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3-EPI-22-DEOXY-20-HYDROXYECDYSONE

Year of first isolation: 1995
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: <br />
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Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: <br />
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3-EPI-22-DEOXY-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCCC(C)(C)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)(CCCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,5R,9R,10R,13R,14S,17S)-17-[(2S)-2,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101915844
InChiKey
[ ChemIDPlus: search ]
KFLDRYHMXLUSFO-FTUASRNISA-N
InChIInChI=1S/C27H44O6/c1-23(2,31)9-6-10-26(5,32)22-8-12-27(33)17-13-19(28)18-14-20(29)21(30)15-24(18,3)16(17)7-11-25(22,27)4/h13,16,18,20-22,29-33H,6-12,14-15H2,1-5H3/t16-,18-,20-,21-,22-,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
FAB-MS m/z487 (M+Na)+
HR-MS 
ESI-MS m/z (relative intensity %)487 (M+Na)+ (0.5), 469 (M+Na-H2O)+ (100)

CARBON NMR

PROTON NMR

CD3OD
0143.2
0272.3
0375.7
0433.8
0557.6
06204.8
07122.0
08168.4
0936.1
1039.8
1121.6
1232.5
1348.3
1485.5
1531.9
1622.1
1753.5
1818.3
1924.0
2076.1
2126.7
2246.0
2321.9
2445.6
2571.6
2629.3
2729.3
CD3OD
01-Ha1.09 (dd, 13.7, 11.9)
01-Hb2.09 (13.7, 4.6)
02-Ha3.64 (ddd 11.9, 9.0, 4.6)
03-Ha3.34 (ddd 11.6, 9.0, 4.4)
04-Ha1.57 (td, 13.1, 11.6)
04-He 1.75 (dt, 13.1, 4.4)
05-H2.09 (dd, 13.1, 4.4)
07-H5.82 (d, 2.8)
09-Ha3.17 (ddd 11.0, 7.2, 2.4)
11-Ha1.69 (qd, 13.1, 4.9)
11-He1.81 (m)
12-Ha2.14 (td, 13.1, 5.0)
12-He1.86 (m)
15-Ha1.62 (ddd 11.9, 9.6, 2.0)
15-Hb1.95 (m)
16-Ha1.86 (m)
16-Hb1.90 (m)
17-H2.35 (t, 9.0)
18-Me0.86 (s)
19-Me0.95 (s)
21-Me1.28 (s)
22-Ha1.36 (m)
22-Hb1.51 (m)
23-Ha1.42 (m)
23-Hb1.42 (m)
24-Ha1.43 (m)
24-Hb1.43 (m)
26-Me1.19 (s)
27-Me1.19 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D27+12 ° (c 0.1; MeOH)
IR (KBr) ν max (cm-1) 
UV ( MeOH) λ max (log ε)242 (2.42)

CHROMATOGRAPHY

NP-HPLCcolumn Nucleosil 100-5, 15 cm long, 4.6 mm i.d., MeOH-CH2Cl2 (7:93), 1 ml.min-1, Ret 23.5 min.
TLC 
GLC 
RP-HPLCcolumn Wakosil 5C18, 25 cm long, 4.6 mm i.d., 45% MeOH, isocratic, 1 ml.min-1, Ret 30 min (E 15 min, 2d20E 22.5 min, 2dE 40 min):

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMAMIYA, Y. et al. (1995) Experientia 51, 363-367 Search more
IdentificationVÁNYOLÓS, A. et al. (2012) Sci. World J. ID 651275, 5p Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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