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9β,20-DIHYDROXYECDYSONE

Year of first isolation: 2004
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Silene italica ssp. nemoralis [Caryophyllaceae] » Images of Silene italica ssp. nemoralis Wikipedia: Silene italica ssp. nemoralis [Caryophyllaceae]
Occurence in animals:
 
9β,20-DIHYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3(C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O)O
Isomeric SMILES
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[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@]2(CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10S,13R,14S,17S)-2,3,9,14-tetrahydroxy-10,13-dimethyl-17-[(2R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID91390253
InChiKey
[ ChemIDPlus: search ]
AHHRNGCAWAPZKG-KCLJKRFISA-N
InChIInChI=1S/C27H44O8/c1-22(2,32)8-7-21(31)25(5,33)19-6-9-26(34)20-13-16(28)15-12-17(29)18(30)14-24(15,4)27(20,35)11-10-23(19,26)3/h13,15,17-19,21,29-35H,6-12,14H2,1-5H3/t15-,17+,18-,19-,21?,23+,24-,25+,26+,27-/m0/s1

MASS SPECTRUM

HRESI-MSMH+ = 497.3119, calculated for C27H45O8, 497.3114
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %)497 (14) [M+H]+, 479 (10), 461 (11), 446 (10), 441 (10), 436 (20), 423 (17), 361 (12), 339 (32), 324 (34), 317 (30), 301 (100)

CARBON NMR

PROTON NMR

DMSO-d5
0135.7
0268.5
0367.7
0425.3
0548.4
06201.2
07122.0
08164.5
0972.8
1042.3
1125.3
1231.4
1344.4
1483.4
1530.6
1620.4
1750.3
1822.5
1920.9
2075.6
2120.5
2276.3
2326.1
2441.4
2568.7
2629.0
2730.0
CD3OD
0137.2
0270.6
0369.9
0426.3
0550.3
06204.4
07124.3
08166.4
0975.3
1044.2
1127.0
1232.9
1346.2
1485.9
1532.3
1621.8
1752.4
1823.4
1921.6
2078.1
2120.8
2278.7
2327.6
2442.6
2571.5
2629.1
2729.8
DMSO-d5
01-Ha1.43 (dt, 14.8, 2.3)
01-He1.74
02-Ha3.67 (q, 2.2)
03-He2.96 (dt, 12.0, 3.5)
04-Ha2.11 (dt, 12.6, 3.5)
04-He1.79 (dt, 12.2, 4.9)
05-H2.52
07-H5.61 (s)
11-Ha1.52 (dd, 13.7, 8.7)
11-He2.21 (dt, 13.4, 9.6)
12-Ha1.86 (dd, 13.6, 9.6)
12-He1.67 (13.8, 8.8)
15-Ha1.65
15-Hb1.75
16-Ha1.55
16-Hb1.89 (qd, 12.0, 1.9)
17-H2.34 (t, 9.1)
18-Me1.13 (s)
19-Me1.24 (s)
21-Me1.07 (s)
22-H3.115 (d, 10.6)
23-Ha1.15
23-Hb1.50
24-Ha1.26 1.444 (ddd, 13.0, 11.7, 4.0)
24-Hb1.66
26-Me1.06 (s)
27-Me1.09 (s)
CD3OD
01-Ha1.67
01-He1.86
02-Ha3.88 (d, 3.1)
03-He3.195 (dt, 12.1, 3.5)
04-Ha2.34 (dt, 13.6, 3.9)
04-He2.01
05-H2.72 (dt, 4.5, 2.3)
07-H5.82 (s)
11-Ha1.69
11-He2.37 (dt, 14.0, 9.8)
12-Ha2.04
12-He1.83
15-Ha1.73*
15-Hb1.97*
16-Ha1.73*
16-Hb1.99*
17-H2.46 (t, 8.8)
18-Me1.235 (s)
19-Me1.37 (s)
21-Me1.21 (s)
22-H3.32
23-Ha1.315
23-Hb1.71
24-Ha 
24-Hb1.81
26-Me1.19 (s)
27-Me1.205 (s)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D24+14 ? ° (c 0.1 ; MeOH)
IR (KBr) ν max (cm-1)3450, 3400, 1660
UV (MeOH) λ max (log ε)206 (1.8) ; 243 (3.8)

CHROMATOGRAPHY

HPLCNP silica, CH2Cl2-iPrOH-H2O (125:40:3)
GLC
HPTLC
TLCsilica gel Merck, EtOAc-EtOH-H2O (8:1:0.5)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2004) Steroids 69(6), 389-394 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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