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ECDYSONOIC ACID

Year of first isolation: 1983
Formula:C27H42O8
Molecular weight:494
Occurence in plants:
 
Occurence in animals:
Schistocerca gregaria [Orthoptera] » Images of Schistocerca gregaria Wikipedia: Schistocerca gregaria [Orthoptera]
Spodoptera littoralis [Lepidoptera] » Images of Spodoptera littoralis Wikipedia: Spodoptera littoralis [Lepidoptera]
Pieris brassicae [Lepidoptera] » Images of Pieris brassicae Wikipedia: Pieris brassicae [Lepidoptera]
ECDYSONOIC ACID

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C(=O)O)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@H](C)[C@@H](CCC(C(=O)[O-])(C)O)O)O)C)C  » JSMol: View in 3D
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(=O)[O-])(C)O)O)O)C)C  » JSMol: View in 3D
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(=O)[O-])(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(5R,6S)-2,5-dihydroxy-2-methyl-6-[(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]heptanoic acid
CAS-RN86583-57-5
PubChem CID101600149
InChiKey
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SIDKGOYPRPHZJH-YAVKZWDVSA-N
InChIInChI=1S/C27H42O8/c1-14(19(28)7-9-26(4,34)23(32)33)15-6-10-27(35)17-11-20(29)18-12-21(30)22(31)13-24(18,2)16(17)5-8-25(15,27)3/h11,14-16,18-19,21-22,28,30-31,34-35H,5-10,12-13H2,1-4H3,(H,32,33)/t14-,15+,16-,18-,19+,21+,22-,24+,25+,26?,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z(of methyl ester)
EI-MS m/z (relative intensity %) 
FAB-MS m/z493 (M-H)-
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 
CD3OD
01-Ha 
01-He 
02-Ha3.85 (m, w1/2=22)
03-He3.95 (m, w1/2=9)
04-Ha 
04-He 
05-H 
07-H5.80
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.71 (s )
19-Me0.96 (s )
21-Me0.91 (d, 10)
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.33 (s )
27-Me--

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC (ion-suppression mode) : Retention volume 12 ml [Waters Resolve column 150 mm x 4.6 mm i.d., solvent MeOH-20 mM Na citrate, pH 6.5, 30:70, flow-rate 1 ml.min-1]

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationISAAC, R.E. et al. (1983) Biochem. J. 213, 261-265 Search more
GeneralLAFONT, R. et al. (1983) Arch. Insect Biochem. Physiol. 1, 41-58 Search more
GeneralISAAC, R.E. et al. (1984) Biochem. J. 221, 459-464 Search more
GeneralDIEHL, P.A. et al. (1985) Methods Enzymol. 111, 377-410 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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