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

5,29-DIHYDROXYCAPITASTERONE

Year of first isolation: 1996
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans var. atropurpurea Wikipedia: Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
5,29-DIHYDROXYCAPITASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H]1C[C@@H]([C@H](C(=O)O1)C)CCO)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(3R,4S,6R)-6-((R)-1-hydroxy-1-((2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl)-4-(2-hydroxyethyl)-3-methyltetrahydro-2H-pyran-2-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
YIZXJSNGUYBWSY-PNUXDPGFSA-N
InChIInChI=1S/C29H44O9/c1-15-16(7-10-30)11-23(38-24(15)34)27(4,35)21-6-9-28(36)18-12-22(33)29(37)14-20(32)19(31)13-26(29,3)17(18)5-8-25(21,28)2/h12,15-17,19-21,23,30-32,35-37H,5-11,13-14H2,1-4H3/t15-,16+,17+,19+,20-,21+,23-,25-,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

MS (thermospray) m/z (relat. intensity %)555 (M+H+NH4)+ (17), 554 (M+NH4)+ (42), 537 (M+H)+ (100), 536 (M)+ (82), 519 (M+H-H2O) (54), 501 (M+H-2H2O)+ (11)
EI-MS m/z (relative intensity %) 

CARBON NMR

PROTON NMR

C5D5N
0134.8
0267.9
0369.9
0435.9
0579.8
06200.9
07120.0
08166.6
0938.2
1044.8
1122.0
1232.0
1347.9
1483.9
1531.6
1621.1
1749.7
1818.0
1917.1
2076.3
2120.7
2283.5
2328.6
2433.5
2541.0
26174.5
2713.7
2831.1
2960.2
C5D5N
01-Ha2.24
01-He2.08
02-Ha4.24 (m)
03-He4.18 (m)
04-Ha2.04
04-He1.95
05-H?
07-H6.26 (d, 2.7)
09-H3.62 (m, w1/2=23)
11-Ha1.87
11-He1.75
12-Ha2.58
12-He1.90
15-Ha2.20
15-Hb1.85
16-Ha2.35 (m)
16-Hb2.07
17-H2.90 (t, 8.8)
18-Me1.11 (s)
19-Me1.16 (s)
21-Me1.44 (s)
22-H4.78 (dd, 11.5, 4.5)
23-Ha2.22
23-Hb1.85
24-H2.22
25-H2.62
27-Me1.25 (d, 7.2)
28-Ha1.83
28-Hb1.55 (m)
29-Hab3.86 (m, w1/2=19, 2H)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3405 (OH), 1714(d-lactone), 1671 (cyclohexenone)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, column Tracer 30x0.78 cm packed with Spherisorb-ODS2 10?m, solvent iPrOH-H2O (13:87), flow-rate 3 mL.min-1, 23°C, Ret 21.2 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCALGANO, M.P. et al. (1996) Tetrahedron 52, 10137-10146 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