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20-HYDROXYECDYSONE-20,22-ACETONIDE 25-ACETATE

Year of first isolation: 2010
Formula:C32H50O8
Molecular weight:562
Occurence in plants:
Silene viridiflora [Caryophyllaceae] » Images of Silene viridiflora Wikipedia: Silene viridiflora [Caryophyllaceae]
Occurence in animals:
 
20-HYDROXYECDYSONE-20,22-ACETONIDE 25-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC(C)(C)CCC1C(OC(O1)(C)C)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O
Isomeric SMILES
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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)OC(=O)C)OC(O1)(C)C)O)C)C » JSMol: View in 3D
IUPAC Name[2-methyl-4-[(4R,5R)-2,2,5-trimethyl-5-[(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-4-yl]butan-2-yl] acetate
CAS-RN 
PubChem CID12094571
InChiKey
[ ChemIDPlus: search ]
BFWMUJOITOHIFF-IBVQXDPUSA-N
InChIInChI=1S/C32H50O8/c1-18(33)38-27(2,3)12-11-26-31(8,40-28(4,5)39-26)25-10-14-32(37)20-15-22(34)21-16-23(35)24(36)17-29(21,6)19(20)9-13-30(25,32)7/h15,19,21,23-26,35-37H,9-14,16-17H2,1-8H3/t19-,21-,23+,24-,25-,26+,29+,30+,31+,32+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HR-ESI-MS 563.35709 [M+H]+, calculated 563.35784 for C32H51O8; 545.34671 [M+H-H2O]+, calculated 545.34728 for C32H49O7
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

D2O
0137.9
0269.9
0369.8
0433.8
0552.9
06*
07123.6
08*
0936.5
1040.7
1122.5
1233.2
1349.4
1487.7
1533.0
1623.6
1752.1
1819.4
1925.7
2088.5
2123.6
2284.7
2325.6
2440.2
2586.7
25-OAc176.1, 24.7 (CH3)
2627.8
2728.1
C(CH3)2110.5, 28.5 (CH3a), 30.8 (CH3b)
D2O
01-Ha1.38 (t, 13)
01-He1.88
02-Ha3.99 (m, w1/2 = 22)
03-He4.07 (m, w1/2 = 8)
04-Ha1.75
04-He1.75
05-H2.36 (t)
07-H5.97 (d, 2.5)
09-H3.11 (m, w1/2 = 22)
11-Ha1.73
11-He1.86
12-Ha1.95
12-He1.95
15-Ha1.68a
15-Hb1.98a
16-Ha2.03b
16-Hb1.93b
17-H2.28 (t, 9)
18-Me0.819 (s)
19-Me1.000 (s)
21-Me1.240 (s)
22-H3.88 (m)
23-Ha1.59
23-Hb1.59
24-Ha1.96
24-Hb1.96
25-OAc2.048 (s) (CH3)
26-Me1.462 (s)
27-Me1.491 (s)
C(CH3)21.407 (s) (CH3a), 1.481 (s) (CH3b)

PHYSICAL PROPERTIES

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

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMAMADALIEVA, N.Z. et al. (2010) Natural Product Communications 5, 1579-1582 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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