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STACHYSTERONE B 14,15-EPOXIDE

Year of first isolation: 2007
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
STACHYSTERONE B 14,15-EPOXIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C15C(O5)CC2C(C)(C(CCC(C)(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]2CC[C@]2([C@]31[C@H](C[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O3)C)C » JSMol: View in 3D
IUPAC Name(2S,4S,6S,7R,10R,11R,13S,14R,16R)-13,14-dihydroxy-7,11-dimethyl-6-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadec-1(18)-en-17-one
CAS-RN 
PubChem CID101431682
InChiKey
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QHRCKMINXNGCBU-GIEIVRAASA-N
InChIInChI=1S/C27H42O7/c1-23(2,32)8-7-21(31)26(5,33)20-12-22-27(34-22)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)6-9-25(20,27)4/h10,14,16,18-22,29-33H,6-9,11-13H2,1-5H3/t14-,16-,18+,19-,20-,21+,22-,24+,25+,26+,27-/m0/s1

MASS SPECTRUM

HRESI-MS478.2924 (calculated for C27H42O7 478.2919)
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %)501 (13) [M+Na]+, 479 (100) [M+H]+, 461 (24) [M+H-H2O]+, 443 (27.5) [M+H-2H2O]+, 425 (2.6) [M+H-3H2O]+, 393 (3), 330 (53)

CARBON NMR

PROTON NMR

CD3OD
0137.1
0268.7
0368.5
0432.8
0552.0
06205.9
07124.0
08159.8
0939.1
1039.7
1121.7
1235.6
1342.4
1473.3
1561.3
1627.9
1748.4
1816.5
1924.5
2077.0
2120.8
2278.4
2327.4
2442.3
2571.4
2629.0
2730.0
CD3OD
01-Ha1.46 (t, 12.8)
01-He1.82 (dd, 13.5, 4.3)
02-Ha3.84 (ddd, 12.1, 4.2, 3.3)
03-He3.95 (q, 3.0)
04-Ha1.66 (dd, 7.8, 3.0)
04-He1.66
05-H2.41 (dd, 9.0, 8.4)
07-H5.89 (d, 2.8)
09-H2.84 (ddd, 10.2, 6.9, 2.8)
11-Ha1.81
11-He1.93
12-Ha2.20 (dd, 9.0, 2.8)
12-He1.81
15-Ha3.97 (s)
16-Ha1.92
16-Hb1.94
17-H1.71 (dd, 10.6, 7.0)
18-Me1.02 (s)
19-Me1.01 (s)
21-Me1.19 (s)
22-H3.29 (dd, 10.5, 1.8)
23-Ha1.28 (td, 11.8, 4.4)
23-Hb1.55 (tdd, 11.8, 4.4, 1.8)
24-Ha1.79 (td, 12.6, 4.6)
24-Hb1.44 (td, 12.4, 4.9)
26-Me1.19 (s)
27-Me1.20 (s)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D28- 5 ° (c 0.1; MeOH)
UV (MeOH) max (log )240 (3.8) ;
IR (KBr) ν max (cm-1)

CHROMATOGRAPHY

HPLCNP-HPLC, solvent cyclohexane-isopropanol-water 100:40:3; RP-HPLC, solvent methanol-water 60:40.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2007) Steroids 72, 751-755 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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