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

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-GALACTOPYRANOSIDE

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 
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
JYWPYPJUPHIBOJ-CREQWTSOSA-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
0137.7
0273.9
0368.6
0429.8
0552.3
06202.3
07121.9
08167.0
0934.6
1039.2
1121.3
1232.0
1348.3
1484.4
1532.2
1621.8
1750.4
1818.1
1924.4
2077.2
2122.0
2277.8
2327.7
2442.9
2570.0
2630.6
2730.3
[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-Ha1.83
01-He2.44
02-Ha4.49
03-He5.65 (br, s)
04-Ha1.98
04-He1.74
05-H2.63 (dd, 14.0, 4.0)
07-H6.21 (d, 2.0)
09-H3.60 (br, s)
11-Ha1.70
11-He2.08
12-Ha2.15
12-He1.85
15-Ha1.96
15-Hb2.51
16-Ha2.45
16-Hb2.05
17-H2.95 (t, 9)
18-Me1.20 (s)
19-Me1.03 (s)
21-Me1.55 (s)
22-H3.87 (d, 9.5)
23-Ha2.15
23-Hb1.85
24-Ha2.30
24-Hb1.81
26-Me1.39 (s)
27-Me1.39 (s)
[sugar] 1' 4.84 (d, 7.5)
[sugar] 2' 4.40 (dd, 9.5, 7.5)
[sugar] 3' 4.10 (dd, 9.5, 3.0)
[sugar] 4' 4.55 (d, 3.0)
[sugar] 5' 4.02 (t, 6.0)
[sugar] 6' 6'' 4.46, 4.42

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+ 21.0 ° (c 0.01; MeOH)
IR (KBr) ν max (cm-1)3420, 2925, 2857, 1647, 1382, 1057
UV (MeOH) λ max (log ε)242 () ;

CHROMATOGRAPHY

GLC
HPTLC
HPLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

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