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11-HYDROXY-SIDISTERONE

Year of first isolation: 2015
Formula:C24H32O7
Molecular weight:432
Occurence in plants:
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] » Images of Ajuga turkestanica Wikipedia: Ajuga turkestanica [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
11-HYDROXY-SIDISTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2C1(OC(=O)C=C1)C)O)C)O)C » JSMol: View in 3D
IUPAC Name5-methyl-5-((2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
RSJRQEANRMFNKN-URTOIKHCSA-N
InChIInChI=1S/C24H32O7/c1-21-10-16(27)15(26)8-12(21)14(25)9-13-20(21)17(28)11-22(2)18(4-7-24(13,22)30)23(3)6-5-19(29)31-23/h5-6,9,12,15-18,20,26-28,30H,4,7-8,10-11H2,1-3H3/t12-,15+,16-,17+,18-,20+,21-,22+,23?,24+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HRESI-MS 455.20418 [M+Na]+, expected 455.20402 for C24H32O7Na
ESI-MS m/z 433 [M+H]+, 415 [MH - H2O]+, 397 [MH - 2H2O]+, 379 [MH - 3H2O]+, 361 [MH - 3H2O]+

CARBON NMR

PROTON NMR

D2O
0139.2
0269.4
0369.4
0433.7
0553.5
06210.5
07124.2
08166.7
0943.4
1040.8
1170.1
1243.2
1348.9
1486.7
1532.3
1623.3
1752.7
1820.4
1925.3
2095.4
2125.8
22167.2
23120.9
24179.0
D2O
01-Ha1.41 (t, 13)
01-He2.50 (dd, 13, 3.9)
02-Ha4.10 (m, w1/2 = 11)
03-He4.10 (m, w1/2 = 11)
04-Ha1.74
04-He1.79
05-H2.33 (dd, 12.1, 5.4)
07-H5.98 (d, 2.6)
09-H3.13 (dd, 8.8, 2.6)
11-Ha4.20 (m)
12-Ha2.13
12-He2.13
15-Ha2.05
15-Hb1.68
16-Ha1.87
16-Hb1.51
17-H2.75 (t, 9.5)
18-Me0.76 (s)
19-Me1.10 (s)
21-Me1.61 (s)
22-H7.92 (d, 5.7)
23-Ha6.15 (d, 5.7)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLC
GLC
TLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGUIBOUT, L. et al. (2015) Phytochemical Analysis 26, 293-300 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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