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3β,5α,14α-TRIHYDROXYERGOSTA-7,22-DIEN-6-ONE

Year of first isolation: 1983
Formula:C28H44O4
Molecular weight:444
Occurence in plants:
 
Occurence in animals:
 
3β,5α,14α-TRIHYDROXYERGOSTA-7,22-DIEN-6-ONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(C)C=CC(C)C1CCC2(C1(CCC3C2=CC(=O)C4(C3(CCC(C4)O)C)O)C)O
Isomeric SMILES
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C1[C@]2([C@](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/[C@@H](C(C)C)C)O)C)O)C » JSMol: View in 3D
IUPAC Name(3S,5R,9R,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5,14-trihydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID21772318
InChiKey
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WWJJKDQPDURSCE-IHEPTZRRSA-N
InChIInChI=1S/C28H44O4/c1-17(2)18(3)7-8-19(4)21-11-14-27(31)23-15-24(30)28(32)16-20(29)9-12-26(28,6)22(23)10-13-25(21,27)5/h7-8,15,17-22,29,31-32H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,21+,22-,25+,26+,27+,28-/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z444 (M)+, 426 (M-H2O)+, 411 (M-H2O-CH3)+, 408 (M-2H2O)+, 393 (M-2H2O-CH3)+, 390 (M-3H2O)+
HR-MS 

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 
28 
CDCl3
01-Ha 
01-Hb 
02-Ha 
02-He 
03-He3.93 (m )
04-Ha 
04-He 
07-H5.81 (d, 2.5)
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.68 (s )
19-Me0.94 (s )
21-Me1.02 (d, 6.2)
22-H 
23-H 
24-H 
25-H 
26-Me0.82 (d, 6.6)
27-Me0.84 (d, 6.6)
28-Me0.92 (d, 6.6)

PHYSICAL PROPERTIES

M.P.267-269 °C ;
[α]D28+ 65 ° (c 0.76; CHCl3).
IR (KBr) ν max (cm-1)3350 (OH), 1620 (C=C), 1670 (cyclohexenone);
UV (EtOH) λ max (log ε)242 (4.16) ;

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

SynthesisVALISOLALAO, J. et al. (1983) Tetrahedron 39, 2779-2785 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
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