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MAKISTERONE C 2,3;20,22-DIACETONIDE

Year of first isolation: 2009
Formula:C35H56O7
Molecular weight:588
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: Silene viridiflora [Caryophyllaceae]
Occurence in animals:
 
MAKISTERONE C 2,3;20,22-DIACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCCC(CC1C(OC(O1)(C)C)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC6C(C5)OC(O6)(C)C)C)C)O)C(C)(C)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@@H]3[C@H]1OC(O3)(C)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@H](OC(O1)(C)C)CC(C(C)(C)O)CC)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@@H]3[C@H]1OC(O3)(C)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@H](OC(O1)(C)C)C[C@H](C(C)(C)O)CC)O)C)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@@H]3[C@H]1OC(O3)(C)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@H](OC(O1)(C)C)C[C@@H](C(C)(C)O)CC)O)C)C » JSMol: View in 3D
IUPAC Name(1R,2R,4S,8R,10R,14S,17S,18R)-17-[(4R,5R)-5-[(2R)-2-ethyl-3-hydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-14-hydroxy-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one
CAS-RN 
PubChem CID70686961
InChiKey
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IRWSUZLZJGRFDN-OKPAJNHESA-N
InChIInChI=1S/C35H56O7/c1-11-20(29(2,3)37)16-28-34(10,42-31(6,7)41-28)27-13-15-35(38)22-17-24(36)23-18-25-26(40-30(4,5)39-25)19-32(23,8)21(22)12-14-33(27,35)9/h17,20-21,23,25-28,37-38H,11-16,18-19H2,1-10H3/t20-,21+,23+,25-,26+,27+,28-,32-,33-,34-,35-/m1/s1

MASS SPECTRUM

HR-ESI-MS611.3913, calculated 611.3924 for C35H56O7Na+
ESI-MS m/z (relative intensity %)627 (42) [M+K]+, 612 (41) [M+H+Na]+, 611 (100) [M+Na]+, 588 (6.4) [M]+, 576 (55) [M+H+Na-2H2O]+, 563 (41), 545 (55), 531 (40) [M+H-Me2CO]+, 513 (42) [M+H-H2O-Me2CO]+, 495 (20) [M+H-2H2O-Me2CO]+, 473 (17) [M+H-2Me2CO]+, 455 (24) [M+H-H2O-2Me2CO]+, 437 (25) [M+H-2H2O-2Me2CO]+, 419 (56) [M+H-3H2O-2Me2CO]+, 391 (86), 381 (28), 338 (25), 333 (29)

CARBON NMR

PROTON NMR

CD3OD
0138.9
0273.8
0373.3
0427.8
0552.6
06205.8
07122.0
08167.0
0935.9
1039.0
1121.8
1232.5
1349.0
1485.4
1531.8
1622.7
1750.4
1817.8
1924.2
2086.1
2122.6
2281.5
2330.9
2450.0
2574.4
2626.8
2727.9
2825.3
2914.9
Me2C [2,3]108.1, 27.2, 29.7
Me2C [20,22]109.6, 26.8, 29.0
CD3OD
01-Ha1.23 (t, ~14.5)
01-He1.99 (d, ~15.0)
02-Ha4.27 (dt, 9.4, 5.0)
03-He4.30 (q, 4.0)
04-Ha1.91-2.01 (m)
04-He1.91-2.01 (m)
05-H2.245 (dd, 9.3, 8.2)
07-H5.80 (d, 2.5)
09-H2.935 (ddd, 11.7, 7.0, 2.5)
11-Ha1.65-1.70 (m)
11-He1.74-1.81 (m)
12-Ha2.105 (td, 13.0, 4.9)
12-He1.81-1.89 (m)
15-Ha1.58-1.67 (m)
15-Hb1.96-2.02 (m)
16-Ha1.83-1.90 (m)
16-Hb2.03-2.10 (m)
17-H2.304 (t, 8.9)
18-Me0.825 (s)
19-Me0.96 (s)
21-Me1.173 (s)
22-H3.834 (d, 10.0)
23-Ha1.16-1.25 (m)
23-Hb1.71-1.79 (m)
24-Ha1.45 (ddd, 12.5, 6.6, 3.0)
26-Me1.16 (s)
27-Me1.18 (s)
28-Ha1.18-1.24 (m)
28-Hb1.63-1.72 (m)
29-Me1.006 (t, 7.5)
Me2C [2,3]1.325 (s); 1.39 (s)
Me2C [20,22]1.320 (s); 1.47 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+65 ° (c 0.005; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)240 (3.4)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2009) Helv. Chim. Acta 92, 753-761 Search more

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