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11α,20,26-TRIHYDROXYECDYSONE

Year of first isolation: 2000
Formula:C27H44O9
Molecular weight:512
Occurence in plants:
Vitex canescens [Lamiaceae (alt. Labiatae)] » Images of Vitex canescens Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
11α,20,26-TRIHYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(CO)O)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102237690
InChiKey
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KLDBEDBIBHZKCM-ZKJAEQJOSA-N
InChIInChI=1S/C27H44O9/c1-23(34,13-28)7-6-21(33)26(4,35)20-5-8-27(36)15-10-16(29)14-9-17(30)18(31)11-24(14,2)22(15)19(32)12-25(20,27)3/h10,14,17-22,28,30-36H,5-9,11-13H2,1-4H3/t14-,17+,18-,19+,20-,21+,22+,23?,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
HR-FAB-MS(negative mode): 511.2906 and 511.2908 for the two epimers, respectivelly, [M-H]- (calc. 511.2907 for C27H44O9 -H)

CARBON NMR

PROTON NMR

C5D5N
0139.65 39.64
0268.20 68.20
0367.94 67.94
0432.64 32.66
0552.26 52.26
06203.74 203.76
07122.02 122.01
08164.07 164.09
0942.53 42.53
1039.30 39.30
1168.62 68.62
1243.93 43.93
1347.96 47.96
1484.01 84.01
1531.65 31.65
1621.40 21.41
1749.78 49.78
1818.68 18.68
1924.65 24.65
2076.62 76.61
2121.29 21.32
2277.29 77.43
2326.57 26.51
2437.35 37.31
2572.41 72.37
2670.63 70.44
2724.32 24.52
C5D5N
01-Ha ?3.43 (dd, 12.4, 3.5) 3.44 (dd, 12.5, 3.5)
01-He 
02-Ha4.58 (m) 4.58 (m)
03-He4.20 (br, s) 4.21 (br, s)
04-Ha 
04-He 
05-H3.00 3.00
07-H6.28 (d, ca. 2) 6.28 (br, s)
09-H3.85-3.89 3.85-3.89
11-Ha4.58 (m) 4.58 (m)
12-Ha3.02 3.02
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.09 (t, 9.1) 3.09 (t, 8.9)
18-Me1.24 (s) 1.24 (s)
19-Me1.30 (s) 1.30 (s)
21-Me1.56 (s) 1.56 (s)
22-H3.85-3.89 3.85-3.89
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-H (2)3.85-3.89 3.85-3.89
26-Me? ?
27-Me1.45 (s) 1.45 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3448, 2952, 1660, 1385, 10535; 3448, 2927, 1660, 1385, 1053
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

TLC 
GLC 
RP-HPLCcolumn ?Bondapak C18, 10 ?m, 300x3.9 mm, solvent MeOH-H2O (18:82), flow-rate 1.0 ml.min-1, Ret 34.4 and 40.8 min.
NP-HPLCcolumn Hypersil Si, 5 ?m, 250x4.6 mm; solvent CHCl3-MeOH (90:10), flow-rate 1.2 ml.min-1, Ret 16.4 min (for both epimers).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSUKSAMRARN, A. et al. (2000) Phytochemistry 53, 921-924 Search more

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© 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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