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3-EPI-RUBROSTERONE

Year of first isolation: 1992
Formula:C19H26O5
Molecular weight:334
Occurence in plants:
Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: Serratula tinctoria [Asteraceae]
Occurence in animals:
 
3-EPI-RUBROSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2=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]2CC[C@]2([C@]1(CCC2=O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,5R,9R,10R,13S,14R)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,12,15,16-decahydrocyclopenta[a]phenanthrene-6,17-dione
CAS-RN 
PubChem CID101642415
InChiKey
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OMQCWEJQYPUGJG-XZDQPVSKSA-N
InChIInChI=1S/C19H26O5/c1-17-9-15(22)14(21)8-12(17)13(20)7-11-10(17)3-5-18(2)16(23)4-6-19(11,18)24/h7,10,12,14-15,21-22,24H,3-6,8-9H2,1-2H3/t10-,12-,14-,15-,17+,18+,19+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z352 (M+H+NH3)+, 335 (M+H)+, 317, 299, 237, 221
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
CD3OD
01-Ha1.12 (dd, 12,13)
01-Hb 
02-Ha3.70 (ddd, 4,9,12)
03-Ha3.42 (ddd, 5,9,12)
04-Ha 
04-He 
05-H2.14
07-H5.92 (d, 2.5)
09-Ha3.18 (ddd, 2.5,7,11)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
18-Me0.88 (s )
19-Me0.98 (s )

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
NP-HPLCRet 13.1 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent iso-C8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml.min-1) (20E 22.6 min, rubrosterone 14.4 min)
RP-HPLCRet 5.7 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent ACN : 1? TFA in H2O 23:77 v/v, flow-rate 1ml.min-1) (20E 5.2 min, rubrosterone 5.3 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationRUDEL, D. et al. (1992) Planta Med. 58, 358-364 Search more

see Important notice
© 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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