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(24R)-24-(2-HYDROXYETHYL)-20-HYDROXYECDYSONE

Year of first isolation: 2002
Formula:C29H48O8
Molecular weight:524
Occurence in plants:
Serratula strangulata [Asteraceae] » Images of Serratula strangulata Wikipedia: Serratula strangulata [Asteraceae]
Occurence in animals:
 
(24R)-24-(2-HYDROXYETHYL)-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(CCO)C(C)(C)O)O)O)O
Isomeric SMILES
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[ 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](C[C@H](C(C)(C)O)CCO)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-17-[(3R)-2,3,6-trihydroxy-5-(2-hydroxyethyl)-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID129829786
InChiKey
[ ChemIDPlus: search ]
NGLFKJFHARGWMY-GBIMCYBUSA-N
InChIInChI=1S/C29H48O8/c1-25(2,35)16(8-11-30)12-24(34)28(5,36)23-7-10-29(37)18-13-20(31)19-14-21(32)22(33)15-26(19,3)17(18)6-9-27(23,29)4/h13,16-17,19,21-24,30,32-37H,6-12,14-15H2,1-5H3/t16?,17?,19-,21+,22-,23+,24+,26+,27+,28?,29+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HREI-MS524.3341, Calculated 524.3349
FAB-MS m/z525 [M+H]+, 510, 507, 492, 389, 371, 189, 171, 145, 127

CARBON NMR

PROTON NMR

DMSO-d6
0136.59
0266.56
0366.74
0431.49
0550.50
06202.59
07120.41
08165.15
0933.15
1037.58
1120.04
1230.26
1346.62
1482.95
1530.82
1620.22
1748.65
1817.07
1923.81
2076.18
2120.92
2275.60
2326.06
2436.55
2568.66
2628.97
2729.92
2841.34
2966.06
DMSO-d6
01-Ha 
01-He1.70-1.84 (m)
02-Ha3.81-3.85 (m)
03-He3.92-3.96 (m)
04-Ha1.61-1.68 (m)
04-He1.70-1.84 (m)
05-H2.37 (dd, J = 12, 5 Hz)
07-H5.61 (s)
09-H3.14-3.18 (m)
11-Ha1.61-1.68 (m)
11-He1.70-1.84 (m)
12-Ha2.10-2.16 (m)
12-He1.84-1.90 (m)
15-Ha1.97-2.03 (m)
15-He1.52-1.58 (m)
16-Ha1.97-2.03 (m)
16-He1.70-1.84 (m)
17-H2.27-2.41 (m)
18-Me0.89 (s)
19-Me0.96 (s)
21-Me1.19 (s)
22-H3.41-3.44 (m)
23-Ha1.41-1.45 (m)
23-Hb1.52-1.58 (m)
24-H1.45-1.55 (m)
26-Me1.20 (s)
27-Me1.21 (s)
28-CH21.37-1.40 (m, 2H)
29-CH23.20-3.26 (m, 2H)

PHYSICAL PROPERTIES

M.P.242-244 °C ;
[α]D24+ 65.2 ° (c 0.04 ; MeOH)
IR (KBr) ν max (cm-1)3387 (OH), 1642 (conjugated carbonyl)
UV (EtOH) λ max (log ε)252 (4.0) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationDAI, J.-Q. et al. (2002) Chin. J. Chem. 20(5), 497-501 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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