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PTEROSTERONE 24-O-β-D-GLUCOSIDE

Year of first isolation: 1988
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Pfaffia iresinoides [Amaranthaceae] » Images of Pfaffia iresinoides Wikipedia: <br />
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Occurence in animals:
 
PTEROSTERONE 24-O-β-D-GLUCOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILES 
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](O)C[C@@H](C(C)C)O[C@@H]1OC([C@H](C(C1O)O)O)CO)O)O)C)C » JSMol: View in 3D
IUPAC Name 
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
WVEMRTZARQEUPR-WHEWAJECSA-N
InChIInChI=1S/C33H54O12/c1-15(2)22(44-29-28(41)27(40)26(39)23(14-34)45-29)12-25(38)32(5,42)24-7-9-33(43)17-10-19(35)18-11-20(36)21(37)13-30(18,3)16(17)6-8-31(24,33)4/h10,15-16,18,20-29,34,36-43H,6-9,11-14H2,1-5H3/t16-,18-,20+,21-,22-,23?,24-,25+,26+,27?,28?,29+,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.0
0268.3
0368.2
0432.6
0551.5
06203.6
07121.7
08166.3
0934.5
1038.8
1121.2
1232.1
1348.1
1484.2
1531.8
1621.6
1749.9
1818.0
1924.6
2076.8
2121.6
2275.4
2336.1
2484.7
2532.1
2617.3
2719.5
glu-1'105.9
glu-2'75.5
glu-3'78.7 *
glu-4'72.1
glu-5'78.2 *
glu-6'63.3
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H2.98 (dd, 13.4, 4.0)
07-H6.22 (d, 2.2)
09-Ha3.55 (br t, 9.0)
11-Ha 
11-He 
12-Ha2.51 (dt, 13.2, 5.0)
12-He 
15-Ha 
15-Hb 
16-Ha2.42 (q, 10.2)
16-Hb 
17-H2.89 (t, 9.0)
18-Me1.17 (s )
19-Me1.04 (s )
21-Me1.56 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.05 (s )
27-Me1.14 (s )
H-1'4.96 (d, 7.6)

PHYSICAL PROPERTIES

M.P.276-277 °C
[α]D15+ 40.9 ° (c 1.5; MeOH)
IR (KBr) ν max (cm-1)3450 (OH), 1650
UV (EtOH) λ max (log ε)243 (4.04)

CHROMATOGRAPHY

HPTLC 
TLCon silica gel, Rf 0.24 (CHCl3-MeOH-H2O 13:7:2)
GLC 
HPLC 
LCsilica gel, solvent CHCl3-MeOH-EtOAc-H2O (2:2:4:1), lower phase

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationNISHIMOTO, N. et al. (1988) Phytochemistry 27, 1665-1668 Search more

see Important notice
© 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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