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11α-HYDROXYPOSTSTERONE

Year of first isolation: 2004
Formula:C21H30O6
Molecular weight:378
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
11α-HYDROXYPOSTSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)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]2C(=O)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-acetyl-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 CID11360938
InChiKey
[ ChemIDPlus: search ]
AXUBMUAOVGJKLY-RUWUBIMMSA-N
InChIInChI=1S/C21H30O6/c1-10(22)11-4-5-21(27)13-7-14(23)12-6-15(24)16(25)8-19(12,2)18(13)17(26)9-20(11,21)3/h7,11-12,15-18,24-27H,4-6,8-9H2,1-3H3/t11-,12+,15-,16+,17-,18-,19+,20-,21-/m1/s1

MASS SPECTRUM

FAB-MS m/z (relative intensity %)379 [M+H]+ (100), 361 [M+H-H2O]+ (88), 343 [M+H-2H2O]+ (40), 325 [M+H-3H2O]+ (10), 299 (11), 282 (32), 277 (13), 246 (80), 231 (20)
HRESI-MS378.2045 (calculated 378.2042 for C21H30O6)
EI-MS m/z (relative intensity %) 

CARBON NMR

PROTON NMR

CD3OD
0139.2
0269.1
0368.7
0433.5
0553.0
06206.6
07123.3
08164.4
0943.1
1040.1
1169.4
1242.3
1348.6
1484.8
1532.3
1622.4
1760.0
1818.4
1924.8
20212.3
2131.6
CD3OD
01-Ha2.60 (dd, 13.0, 4.2)
01-He1.38 (t, 12.3)
02-Ha4.015 (dt, 11.8, 3.8)
03-He3.96 (q, 2.9)
04-Ha1.70
04-He1.775 (td, 13.6, 2.4)
05-H2.345 (dd, 13.1, 4.1)
07-H5.807 (d, 2.7)
09-H3.18 (dd, 8.9, 2.7)
11-Ha4.08 (ddd, 10.8, 8.9, 5.8)
12-Ha2.406 (t, 11.4)
12-He2.08 (dd, 12.0, 5.8)
15-Ha1.68
15-Hb2.00
16-Ha1.90
16-Hb2.245
17-H3.36 (dd, 9.4, 8.1)
18-Me0.61 (s)
19-Me1.05 (s)
21-Me2.16 (s)

PHYSICAL PROPERTIES

M.P.174-176 °C ;
[α]D28+ 12 ° (c 0.1 ; MeOH)
IR (KBr) ν max (cm-1)3320, 1718, 1653
UV (MeOH) λ max (log ε)240 (4.116) ;

CHROMATOGRAPHY

LCLow pressure RP, MeOH-H2O (40:60)
HPLC
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHUNYADI, A. et al. (2004) J. Nat. Prod. 67, 1072-1072 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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