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3-EPI-2-DEOXY-20-HYDROXYECDYSONE

Year of first isolation: 1989
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Tinospora capillipes [Menispermaceae] » Images of Tinospora capillipes Wikipedia: <br />
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Occurence in animals:
Hirudo medicinalis [leech] » Images of Hirudo medicinalis Wikipedia: <br />
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3-EPI-2-DEOXY-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)O)O)O)C)O
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@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-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-RN22785-88-2
PubChem CID11812630
InChiKey
[ ChemIDPlus: search ]
JNTQSSGVHLUIBL-MBYAXLKMSA-N
InChIInChI=1S/C27H44O6/c1-23(2,31)10-9-22(30)26(5,32)21-8-13-27(33)18-15-20(29)19-14-16(28)6-11-24(19,3)17(18)7-12-25(21,27)4/h15-17,19,21-22,28,30-33H,6-14H2,1-5H3/t16-,17+,19+,21+,22-,24-,25-,26-,27-/m1/s1

MASS SPECTRUM

FAB-MS (positive mode) m/z465.3217 [M+H] +
CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)464 (M) +

CARBON NMR

PROTON NMR

C5D5N
0131.71
0227.43
0368.07
0438.62
0551.34
06203.43
07121.63
08166.02
0934.46
1037.95
1121.09
1231.99
1348.09
1484.18
1532.37
1621.40
1750.08
1817.84
1924.41
2076.85
2121.09
2277.54
2327.40
2442.56
2569.56
2629.96
2729.96
D2O
01-Ha1.22
01-He1.11
02-Ha1.4
02-He1.95
03-Ha3.54 (m, w1/2 = 25)
04-Ha1.43
04-He1.73
05-H2.13 (dd, 13, 4)
07-H5.97 (d, 2.5)
09-Ha3.20 (m, w1/2 = 22)
11-Ha1.8
11-He1.72
12-Ha 
12-He1.68
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.33 (dd, 9, 9)
18-Me0.86 (s )
19-Me0.92 (s )
21-Me1.23 (s )
22-H3.43 (dd, 10, 2)
23-Ha1.32
23-Hb1.68
24-Ha 
24-Hb 
26-Me1.22 (s )
27-Me1.23 (s )
C5D5N
01-Ha 
01-He 
02-Ha 
02-He 
03-Ha3.83
04-Ha 
04-He 
05-H2.29
07-H6.23
09-Ha3.70
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.02 (t, 9)
18-Me1,22 (s)
19-Me0.98 (s)
21-Me1.59 (s)
22-H3.88 (brd, 10.1)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.37 (s)
27-Me1.37 (s)

PHYSICAL PROPERTIES

M.P.247 °C
[α]D28+ 60.6 ° (c 0.201; MeOH)
IR (KBr) ν max (cm-1)3340, 2960, 1640, (enone), 1558, 1408, 1381, 1299, 1054, 963
UV (EtOH) λ max (log ε)243 (4.09)

CHROMATOGRAPHY

HPTLC 
TLC(silica gel Merck plates), solvent CHCl3-MeOH (4:1 v/v) Rf 0.30 (2D20E 0.53)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Calliphora assay: 33% (20-hydroxyecdysone = 100%)

REFERENCES

GeneralGALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1059-1067 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
First isolationGARCIA, M. et al. (1989) Invertebr. Reprod. Devel. 15, 57-68 Search more
First isolationSONG, C. et al. (1991) Chin. Chem. Lett. 2, 13-14 Search more
GeneralSUKSAMRARN, A. et al. (1997) Tetrahedron 53, 3145-3154 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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