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20-HYDROXYECDYSONE 22-GLYCOLATE

Year of first isolation: 1986
Formula:C29H46O9
Molecular weight:538
Occurence in plants:
 
Occurence in animals:
Pycnogonum litorale [pantopod] » Images of Pycnogonum litorale Wikipedia: Pycnogonum litorale [pantopod]
20-HYDROXYECDYSONE 22-GLYCOLATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)OC(=O)CO)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)CO)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2R,3R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,5R,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] 2-hydroxyacetate
CAS-RN 
PubChem CID21775774
InChiKey
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DWTMLGDZGORWQW-NVKGGLFYSA-N
InChIInChI=1S/C29H46O9/c1-25(2,35)9-8-23(38-24(34)15-30)28(5,36)22-7-11-29(37)17-12-19(31)18-13-20(32)21(33)14-26(18,3)16(17)6-10-27(22,29)4/h12,16,18,20-23,30,32-33,35-37H,6-11,13-15H2,1-5H3/t16?,18-,20+,21-,22-,23+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z556 (MH + NH3)+, 539 (MH)+, 521, 503, 480, 463 (MH-glycolic acid)+, 445, 427, 409, 363 (M- side-chain), 345.
EI-MS m/z (relative intensity %) 
HR-MS 

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 
D2O
01-Ha 
01-Hb 
02-Ha3.99 (m, w1/2=21)
03-He4.07 (m, w1/2=8)
04-Ha 
04-He 
05-H 
07-H5.98 (d, 2.5)
09-Ha3.11 (m, w1/2=22)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.86 (s )
19-Me1.00 (s )
21-Me1.33 (s )
22-H4.93 (d, w1/2=14)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.21 (s )
27-Me1.21 (s )
OCOCH2O4.31 (s, 2H)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCNP-HPLC (Merck Lichrosorb Si 60) solvent CH2Cl2-iPrOH-H2O (125:30:2) Ret. 28.2 ml (20E = 27.6 ml).RP-HPLC (Merck Supersphere RP18, 15 cm long, 4 mmcratic for 10 min, then linear gradient 16:84 to 40:60 in 25 min) Ret 7.7 min (20E 7.3 min).

BIOLOGICAL ACTIVITIES

Musca assay: 516% (20-hydroxyecdysone = 100%)

REFERENCES

BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
First isolationBÜCKMANN, D. et al. (1986) J. Comp. Physiol., B 156, 759-765 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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