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22-OXO-TURKESTERONE

Year of first isolation: 2015
Formula:C27H42O8
Molecular weight:494
Occurence in plants:
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] » Images of Ajuga turkestanica Wikipedia: Ajuga turkestanica [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
22-OXO-TURKESTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(=O)CCC(C)(C)O)O)O)O
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]2[C@](C)(C(=O)CCC(C)(C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 170325766
InChiKey
[ ChemIDPlus: search ]
UIIGNDUXNWFJEC-RFKQUTSUSA-N
InChIInChI=1S/C27H42O8/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4/h11,14,17-20,22,29-31,33-35H,6-10,12-13H2,1-5H3/t14-,17+,18-,19+,20-,22+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HRESI-MS 517.27681 [M+Na]+, expected 517.27719 for C27H42O8Na
ESI-MS m/z 495 [M+H]+, 477 [MH - H2O]+, 459 [MH - 2H2O]+, 441 [MH - 3H2O]+, 423 [MH - 4H2O]+

CARBON NMR

PROTON NMR

D2O
0139.2
0269.3
0369.3
0433.6
0553.4
06210.4
07123.9
08166.8
0943.4
1040.8
1170.2
1243.7
1349.5
1486.8
1532.4
1622.3
1751.7
1819.6
1925.3
2084.0
2125.6
22220.4
2334.1
2438.6
2573.2
2629.6
2729.6
D2O
01-Ha1.40 (t, 12.8)
01-He2.48 (dd, 13, 3.9)
02-Ha4.10 (m, w1/2 = 12)
03-He4.10 (m, w1/2 = 12)
04-Ha1.74
04-He1.79
05-H2.31 (dd, 12.3, 5.3)
07-H5.97 (d, 2.6)
09-H3.14 (dd, 8.8, 2.6)
11-Ha4.24 (m, w1/2 = 27, ddd, 11, 9, 6.1)
12-Ha2.16 (t, 12.3)
12-He2.28 (dd, 12.5, 6.1)
15-Ha2.05 (m, w1/2 = 26)
15-Hb1.65
16-Ha1.68
16-Hb1.60
17-H2.62 (t, 9.4)
18-Me0.84 (s)
19-Me1.10 (s)
21-Me1.51 (s)
22-H 
23-Ha2.79 (m, w1/2 = 12)
23-Hb2.79 (m, w1/2 = 12)
24-Ha1.76
24-Hb1.76
26-Me1.24 (s)
27-Me1.24 (s)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

TLC
HPTLC
HPLC
GLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

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