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

20,22-O-(R-3-METHOXYCARBONYL) PROPYLIDENE-20-HYDROXYECDYSONE

Year of first isolation: 2012
Formula:C32H50O9
Molecular weight:578
Occurence in plants:
Achyranthes bidentata [Amaranthaceae] » Images of Achyranthes bidentata Wikipedia: Achyranthes bidentata [Amaranthaceae]
Occurence in animals:
 
20,22-O-(R-3-METHOXYCARBONYL) PROPYLIDENE-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C5(C(OC(O5)CCC(=O)OC)CCC(C)(C)O)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](O[C@H](O1)CCC(=O)OC)CCC(C)(C)O)O)C)C » JSMol: View in 3D
IUPAC Namemethyl 3-[(2R,4R)-5-(3-hydroxy-3-methylbutyl)-4-methyl-4-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,3-dioxolan-2-yl]propanoate
CAS-RN 
PubChem CID123962103
InChiKey
[ ChemIDPlus: search ]
SEQDERYTYFVWJV-WDHGFTPFSA-N
InChIInChI=1S/C32H50O9/c1-28(2,37)12-11-25-31(5,41-27(40-25)8-7-26(36)39-6)24-10-14-32(38)19-15-21(33)20-16-22(34)23(35)17-29(20,3)18(19)9-13-30(24,32)4/h15,18,20,22-25,27,34-35,37-38H,7-14,16-17H2,1-6H3/t18-,20-,22+,23-,24-,25?,27+,29+,30+,31+,32+/m0/s1

MASS SPECTRUM

EIS-MS (-) m/z 577 [M-H]-
ESI-MS (+) m/z 601 [M+Na]+, 579 [M+H]+
HREI-MS m/z578.3450 [M]+ (calcd. for C32H50O9, 578.3449)
CI-MS (NH3) m/z 

CARBON NMR

PROTON NMR

CD3OD
0137.3 (t)
0268.7 (d)
0368.5 (d)
0432.8 (t)
0551.8 (d)
06206.5 (s)
07122.2 (d)
08167.6 (s)
0935.1 (d)
1039.2 (s)
1121.5 (t)
1232.2 (t)
1349.0 (s)*
1485.2 (s)
1531.7 (t)
1622.6 (t)
1751.4 (d)
1817.6 (q)
1924.4 (q)
2085.3 (s)
2123.4 (q)
2286.6 (d)
2324.6 (t)
2442.2 (t)
2571.1 (s)
2629.5 (q)
2728.9 (q)
[MCP]-1'103.9 (d)
[MCP]-2'31.0 (t)
[MCP]-3'29.2 (t)
[MCP]-4'175.6 (s)
[MC]-OMe52.1 (q)
CD3OD
01-Ha1.41 (m)
01-He1.78 (m)
02-Ha3.82 (m)
03-He3.94 ((m)
04-Ha1.71 (m)
04-He1.71 (m)
05-H2.36 (m)
07-H5.81 (s)
09-H3.13 m)
11-Ha1.68 (m)
11-He1.79 (m)
12-Ha2.09 (m)
12-He1.83 (m)
15-Ha1.61 (m)
15-Hb1.91 (m)
16-Ha1.92 (m)
16-Hb1.92 (m)
17-H2.34 (m)
18-Me0.84 (s)
19-Me0.95 (s)
21-Me1.15 (s)
22-H3.64 (m)
23-Ha1.54 (m)
23-Hb1.54 (m)
24-Ha1.72 (m)
24-Hb1.45 (m)
26-Me1.19 (s)
27-Me1.20 (s)
[MCP]-H1'4.97 (t, 4.0)
[MCP]-H2'1.90 (m)
[MCP]-H3'2.41 (t, 7.2)
[MC]-OMe3.65 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 34.0 ° (c = 0.20 ; MeOH)
IR (KBr) ν max (cm-1)3423, 2964, 1737, 1654, 1382, 1139, 1058
UV (MeOH) λ max (log ε) nm242 (3.75) ;

CHROMATOGRAPHY

RP-HPLCColumn Fuji-C18 10 m, mobile phase MeOH-H20 (70:30 v/v), flow rate 10 mL/min, Ret 41 min
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZHANG, M. et al. (2012) Molecules 17, 3324-3332 Search more
GeneralZHANG, M. et al. (2012) Personal communication to Ecdybase editors 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