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26-HYDROXYMAKISTERONE C

Year of first isolation: 2008
Formula:C29H48O8
Molecular weight:524
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
26-HYDROXYMAKISTERONE C

STRUCTURE DESCRIPTORS

Canonical SMILESCCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)(CO)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](CC(C(CO)(C)O)CC)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)([C@@H](C[C@H]([C@@](CO)(C)O)CC)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)([C@@H](C[C@H]([C@](CO)(C)O)CC)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)([C@@H](C[C@@H]([C@@](CO)(C)O)CC)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)([C@@H](C[C@@H]([C@](CO)(C)O)CC)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101851587
InChiKey
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ZBEOVYLJIQOXKK-YPNFDIQASA-N
InChIInChI=1S/C29H48O8/c1-6-16(27(4,35)15-30)11-24(34)28(5,36)23-8-10-29(37)18-12-20(31)19-13-21(32)22(33)14-25(19,2)17(18)7-9-26(23,29)3/h12,16-17,19,21-24,30,32-37H,6-11,13-15H2,1-5H3/t16-,17+,19+,21-,22+,23+,24-,25-,26-,27?,28-,29-/m1/s1

MASS SPECTRUM

HR-ESI-MS m/z547.3276 [M+Na]+ (calculated for C29H48O8Na : 547.3247)
ESI-MS/MS m/z525 [M+H]+, 507 [M+H-H20]+, 489 [M+H-2H20]+, 471 [M+H-3H2O]+, 453 [M+H-4H2O]+

CARBON NMR

PROTON NMR

CD3OD
0137.36
0268.71
0368.51
0432.87
0551.80
06206.44
07122.14
08167.86
0935.10
1039.26
1121.63
1232.49
13~49.17
1485.19
1531.81
1621.63
1750.39
1818.03
1924.41
2077.91
2120.82
2277.57
2333.40
2445.30
2576.41
2669.08
2721.01
2825.04
2914.30
CD3OD
01-Ha1.43
01-He1.79
02-Ha3.84 (ddd, 12.0, 4.2, 3.0)
03-He3.95 (q, 3, 3, 3)
04-Ha1.68-1.76
04-He1.68-1.76
05-H2.39 (dd, 12.8, 4.8)
07-H5.81 (d, 2.6)
09-Ha3.16 (m, 11.5, 7, 2.6)
11-Ha1.71
11-He1.80
12-Ha2.13 (td, 13, 13, 5)
12-He1.87
15-Ha1.96
15-Hb1.62
16-Ha1.78
16-Hb2.04
17-H2.39 (dd, 10.0, 8.8)
18-Me0.896 (s)
19-Me0.967 (s)
21-Me1.196 (s)
22-H3.45 (dd, 10.8, 2.4)
23-Ha1.45
23-Hb1.37
24-H1.66
26-Ha3.58 (d, 11.7)
26-Hb3.35 (d, 11.7)
27-Me1.061 (s)
28-Ha1.79
28-Hb1.20
29-Me1.030 (t, 7.4, 7.4)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 64.0 ° (c 0.075; EtOH)
IR (KBr) ν max (cm-1)3409 (OH), 1654 (C=O), 1056 (C-O)
UV (MeOH) λ max (log ε)

CHROMATOGRAPHY

HPLCRP-HPLC Separon SGX C-18 (250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min (Ret 55.0 min); NP-HPLC Silasorb 600 (250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min (Ret 28.0 min); and two other systems.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationBUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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