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20-HYDROXYECDYSONE 3-ACETATE

Year of first isolation: 1984
Formula:C29H46O8
Molecular weight:522
Occurence in plants:
Lychnis flos-culculi [Caryophyllaceae] » Images of Lychnis flos-culculi Wikipedia: Lychnis flos-culculi [Caryophyllaceae]
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans var. atropurpurea Wikipedia: Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)]
Occurence in animals:
Locusta migratoria [Orthoptera] » Images of Locusta migratoria Wikipedia: Locusta migratoria [Orthoptera]
20-HYDROXYECDYSONE 3-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC1CC2C(=O)C=C3C(C2(CC1O)C)CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)O)O)O)C
Isomeric SMILES
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[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
CAS-RN 
PubChem CID10951463
InChiKey
[ ChemIDPlus: search ]
UWFCFVQTAHITKV-OQQOFWQASA-N
InChIInChI=1S/C29H46O8/c1-16(30)37-22-14-19-20(31)13-18-17(26(19,4)15-21(22)32)7-11-27(5)23(8-12-29(18,27)36)28(6,35)24(33)9-10-25(2,3)34/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21-,22+,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z540, 523 (MH)+, 505, 487, 469, 405 (MH - C22 -C27)+, 387, 345, 329
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.64
0266.06
0371.20
0429.62
0551.88
06202.24
07121.55
08166.48
0934.25
1038.48
1121.05
1231.85
1347.99
1484.06
1531.65
1621.38
1750.00
1817.81
1924.21
2076.77
2121.63
2277.48
2327.39
2442.56
2569.49
2629.88
2730.06
CDCl3
01-Ha1.3
01-He1.9
02-Ha4.02 (m, w1/2=22)
03-He5.21 (m, w1/2=8)
04-Ha1.6
04-He1.85
05-H2.3
07-H5.85 (d, 2.5)
09-Ha3.01 (m, w1/2=22)
11-Ha1.70
11-He1.80
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha2.0
16-Hb1.75
17-H2.33 (m )
18-Me0.87 (s )
19-Me1.01 (s )
21-Me1.21 (s )
22-H3.44 (d, 10)
23-Ha1.35
23-Hb1.65
24-Ha 
24-Hb 
26-Me1.24 (s )
27-Me1.25 (s )
O-Ac2.12 (s)
C5D5N
01-Ha1.81*
01-He2.25*
02-Ha4.30 (w1/2=22)
03-He5.51 (w1/2=8)
04-Ha1.80$
04-He1.97$
05-H2.67
07-H6.24
09-Ha3.57
11-Ha 
11-He 
12-Ha2.57
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.00 ( t, w1/2=23)
18-Me1.23
19-Me1.08
21-Me1.60
22-H3.88 (w1/2=14.7)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.37
27-Me1.37
O-Ac1.98

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel, Rf 0.35 (CHCl3-EtOH 4:1).
GLC 
HPLC1- Retention time 8.7 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min)2-Retention time 13.8 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min)3-Retention time 10.8 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 4.7 x 10-7M

REFERENCES

GeneralGALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1045-1046 Search more
First isolationMODDE, J.-F. et al. (1984) Int. J. Invertebr. Reprod. Develop. 7, 161-183 Search more
GeneralGIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 Search more
GeneralCALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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