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26-HYDROXYPINNATASTERONE

Year of first isolation: 2001
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Vitex cymosa [Lamiaceae (alt. Labiatae)] » Images of Vitex cymosa Wikipedia: Vitex cymosa [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
26-HYDROXYPINNATASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCC(C(C)(CO)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)(CCC(C(CO)(C)O)O)O)O)C)C  » JSMol: View in 3D
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)(CC[C@H]([C@](CO)(C)O)O)O)O)C)C  » JSMol: View in 3D
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)(CC[C@H]([C@@](CO)(C)O)O)O)O)C)C  » JSMol: View in 3D
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)(CC[C@@H]([C@](CO)(C)O)O)O)O)C)C  » JSMol: View in 3D
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)(CC[C@@H]([C@@](CO)(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-[(2S)-2,5,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 152755867
InChiKey
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ZHWWWLBWFJXRQS-NSPYQFHBSA-N
InChIInChI=1S/C27H44O8/c1-23-13-20(31)19(30)12-17(23)18(29)11-16-15(23)5-8-24(2)21(6-10-27(16,24)35)25(3,33)9-7-22(32)26(4,34)14-28/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22?,23+,24+,25-,26?,27+/m0/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)460 (1), 442 (5), 363 (5), 345 (12), 327 (11), 301 (8), 285 (5), 267 (8), 259 (5), 225 (6), 211 (6), 173 (10), 129 (9), 115 (36), 105 (8), 97 (18), 91 (10), 69 (34), 55 (25), 43 (100)
FAB-MS m/z (relative intensity %)519 (100), 497 (31), 460 (60), 385 (34), 363 (48), 301 (18)

CARBON NMR

PROTON NMR

C5D5N
0137.8
0267.9
0367.8
0432.3
0551.2
06203.3
07121.4
08166.0
0934.2
1038.5
1120.9
1231.8
1347.9
1484.0
1531.6
1621.3
1749.9
1817.7
1924.3
2076.7
2121.5
2237.4
2326.5
2477.5
2571.4
2664.6
2724.5
C5D5N (2 epimers)
01-Ha 
01-Hb 
02-Ha4.25
03-He4.25
04-Ha 
04-He 
05-H3.02 (dd, 13, 4)
07-H6.28 (d, 1.7)
09-Ha3.69 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H3.07 (t, 9)
18-Me1.24 (s)
19-Me1.08 (s)
21-Me1.59 (s), 1.60 (s)
22-Ha 
22-Hb 
23-Ha 
23-Hb 
24-H3.89 (br dd, 10, 3)
26-CH2OH4.25
27-Me1.49 (s), 1.50 (s)

PHYSICAL PROPERTIES

M.P.- °C
[α]D25+ 36.0 ° (c 1%; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)

CHROMATOGRAPHY

HPLCRP-HPLC column Lichrosorb RP-18, 5 ?m, 4 mm i.d., 250 mm long, solvent MeOH-H2O 30:70, flow-rate 1.2 ml.min-1, Ret 8.24 and 8.59 min (2 isomers).
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationDOS SANTOS, T.C. et al. (2001) Fitoterapia 72, 215-220 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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