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28-EPI-CYASTERONE

Year of first isolation: 2004
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
Eriophyton wallchii [Lamiaceae (alt. Labiatae)] » Images of Eriophyton wallchii Wikipedia: Eriophyton wallchii [Lamiaceae (alt. Labiatae)]
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: Cyathula capitata [Amaranthaceae]
Occurence in animals:
 
28-EPI-CYASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)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]1[C@@H](C(=O)O[C@H]1C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,4S,5S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one
CAS-RN 
PubChem CID11260931
InChiKey
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NEFYSBQJYCICOG-OENMBAOESA-N
InChIInChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15-,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
FAB-MS m/z521 [M+1]+, 503 [M+1-H2O]+, 485 [M+1-H2O]+, 449, 431, 363, 347, 345, 303, 285, 249, 201, 183, 157, 121
HR-FABMS m/z521.3152 [M+H]+, C29H45O8 requires 521.3114
HRAPCIMS m/z543.2968 [M+Na]+, C29H44O8Na, calcd. 543.2933

CARBON NMR

PROTON NMR

C5D5N
0138.0
0268.1
0368.0
0432.5
0551.4
06203.4
07121.8
08165.7
0934.5
1038.7
1121.0
1232.1
1348.2
1484.1
1531.9
1621.4
1750.1
1817.9
1924.5
2076.8
2121.0
2276.5
2330.9
2446.1
2538.7
26179.1
2716.4
2878.7
2914.4
C5D5N
01-Ha1.92 (m) 1.92
01-He2.14 (d, 13.2) 2.13 (dd, 13.3, 4.6)
02-Ha4.16 (d, 11.5) 4.16 (dt, 11.0, 3.6)
03-He4.21 (br s) 4.22 (brs, w1/2=9.4)
04-Ha1.79 (m) 1.81
04-He1.79 (m) 2.03
05-H3.00 (dd, 10.2, 2.8) 3.00 (dd, 13.2, 3.7)
07-H6.28 (s) 6.25 (d, 2.3)
09-H3.59 (m) 3.59 (brt, 8.6)
11-Ha1.76 (m) 1.75
11-He1.76 (m) 1.90
12-Ha2.63 (m) 2.60 (td, 13.0, 4.7)
12-He2.06 (m) 2.03
15-Ha2.22 (m) 1.92
15-Hb2.22 (m) 2.22
16-Ha2.46 (m) 2.47
16-Hb2.06 (m) 2.03
17-H2.87 (br t, 9.6) 2.86 (t, 9.2)
18-Me1.24 (s) 1.21 (s)
19-Me1.07 (s) 1.05 (s)
21-Me1.57 (s) 1.58 (s)
22-H3.88 (d, 10.6) 3.89 (dd, 11.0, 2.1)
23-Ha1.79 (m) 1.64
23-Hb1.79 (m) 1.80
24-H2.46 (m) 2.47
25-H2.33 (dq, 11.5, 6.5) 2.34 (dq, 11.5, 7.0)
27-Me1.30 (d, 6.5) 1.18 (d, 7.0)
28-H4.98 (t, 6.8) 4.98 (dq, 6.8, 6.6)
29-Me1.17 (d, 7.0) 1.29 (d, 6.6)

PHYSICAL PROPERTIES

M.P.248-250 °C ;
[α]D20? ° (c ; MeOH)
UV (MeOH) lmax (log e)242 (4.11) ;
IR (KBr) ν max (cm-1)3340, 2939, 2877, 1755 (?-lactone), 1665 (???-unsaturated ketone), 1652, 1446, 1385, 1319, 1262, 1228, 1191, 1148, 1053, 953, 927, 878

CHROMATOGRAPHY

HPLCRP-HPLC, column Shimadzu STR PREP-ODS, 6x15 mm i.d.), solvent MeOH-H2O (10:8), flow-rate 1 ml.min-1, ret. 15.2 min (cyasterone : 13.8 min)
GLC
HPTLC
TLCSilica plates, solvent CHCl3-MeOH (10:1), developed 3 times, Rf 0.38

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationYI, J. et al. (2004) Steroids 69, 809-815 Search more
GeneralOKUZUMI, K. et al. (2005) Org. Biomol. Chem. 3, 1227-1232 Search more

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