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24-EPI-PTEROSTERONE

Year of first isolation: 1996
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Athyrium yokocense [Athyriaceae] » Images of Athyrium yokocense Wikipedia: Athyrium yokocense [Athyriaceae]
Occurence in animals:
 
24-EPI-PTEROSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)O
Isomeric SMILES
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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@@H](C[C@H](C(C)C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID11027254
InChiKey
[ ChemIDPlus: search ]
UMMBJCYNGLCGEF-GCOWLVGZSA-N
InChIInChI=1S/C27H44O7/c1-14(2)18(28)12-23(32)26(5,33)22-7-9-27(34)16-10-19(29)17-11-20(30)21(31)13-24(17,3)15(16)6-8-25(22,27)4/h10,14-15,17-18,20-23,28,30-34H,6-9,11-13H2,1-5H3/t15-,17-,18+,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %) 
HR-MS481.3172 [M+H]+
SI-MS m/z481 (M+H)+, 463, 445, 427

CARBON NMR

PROTON NMR

C5D5N
0138.0
0268.1
0368.1
0432.4
0551.4
06203.4
07121.7
08166.1
0934.4
1038.7
1121.1
1232.0
1348.1
1484.2
1531.8
1621.7
1750.0
1817.9
1924.4
2076.8
2121.3
2273.4
2337.5
2473.5
2535.0
2619.5
2718.6
C5D5N
01-Ha1.97 (m )
01-Hb2.17 (m )
02-Ha4.19 (br, d, 11.9)
03-He4.24 (br, s)
04-Ha1.80 (m )
04-He2.02 (m )
05-H3.03 (m )
07-H6.25 (d )
09-Ha3.60 (m )
11-Ha1.80 (m )
11-He1.90 (m )
12-Ha2.10 (m )
12-He2.66 (m )
15-Ha1.89 (m )
15-Hb1.89 (m )
16-Ha2.36 (m )
16-Hb2.50 (m )
17-H3.08 (m )
18-Me1.25 (s )
19-Me1.09 (s )
21-Me1.66 (s )
22-H4.13 (br, s )
23-Ha1.87 (m )
23-Hb2.03 (m )
24-H4.50 (br, d, 10.1)
25-H1.85 (m )
26-Me1.01 (d, 6.4)
27-Me1.10 (d, 6.4)

PHYSICAL PROPERTIES

M.P.151-152 °C
[α]D25+ 66 ° (c 0.63 ; MeOH)
IR (KBr) ν max (cm-1)3400 (OH), 1660 (C=Oand C=C);
UV (EtOH) λ max (log ε)2.43 (4.03); 336 (2)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC (ODS) using MeOH-H2O (1:1)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationOHTA, S. et al. (1996) Phytochemistry 41, 745-747 Search more
SynthesisSUKSAMRARN, A. et al. (1999) Tetrahedron 55, 255-260 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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