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|LipidBank=XPR6201
|LipidBank=XPR6201
|LipidMaps=-
|LipidMaps=-
|SysName= (S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid
|SysName= 12S-Hydroxy- (cis-5,trans-8,trans-10) -heptadecatrienoic acid
|Common Name=&&(S) , (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid&&
|Common Name=&&12S-Hydroxy- (5Z,8E,10E) -heptadecatrienoic acid&&(S)- (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid&&
|Reflactive=METHYL ESTER ; [<FONT FACE=""Symbol"">a</FONT>]X<sub>D</sub><sup>25</sup> =+7.5°(C=0.2, CHLOROFORM) [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|Optical=METHYL ESTER ; [ alpha ]^{25}_D  =+7.5°(C=0.2, CHLOROFORM) [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|Solubility=DIETHYL ETHER [[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]
|Solubility=DIETHYL ETHER [[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]
|Mass Spectra=METHYL ESTER TMS ETHER ; m/e 366(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 335, 295, 276, 225, 173, (128)[[Reference:Hamberg_M:Svensson_J:Wakabayashi_T:Samuelsson_B:,Proc. Nat. Acad. Sci. USA,1974,71,345|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Svensson_J:Wakabayashi_T:Samuelsson_B:,Proc. Nat. Acad. Sci. USA,1974,71,345}}]] METHYL ESTER ; 298(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 224 [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|Mass Spectra=METHYL ESTER TMS ETHER ; m/e 366(M^+ ), 335, 295, 276, 225, 173, (128)[[Reference:Hamberg_M:Svensson_J:Wakabayashi_T:Samuelsson_B:,Proc. Nat. Acad. Sci. USA,1974,71,345|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Svensson_J:Wakabayashi_T:Samuelsson_B:,Proc. Nat. Acad. Sci. USA,1974,71,345}}]] METHYL ESTER ; 298(M^+ ), 224 [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|UV Spectra=METHYL ESTER ; ETHANOL : 232nm(<FONT FACE=""Symbol"">e</FONT> 33,400)[[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]. METHANOL : 240nm [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|UV Spectra=METHYL ESTER ; ETHANOL : 232nm( epsilon  33,400)[[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]. METHANOL : 240nm [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|NMR Spectra=METHYL ESTER ; <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE=""Symbol"">d</FONT> 6.17(dd, J=15.11, 10.36Hz, 1H, 10-CH), 6.04(dd, J=15,05, 10.52Hz, 1H, 9-CH), 5.66(dt, J=15.16, 6.48Hz, 1H), 5.60(dd, J=17.17, 7.04Hz, 1H, 11-CH), 5.42(m, 2H, 5-CH, 6-CH), 4.1(m, 1H, 12-CH), 3.66(s, 3H, COOCH<SUB><FONT SIZE=-1>3</FONT></SUB>), 2.81(m, 2H, 7-CH), 2.36(t, J=7.51Hz, 2H, 2-CH), 2.1-0.85(m, 16H, CH<SUB><FONT SIZE=-1>2</FONT></SUB> and CH<SUB><FONT SIZE=-1>3</FONT></SUB>) [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|NMR Spectra=METHYL ESTER ; ^1 H-NMR(CDCl_3 ) : delta  6.17(dd, J=15.11, 10.36Hz, 1H, 10-CH), 6.04(dd, J=15,05, 10.52Hz, 1H, 9-CH), 5.66(dt, J=15.16, 6.48Hz, 1H), 5.60(dd, J=17.17, 7.04Hz, 1H, 11-CH), 5.42(m, 2H, 5-CH, 6-CH), 4.1(m, 1H, 12-CH), 3.66(s, 3H, COOCH_3 ), 2.81(m, 2H, 7-CH), 2.36(t, J=7.51Hz, 2H, 2-CH), 2.1-0.85(m, 16H, CH_2  and CH_3 ) [[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]]
|Source=
|Source=
|Chemical Synthesis=[[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]] {{Image200|LBF17307HO02FT0001.gif}}
|Chemical Synthesis=[[Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131|{{RelationTable/GetFirstAuthor|Reference:Nicolaou_KC:Stylianides_NA:Ramphal_JY:,J. Chem. Soc. Perkin Trans. I,1989,,2131}}]] {{Image200|LBF17307HO02FT0001.gif}}
|Metabolism=When prostaglandin H2 reacts with thromboxane A synthase and the endoperoxide moiety is cleaved, the production of thromboxane A2 is accompanied by the formation of 12(S)-hydroxy-5,8,10-heptadecatrienoic acid in an almost equimolar amount liberating malondialdehyde [[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]. This compound is also a product of non-enxymatic degradation of prostaglandin H2 [[Reference:Nugteren_DH:Hazelhof_E:,Biochim. Biophys. Acta,1973,326,448|{{RelationTable/GetFirstAuthor|Reference:Nugteren_DH:Hazelhof_E:,Biochim. Biophys. Acta,1973,326,448}}]].
|Metabolism=When prostaglandin H2 reacts with thromboxane A synthase and the endoperoxide moiety is cleaved, the production of thromboxane A2 is accompanied by the formation of 12(S)-hydroxy-5,8,10-heptadecatrienoic acid in an almost equimolar amount liberating malondialdehyde [[Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1974,71,3400}}]]. This compound is also a product of non-enxymatic degradation of prostaglandin H2 [[Reference:Nugteren_DH:Hazelhof_E:,Biochim. Biophys. Acta,1973,326,448|{{RelationTable/GetFirstAuthor|Reference:Nugteren_DH:Hazelhof_E:,Biochim. Biophys. Acta,1973,326,448}}]].
|Symbol=HHT
|Biological Activity=The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes [[Reference:Goetzl_EJ:Gorman_RR:,J. Immunol.,1978,120,526|{{RelationTable/GetFirstAuthor|Reference:Goetzl_EJ:Gorman_RR:,J. Immunol.,1978,120,526}}]].
}}
}}


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{{Lipid/Footer}}

Latest revision as of 15:24, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR6201
LipidMaps -
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF17307HO02
12S-Hydroxy- (5Z,8E,10E) -heptadecatrienoic acid
Structural Information
12S-Hydroxy- (cis-5,trans-8,trans-10) -heptadecatrienoic acid
  • 12S-Hydroxy- (5Z,8E,10E) -heptadecatrienoic acid
  • (S)- (Z,E,E) -12-Hydroxy-5,8,10-heptadecatrienoic acid
 HHT
Formula C17H28O3
Exact Mass 280.203844762
Average Mass 280.40242
SMILES CCCCC[C@H](O)C=CC=CCC=CCCCC(O)=O
Physicochemical Information
METHYL ESTER ; [ α ]25
D   =+7.5°(C=0.2, CHLOROFORM) Nicolaou_KC et al.
DIETHYL ETHER HambergMet al.
Nicolaou_KC et al.

When prostaglandin H2 reacts with thromboxane A synthase and the endoperoxide moiety is cleaved, the production of thromboxane A2 is accompanied by the formation of 12(S)-hydroxy-5,8,10-heptadecatrienoic acid in an almost equimolar amount liberating malondialdehyde Hamberg_M et al.. This compound is also a product of non-enxymatic degradation of prostaglandin H2 Nugteren_DH et al..
The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes Goetzl_EJ et al..
Spectral Information
Mass Spectra METHYL ESTER TMS ETHER ; m/e 366(M+), 335, 295, 276, 225, 173, (128) HambergMet al. METHYL ESTER ; 298(M+), 224 Nicolaou_KC et al.
UV Spectra METHYL ESTER ; ETHANOL : 232nm( ε 33,400) HambergMet al.. METHANOL : 240nm Nicolaou_KC et al.
IR Spectra
NMR Spectra METHYL ESTER ; 1H-NMR(CDCl3) : δ 6.17(dd, J=15.11, 10.36Hz, 1H, 10-CH), 6.04(dd, J=15,05, 10.52Hz, 1H, 9-CH), 5.66(dt, J=15.16, 6.48Hz, 1H), 5.60(dd, J=17.17, 7.04Hz, 1H, 11-CH), 5.42(m, 2H, 5-CH, 6-CH), 4.1(m, 1H, 12-CH), 3.66(s, 3H, COOCH3), 2.81(m, 2H, 7-CH), 2.36(t, J=7.51Hz, 2H, 2-CH), 2.1-0.85(m, 16H, CH2 and CH3) Nicolaou_KC et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF17307HO02 See above. Goetzl_EJ et al. 1978
n.a. LBF17307HO02 See above. Hamberg_M et al. 1974
n.a. LBF17307HO02 See above. Hamberg_M et al. 1974
n.a. LBF17307HO02 See above. Hamberg_M et al. 1974
n.a. LBF17307HO02 See above. Nicolaou_KC et al. 1989
n.a. LBF17307HO02 See above. Nugteren_DH et al. 1973


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