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20-HYDROXYECDYSONE 22-STEARATE

Year of first isolation: 1985
Formula:C45H78O8
Molecular weight:746
Occurence in plants:
 
Occurence in animals:
Ornithodoros moubata [Argasidae] » Images of Ornithodoros moubata Wikipedia: Ornithodoros moubata [Argasidae]
Heliothis virescens [Lepidoptera] » Images of Heliothis virescens Wikipedia: Heliothis virescens [Lepidoptera]
20-HYDROXYECDYSONE 22-STEARATE

STRUCTURE DESCRIPTORS

Canonical SMILESCCCCCCCCCCCCCCCCCC(=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)CCCCCCCCCCCCCCCCC)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,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] octadecanoate
CAS-RN 
PubChem CID11973422
InChiKey
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UVOWKMPZDFLQSZ-KMVKICEVSA-N
InChIInChI=1S/C45H78O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-40(49)53-39(25-26-41(2,3)50)44(6,51)38-24-28-45(52)33-29-35(46)34-30-36(47)37(48)31-42(34,4)32(33)23-27-43(38,45)5/h29,32,34,36-39,47-48,50-52H,7-28,30-31H2,1-6H3/t32?,34?,36-,37+,38+,39?,42-,43-,44-,45-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z764 (M+H+NH3)+, 747 (M+H)+, 729, 711, 693, 463 (M-fatty acid)+, 445, 427, 409, 363, 345
EI-MS m/z (relative intensity %) 
SI-MS m/z747 (M+H)+, 729, 711, 693, 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-He3.89 (m )
03-He4.05 (m )
04-Ha 
04-He 
05-H2.44 (m )
07-H5.85 (d, 1.6)
09-Ha3.00 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.86 (s )
19-Me0.99 (s )
21-Me1.21 (s )
22-H4.88 (d, 9.4)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.23 (s )
27-Me1.23 (s )
O-CO-CH22.37 (t, 7.2)
termin CH3 0.88 (t, 6.7)

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 48.5 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]

BIOLOGICAL ACTIVITIES

 

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

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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