Welcome to online ecdysteroids database ! . .
Access data · History · Contact

3-EPI-2-DEOXYECDYSONE

Year of first isolation: 1981
Formula:C27H44O5
Molecular weight:448
Occurence in plants:
Blechnum vulcanicum [Blechnaceae] » Images of Blechnum vulcanicum Wikipedia: Blechnum vulcanicum [Blechnaceae]
Acanthophyllum gypsophiloides [Caryophyllaceae] » Images of Acanthophyllum gypsophiloides Wikipedia: Acanthophyllum gypsophiloides [Caryophyllaceae]
Occurence in animals:
Schistocerca gregaria [Orthoptera] » Images of Schistocerca gregaria Wikipedia: Schistocerca gregaria [Orthoptera]
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
3-EPI-2-DEOXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C)O)C(CCC(C)(C)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID21724361
InChiKey
[ ChemIDPlus: search ]
CRAPXAGGASWTPU-DUIYOXMUSA-N
InChIInChI=1S/C27H44O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28-29,31-32H,6-14H2,1-5H3/t16-,17+,18+,19-,21-,22+,25+,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)448 (M)+ (0.2), 430 (2), 412 (5), 397 (5), 396 (3), 379 (3), 361 (1), 332 (8), 314 (11), 299 (5), 284 (6), 283 (9), 263 (8), 251 (5), 99 (100), 81 (54).
EI* m/z (relative intenzity %)430 (4), 394 (4), 343 (5), 332(8), 284 (18), 99 (100), 81 (68)
CI-MS (isobutane) m/z449 (M+H)+

CARBON NMR

PROTON NMR

C5D5N
0135.6 (t )
0231.2 (t )
0369.1 (d )
0434.3 (t )
0557.2 (d )
06201.9 (s )
07121.3 (d )
08165.8 (s )
0934.0 (d )
1036.8 (s )
1120.8 (t )
1231.6 (t )
1347.6 (s )
1483.8 (s )
1531.9 (t )
1626.7 (t )
1748.3 (d )
1815.8 (q )
1923.9 (q )
2043.0 (d )
2115.7 (q )
2274.0 (d )
2325.6 (t )
2442.5 (t )
2569.7 (s )
2630.0 (q )
2730.3 (q )
DMSO-d6
0128.40
0227.91
0362.61
0431.75
0550.18
06201.96
07119.93
08164.84
0933.16
1035.77
1120.30
1230.43
1346.92
1482.75
1530.16
1625.45
1746.92
1815.03
1923.45
2041.49
2112.60
2272.27
2324.14
2440.96
2568.55
2629.49
2728.97
DMSO-d6
01-Ha1.375
01-He1.488
02-Ha1.643
02-He1.529
03-He3.827
04-Ha1.692
04-He1.405
05-H2.274
07-H5.643
09-Ha3.076
11-Ha1.635
11-He1.503
12-Ha2.026
12-He1.623
15-Ha1.847
15-Hb1.527
16-Ha1.843
16-Hb1.383
17-H1.952
18-Me0.617
19-Me0.881
20-H1.616
21-Me0.851
22-H3.430
23-Ha1.366
23-Hb1.177
24-Ha1.655
24-Hb1.281
26-Me1.094
27-Me1.080
CD3OD
01-Ha 
01-He 
02-Ha 
03-Ha3.57 (m, w1/2=22)
04-Ha 
04-He 
05-H 
07-H5.82 (d, 2.2)
09-Ha3.18 (m )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.726 (s)
19-Me0.915 (s)
21-Me0.944 (d, 6)
22-H3.59 (brd, 10.5)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.186 (s)
27-Me1.186 (s)

PHYSICAL PROPERTIES

M.P.264-265 °C ;
[α]D20+ 98 ° (CHCl3)
IR (KBr) ν max (cm-1)3450 (OH), 1650 (cyclohexenone) ;
UV (EtOH) λ max (log ε)243 (4.061) ;

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel, Rf 0.60 (CHCl3-MeOH 4:1 v/v) (0.56 for 2DE)
GLC 
NP-HPLCCH2Cl2-iPrOH-MeOH 87:10:3 v/v/v (Russel et al.);
RP-HPLCReverse-phase column (15 cm long, 4.6 mm i.d.) eluted at 1 ml.min-1 with a linear gradient (20 min) 40-> 80% methanol in H2O, retention time 20.0 min) (20E 9.4 min).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationRUSSEL, G.B. et al. (1981) Phytochemistry 20, 2407-2410 Search more
First isolationISAAC, R.E. et al. (1981) Chem. Commun., 418-420 Search more
GeneralHETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 Search more
GeneralREES, H.H. et al. (1985) Methods Enzymol. 111, 377-410 Search more
First isolationKAMBA, M. et al. (1995) J. Seric. Sci. Jpn. 64, 333-343 Search more
IdentificationTULEUOV, B.I. et al. (2018) Russian Chemical Bulletin, International Edition 67(4): 633-666 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE