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9α,20-DIHYDROXYECDYSONE

Year of first isolation: 2003
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:
 
9α,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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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,9S,10S,13R,14S,17S)-2,3,9,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-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 CID10097359
InChiKey
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AHHRNGCAWAPZKG-GLRNUJIGSA-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

EI-MS m/z (relative intensity %)460 (2), 442 (2), 424 (2), 410 (4), 392 (4), 379 (1), 374 (6), 361 (59), 343 (43), 325 (19), 316 (1), 301 (94), 283 (96), 250 (54), 232 (28), 211 (40), 161 (22), 143 (46), 125 (40), 99 (62), 81 (100), 69 (63)
ESI-MS-MS m/z503 [M + Li]+ , 485 [M + Li - H2O]+
HREI-MS460.5998 [M - 2 H20]+, calculated for C27H40O6 460.5962

CARBON NMR

PROTON NMR

CD3OD
0137.6
0269.7
0369.8
0436.3
0551.4
06206.7
07123.8
08162.6
0976.6
1043.0
1130.9
1229.6
1349.1
1487.2
1531.6
1621.4
1750.4
1818.5
1929.6
2078.0
2121.2
2278.6
2327.5
2442.5
2571.4
2629.1
2729.9
CD3OD
01-Ha1.38 (t)
01-He2.06 (d)
02-Ha4.45 (dt 10.4, 3.9)
03-He3.96 (q, 2.6)
04-Ha2.44 (td, 13.3, 2.3)
04-He1.74 (d)
05-H2.56 (dd, 13.3, 3.9)
07-H5.85 (s)
11-Ha1.95
11-He2.04
12-Ha2.19 (td, 13.1, 4.6)
12-He1.83 (d)
15-Ha1.67
15-Hb1.98
16-Ha1.71
16-Hb2.01
17-H2.45
18-Me0.89 (s)
19-Me1.01 (s)
21-Me1.22 (s)
22-H3.32 (dd)
23-Ha1.31 (q)
23-Hb1.66 (t)
24-Ha1.44 (td, 11.6, 4.2)
24-Hb1.81 (t)

PHYSICAL PROPERTIES

M.P.269-271 °C ;
[α]D24- 10 ° (c 0.05; MeOH)
IR (KBr) ν max (cm-1)3460, 3380, 1660
UV (MeOH) λ max (log ε)228 (3.7) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

GeneralSUKSAMRARN, A et al. (1994) Tetrahedron 35, 4445-4448 Search more
First isolationPONGRÁCZ, Z. et al. (2003) J. Nat. Prod. 66(3), 450-451 Search more
GeneralSIMON, A. et al. (2004) Steroids 69(6), 389-394 Search more

see Important notice
© 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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