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14-EPI-20-HYDROXYECDYSONE

Year of first isolation: 2007
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
14-EPI-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(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](CCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID11386092
InChiKey
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NKDFYOWSKOHCCO-MQVWFXNHSA-N
InChIInChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27-/m0/s1

MASS SPECTRUM

FAB-MS m/z (relative intensity %)503 [M+Na](34), 481 [M+H](41), 463 [M+H-H2O](25), 445 [M+H-2H2O](65), 427 [M+H-3H2O](37), 363 (41), 303 (71), 279 (80), 211 (100).
HR-MS481.3158 for C27H45O7, calculated 481.3165
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CD3OD
0137.23
0268.66
0368.41
0433.34
0551.01
06206.12
07123.12
08167.68
0937.41
1039.27
1122.25
1241.67
1352.64
1485.68
1540.75
1624.64
1756.61
1819.24
1924.64
2077.64
2120.45
2278.44
2327.41
2442.20
2571.24
2628.84
2729.88
CD3OD
01-Ha1.43
01-He1.80
02-Ha3.86
03-He3.94
04-Ha1.59
04-He1.73
05-H2.36
07-H6.29
09-H2.85
11-Ha1.68
11-He1.79
12-Ha1.77
12-He1.67
15-Ha2.28
15-Hb1.43
16-Ha2.08
16-Hb1.89
17-H1.98
18-Me1.26
19-Me0.94
21-Me1.29
22-H3.50
23-Ha1.58
23-Hb1.29
24-Ha1.80
24-Hb1.43
26-Me1.19
27-Me1.21

PHYSICAL PROPERTIES

M.P.C ;
[α]D20+- ° (c ; MeOH)
IR (KBr) ν max (cm-1)3380 (OH), 1653 (C=O), 1063 (C-O)
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLCNP-HPLC column Zorbax-SIL (250x4.6 mm), solvent cyclohexane-iso-PrOH-H2O (100:40:3), flow-rate 1 ml/min, ret. 22.1 min (20E : 21.0 min).
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

GeneralHARMATHA, J. et al. (2002) Steroids 67, 123-135 Search more
First isolationHUNYADI, A. et al. (2007) J. Chrom. Sci. 45, 76-86 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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