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2,22-DIDEOXY-23-HYDROXYECDYSONE

Year of first isolation: 2000
Formula:C27H44O5
Molecular weight:448
Occurence in plants:
 
Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
2,22-DIDEOXY-23-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)C[C@@H](CC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14S,17R)-17-((2R,4S)-4,6-dihydroxy-6-methylheptan-2-yl)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
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DOODXECBAIMQQQ-SKYCAMSBSA-N
InChIInChI=1S/C27H44O5/c1-16(12-18(29)15-24(2,3)31)19-8-11-27(32)21-14-23(30)22-13-17(28)6-9-25(22,4)20(21)7-10-26(19,27)5/h14,16-20,22,28-29,31-32H,6-13,15H2,1-5H3/t16-,17+,18+,19-,20+,22+,25-,26-,27-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)448 [M]+, 430, 420, 415, 412, 402, 397, 384, 346, 344, 313 (C20 -C22 cleavage - H2O), 303 (C17-C20 cleavage), 285 (C17-C20 cleavage - H2O), 273, 257, 233, 215, 207
FAB-MS m/z449 [M+H]+

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-Ha 
02-He 
03-He3.97 (m, w1/2 = 9)
04-Ha 
04-He 
05-H2.41 (dd, 12.8, 3.7)
07-H5.80 (d, 2.4)
09-H 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.719 (s)
19-Me0.959 (s)
20-H 
21-Me0.993 (d, 5.9)
22-Ha 
23-H4.03 (m)
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.276 (s)
27-Me1.236 (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 50% aqueous MeOH for 30 min, then 60% MeOH, Ret 51.5 min (2dE 25.0 min); solvent 55% MeOH, Ret 53.3 min (2dE 18.6 min).
GLC
TLCMerck Kieselgel 60 F254 (20x20 cm, 1 mm thick), developed twice with CHCl3-MeOH (4:1, v/v), Rf 0.75 (2dE 0.79)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKAMBA, M. et al. (2000) Nat. Product Lett. 14, 349-356 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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