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22-OXO-20-HYDROXYECDYSONE

Year of first isolation: 1992
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Serratula tinctoria [Asteraceae] » Images of Serratula tinctoria Wikipedia: <br />
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Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: <br />
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Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: <br />
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Occurence in animals:
 
22-OXO-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(=O)CCC(C)(C)O)O)O
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(CC[C@@H]2[C@](C)(C(=O)CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-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 CID14442966
InChiKey
[ ChemIDPlus: search ]
IILSBUXFTVZCJS-DPROJNMLSA-N
InChIInChI=1S/C27H42O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-21,29-30,32-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z496 (M+H+NH3)+, 479 (M+H)+, 461, 443, 425, 363, 345, 329, 327, 320
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.0
0268.1
0368.1
0432.7
0551.4
06203.4
07121.8
08165.6
0932.4
1038.7
1121.7
1231.8
1348.2
1484.1
1531.9
1621.7
1751.6
1817.7
1924.4
2081.4
2125.7
22217.0
2345.9
2438.4
2569.0
2630.0
2729.9
CD3OD
0137.37
0268.70
0368.51
0432.74
0551.80
06206.36
07122.19
08167.58
0935.11
1039.28
1121.51
1232.48
13=49.0
1485.14
1531.81
1621.69
1751.64
1817.91
1924.39
2082.02
2125.37
22217.29
2332.86
2438.14
2570.68
2629.21
2729.21
D2O
01-Ha1.40 (dd, 13,12)
01-Hb1.89
02-Ha3.88 (m, w1/2=22)
03-He3.04 (m, w1/2=8)
04-Ha1.78
04-He1.78
05-H2.42 (dd, 14,4.5)
07-H5.84 (d, 2.5)
09-Ha2.98 (m, w1/2=22)
11-Ha1.78
11-He1.93
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha1.64
16-Hb1.78
17-H2.59 (m )
18-Me0.87 (s )
19-Me1.02 (s )
21-Me1.51 (s )
23-Ha2.80 (m, w1/2=19)
23-Hb2.80 (m )
24-Ha1.76
24-Hb1.76
26-Me1.25 (s )
27-Me1.25 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCNP-HPLC, Ret 10.2 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O, 125:25:2 v/v/v, flow-rate 1ml.min-1) (20E 25.2 min); Ret 16.7 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent isoC8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml. min-1) (20E 22.6 min). RP-HPLC, Ret 14.0 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent linear gradient 20 to 70% ACN in 1? TFA in H2O, flow-rate 1ml.min-1) (20E 12.3 min)

BIOLOGICAL ACTIVITIES

 

REFERENCES

GeneralHEDTMAN, U. et al. (1989) Angew. Chem., Int. Ed. Engl. 28, 1515-1518 Search more
GeneralHEDTMAN, U. et al. (1991) Tetrahedron 47, 3753-3772 Search more
First isolationRUDEL, D. et al. (1992) Planta Med. 58, 358-364 Search more
IdentificationVOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 Search more
IdentificationKIUCHI, M. et al. (2003) Arch. Insect Biochem. Physiol. 52, 35-44 Search more
IdentificationTAN, C. et al. (2003) Acta Pharm. Sinica 83, 760-762 Search more

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