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2,22-DIDEOXY-20-HYDROXYECDYSONE 25-O-β-D-GLUCOPYRANOSIDE

Year of first isolation: 2009
Formula:C33H54O10
Molecular weight:610
Occurence in plants:
Froelichia floridana [Amaranthaceae] » Images of Froelichia floridana Wikipedia: Froelichia floridana [Amaranthaceae]
Occurence in animals:
 
2,22-DIDEOXY-20-HYDROXYECDYSONE 25-O-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(CCCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)O)O)C)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-17-[(2S)-2-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID42611661
InChiKey
[ ChemIDPlus: search ]
VKAFQILVRDFOIB-DMLNGFPFSA-N
InChIInChI=1S/C33H54O10/c1-29(2,43-28-27(39)26(38)25(37)23(17-34)42-28)10-6-11-32(5,40)24-9-14-33(41)20-16-22(36)21-15-18(35)7-12-30(21,3)19(20)8-13-31(24,33)4/h16,18-19,21,23-28,34-35,37-41H,6-15,17H2,1-5H3/t18-,19-,21-,23+,24-,25+,26-,27+,28-,30+,31+,32-,33+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z
HR-ESI-MS m/z[M+Li]+ 617.3881, calculated for C33H54O10Li, 617.3877

CARBON NMR

PROTON NMR

DMSO-d6
0129.1
0228.2
0362.8
0432.1
0550.8
06203.4
07120.3
08165.8
0932.1
1036.1
1120.1
1230.7
1348.6
1485.0
1529.9
1620.7
1751.2
1817.7
1923.8
2073.6
2126.6
2244.5
2318.2
2442.1
2576.5
2626.3
2726.2
[glu]  1'97.1
[glu]  2'73.3
[glu]  3'77.0
[glu]  4'70.3
[glu]  5'76.5
[glu]  6'61.2
DMSO-d6
01-Ha1.22 (m)
01-He1.49 (m)
02-Ha1.63 (m)
02-He1.32 (m)
03-He3.84 (br, s, w1/2 = 15.6)
04-Ha1.37 (m)
04-He 
05-H2.27 (dd, 12.1, 3.7)
07-H5.63 (d, 3.0)
09-H3.07 (m)
11-Ha1.59 (m)
11-He1.47 (m)
12-Ha1.99 (dd, 11.8, 7.8)
12-He1.66 (m)
15-Ha1.50 (m)
15-Hb1.79 (m)
16-Ha1.82 (m)
16-Hb1.67 (m)
17-H2.17 (t, 9.0)
18-Me0.73 (s)
19-Me0.85 (s)
21-Me1.13 (s)
22-Ha1.33 (m)
22-Hb1.26 (m)
23-Ha1.38 (m)
23-Hb1.27 (m)
24-Ha1.38 (m)
24-Hb 
26-Me1.15 (s)
27-Me1.15 (s)
[glu]  H14.26 (d, 7.7)
[glu]  H22.90 (m)
[glu]  H33.13 (m)
[glu]  H43.01 (m)
[glu]  H53.04 (m)
[glu]  H6'3.76 (d, 11.0)
[glu]  H6''3.63 (m)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D21+ 26 ° (c 0.07; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)246 () ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWANG, P. et al. (2009) Phytochemistry 70, 430-436 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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