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20-HYDROXYECDYSONE 2-CINNAMATE

Year of first isolation: 1971
Formula:C36H50O8
Molecular weight:610
Occurence in plants:
Dacrydium intermedium [Podocarpaceae] » Images of Dacrydium intermedium Wikipedia: Dacrydium intermedium [Podocarpaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE 2-CINNAMATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)OC(=O)C=CC5=CC=CC=C5)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)/C=C/c1ccccc1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] (E)-3-phenylprop-2-enoate
CAS-RN 
PubChem CID101704303
InChiKey
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DXVLKBLMTNJMNC-JPKZWUAGSA-N
InChIInChI=1S/C36H50O8/c1-32(2,41)16-15-30(39)35(5,42)29-14-18-36(43)24-19-26(37)25-20-27(38)28(21-33(25,3)23(24)13-17-34(29,36)4)44-31(40)12-11-22-9-7-6-8-10-22/h6-12,19,23,25,27-30,38-39,41-43H,13-18,20-21H2,1-5H3/b12-11+/t23-,25-,27+,28-,29-,30+,33+,34+,35+,36+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)610 [M]+, 592, 574, 556, 494 [M-116 (side chain)]+, 426 [M-148 (cinnamic acid) - 36]+, 345 [M-148 -117]+, 148 (cinnamic acid), 147 (100%) (cinnamoyloxy), 131 (cinnamoyl).
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
C5D5N
01-Ha 
01-Hb 
02-Ha5.42 (m, w1/2=20)
03-He4.37 (m, w1/2=9)
04-Ha 
04-He 
05-H 
07-H6.25
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.21 (s )
19-Me1.11 (s )
21-Me1.57 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me1.38 (s )
27-Me1.38 (s )
Othervinylic 6.60, 7.92 (d, 16); aromatic 7.38

PHYSICAL PROPERTIES

M.P.258-260 °C ;
[α]D20 
IR (KBr) ν max (cm-1)3400 (OH), 1700 (carbonyl), 1646 (cyclohexenone).
UV (EtOH) λ max (log ε)276 (4.332), 248 (sh), 223 (4.301), 200 (4.301);

CHROMATOGRAPHY

HPTLC 
TLC on silicaRf 0.44 (CHCl3-EtOH 9:1 v/v, two elutions); Rf 0.53 (CHCl3-EtOH 4:1) RP-TLC on paraffin coated silica gel Rf 0.00 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.00 (MeOH-H2O 65:35)
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Musca assay: 10% (20-hydroxyecdysone = 100%)

REFERENCES

First isolationRUSSEL, G.B. et al. (1971) J. Chem. Soc., Chem. Commun., 71 Search more
GeneralRUSSEL, G.B. et al. (1972) Aust. J. Chem. 25, 1935-1941 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 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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