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PONASTERONE A 20,22-ACETONIDE

Year of first isolation: 2010
Formula:C30H48O6
Molecular weight:504
Occurence in plants:
Taxus canadensis [Taxaceae] » Images of Taxus canadensis Wikipedia: Taxus canadensis [Taxaceae]
Occurence in animals:
 
PONASTERONE A 20,22-ACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC1C(OC(O1)(C)C)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)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@]1(C)[C@@H](CCC(C)C)OC(O1)(C)C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(4R,5R)-2,2,4-trimethyl-5-(3-methylbutyl)-1,3-dioxolan-4-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID11466242
InChiKey
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GZBAPTXUYWCGFX-WNKNHJGZSA-N
InChIInChI=1S/C30H48O6/c1-17(2)8-9-25-29(7,36-26(3,4)35-25)24-11-13-30(34)19-14-21(31)20-15-22(32)23(33)16-27(20,5)18(19)10-12-28(24,30)6/h14,17-18,20,22-25,32-34H,8-13,15-16H2,1-7H3/t18-,20-,22+,23-,24-,25+,27+,28+,29+,30+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HR-MS ((+)-FAB) m/z 505.3528 (calculated 505.3529 for C30H49O6, [M+H] +)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CDCl3
0136.8
0267.6
0367.3
0431.3
0549.8
06206.4
07121.6
08167.9
0933.6
1038.2
1120.2
1230.8
1348.2
1485.5
1531.4
1620.9
1748.7
1817.0
1923.8
2084.5
2121.8
2278.8
2333.2
2435.2
2532.8
2617.7
2720.3
iPr106.5, 28.9, 26.7
CDCl3
01-Ha1.41 (m)
01-He1.85 (m)
02-Ha3.90 (~dt)
03-He4.06 (br, s)
04-Ha1.88(m)
04-He1.65 (m)
05-H2.44 (dd)
07-H5.86 (d)
09-H2.99 (t)
11-Ha1.66 (m)
11-He1.78 (m)
12-Ha2.02 (m)
12-He1.84 (m)
15-Ha1.56 (m)
15-Hb2.05 (m)
16-Ha2.04 (m)
16-Hb1.80 (m)
17-H2.16 (m)
18-Me0.80 (s)
19-Me0.99 (s)
21-Me1.12 (s)
22-H3.73 (d)
23-Ha1.49 (m)
23-Hb1.04 (m)
24-Ha1.58 (m)
24-Hb1.58 (m)
25-H1.60 (m)
26-Me0.83 (d)
27-Me0.89 (d)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D22+ 67 ° (c = 0.10, MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLCWhatman Partisil 10 ODS-2Mag-20 preparative column (500 mm long, 22 mm i.d.) eluted with a linear gradient of acetonitrile in water, 25% to 100% in 50 min, flow-rate 18 mL/min.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationFANG, Yu. et al. (2010) Z. Naturforsch. 65b, 1401-1405 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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