LBF20407HO07: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
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|LipidBank=XPR6103
|LipidBank=XPR6103
|LipidMaps=-
|LipidMaps=-
|SysName=15 (S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid
|SysName=15S-Hydroxy- (cis-5,cis-8,cis-11,trans-13) -eicosatetraenoic acid
|Solubility=DIETHYL ETHER <<1086>>
|Common Name=&&15S-Hydroxy- (5Z,8Z,11Z,13E) -eicosatetraenoic acid&&15(S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid&&
|Mass Spectra=METHYL ESTER TMS ETHER ; m/e 406(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 391, 335, 316, 305, 225, 173 <<1086>>
|Solubility=DIETHYL ETHER [[Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115|{{RelationTable/GetFirstAuthor|Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115}}]]
|UV Spectra=METHYL ESTER ; <FONT FACE="Symbol">l</FONT> (ISOOCTANE) = 236nm(<FONT FACE="Symbol">e</FONT> 27200) <<1086>>
|Mass Spectra=METHYL ESTER TMS ETHER ; m/e 406(M^+ ), 391, 335, 316, 305, 225, 173 [[Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115|{{RelationTable/GetFirstAuthor|Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115}}]]
|NMR Spectra=METHYL ESTER ; <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(90MHz) : <FONT FACE="Symbol">d</FONT> 6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH<SUB><FONT SIZE=-1>3</FONT></SUB>), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) <<1086>>
|UV Spectra=METHYL ESTER ; lambda  (ISOOCTANE) = 236nm( epsilon  27200) [[Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115|{{RelationTable/GetFirstAuthor|Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115}}]]
|NMR Spectra=METHYL ESTER ; ^1 H-NMR(90MHz) : delta  6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH_3 ), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) [[Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115|{{RelationTable/GetFirstAuthor|Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115}}]]
|Source=
|Chemical Synthesis=[[Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115|{{RelationTable/GetFirstAuthor|Reference:Baldwin_JE:Davies_DI:Hughes_L:Gutterridge_NJA:,J. Chem. Soc. Perkin I,1979,,115}}]] {{Image200|LBF20407HO07FT0001.gif}}
|Metabolism=When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced [[Reference:Bryant_RW:Bailey_JM:Schewe_T:Rapoport_SM:,J. Biol. Chem.,1982,257,6050|{{RelationTable/GetFirstAuthor|Reference:Bryant_RW:Bailey_JM:Schewe_T:Rapoport_SM:,J. Biol. Chem.,1982,257,6050}}]]. The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.
|Symbol=15S-HETE
|Biological Activity=In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling [[Reference:Kuhn_H:Thiele_BJ:,J. Lipid Mediat. Cell Signal.,1995,12,157|{{RelationTable/GetFirstAuthor|Reference:Kuhn_H:Thiele_BJ:,J. Lipid Mediat. Cell Signal.,1995,12,157}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 07:35, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR6103
LipidMaps -
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20407HO07
15S-Hydroxy- (5Z,8Z,11Z,13E) -eicosatetraenoic acid
LBF20407HO07.png
Structural Information
15S-Hydroxy- (cis-5,cis-8,cis-11,trans-13) -eicosatetraenoic acid
  • 15S-Hydroxy- (5Z,8Z,11Z,13E) -eicosatetraenoic acid
  • 15(S) -Hydroxy-5,8,11,13- (Z,Z,Z,E) -eicosatetraenoic acid
 15S-HETE
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC[C@@H](C=CC=CCC=CCC=CCCCC(O)=O)O)CC
Physicochemical Information
DIETHYL ETHER Baldwin_JE et al.
Baldwin_JE et al.
LBF20407HO07FT0001.gif
 When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced Bryant_RW et al.. The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.
In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling Kuhn_H et al..
Spectral Information
Mass Spectra METHYL ESTER TMS ETHER ; m/e 406(M+), 391, 335, 316, 305, 225, 173 Baldwin_JE et al.
UV Spectra METHYL ESTER ; λ (ISOOCTANE) = 236nm( ε 27200) Baldwin_JE et al.
IR Spectra
NMR Spectra METHYL ESTER ; 1H-NMR(90MHz) : δ 6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH3), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) Baldwin_JE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20407HO07 See above. Baldwin_JE et al. 1979
n.a. LBF20407HO07 See above. Bryant_RW et al. 1982
n.a. LBF20407HO07 See above. Kuhn_H et al. 1995


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