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INOKOSTERONE 26-ACETATE

Year of first isolation: 2005
Formula:C29H46O8
Molecular weight:522
Occurence in plants:
Serratula coronata [Asteraceae] » Images of Serratula coronata Wikipedia: Serratula coronata [Asteraceae]
Occurence in animals:
 
INOKOSTERONE 26-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)COC(=O)C
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)COC(=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@](C)([C@@H](CCC(C)COC(=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@](C)([C@@H](CCC(C)COC(=O)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,5R,6R)-5,6-dihydroxy-2-methyl-6-[(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]heptyl] acetate
CAS-RN 
PubChem CID11591734
InChiKey
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FARFYWFUAMLBAX-CZDBYVCJSA-N
InChIInChI=1S/C29H46O8/c1-16(15-37-17(2)30)6-7-25(34)28(5,35)24-9-11-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,3)18(19)8-10-27(24,29)4/h12,16,18,20,22-25,32-36H,6-11,13-15H2,1-5H3/t16-,18-,20-,22+,23-,24-,25+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z540 [M + H + NH3]+, 522 [M]+, 505, 498, 480, 464, 434, 416, 352, 308, 291, 220, 176, 153, 116.

CARBON NMR

PROTON NMR

D2O
0136.6 (t)
0268.5 (d)
0368.2 (d)
0432.4 (t)
0551.7 (d)
06209.8 (s)
07122.1 (d)
08?
0934.9 (d)
1039.3 (s)
1121.3 (t)
1232.0 (t)
1348.3 (s)
1486.1 (s)
1531.5 (t)
1621.3 (t)
1750.3 (d)
1818.0 (q)
1924.2 (q)
2079.3 (s)
2120.7 (q)
2278.2 (d)
2329.1 (t)
2431.5 (t)
2533.2 (d)
2671.2 (t)
2717.3 (q)
CH321.7 (q)
CO?
D2O
01-Ha1.38 (t, 13.4)
01-He1.88 (m)
02-Ha3.99 (m, w1/2 = 22)
03-He4.07 (m, w1/2 = 8)
04-Ha1.75 (t)
04-He1.75 (t)
05-H2.34 (t)
07-H5.97 (d, 2.0)
09-H3.11 (m, w1/2 = 22)
11-Ha1.73 (m)
11-He1.86 (m)
12-Ha1.95 (m)
12-He1.75 (m)
15-Ha1.65 (m)
15-Hb2.05 (m)
16-Ha1.75* (m)
16-Hb1.86* (m)
17-H2.31 (t, 9.0)
18-Me0.86 (s)
19-Me1.00 (s)
21-Me1.22 (s)
22-H3.43 (dd, 10.0, 1.0)
23-Ha1.24 (m)
23-Hb1.65 (m)
24-Ha1.27 (m)
24-Hb1.65 (m)
25-H1.87 (m)
26-Ha4.05 (dd, 11.0, 6.0)
26-Hb3.95 (dd, 11.0, 6.5)
27-Me0.96 (d, 6.9)

PHYSICAL PROPERTIES

M.P.? °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)242 nm (?) ;

CHROMATOGRAPHY

HPLCNP-HPLC Zorbax-SIL (250 x 9.4 mm) solvent dichloromethane-isopropanol-water (125:15:1), flow-rate 4 ml/min (Ret 19.0 min); Kromasil (250x 4.6 mm), solvent cyclohexane-isopropanol-water (100:30:2), flow-rate 1 ml/min (Ret 4.5 min). RP-HPLC Spherisorb 5ODS2, solvent methanol-water (60:40), flow-rate 1 ml/min (Ret 10.8 min).
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationODINOKOV, V.N. et al. (2005) Collect. Czech. Chem. Commun. 70, 2038-2052 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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