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

SERFUROSTERONE A

Year of first isolation: 2008
Formula:C33H48O9
Molecular weight:588
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
SERFUROSTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C5(C(OC(O5)C6=CC=C(O6)CO)CCC(C)(C)O)C)O
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@]1(C)[C@H](O[C@H](O1)c1oc(cc1)CO)CCC(C)(C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(2R,4R,5R)-5-(3-hydroxy-3-methylbutyl)-2-[5-(hydroxymethyl)furan-2-yl]-4-methyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101838581
InChiKey
[ ChemIDPlus: search ]
DOEMUYSOEFOKLD-GEEPUZIISA-N
InChIInChI=1S/C33H48O9/c1-29(2,38)11-10-27-32(5,42-28(41-27)25-7-6-18(17-34)40-25)26-9-13-33(39)20-14-22(35)21-15-23(36)24(37)16-30(21,3)19(20)8-12-31(26,33)4/h6-7,14,19,21,23-24,26-28,34,36-39H,8-13,15-17H2,1-5H3/t19-,21-,23+,24-,26-,27+,28+,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z 
HR-ESI-MS589.3393 [M+H]+ (calculated for C33H49O9 : 589.3363)

CARBON NMR

PROTON NMR

CD3OD
0137.3
0268.5
0368.3
0432.7
0552.1
06
07122.0
08
0935.0
1039.1
1131.7
1232.2
1348.0
1485.4
15
16
1751.1
1817.5
1924.1
2085.6
2123.6
2285.7
23
2441.7
2571.4
2628.7
2729.2
2898.2
29
30 
31 
32 
3357.2
CD3OD
01-Ha1.42 (dd, 13.2, 12.0)
01-He1.79 (dt, 13.2, 4.2)
02-Ha3.84 (dt, 12.0, 3.4)
03-He3.95 (s, br)
04-Ha1.75
04-He1.75
05-H2.39 (dd, 12.6, 4.2)
07-H5.82 (d, 2.6)
09-Ha3.15 (ddd, 8.9, 2.6, 10.8)
11-Ha1.62
11-He1.62
12-Ha2.11 (td, 12.6, 4.2)
12-He1.85
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.41 (t, 9.1)
18-Me0.86 (s)
19-Me0.96 (s)
21-Me1.30 (s)
22-H3.79 (dd, 9.4, 2.3)
23-Ha 
23-Hb 
24-Ha1.53
24-Hb1.53
26-Me1.20 (s)
27-Me1.21 (s)
28-H5.79 (s)
30-H6.42 (d, 3.0)
31-H6.28 (d, 3.0)
33-H4.51 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25.5+ 56 ° (c 0.0025; DMSO)
IR (KBr) ν max (cm-1)
UV (DMSO) λ max (log ε)258.7 (3.925) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationLIKTOR-BUSA, E. et al. (2008) Tetrahedron Lett. 49, 1738-1740 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