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1-HYDROXY-22-DEOXY-20,21-DEHYDRO-ECDYSONE

Year of first isolation: 2010
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
1-HYDROXY-22-DEOXY-20,21-DEHYDRO-ECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C1(CCC2C(=C)CCCC(C)(C)O)O
Isomeric SMILES
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[ ChemSpider: search ]
[C@@H]1([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]2C(=C)CCCC(C)(C)O)O)C)C)O » JSMol: View in 3D
IUPAC Name(1S,2R,3R,5R,9R,10R,13R,14S,17R)-1,2,3,14-tetrahydroxy-17-(6-hydroxy-6-methylhept-1-en-2-yl)-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID70691107
InChiKey
[ ChemIDPlus: search ]
HGRUQPLUHLGTLO-AISGDZIMSA-N
InChIInChI=1S/C27H42O6/c1-15(7-6-10-24(2,3)32)16-9-12-27(33)18-13-20(28)19-14-21(29)22(30)23(31)26(19,5)17(18)8-11-25(16,27)4/h13,16-17,19,21-23,29-33H,1,6-12,14H2,2-5H3/t16-,17+,19+,21-,22-,23-,25-,26-,27-/m1/s1

MASS SPECTRUM

HRESI-MS 463.3065 [M+H]+ (calculated for C27H43O6, 463.3059)
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %) 501 (44) [M+K]+, 485 (100) [M+Na]+, 463 (5) [M+H]+, 445 (7) [M+H-H2O]+, 427 (16) [M+H-2H2O]+ , 409 (9) [M+H-3H2O]+

CARBON NMR

PROTON NMR

CD3OD
0176.6
0268.6
0371.1
0433.7
0547.0
06205.9
07122.0
08166.9
0935.9
1044.0
1122.2
1231.3
1348.5
1485.1
1532.3
1625.3
1751.1
1817.6
1920.2
20150.3
21111.2
2239.9
2324.5
2444.7
2571.6
2629.32
2729.36
CD3OD
01-He3.82 (s, br)
02-Ha3.88 (t, 3.1)
03-He4.05 (s, br)
04-Ha1.77
04-He1.82 (t, 13.0, br)
05-H2.62 (dd, 13.0, 4.3)
07-H5.84 (d, 2.6)
09-H3.11 (t, 8.2, br)
11-Ha1.77
11-He1.71
12-Ha2.11 (d, 13.3, 4.8)
12-He1.56
15-Ha2.06
15-Hb1.67
16-Ha1.91
16-Hb1.91
17-H2.61
18-Me0.61 (s)
19-Me1.07 (s)
20-H2.99 (t, 9.2)
21-CH2=4.91 (s) (Z); 4.95 (s) (E)
22-Ha2.03
22-Hb2.09
23-Ha1.50
23-Hb1.58
24-Ha1.43 (td, 12.5, 4.7)
24-Hb1.49
26-Me1.18 (s)
27-Me1.18 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25.5+30 ° (c = 0.1; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)241.3 (3.9)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTAKÁCS, M. et al. (2010) Magn. Reson. Chem. 48, 386-391 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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