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3-EPI-22-DEOXY-16β,20-DIHYDROXYECDYSONE

Year of first isolation: 2000
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
 
Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: <br />
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3-EPI-22-DEOXY-16β,20-DIHYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ 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(C[C@@H]([C@@H]2[C@](C)(CCCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name 
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
JLGSDRXEKUKFKR-CAZXMIBQSA-N
InChIInChI=1S/C27H44O7/c1-23(2,32)8-6-9-26(5,33)22-21(31)14-27(34)16-11-18(28)17-12-19(29)20(30)13-24(17,3)15(16)7-10-25(22,27)4/h11,15,17,19-22,29-34H,6-10,12-14H2,1-5H3/t15-,17-,19-,20-,21-,22-,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
FAB-MS m/z503 [M+Na]+, 481 [M+H]+, 463 [M+H-H2O]+, 445 [M+H-2H2O]+, 427 [M+H-3H2O]+

CARBON NMR

PROTON NMR

C5D5N
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
CD3OD
01-Ha 
01-He 
02-Ha3.62 (m, w1/2 = 22)
03-Haoverlap with solvent
04-Ha 
04-He 
05-H2.08 (dd, 13.2, 4.6)
07-H5.81 (d, 2.4)
09-H3.17 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Haoverlap with solvent
17-H 
18-Me1.10 (s)
19-Me0.97 (s)
21-Me1.27 (s)
22-Ha 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.19 (s)
27-Me1.19 (s)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)243 nm (-) ;

CHROMATOGRAPHY

HPLCRP-HPLC column Wakosil 5C18, 250x4.6 mm, flow-rate 1 ml/min, solvent 45 % aqueous MeOH, Ret 15.5 min (20E 8.9 min).
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKAMBA, M. et al. (2000) Nat. Prod. Lett. 14, 469-476 Search more

see Important notice
© 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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