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TURKESTERONE 2-O-CINNAMATE

Year of first isolation: 2019
Formula:C36H50O9
Molecular weight:626
Occurence in plants:
Rhaponticum uniflorum [Menispermaceae] » Images of Rhaponticum uniflorum
Occurence in animals:
 
TURKESTERONE 2-O-CINNAMATE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)/C=C/c1ccccc1)O)C(=O)C=C1C2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@]([C@@H](CCC(C)(C)O)O)(O)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,11R,13R,14S,17S)-3,11,14-trihydroxy-10,13-dimethyl-6-oxo-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-2-yl cinnamate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
QZGAWXSFLXUDMD-WOOHFCDMSA-N
InChIInChI=1S/C36H50O9/c1-32(2,42)15-14-29(40)35(5,43)28-13-16-36(44)23-18-24(37)22-17-25(38)27(45-30(41)12-11-21-9-7-6-8-10-21)20-33(22,3)31(23)26(39)19-34(28,36)4/h6-12,18,22,25-29,31,38-40,42-44H,13-17,19-20H2,1-5H3/b12-11+/t22-,25+,26+,27-,28-,29+,31?,33-,34+,35+,36+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
ESI-MS m/z 665 (M+K)+, 649 (M+Na)+, 627 (M+H)+, 609 (M+H-H2O)+, 591 (M+H-2H2O)+, 573 (M+H-3H2O)+, 556 (M+H-C4H7O)+, 555 (M+H-4H2O)+, ...
HR-ESI-MS 

CARBON NMR

PROTON NMR

CD3OD
0134.6
0273.4
0366.7
0432.4
0552.2
06206.4
07122.9
08166.3
0943.1
1039.6
1169.4
1243.5
1349.1
1485.1
1531.6
1621.3
1750.4
1818.4
1924.2
2078.6
2127.5
2278.6
2327.5
2442.5
2571.6
2628.6
2729.6
Cinnamate 1'133.7
Cinnamate 2'128.5
Cinnamate 3'129.7
Cinnamate 4'131.0
Cinnamate 5'129.7
Cinnamate 6'128.5
Cinnamate 7'146.7
Cinnamate 8'117.0
Cinnamate 9'168.5
CD3OD
01-Ha1.40 (dd, 12.9, 12.0)
01-He2.63 (dd, 13.9, 4.2)
02-Ha5.39 (ddd, 12.0, 4.2, 3.2)
03-He4.27-4.37 (m)
04-Ha1.72-1.74 (m)
04-He1.80-1.82 (m)
05-H2.37 (dd, 13.1, 4.1)
07-H5.83 (dd, 2.6, 1.0)
09-H3.05 (dd, 9.0, 2.9)
11-H4.12 (ddd, 10.7, 9.1, 6.1)
12-Ha2.25 (dd, 12.1, 10.7)
12-He2.14 (dd, 12.1, 6.1)
15-Ha1.95-1.98 (m)
15-Hb1.57-1.60 (m)
16-Ha1.75-1.78 (m)
16-Hb1.99-2.01 (m)
17-H2.34 (t, 11.2)
18-Me0.89 (s)
19-Me1.05 (s)
21-Me1.23 (s)
22-H3.30 (dd, 11.1, 1.5)
23-Ha1.31-1.36 (m)
23-Hb1.83-1.84 (m)
24-Ha1.43-1.46 (m)
24-Hb1.15 (m)
25-H-
26-Me1.20 (s)
27-Me1.21 (s)
Cinnamate 2'7.51 (d, 8.0)
Cinnamate 3'6.62 (d, 8.0)
Cinnamate 4'7.26 (m)
Cinnamate 5'6.62 (d, 8.0)
Cinnamate 6'7.51 (d, 8.0)
Cinnamate 7'7.72 (d, 16.2), 6.27 (d, 16.2)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3351, 1685, 1635
UV (MeOH) λ max (log ε)245 ; 278

CHROMATOGRAPHY

HPTLC
TLC
HPLC
GLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationOLENNIKOV, D.N. et al. (2019) Chem. Nat. Compd. 55 (2), 256-264 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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