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|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(250MHz, ACETONE-D<SUB><FONT SIZE=-1>6</FONT></SUB>) ; <FONT FACE="Symbol">d</FONT> 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) [[Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789|{{RelationTable/GetFirstAuthor|Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789}}]]. <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>NMR(C<SUB><FONT SIZE=-1>6</FONT></SUB>D<SUB><FONT SIZE=-1>6</FONT></SUB>) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 [[Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789|{{RelationTable/GetFirstAuthor|Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(250MHz, ACETONE-D<SUB><FONT SIZE=-1>6</FONT></SUB>) ; <FONT FACE="Symbol">d</FONT> 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) [[Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789|{{RelationTable/GetFirstAuthor|Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789}}]]. <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>NMR(C<SUB><FONT SIZE=-1>6</FONT></SUB>D<SUB><FONT SIZE=-1>6</FONT></SUB>) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 [[Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789|{{RelationTable/GetFirstAuthor|Reference:Leblanc_Y:Fitzsimmons_BJ:Adams_J:Perez_F:Rokach_J:,J. Org. Chem.,1986,51,789}}]]
|Source=
|Source=
|Chemical Synthesis=[[Reference:Corey_EJ:Niwa_H:Knolle_J:,J. Am. Chem. Soc.,1978,100,1942|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Niwa_H:Knolle_J:,J. Am. Chem. Soc.,1978,100,1942}}]];> {{Image200|LBF20406HO21FT0001.gif}}
|Chemical Synthesis=[[Reference:Corey_EJ:Niwa_H:Knolle_J:,J. Am. Chem. Soc.,1978,100,1942|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Niwa_H:Knolle_J:,J. Am. Chem. Soc.,1978,100,1942}}]] {{Image200|LBF20406HO21FT0001.gif}}
|Metabolism=When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced [[Reference:Yamamoto_S:Suzuki_H:Ueda_N:,Prog. Lipid Res.,1997,36,23|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_S:Suzuki_H:Ueda_N:,Prog. Lipid Res.,1997,36,23}}]];>. The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.
|Metabolism=When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced [[Reference:Yamamoto_S:Suzuki_H:Ueda_N:,Prog. Lipid Res.,1997,36,23|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_S:Suzuki_H:Ueda_N:,Prog. Lipid Res.,1997,36,23}}]]. The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.
}}
}}


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Upper classes: LB LBF



IDs and Links
LipidBank XPR6102
LipidMaps -
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406HO21
12 (S) -Hydoxy-5,8,10,14- (Z,E,Z,Z) -eicosatetraenoic acid
Structural Information
12 (S) -Hydoxy-5,8,10,14- (Z,E,Z,Z) -eicosatetraenoic acid
  • 12 (S) -Hydoxy-5,8,10,14- (Z,E,Z,Z) -eicosatetraenoic acid
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC=CC[C@@H](C=CC=CCC=CCCCC(O)=O)O)CCC
Physicochemical Information
DIETHYL ETHER , ACETONE , BENZENE LeblancYet al.
Corey_EJ et al.

When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced Yamamoto_S et al.. The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.
Spectral Information
Mass Spectra METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) JustGet al.
UV Spectra METHYL ESTER ; l MeOHmax = 234nm JustGet al.METHYL ESTER ; l EtOHmax = 237nm(e 30500) HambergMet al.
IR Spectra NEAT : n 3480b, 1710, 1460, 1400cm-1 LeblancYet al.
NMR Spectra 1H-NMR(250MHz, ACETONE-D6) ; d 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) LeblancYet al.. 13NMR(C6D6) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 LeblancYet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HO21 See above. Corey_EJ et al. 1978
n.a. LBF20406HO21 See above. Hamberg_M et al. 1974
n.a. LBF20406HO21 See above. Just_G et al. 1986
n.a. LBF20406HO21 See above. Leblanc_Y et al. 1986
n.a. LBF20406HO21 See above. Yamamoto_S et al. 1997
n.a. LBF20406HO21 See above. Yoshimoto_T et al. 1995


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