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2,22-DIDEOXYECDYSONE 25-O-β-D-GLUCOPYRANOSYL-(1->2)-β-D-GLUCOPYRANOSIDE

Year of first isolation: 2009
Formula:C39H64O14
Molecular weight:756
Occurence in plants:
Froelichia floridana [Amaranthaceae] » Images of Froelichia floridana Wikipedia: Froelichia floridana [Amaranthaceae]
Occurence in animals:
 
2,22-DIDEOXYECDYSONE 25-O-β-D-GLUCOPYRANOSYL-(1->2)-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CCCC(C)(C)OC1C(C(C(C(O1)CO)O)O)OC2C(C(C(C(O2)CO)O)O)O)C3CCC4(C3(CCC5C4=CC(=O)C6C5(CCC(C6)O)C)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@H](C)CCCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14S,17R)-17-[(2R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID42611662
InChiKey
[ ChemIDPlus: search ]
SVMJZCACKKJCOO-HEQJLXOMSA-N
InChIInChI=1S/C39H64O14/c1-19(21-10-14-39(49)23-16-25(43)24-15-20(42)8-12-37(24,4)22(23)9-13-38(21,39)5)7-6-11-36(2,3)53-35-33(31(47)29(45)27(18-41)51-35)52-34-32(48)30(46)28(44)26(17-40)50-34/h16,19-22,24,26-35,40-42,44-49H,6-15,17-18H2,1-5H3/t19-,20+,21-,22+,24+,26-,27-,28-,29-,30+,31+,32-,33-,34+,35+,37-,38-,39-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z
HR-ESI-MS m/z[M+Li]+ 763.4463, calculated for C39H64O14Li, 763.4456

CARBON NMR

PROTON NMR

DMSO-d6
0128.8
0227.7
0362.0
0432.2
0550.7
06205.0
07120.4
08167.0
0931.7
1036.5
1120.6
1230.9
1349.1
1484.0
1530.8
1626.9
1750.4
1815.8
1924.1
2035.4
2119.2
2236.7
2320.6
2442.3
2578.0
2625.7
2726.9
[glu 1] 195.9
[glu 1] 282.1
[glu 1] 376.7
[glu 1] 470.4
[glu 1] 577.3
[glu 1] 661.3
[glu 2] 1'104.3
[glu 2] 2'75.4
[glu 2] 3'76.3
[glu 2] 4'70.2
[glu 2] 5'76.3
[glu 2] 6'61.4
DMSO-d6
01-Ha1.26 (m)
01-He1.42 (m)
02-Ha1.56 (m)
02-He1.43 (m)
03-He3.78 (br, s, w1/2 = 15.7)
04-Ha1.32 (m)
04-He 
05-H2.19 (dd, 12.3, 3.3)
07-H5.59 (s)
09-H3.07 (m)
11-Ha1.51 (m)
11-He1.37 (m)
12-Ha1.86 (m)
12-He1.53 (m)
15-Ha1.42 (m)
15-Hb1.73 (m)
16-Ha1.86 (m)
16-Hb1.19 (m)
17-H1.79 (t, 9.0)
18-Me0.50 (s)
19-Me0.78 (s)
20-H1.28 (m)
21-Me0.79 (d, 6.7)
22-Ha1.25 (m)
22-Hb0.87 (m)
23-Ha1.99 (m)
23-Hb1.25 (m)
24-Ha1.37 (m)
24-Hb1.25 (m)
26-Me1.08 (s)
27-Me1.08 (s)
[glu 1] H14.38 (d, 7.4)
[glu 1] H23.14 (d, 8.4)
[glu 1] H33.34 (d, 8.3)
[glu 1] H43.04 (m)
[glu 1] H53.07 (m)
[glu 1] H63.60 (d, 11.6), 3.43 (m)
[glu 2] H1'4.33 (d, 7.7)
[glu 2] H2'2.96 (t, 8.4)
[glu 2] H3'3.13 (m)
[glu 2] H4'3.07 (m)
[glu 2] H5'3.06 (m)
[glu 2] H6'3.55 (d, 11.6), 3.37 (m)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D21+ 48 ° (c 0.92; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)248 () ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

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

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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