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

HERKESTERONE

Year of first isolation: 2004
Formula:C27H42O8
Molecular weight:494
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
HERKESTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CC=C3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1C2=CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,12,15,16,17-octahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102157616
InChiKey
[ ChemIDPlus: search ]
IPPARPMLJLUMNP-CVFUVVIBSA-N
InChIInChI=1S/C27H42O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h6,12,17-20,28-30,32-35H,7-11,13-14H2,1-5H3/t17-,18+,19-,20+,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

FAB-MS m/z (relative intensity %)495 [M+H]+ (9), 477 [M+H-H2O]+ (10), 459 [M+H-2H2O]+ (23), 443 (26), 440 (11), 422 (8), 407 (49), 394 (17), 378 (9), 361 (26), 359 (10), 323 (18), 300 (100), 199 (11)
EI-MS m/z (relative intensity %)
HRE-SIMS m/z494.2885 (calculated 494.2880 for C27H42O8)

CARBON NMR

PROTON NMR

CD3OD
0134.5
0268.6
0370.3
0439.2
0580.5
06203.1
07117.9
08156.5
09137.9
1046.4
11134.3
1239.2
1348.0
1484.5
1531.5
1621.8
1750.7
1818.2
1926.5
2077.8
2120.9
2278.6
2327.5
2442.5
2571.4
2629.1
2729.9
DMSO-d6
01 
02 
03 
04 
0578.4
06 
07116.5
08 
09136.3
10 
11131.7
1237.5
1346.3
1482.0
15 
1620.4
1748.7
1817.3
1925.8
2075.5
2120.7
2276.3
2326.1
2441.4
2568.7
2629.0
2730.0
CD3OD
01-Ha2.05
01-He2.05
02-Ha3.83 (ddd, 10.7, 5.4, 3.2)
03-He3.88 (q, 3.0)
04-Ha1.77 (dd, ?, 3.4)
04-He1.92 (dd, 14.5, 2.8)
05-H-
07-H5.83 (t, 1.2)
09-H-
11-H6.34 (dt, 6.7, 2.0)
12-Ha2.726 (dd, 18.0, 1.8)
12-He2.436 (dd, 18.2, 6.7)
15-Ha1.80
15-Hb1.98
16-Ha1.79
16-Hb1.99
17-H2.49 (t, 9.0)
18-Me0.90 (s)
19-Me1.05 (s)
21-Me1.208 (s)
22-H3.35 (dd, 10.3, 1.8)
23-Ha1.30
23-Hb1.68
24-Ha1.44 (ddd, 13.3, 11.6, 4.2)
24-Hb1.81
26-Me1.19 (s)
27-Me1.206 (s)
DMSO-d6
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H5.65 (s)
09-H 
11-H6.18 (s, br)
12-Ha2.59 (d, 17.8)
12-He2.29 (dd, 17.8, 6.6)
15-Ha 
15-Hb 
16-Ha1.60*
16-Hb1.89*
17-H2.36 (t, 9.3)
18-Me0.77 (s)
19-Me0.96 (s, b)
21-Me1.075 (s)
22-H3.13 (d, 10.2)
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.06 (s)
27-Me1.09 (s)

PHYSICAL PROPERTIES

M.P.218 °C (dec.) ;
[α]D28+ 59 ° (c 0.1 ; DMSO)
IR (KBr) ν max (cm-1)3560-3200, 1650, 1602
UV (MeOH) λ max (log ε)296 (4.02) ;

CHROMATOGRAPHY

LCLow pressure RP, MeOH-H2O (45:55)
HPLCNP on silica (Zorbax-SIL), solvent CH2Cl2-iPrOH-H2O (125:40:3)
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHUNYADI, A. et al. (2004) J. Nat. Prod. 67, 1072-1072 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