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22-DEHYDRO-12-HYDROXY-29-NOR-CYASTERONE

Year of first isolation: 1995
Formula:C28H40O9
Molecular weight:520
Occurence in plants:
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans var. atropurpurea Wikipedia: Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
22-DEHYDRO-12-HYDROXY-29-NOR-CYASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(COC1=O)CC(=O)C(C)(C2CCC3(C2(C(CC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)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]2C[C@H]([C@]2([C@]1(CC[C@@H]2[C@](C)(C(=O)C[C@@H]1COC(=O)[C@H]1C)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(9R,10R,13S,14R,17S)-2,3,12,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one
CAS-RN 
PubChem CID129681947
InChiKey
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UYTJADWYDZXNQA-WUOSKBNASA-N
InChIInChI=1S/C28H40O9/c1-13-14(12-37-24(13)34)7-23(33)27(4,35)21-5-6-28(36)16-8-18(29)17-9-19(30)20(31)11-25(17,2)15(16)10-22(32)26(21,28)3/h8,13-15,17,19-22,30-32,35-36H,5-7,9-12H2,1-4H3/t13?,14-,15+,17?,19?,20?,21+,22?,25-,26+,27-,28-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %) 
HR-MS 
MS (thermospray) m/z (negative ions)565 (M+HCOO)-, 547 M+HCOO-H2O).

CARBON NMR

PROTON NMR

C5D5N
0137.9
0267.9
0367.8
0432.3
0551.2
06203.3
07122.3
08163.1
0934.5
1038.8
1129.7
1270.9
1351.9
1485.9
1531.6
1622.9
1759.3
1812.2
1924.3
2078.9
2128.7
22219.0
2342.8
2439.7
2539.2
26179.4
2713.8
2871.4
C5D5N
01-Ha2.13
01-He1.98
02-Ha4.15 (m, w1/2=26)
03-He4.23 (m, w1/2=12)
04-Ha2.01
04-He1.74 (t, 15.0)
05-H3.05 (dd, 13.0, 3.5)
07-H6.30 (d, 2.0)
09-H3.75 (m, w1/2=16)
11-Ha2.46 (m)
11-He1.92
12-He5.04
15-Ha2.16
15-Hb1.94
16-Ha2.81 (m)
16-Hb2.25
17-H3.39 (t, 9.5)
18-Me0.77 (s)
19-Me1.10 (s)
21-Me1.56 (s)
22-H?
23-Ha3.63 (dd, 19.0, 3.5)
23-Hb3.30 (dd, 19.0, 10.0)
24-Ha2.65 (m)
25-H2.33 (dq, 11.0, 7.0)
27-Me1.18 (d, 7.0)
28-Ha4.78 (t, 8.5)
28-Hb3.84 (t, 8.5)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3394, 1754, 1705, 1652
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, column Spherisorb ODS-2, 10 ?m, 300 x 7.8 mm, flow-rate 3 ml.min-1, solvent iPrOH-H2O 1:5.6, temp. 23°C, Ret. 29.3 min (20E 17.2 min).

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCALGANO, M.P. et al. (1995) Tetrahedron 51, 12119-12126 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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