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20,26-DIHYDROXYECDYSONE 2,22-DIACETATE

Year of first isolation: 2004
Formula:C31H48O10
Molecular weight:580
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: Silene viridiflora [Caryophyllaceae]
Occurence in animals:
 
20,26-DIHYDROXYECDYSONE 2,22-DIACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC1CC2(C3CCC4(C(CCC4(C3=CC(=O)C2CC1O)O)C(C)(C(CCC(C)(CO)O)OC(=O)C)O)C)C
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)OC(=O)C)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC[C@@](CO)(C)O)OC(=O)C)O)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC[C@](CO)(C)O)OC(=O)C)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-3-acetyloxy-2,6,7-trihydroxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] acetate
CAS-RN 
PubChem CID152751345
InChiKey
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GFXSCYFAJXZMRJ-HZOCAVHQSA-N
InChIInChI=1S/C31H48O10/c1-17(33)40-24-15-28(4)19-7-11-29(5)25(30(6,38)26(41-18(2)34)9-10-27(3,37)16-32)8-12-31(29,39)20(19)13-22(35)21(28)14-23(24)36/h13,19,21,23-26,32,36-39H,7-12,14-16H2,1-6H3/t19-,21-,23+,24-,25-,26+,27?,28+,29+,30+,31+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
FAB-MS m/z603.3 [M+Na]+, 581.3 [M+H]+, 563.3 [M+H-H2O]+
CI-MS (NH3) m/z682, 664, 640, 622, 598, 580, 562, 556, 538, 520, 502, 496, 478, 461, 443, 422, 404, 236, 218, 192 174, 136, 132, 77

CARBON NMR

PROTON NMR

D2O
0139.2
0274.5
0367.8
04n.d.
0553
06n.d.
07123.8
08n.d.
0936.6
1041.0
11n.d.
1233.8
1350.2
1488.1
1533.1
1622.9
1752.1
1819.7
1925.6
2079.9
2123.0
2282.9
22-Ac23.4/177.6
23n.d.
2437.4
2576.0
2671.3
2724.6
3-Ac23.6/176.5
D2O
01-Ha1.53
01-He1.96
02-Ha5.08 (m, w1/2 = 22)
03-He4.22 (m, w1/2 = 8)
04-Ha1.80
04-He1.83
05-H2.41 (dd, 5, 13)
07-H5.99 (d, 2.5)
09-H3.18 (m, w1/2 = 24)
11-Ha1.73
11-He1.86
12-Ha1.76
12-He1.96
15-Ha1.67
15-Hb2.06
16-Ha1.88*
16-Hb1.80*
17-H2.31 (t, 9.5)
18-Me0.86 (s)
19-Me1.02 (s)
2-Ac2.127 (s)
21-Me1.34 (s)
22-Ac2.167 (s)
22-H4.85 (dd, 10.5, 2)
23-Ha1.56
23-Hb1.76
24-Ha1.75
24-Hb1.46
26-CH2OH3.42 (s)
27-Me1.15 (s)

PHYSICAL PROPERTIES

M.P.- ?C ;
[α]D20? ? (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)- (-) ;

CHROMATOGRAPHY

HPLCNP-HPLC column Zorbax-SIL (250 mm long, 4.6 mm i.d.) eluted with dichloromethane-isopropanol-water (125:25:1 v/v/v), flow-rate 2 ml/min, ret 15.0 min. RP-HPLC column Ultrasphere 5ODS2 (250 mm long, 4.6 mm i.d.) eluted with a linear gradient (40-100% over 30 min) of methanol in water (containing 0.1% TFA), flow-rate 1 ml/min, ret 12.9 min.
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMAMADALIEVA, N.Z. et al. (2004) Collect. Czech. Chem. Commun. 69(8), 1675-1680 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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