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29-NORCYASTERONE 3-ACETATE

Year of first isolation: 1985
Formula:C30H44O9
Molecular weight:548
Occurence in plants:
Ajuga reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans Wikipedia: <br />
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Occurence in animals:
 
29-NORCYASTERONE 3-ACETATE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C[C@@H]1COC(=O)[C@H]1C)O)O)C)C » JSMol: View in 3D
IUPAC Name 
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
PEHHOWZJLAZZNB-CCQDXIEQSA-N
InChIInChI=1S/C30H44O9/c1-15-17(14-38-26(15)35)10-25(34)29(5,36)24-7-9-30(37)19-11-21(32)20-12-23(39-16(2)31)22(33)13-27(20,3)18(19)6-8-28(24,30)4/h11,15,17-18,20,22-25,33-34,36-37H,6-10,12-14H2,1-5H3/t15-,17+,18-,20-,22-,23+,24-,25+,27+,28+,29+,30+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)548 (M)+ (1.9),
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0138.70 *
0266.07
0371.20
0429.65
0551.93
06202.15
07121.55
08166.28
0934.40
1038.57 *
1121.07
1231.78
1348.14
1484.05
1531.94
1621.35
1750.11
1817.88
1924.26
2076.64
2121.26 "
2275.97
2334.75
2440.68
2543.32
26179.78
2714.44
2872.89
CH3COO 21.07 ", 170.56
C5D5N
01-Ha 
01-He 
02-Ha4.28 (br, d, w1/2 = 21.0)
03-He5.49 (br, w1/2 = 9.0)
04-Ha 
04-He 
05-H2.67 (dd, 13.5, 4.2)
07-H6.26 (d, 1.8)
09-Ha3.59 (bt, w1/2 = 23.0)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.87 (bt, 9.0)
18-Me1.24 (s )
19-Me1.08 (s )
21-Me1.57 (s )
22-H3.89 (brd, w1/2 = 19.6)
23-Ha 
23-Hb 
24-H 
25-H2.22 (dq, 10.8, 6.9)
26-Me-
27-Me1.16 (d, 6.9)
28-Ha4.65 (dd, ca. 9.2, 7.6)
28-Hb3.96 (dd, ca. 10.4, 8.8)
O-Ac1.96 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC 
HPLCRP-HPLC, Column LiChroCART 4x125 mm packed with Lichrospher 100 RP-18, 5?m, with a guard column Waters 4x24 mm packed with Bondapak C-18, 10 ?m, temperature 55°C, solvent iPrOH-H2O 1:10, flow-rate 1 ml.min-1. Ret 15.68 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCAMPS, F. et al. (1985) J. Chem. Res. (S), 14-15 Search more
GeneralCAMPS, F. et al. (1985) J. Chem. Res. (M), 241-266 Search more
GeneralCALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 Search more

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© 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
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