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

Year of first isolation: 2008
Formula:C30H48O8
Molecular weight:536
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: Silene viridiflora [Caryophyllaceae]
Occurence in animals:
 
2-DEOXY-5,20,26-TRIHYDROXYECDYSONE 20,22-ACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CCC(C5)O)C)O)C)O)CCC(C)(CO)O)C
Isomeric SMILES
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C1[C@]2([C@@](C[C@H](C1)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](C1)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@@H](CC[C@@](CO)(C)O)OC(O1)(C)C)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@](C[C@H](C1)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@@H](CC[C@](CO)(C)O)OC(O1)(C)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(3S,5S,9R,10R,13R,14S,17S)-17-[(4R,5R)-5-(3,4-dihydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3,5,14-trihydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102477128
InChiKey
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MENIOZHCBSKIIJ-FHOYITCCSA-N
InChIInChI=1S/C30H48O8/c1-24(2)37-23(10-11-25(3,34)17-31)28(6,38-24)21-9-14-29(35)20-15-22(33)30(36)16-18(32)7-12-26(30,4)19(20)8-13-27(21,29)5/h15,18-19,21,23,31-32,34-36H,7-14,16-17H2,1-6H3/t18-,19-,21-,23+,25?,26+,27+,28+,29+,30+/m0/s1

MASS SPECTRUM

HR-ESI-MS537.3420 [M+H]+ (calc. for C30H49O8, 537.3414)
ESI-MS m/z (relative intensity %)559 [M+Na]+ (100), 541 [M+Na-H2O]+ (12), 537 [M+H]+ (36), 518 [M-H2O]+ (3), 501 [M+H-2H2O]+ (2), 445 (10), 385 [M+H-H2O-C6O3H14]+ (3), 315 (12), 304 (24)

CARBON NMR

PROTON NMR

CD3OD
0125.6
0229.3
0367.2
0436.9
0581.2
06
07120.7
08
0938.1
1043.25
1122.5
1232.6
1348.7
1485.4
1531.8
1622.5
1750.6
1817.8
1917.3
2086.0
2122.7
2283.6
2324.05
2437.2
2573.6
2670.7
2723.8
28-C108.2
29-Me27.3
30-Me29.5
CD3OD
01-Ha1.50 (m)
01-He1.84 (m)
02-Ha1.77 (m)
02-He1.96 (m)
03-He4.08 (s, br)
04-Ha1.61 (m)
04-He2.035 (m)
07-H5.86 (s, br)
09-H3.28 (m)
11-Ha1.73 (m)
11-He 
12-Ha2.12 (td, 12.4, 5.7)
12-He1.86 (m)
15-Ha1.61 (m)
15-Hb1.97 (m)
16-Ha1.88 (m)
16-Hb2.04 (m)
17-H2.2 (t, 8.7)
18-Me0.83 (s)
19-Me0.89 (s)
21-Me1.18 (s)
22-H3.70 (m)
23-Ha1.55 (m)
23-Hb1.55 (m)
24-Ha1.53 (m)
24-Hb1.72 (m)
26-CH2OH3.37 (d, 11), 3.36 (d, 11)
27-Me1.15 (s)
[Me2CO]1.39 (s), 1.32 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+ 25° (c 0.05; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)238 (4.08) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

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

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