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POLYPODINE B 20,22-ACETONIDE

Year of first isolation: 1994
Formula:C30H48O8
Molecular weight:536
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
POLYPODINE B 20,22-ACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)CCC(C)(C)O)C
Isomeric SMILES
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C1[C@]2([C@@](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@@H](CCC(C)(C)O)OC(O1)(C)C)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID70689030
InChiKey
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HZCBCWUIZCCMEB-HUSZLGJPSA-N
InChIInChI=1S/C30H48O8/c1-24(2,34)11-10-23-28(7,38-25(3,4)37-23)21-9-13-29(35)18-14-22(33)30(36)16-20(32)19(31)15-27(30,6)17(18)8-12-26(21,29)5/h14,17,19-21,23,31-32,34-36H,8-13,15-16H2,1-7H3/t17-,19-,20+,21-,23+,26+,27+,28+,29+,30+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)503 (1), 485 (1), 443 (2), 425 (2), 379 (20), 361 (2)
FAB-MS m/z559 (M+Na)+ (40), 537 (M+H)+ (60), 520 (10), 479 (5), 461 (7), 443 (2), 425 (8)
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0136.18
0270.22
0368.41
0434.19
0580.28
06202.35
07120.57
08167.16
0939.02
1045.37
1122.50
1232.40
1348.45
1485.10
1531.67
1622.38
1750.40
1817.68
1916.98
2085.83
2122.58
2283.31
2324.70
2442.21
2571.11
2629.50
2729.34
iPr-(20,22)108.02, 28.96, 27.18
Me2CO-d6
01-Ha 
01-Hb 
02-Ha3.82 (m )
03-He3.82 (m )
04-Ha 
04-He 
07-H5.87 (d, 2.5)
09-Ha3.24 (ddd, 12.0, 7.0, 2.5)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.37 (dd, 9.0, 8.5)
18-Me0.840 (s )
19-Me0.871 (s )
21-Me1.179 (s )
22-H3.68 (dd, 7.0, 5.5)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.179 (s )
27-Me1.168 (s )
iPr-20,221.362 (s ), 1.297 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3599, 3439 (OH), 1673 (enone), 1171, 1061 (dioxolane ring)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCNormal-phase (Separon SGX silica 7 ?m) (CH2Cl2-MeOH-H2O 88:11:1)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationPIS, J. et al. (1994) Phytochemistry 37, 707-711 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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