, A. et al. (2002) Insect Biochem. Molec. Biol. 32, 193-197 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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