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

24-METHYLENESHIDASTERONE

Year of first isolation: 2007
Formula:C28H42O6
Molecular weight:474
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
24-METHYLENESHIDASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(C(=C)CC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
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@](C)(C1OC(C(=C)C1)(C)C)O)O)C)C  » JSMol: View in 3D
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@](C)(C1OC(C(=C)C1)(C)C)O)O)C)C  » JSMol: View in 3D
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@](C)(C1OC(C(=C)C1)(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R)-5,5-dimethyl-4-methylideneoxolan-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101431681
InChiKey
[ ChemIDPlus: search ]
IPJLOFDOKBDRGY-IJYGRGDZSA-N
InChIInChI=1S/C28H42O6/c1-15-11-23(34-24(15,2)3)27(6,32)22-8-10-28(33)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,16,18,20-23,30-33H,1,7-11,13-14H2,2-6H3/t16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1

MASS SPECTRUM

HRESI-MS474.2975 (calculated for C28H42O6 474.2970)
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %)497 (10) [M+Na]+, 475 (100) [M+H]+, 457 (72) [M+H-H2O]+, 439 (5.7) [M+H-2H2O]+, 421 (3) [M+H-3H2O]+, 364 (2)

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.9
0368.7
0433.2
0551.9
06206.6
07122.3
08168.1
0935.3
1039.4
1121.6
1232.45
1348.4
1485.4
1531.8
1622.0
1752.0
1818.35
1924.5
2076.8
2120.7
2282.4
2335.6
24158.3
2583.2
2627.9
2729.7
28 CH2=104.1
CD3OD
01-Ha1.43 (dt, 13.1, 12.5)
01-He1.795
02-Ha3.84 (ddd, 12.1, 4.3, 3.3)
03-He3.95 (q, 2.9)
04-Ha1.72*
04-He1.76*
05-H2.38 (dt, 8.1, 4.7)
07-H5.81 (d, 2.7)
09-H3.15 (ddd, 11.3, 7.1, 2.7)
11-Ha1.67
11-He1.80
12-Ha2.165 (td, 13.3, 4.8)
12-He1.84
15-Ha1.62
15-Hb1.97
16-Ha1.83
16-Hb2.00
17-H2.42 (dd, 9.5, 8.2)
18-Me0.84 (s)
19-Me0.96 (s)
21-Me1.21 (s)
22-H3.91 (t, 8.1)
23-Ha2.545 (dt, 8.2, 2.2)
23-Hb2.545 (dt, 8.2, 2.2)
26-Me1.28 (s)
27-Me1.33 (s)
28 CH2=4.805 (t, 2.3), 4.895 (t, 2.2)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D28+3 ° (c 0.05 ; MeOH) ; different for Japonicone (isomeric ?)
UV (MeOH) max (log )241.8 (3.7) ;
IR (KBr) ν max (cm-1)

CHROMATOGRAPHY

HPLCNP-HPLC, solvent cyclohexane-isopropanol-water 100:40:3; RP-HPLC, solvent methanol-water 60:40.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2007) Steroids 72, 751-755 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