Welcome to online ecdysteroids database ! . .
Access data · History · Contact

20-HYDROXYECDYSONE 20,22-ETHYLIDENE

Year of first isolation: 2005
Formula:C29H46O7
Molecular weight:506
Occurence in plants:
Serratula coronata [Asteraceae] » Images of Serratula coronata Wikipedia: Serratula coronata [Asteraceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 20,22-ETHYLIDENE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)CCC(C)(C)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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@]1(C)[C@@H](CCC(C)(C)O)OC(O1)C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(2R,4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,4-dimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID12094560
InChiKey
[ ChemIDPlus: search ]
NCPGKYAKIIXLRA-RUVATRSJSA-N
InChIInChI=1S/C29H46O7/c1-16-35-24(9-10-25(2,3)33)28(6,36-16)23-8-12-29(34)18-13-20(30)19-14-21(31)22(32)15-26(19,4)17(18)7-11-27(23,29)5/h13,16-17,19,21-24,31-34H,7-12,14-15H2,1-6H3/t16-,17+,19+,21-,22+,23+,24-,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z524 [M + H + NH3]+, 507 [M + H]+, 489, 471, 463, 445, 427, 411, 409, 391, 370, 346, 279, 272, 246, 299, 187, 160, 143, 124, 99

CARBON NMR

PROTON NMR

D2O
0136.1 (t)
0268.5 (d)
0368.5 (d)
0432.3 (t)
0551.4 (d)
06?
07122.1 (d)
08?
0934.9 (d)
1039.1 (s)
11?
1231.7 (t)
1348.2 (s)
1486.1 (s)
15?
16?
1751.1 (d)
1818.0 (q)
1924.3 (q)
2087.3 (s)
2124.9 (q)
2286.1 (d)
23?
2441.7 (t)
2572.8 (s)
2629.0 (qq)
2729.0 (q)
MeCH<21.3 (q), 102.5 (d)
D2O
(minor)1.35 (d, 5.0); 5.36 (q, 5.0)
01-Ha1.38 (t, 13.4)
01-He1.88 (m)
02-Ha3.99 (m, w1/2 = 22)
03-He4.07 (m, w1/2 = 8)
04-Ha1.75 (t)
04-He1.75 (t)
05-H2.36 (t)
07-H5.97 (d, 2.5)
09-Ha3.11 (m, w1/2 = 22)
11-Ha1.73 (m)
11-He1.86 (m)
12-Ha1.95 (m)
12-He1.75 (m)
15-Ha1.65 (m)
15-Hb2.05 (m)
16-Ha1.88* (m)
16-Hb1.74* (m)
17-H2.31 (t, 9)
18-Me0.86 (s)
19-Me1.00 (s)
21-Me1.25 (s)
22-H3.85 (m, w1/2=18)
23-Ha1.63 (m)
23-Hb1.63 (m)
24-Ha1.75 (m)
24-Hb1.75 (m)
26-Me1.24 (s)
27-Me1.25 (s)
MeCH<1.40 (d, 5.0); 5.15 (q, 5.0)

PHYSICAL PROPERTIES

M.P.? °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)? (?) ;

CHROMATOGRAPHY

HPLCNP-HPLC Zorbax-SIL (250 x 9.4 mm) solvent dichloromethane-isopropanol-water (125:15:1), flow-rate 4 ml/min (Ret 35.5 min); Kromasil (250x 4.6 mm), solvent cyclohexane-isopropanol-water (100:30:2), flow-rate 1 ml/min (Ret 15.3 min).
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationODINOKOV, V.N. et al. (2005) Collect. Czech. Chem. Commun. 70, 2038-2052 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE