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28-EPI-SENGOSTERONE

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: <br />
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Occurence in animals:
 
28-EPI-SENGOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)O
Isomeric SMILES
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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](C[C@H]1[C@@H](C(=O)O[C@H]1C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(3S,4S,5S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one
CAS-RN 
PubChem CID101355230
InChiKey
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YQCOGGGDJXBMBU-ZHDQNANASA-N
InChIInChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15-,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
MS (thermospray) m/z (relat. intensity %)554 (M+NH4)+ (25), 537 (M+H) (100), 536 (M)+ (82), 519 (M+H-H20) (34), 501 (M+H-2H2O) (21)

CARBON NMR

PROTON NMR

C5D5N
0134.8
0267.9
0369.8
0435.9
0579.8
06200.9
07120.0
08166.6
0938.2
1044.8
1122.0
1232.1
1348.2
1483.9
1531.6
1621.3
1750.0
1817.9
1917.1
2076.7
2121.1
2276.4
2330.8
2446.0
2538.7
26179.1
2716.3
2878.7
2914.3
C5D5N
01-Ha 
01-He 
02-Ha4.27 (m, w1/2=24)
03-He4.18 (m, w1/2=15)
04-Ha 
04-He 
05-H?
07-H6.27 (d, 2.1)
09-H3.66 (m, w1/2=24)
11-Ha 
11-He 
12-Ha2.62
12-He2.08
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.88 (t, 8.4)
18-Me1.24 (s)
19-Me1.18 (s)
21-Me1.61 (s)
22-H3.90 (m, w1/2=20)
23-Ha1.81
23-Hb1.69
24-H2.48
25-H2.33 (dq, 11.4, 6.9)
27-Me1.17 (d, 7)
28-H5.01
29-Me1.31 (d, 6)
H-2 OH5.56 (w1/2=15)
H-22 OH5.56 W1/2=8)
H-3 OH5.88 (d, 8.1)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3416 (OH), 1749 (?-lactone), 1670 (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 22.5 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

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

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© Université Pierre & Marie Curie, Paris 6, France
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