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

7,8-DIHYDROAJUGASTERONE C

Year of first isolation: 1996
Formula:C27H46O7
Molecular weight:482
Occurence in plants:
Nierembergia hippomanica [Solanaceae] » Images of Nierembergia hippomanica Wikipedia: Nierembergia hippomanica [Solanaceae]
Occurence in animals:
 
7,8-DIHYDROAJUGASTERONE C

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)CC1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@H]1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C  » JSMol: View in 3D
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@@H]1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,8R,9S,10R,11R,13R,14R,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID15250834
InChiKey
[ ChemIDPlus: search ]
DFFFEFCBFYMSHZ-KGMAXRKNSA-N
InChIInChI=1S/C27H46O7/c1-14(2)6-7-22(32)26(5,33)21-8-9-27(34)16-11-17(28)15-10-18(29)19(30)12-24(15,3)23(16)20(31)13-25(21,27)4/h14-16,18-23,29-34H,6-13H2,1-5H3/t15-,16+,18+,19-,20+,21-,22+,23+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)467 ([M-15]+, 2), 464 ([M-18]+, 5), 428 (5M-3x18], 2), 413 (2), 381 (4), 363 (84), 345 (41), 327 (28), 309 (16), 285 (8), 267 (10), 189 (12), 157 (11), 145 (41), 127 (9), 109 (33), 101 (2), 83 (75), 71 (36), 67 (33), 55 (100), 43 (94).
FAB-MS483 [MH]+

CARBON NMR

PROTON NMR

C5D5N
0143.9 c
0265.2
0367.8 d
0432.3 a
0555.4
06214.5
0740.6
0837.7 b
0951.4
1041.2
1167.5 d
1243.5 c
1360.1
1493.8
1537.9 b
1632.9 a
1753.3
1826.9
1916.4
2076.7 e
2121.5
2277.0 e
2331.8
2436.4
2528.7
2622.6
2722.0
C5D5N
01-Ha2.00 (m )
01-He3.45 (dd, 16, 4)
02-Ha4.60 (m )
03-He4.30 (m )
04-Ha1.80 (m )
04-He2.20 (dt, 4, 14)
05-H3.20 (m )
07-Ha2.23 (dd, 4, 14)
07-He1.85 (m )
08-H2.30 (m )
09-H3.90 (t, 9)
11-Ha4.68 (m )
12-Ha3.42 (t, 12)
12-He2.70 (dd, 12, 6)
15-Ha1.95 (m )
15-Hb2.10 (m )
16-Ha2.10 (m )
16-Hb2.50 (m )
17-H3.00 (t, 8)
18-Me1.23 (s )
19-Me1.40 (s )
21-Me1.53 (s )
22-H3.80 (dd, 5, 10)
23-Ha ~1.40
23-Hb1.68 (m )
24-Ha ~1.50
24-Hb1.71 (m )
25-H1.58 (m )
26-Me0.82 (d, 6)
27-Me0.82 (d, 6)

PHYSICAL PROPERTIES

M.P. 
[α]D22+ 43.2 ° (c 0.01; CHCl3)
IR (KBr) ν max (cm-1)3350 (OH), 2870 (C-C), 1695 (C=O), 2445, 1375, 1265, 1230
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCsilica gel, Rf 0.37 (CHCl3-Me2CO, 35:65) (20E : 0.24)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationPOMILIO, A.B. et al. (1996) Phytochemistry 41, 1393-1398 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