Welcome to online ecdysteroids database ! . .
Access data · History · Contact

25-HYDROXYPANUOSTERONE

Year of first isolation: 1995
Formula:C28H46O8
Molecular weight:510
Occurence in plants:
Tapinella panuoides [Fungi] » Images of Tapinella panuoides Wikipedia: Tapinella panuoides [Fungi]
Occurence in animals:
 
25-HYDROXYPANUOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(C)(C(C)(C)O)O)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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](CC(C(C)(C)O)(C)O)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](C[C@@](C(C)(C)O)(C)O)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](C[C@](C(C)(C)O)(C)O)O)O)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-[(2R,3R)-2,3,5,6-tetrahydroxy-5,6-dimethylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID100953176
InChiKey
[ ChemIDPlus: search ]
SJBJYCZFHXEDBY-DSDITLTGSA-N
InChIInChI=1S/C28H46O8/c1-23(2,33)26(5,34)14-22(32)27(6,35)21-8-10-28(36)16-11-18(29)17-12-19(30)20(31)13-24(17,3)15(16)7-9-25(21,28)4/h11,15,17,19-22,30-36H,7-10,12-14H2,1-6H3/t15-,17-,19+,20-,21-,22+,24+,25+,26?,27+,28+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %) 
FAB-MS m/z533 (M+Na)+ (3), 511 (M+H)+ (1), 494 (1), 493 (1), 457 (2), 413 (2), 385 (2), 383 (2), 331 (2), 311 (5), 283 (5), 173 (6), 149 (12), 115 (17), 109 (23), 95 (41), 81 (53), 69 (79), 55 (100)
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0137.37
0268.72
0368.53
0432.64
0551.80
06204.46
07122.29
08167.84
0935.13
1039.30
1121.51
1232.41
13a
1485.48
1531.79
1621/32
1750.02
1817.96
1924.39
2077.91
2120.69
2274.02
2339.96
2476.27
2577.51
2625.25
2725.25
2822.41
CD3OD
01-Ha1.43 (dd, 13.0, 12.0)
01-He1.72
02-Ha3.84 (ddd, 12.0, 4.5, 3.0)
03-He3.95 (q )
04-Ha1.76
04-He1.69
05-H2.38 (dd, 13.0, 4.4)
07-H5.82 (d, 2.5)
09-H3.15 (ddd, 10.0, 7.0, 2.5)
11-Ha1.79
11-He1.70
12-Ha2.13 (dt, 13.0, 13.0, 4.5)
12-He1.87
15-Ha1.95
15-Hb1.59
16-Ha2.02
16-Hb1.88
17-H2.34 (t, 9.0, 9.0)
18-Me0.899 (s )
19-Me0.969 (s )
21-Me1.207 (s )
22-H3.73 (d, 9.2)
23-Ha1.83 (d, 14.6)
23-Hb1.53 (dd, 14.6, 9.2)
26-Me1.257 (s )
27-Me1.242 (s )
28-Me1.199 (s )

PHYSICAL PROPERTIES

M.P.248-256 °C
[α]D20 
IR (KBr) ν max (cm-1)3406 (OH), 1653 (cyclohexenone)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

NP-HPLCcolumn Silasorb 600 (4 x 250 mm), flow-rate 0.8 ml.min-1, solvent Et2O-hexane-MeOH-H2O (440:430:120:10), Ret 57.6 min (20E 47.5 min); solvent Et2O-CH3CN-H2O (780:190: 30), Ret 40.5 min (20E 31.7 min)
RP-HPLCcolumn Separon SIX C18 (4 x 250 mm), solvent MeOH-H2O, linear gradient 10 to 70 % MeOH in 50 min, flow-rate 0.6 ml.min-1, Ret 40.6 min (20E 42.7 min).
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationVOKÁČ, K. et al. (1995) 16th Conference on Isoprenoids, Prague, Abstracts, pp. 77-78 Search more
First isolationVOKÁČ, K. et al. (1998) Phytochemistry 49, 2109-2114 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE