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

5,20,26-TRIHYDROXYECDYSONE 20,22-ACETONIDE

Year of first isolation: 2008
Formula:C30H48O9
Molecular weight:552
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: <br />
<b>Warning</b>:  preg_replace() [<a href='function.preg-replace'>function.preg-replace</a>]: No ending delimiter '&' found in <b>/usr/local/www/apache22/data/ecdybase.org/www/sheet.inc</b> on line <b>60</b><br />
Occurence in animals:
 
5,20,26-TRIHYDROXYECDYSONE 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)(CO)O)C
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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)[C@@H](CCC(CO)(C)O)OC(O1)(C)C)O)C)O)C  » JSMol: View in 3D
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)[C@@H](CCC(CO)(C)O)OC(O1)(C)C)O)C)O)C  » JSMol: View in 3D
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)[C@@H](CCC(CO)(C)O)OC(O1)(C)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-17-[(4R,5R)-5-(3,4-dihydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,3,5,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID70684797
InChiKey
[ ChemIDPlus: search ]
ZJNBRMJTFYQDIR-CUWPXVPYSA-N
InChIInChI=1S/C30H48O9/c1-24(2)38-23(9-10-25(3,35)16-31)28(6,39-24)21-8-12-29(36)18-13-22(34)30(37)15-20(33)19(32)14-27(30,5)17(18)7-11-26(21,29)4/h13,17,19-21,23,31-33,35-37H,7-12,14-16H2,1-6H3/t17-,19-,20+,21-,23+,25?,26+,27+,28+,29+,30+/m0/s1

MASS SPECTRUM

ESI-MS m/z (relative intensity %)575 [M+Na]+ (46), 553 [M+H]+ (100), 537 [M-CH3]+ (5), 535 [M+H-H2O]+ (3), 520 [M+H-H2O-CH3]+ (2), 495 [M+H-acetone]+ (59), 481 (1), 477 (3), 437 (3), 359 (3), 328 (14)
HR-ESI-MS m/z553.3366 [M+H]+ (calc. for C30H49O9, 553.3363)

CARBON NMR

PROTON NMR

CD3OD
0134.3
0268.6
0370.4
0436.3
0580.4
06202.5
07120.7
08167.4
0939.2
1045.5
1122.65
1232.6
1348.7
1485.3
1531.8
1622.5
1750.5
1817.8
1917.1
2086.0
2122.7
2283.6
2324.0
2437.2
2573.6
2670.7
2723.9
2xMe 
Me227.3, 29.5
O-C-O108.2
CD3OD
01-Ha1.73 (m)
01-He1.73 (m)
02-Ha3.95 (ddd, 10.0, 7.4, 3.6)
03-He3.99 (q, 3)
04-Ha1.77 (dd, 14.9, 3.0)
04-He2.075 (dd, 14.7, 3.0)
07-H5.86 (d, 2.8)
09-H3.19 (ddd, 11.3, 7.0, 2.7)
11-Ha1.74 (m)
11-He1.81 (m)
12-Ha2.12 (td, 13.1, 5.0)
12-He1.86 (m)
15-Ha1.61 (m)
15-Hb1.97 (m)
16-Ha1.87 (m)
16-Hb2.03 (m)
17-H2.31 (dd, 9.4, 8.1)
18-Me0.83 (s)
19-Me0.915 (s)
21-Me1.18 (s)
22-H3.695 (t, 6)
23-Ha1.53 (m)
23-Hb1.55 (m)
24-Ha1.52 (m)
24-Hb1.71 (m)
26-CH2OH3.375 (d, 11), 3.355 (d, 11)
27-Me1.15 (s)
Me2CO1.39 (s), 1.32 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+ 89 ° (c 0.05; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)242 (3.76) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTÓTH, N. et al. (2008) J. Nat. Prod. 71, 1461-1463 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