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VITEXIRONE

Year of first isolation: 1990
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Vitex fisherii [Lamiaceae] » Images of Vitex fisherii Wikipedia: <br />
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Occurence in animals:
 
VITEXIRONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O)C
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC=C(C)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylhept-5-en-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN130369-79-8
PubChem CID101940101
InChiKey
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KEADWWVWWCWINS-UKTRSHMFSA-N
InChIInChI=1S/C27H42O7/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/h6,11,15,18-23,29-34H,7-10,12-13H2,1-5H3/t15-,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 %)461 [M+1-H2O]
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0139.9
0268.2
0368.9
0432.9
0552.5
06203.6
07122.3
08164.2
0942.8
1039.5
1168.9
1244.1
1348.2
1484.2
1531.9
1621.5
1750.0
1819.0
1924.9
2076.9
2121.5
2276.7
2331.8
24123.7
25131.9
2618.0
2725.9
C5D5N
01-Ha3.44
01-Hb 
02-Ha4.60
03-He4.22
04-Ha 
04-He 
05-H3.03
07-H6.29
09-Ha3.88
11-He4.60
12-Ha3.03
12-He2.71
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.33
19-Me1.26
21-Me1.59
22-H3.88
23-Ha 
23-Hb 
24-H5.53
26-Me1.59
27-Me1.66

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3400, 1655
UV (EtOH) λ max (log ε)234 (?)

CHROMATOGRAPHY

TLC 
DCCCsolvent system CHCl3-MeOH-H2O (13:7:4, v/v/v), upper phase as mobile phase
GLC 
HPLCrecycle HPLC column Asahipack GS-320 (50 cm x 2.5 cm, 5?m) MeOH as eluent (3 ml.min-1). This column is packed with a polyvinyl alcohol resin and separation depends princi-pally on molecular size.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKUBO, I. et al. (1990) J. Chem. Ecol. 16, 2581-2588 Search more

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