Welcome to online ecdysteroids database ! . .
Access data · History · Contact

3-O-ACETYL-20-HYDROXYECDYSONE 2-O-β-D-GLUCOPYRANOSIDE

Year of first isolation: 2017
Formula:C35H56O13
Molecular weight:684
Occurence in plants:
Serratula chinensis [Asteraceae] » Images of Serratula chinensis Wikipedia: Serratula chinensis [Asteraceae]
Occurence in animals:
 
3-O-ACETYL-20-HYDROXYECDYSONE 2-O-β-D-GLUCOPYRANOSIDE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-14-hydroxy-10,13-dimethyl-6-oxo-2-(((2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
JYWPYPJUPHIBOJ-VCWLNJAPSA-N
InChIInChI=1S/C35H56O13/c1-17(37)46-22-14-20-21(38)13-19-18(32(20,4)15-23(22)47-30-29(42)28(41)27(40)24(16-36)48-30)7-11-33(5)25(8-12-35(19,33)45)34(6,44)26(39)9-10-31(2,3)43/h13,18,20,22-30,36,39-45H,7-12,14-16H2,1-6H3/t18-,20-,22+,23-,24?,25-,26+,27+,28?,29?,30+,32+,33+,34+,35+/m0/s1

MASS SPECTRUM

HRESI-MS707.3609 [M+Na]+, calculated 707.3613 for C35H56O13Na

CARBON NMR

PROTON NMR

C5D5N
0137.5
0274.1
0368.6
0429.8
0552.1
06202.6
07122.2
08167.3
0934.6
1039.0
1121.2
1232.0
1348.2
1484.5
1532.1
1621.8
1750.3
1818.1
1924.3
2077.1
2122.0
2277.9
2327.7
2442.9
2570.0
2630.5
2730.2
[sugar] 1' 104.4
[sugar] 2' 72.8
[sugar] 3' 75.6
[sugar] 4' 70.4
[sugar] 5' 77.2
[sugar] 6' 62.5
C5D5N
01-Ha1.87
01-He2.46
02-Ha4.57
03-He5.70 (br, s)
04-Ha2.04
04-He1.84
05-H2.66 (dd, 14.0, 4.0)
07-H6.24 (d, 2.0)
09-H3.63 (br, s)
11-Ha1.73
11-He2.07
12-Ha2.54
12-He1.91
15-Ha1.92
15-Hb2.13
16-Ha2.54
16-Hb1.91
17-H2.97 (t, 9.0)
18-Me1.21 (s)
19-Me1.04 (s)
21-Me1.57 (s)
22-H3.89 (d, 10.0)
23-Ha2.18
23-Hb1.87
24-Ha2.33
24-Hb1.83
26-Me1.41 (s)
27-Me1.42 (s)
[sugar] 1' 4.95 (d, 7.5)
[sugar] 2' 4.00 (t, 8.0)
[sugar] 3' 4.23
[sugar] 4' 4.25
[sugar] 5' 3.94
[sugar] 6' 6'' 4.55 (dd, 11.0, 2.5), 4.38 (dd, 11.0, 5.0)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+ 13.4 ° (c 0.01; MeOH)
IR (KBr) ν max (cm-1)33423, 2962, 2929, 1728, 1660, 1382, 1051
UV (MeOH) λ max (log ε)242 () ;

CHROMATOGRAPHY

TLC
GLC
HPTLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZHANG, Z.-Y. et al. (2017) J. Asian Nat. Prod. Res. 19, 208-214 Search more

see Important notice
© 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE