Welcome to online ecdysteroids database ! . .
Access data · History · Contact

3-EPI-SHIDASTERONE

Year of first isolation: 2012
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
3-EPI-SHIDASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(CCC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]1OC(CC1)(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,5R,9R,10R,13R,14S,17S)-17-((R)-1-((R)-5,5-dimethyltetrahydrofuran-2-yl)-1-hydroxyethyl)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
JWXMXJQGIRXWDG-ZKSFWNCQSA-N
InChIInChI=1S/C27H42O6/c1-23(2)9-8-22(33-23)26(5,31)21-7-11-27(32)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-32H,6-11,13-14H2,1-5H3/t15-,17-,19-,20-,21-,22+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

HR-ESI-MS 462.29702, calculated 462.29759 for C27H42O6
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %) 485 (15) (M+Na)+, 463 (41) (M+H), 445 (68) (M+H-H2O), 427 (13) (M+H-2H2O), 99 (100) (C22-C27)

CARBON NMR

PROTON NMR

CD3OD
0143.2
0272.3
0375.5
0433.8
0557.6
06204.8
07122.1
08168.2
0936.1
1039.7
1121.7
1232.5
1348.5
1485.3
1531.9
1621.9
1752.0
1818.3
1924.0
2077.2
2120.9
2285.7
2328.6
2439.8
2581.9
2628.5
2729.1
CD3OD
01-Ha1.08 (dd, 13.5, 11.9)
01-He2.09 (d, 13.5, 4.2)
02-Ha3.64 (ddd, 11.9, 8.8, 4.2)
03-He3.35 (m)
04-Ha1.56 (m)
04-He1.76 (m)
05-H2.09 (dd, 13.5, 4.2)
07-H5.82 (d, 2.7)
09-H3.17 (ddd, 11.7, 7.4, 2.7)
11-Ha1.70 (m)
11-He1.82 (m)
12-Ha2.16 (td, 13.0, 4.5)
12-He1.86 (m)
15-Ha1.61 (m)
15-Hb1.97 (dd, 12.7, 6.4)
16-Ha1.82 (m)
16-Hb2.02 (dtm, 12.6, 10.0)
17-H2.37 (t, 9.2)
18-Me0.85 (s)
19-Me0.95 (s)
21-Me1.22 (s)
22-H3.92 (dd, 8.4, 6.2)
23-Ha1.76 (m)
23-Hb1.90 (m)
24-Ha1.75 (m)
24-Hb1.75 (m)
26-Me1.24 (s)
27-Me1.25 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D27° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)245 (3.84) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationVÁNYOLÓS, A. et al. (2012) The Scientific World Journal article ID 651275, 5p 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE