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20-HYDROXY-24-HYDROXYMETHYLECDYSONE

Year of first isolation: 2003
Formula:C28H46O8
Molecular weight:510
Occurence in plants:
Sida spinosa [Malvaceae] » Images of Sida spinosa Wikipedia: Sida spinosa [Malvaceae]
Occurence in animals:
 
20-HYDROXY-24-HYDROXYMETHYLECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(CO)C(C)(C)O)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@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(C)(C)O)CO)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,6-trihydroxy-5-(hydroxymethyl)-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID12084879
InChiKey
[ ChemIDPlus: search ]
IDVDSLXRLYXWHQ-TUVIPRGISA-N
InChIInChI=1S/C28H46O8/c1-24(2,34)15(14-29)10-23(33)27(5,35)22-7-9-28(36)17-11-19(30)18-12-20(31)21(32)13-25(18,3)16(17)6-8-26(22,28)4/h11,15-16,18,20-23,29,31-36H,6-10,12-14H2,1-5H3/t15-,16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

FAB-MS511 [M+H]+
EI-MS m/z (relative intensity %)460 [M-51]+ (2), 446 (3), 363 (37), 345 (49), 327 (27), 301 (15), 269 (17), 250 (49), 231 (16), 191 (13), 183 (11), 173 (27), 165 (9), 147 (289), 129 (18), 81 (100)
CI-MS (NH3) m/z-

CARBON NMR

PROTON NMR

DMSO
0136.8 (t)
0266.8 (d)
0367.0 (d)
0431.9 (t)
0548.9 (d)
06203.0 (s)
07120.7 (d)
08165.5 (s)
0933.4 (d)
1037.9 (s)
1120.5 (t)
1231.7 (t)
1347.1 (s)
1483.2 (s)
1530.6 (t)
1620.3 (t)
1750.4 (d)
1817.4 (q)
1924.6 (q)
2076.0 (s)
2121.8 (q)
2276.2 (d)
2331.1 (t)
2448.9 (d)
2569.0 (s)
2630.4 (q)
2729.2 (q)
2863.3 (t)
DMSO
01-Ha1.26 (t, 9)
01-He1.60
02-Ha3.60
03-He3.74
04-Ha1.48
04-He1.60
05-H2.20 (dd, 13, 4)
07-H5.63 (d, 2.5)
09-H3.03 (ddd, 9, 7.2, 2)
11-Ha1.55
11-He1.78
12-Ha2.06 (ddd, 13, 13, 4.8)
12-He1.74
15-Ha1.80
15-Hb1.50
16-Ha1.88
16-Hb1.64
17-H2.22 (t, 8)
18-Me0.76 (s)
19-Me0.83 (s)
21-Me1.05 (s)
22-Hb3.15 (br, d, 10)
23-Ha1.45 (ddd)
23-Hb1.57
24-Ha1.75
24-Hb-
26-Me1.03 (s)
27-Me1.06 (s)

PHYSICAL PROPERTIES

 

CHROMATOGRAPHY

 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationDARWISH, F.M.M. et al. (2003) Phytochemistry 62, 1179-1184 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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