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11α-HYDROXYRUBROSTERONE

Year of first isolation: 2003
Formula:C19H26O6
Molecular weight:350
Occurence in plants:
Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: <br />
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Occurence in animals:
 
11α-HYDROXYRUBROSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CC(C(CC1C(=O)C=C3C2C(CC4(C3(CCC4=O)O)C)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(CCC2=O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,11R,13S,14R)-2,3,11,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,9,11,12,15,16-decahydrocyclopenta[a]phenanthrene-6,17-dione
CAS-RN 
PubChem CID11473564
InChiKey
[ ChemIDPlus: search ]
ZSDODXGPSKCBIM-JYRIXWCESA-N
InChIInChI=1S/C19H26O6/c1-17-7-13(22)12(21)5-9(17)11(20)6-10-16(17)14(23)8-18(2)15(24)3-4-19(10,18)25/h6,9,12-14,16,21-23,25H,3-5,7-8H2,1-2H3/t9-,12-,13+,14-,16-,17+,18-,19-/m1/s1

MASS SPECTRUM

HREI-MS m/z350.1718 [M]+ (calcd. 350.1729)
EI-MS m/z (relative intensity %)350 [M]+ (18), 332 [M-H2O]+ (77), 314 [M-2H2O]+ (25), 304 (M-H2O-CO]+ (23), 286 [M-2H2O-CO]+ (21), 271 [M-2H2O-CO-CH3]+ (22), 249 (35), 227 (64), 185 ((93), 161 (48), 91 (97), 77 (63), 69 (41), 55 (100), 43 (90)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

C5D5N
0139.7
0268.1
0368.0
0432.9
0552.7
06203.7
07122.6
08161.3
0943.5
1039.8
1168.3
1236.2
1353.3
1479.5
1533.7
1629.1
17216.5
1817.9
1924.9
C5D5N
01-Ha3.41 (dd, 4.0, 12.6)
01-He2.02 (m)
02-Ha4.54 (m)
03-He4.54 (m)
04-Ha 
04-He 
05-H3.08 (m)
07-H6.32 (d, 2.2)
09-H3.82 (dd, 2.2, 8.6)
11-Ha4.21 (m)
12-Ha2.46 (m)
12-He3.05 (m)
15-Ha2.62 (m)*
15-Hb2.62 (m)*
16-Ha2.24 (m)$
16-Hb2.31 (m)$
18-Me0.90 (s)
19-Me1.29 (s)

PHYSICAL PROPERTIES

M.P.251-253 °C ;
[α]D20+ 1.07 ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)- (-) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTAN, C.-Y. et al. (2003) J. Asian Nat. Prod. Res. 5(4), 237-240 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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