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POSTSTERONE 2-ACETATE

Year of first isolation: 2009
Formula:C23H32O6
Molecular weight:404
Occurence in plants:
Cyanotis longifolia [Commelinaceae] » Images of Cyanotis longifolia Wikipedia: Cyanotis longifolia [Commelinaceae]
Occurence in animals:
 
POSTSTERONE 2-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)OC(=O)C)C)C)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2C(=O)C)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17S)-17-acetyl-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] acetate
CAS-RN 
PubChem CID15168048
InChiKey
[ ChemIDPlus: search ]
GHVFPBQIXUAGPE-JKCRNPTCSA-N
InChIInChI=1S/C23H32O6/c1-12(24)14-6-8-23(28)16-9-18(26)17-10-19(27)20(29-13(2)25)11-21(17,3)15(16)5-7-22(14,23)4/h9,14-15,17,19-20,27-28H,5-8,10-11H2,1-4H3/t14-,15+,17+,19-,20+,21-,22-,23-/m1/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z 422 [M+NH4]+, 405 [MH]+, 344 [M-CH3COOH]+

CARBON NMR

PROTON NMR

D2O
0135.1
0274.1
0367.6
0433.6
0552.8
06n.d.
07123.9
08n.d.
0936.1
1040.0
1122.6
1231.9
1350.2
1486.9
1533.2
1623.2
1761.7
1819.0
1925.4
20221.4
2133.7
Ac [CH3]23.2
Ac [CO]175.7
D2O
01-Ha1.56 (t, 13.1)
01-He1.99
02-Ha5.10 (m, w1/2 = 22)
03-He4.24 (m, w1/2 = 8)
04-Ha1.80
04-He1.84
05-H2.44 (dd, 13.8, 4.4)
07-H6.02 (d, 2.2)
09-H3.22 (m, w1/2 = 22)
11-Ha1.73*
11-He1.96*
12-Ha1.92*
12-He2.20*
15-Ha2.12*
15-Hb1.76*
16-Ha1.91*
16-Hb2.22*
17-H3.34 (t, 8.5)
18-Me0.64 (s)
19-Me1.03 (s)
21-Me2.26 (s)
CH3CO2.13 (s)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

RP-HPLCcolumn YMC C18, 250 mm x 20.2 mm i.d, solvent MeOH/H2O 1:1, flow-rate 10 ml/min, Ret 30.6 min (20E : 12.4 min)
HPLC
NP-HPLCcolumn Zorbax-SIL 250 mm x 4.6 mm i.d., solvent cyclohexane-isopropanol-water, flow-rate 1 mL/min, Ret 7.1 min (20E : 15.8 min)
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCROUZET, S. et al. (2009) Arch. Insect Biochem. Physiol. 72, 194-209 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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