LBF20406HO22: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


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|LipidBank=XPR6114
|LipidBank=XPR6114
|LipidMaps=LMFA03060021
|LipidMaps=LMFA03060021
|SysName= (R) , (Z,E,Z,Z) -8-Hydroxy-5,9,11,14-eicosatetraenoic acid
|SysName=8R-Hydroxy- (cis-5,trans-9,cis-11,cis-14) -eicosatetraenoic acid
|Common Name=&&(R) , (Z,E,Z,Z) -8-Hydroxy-5,9,11,14-eicosatetraenoic acid&&
|Common Name=&&8R-Hydroxy- (5Z,9E,11Z,14Z) -eicosatetraenoic acid&&(R) , (Z,E,Z,Z) -8-Hydroxy-5,9,11,14-eicosatetraenoic acid&&
|Reflactive=8(S)-ISOMER METHYL ESTER ; [<FONT FACE=""Symbol"">a</FONT>]X<sub>D</sub><sup>22</sup>=-4.75°(C=0.4, CHLOROFORM) [[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]]
|Optical=8(S)-ISOMER METHYL ESTER ; [ alpha ]^{22}_D =-4.75°(C=0.4, CHLOROFORM) [[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]]
|Solubility=ETHYL ACETATE [[Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747}}]]
|Solubility=ETHYL ACETATE [[Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747}}]]
|Mass Spectra=METHYL ESTER, TMS ETHER ; m/e 265 [[Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747}}]]. 8(S)-ISOMER METHYL ESTER TMS ETHER ; m/e 406, 391, 316, 265, 243 [[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]]
|Mass Spectra=METHYL ESTER, TMS ETHER ; m/e 265 [[Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747}}]]. 8(S)-ISOMER METHYL ESTER TMS ETHER ; m/e 406, 391, 316, 265, 243 [[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]]
|UV Spectra=METHYL ESTER ; <FONT FACE=""Symbol"">l</FONT> <SUB><FONT SIZE=-1>m</FONT></SUB><SUB><FONT SIZE=-1>a</FONT></SUB><SUB><FONT SIZE=-1>x</FONT></SUB> = 235.8nm (<FONT FACE=""Symbol"">e</FONT> 28,000)[[Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747}}]]
|UV Spectra=METHYL ESTER ; lambda  _{max} = 235.8nm ( epsilon  28,000)[[Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Nidy_EG:Epps_DE:Mizsak_SA:Wnuk_RJ:,J. Biol. Chem.,1986,261,747}}]]
|NMR Spectra=8(S)-ISOMER METHYL ESTER ; <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE=""Symbol"">d</FONT> 6.56(dd, J=14.5, 11.1Hz, 1H, 10-CH), 6.00(brt, J=11.1, 9.7Hz, 1H, 11-CH), 5.72(dd, J=7.3, 14.5Hz, 1H, 9-CH), 5.59-5.16(m, 5H), 4.23(q, 1H,8-CH), 3.71(s, 3H,OCH<SUB><FONT SIZE=-1>3</FONT></SUB>), 2.95(t, 2H,13-CH), 2.35(t, 4H, 4,7-CH), 2.11(sextet, 4H), 1.73(pentet, 2H, 3-CH), 1.56(brs, S, 1H, OH), 1.32(m, 6H), 0.91(t, 3H, 20-CH) [[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]]
|NMR Spectra=8(S)-ISOMER METHYL ESTER ; ^1 H-NMR(CDCl_3 ) : delta  6.56(dd, J=14.5, 11.1Hz, 1H, 10-CH), 6.00(brt, J=11.1, 9.7Hz, 1H, 11-CH), 5.72(dd, J=7.3, 14.5Hz, 1H, 9-CH), 5.59-5.16(m, 5H), 4.23(q, 1H,8-CH), 3.71(s, 3H,OCH_3 ), 2.95(t, 2H,13-CH), 2.35(t, 4H, 4,7-CH), 2.11(sextet, 4H), 1.73(pentet, 2H, 3-CH), 1.56(brs, S, 1H, OH), 1.32(m, 6H), 0.91(t, 3H, 20-CH) [[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]]
|Source=
|Chemical Synthesis=[[Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039|{{RelationTable/GetFirstAuthor|Reference:Yadagiri_P:Lumin_S:Mosset_P:Capdevila_J:Falck_JR:,Tetrah. Lett.,1986,27,6039}}]] {{Image200|LBF20406HO22FT0001.gif}}
|Metabolism=
|Symbol=8(R)-HETE
|Biological Activity=The compound is involved in the maturation of starfish oocyte [[Reference:Meijer_L:Brash_AR:Bryant_RW:Ng_K:Maclouf_J:Sprecher_H:,J. Biol. Chem.,1986,261,17040|{{RelationTable/GetFirstAuthor|Reference:Meijer_L:Brash_AR:Bryant_RW:Ng_K:Maclouf_J:Sprecher_H:,J. Biol. Chem.,1986,261,17040}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 07:28, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR6114
LipidMaps LMFA03060021
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406HO22
8R-Hydroxy- (5Z,9E,11Z,14Z) -eicosatetraenoic acid
LBF20406HO22.png
Structural Information
8R-Hydroxy- (cis-5,trans-9,cis-11,cis-14) -eicosatetraenoic acid
  • 8R-Hydroxy- (5Z,9E,11Z,14Z) -eicosatetraenoic acid
  • (R) , (Z,E,Z,Z) -8-Hydroxy-5,9,11,14-eicosatetraenoic acid
 8(R)-HETE
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC=CCC=CC=C[C@H](CC=CCCCC(O)=O)O)CCC
Physicochemical Information
8(S)-ISOMER METHYL ESTER ; [ α ]22
D   =-4.75°(C=0.4, CHLOROFORM) YadagiriPet al.
ETHYL ACETATE Bundy_GL et al.
Yadagiri_P et al.
LBF20406HO22FT0001.gif
The compound is involved in the maturation of starfish oocyte Meijer_L et al..
Spectral Information
Mass Spectra METHYL ESTER, TMS ETHER ; m/e 265 Bundy_GL et al.. 8(S)-ISOMER METHYL ESTER TMS ETHER ; m/e 406, 391, 316, 265, 243 YadagiriPet al.
UV Spectra METHYL ESTER ; λ max = 235.8nm ( ε 28,000) Bundy_GL et al.
IR Spectra
NMR Spectra 8(S)-ISOMER METHYL ESTER ; 1H-NMR(CDCl3) : δ 6.56(dd, J=14.5, 11.1Hz, 1H, 10-CH), 6.00(brt, J=11.1, 9.7Hz, 1H, 11-CH), 5.72(dd, J=7.3, 14.5Hz, 1H, 9-CH), 5.59-5.16(m, 5H), 4.23(q, 1H,8-CH), 3.71(s, 3H,OCH3), 2.95(t, 2H,13-CH), 2.35(t, 4H, 4,7-CH), 2.11(sextet, 4H), 1.73(pentet, 2H, 3-CH), 1.56(brs, S, 1H, OH), 1.32(m, 6H), 0.91(t, 3H, 20-CH) YadagiriPet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HO22 See above. Bundy_GL et al. 1986
n.a. LBF20406HO22 See above. Meijer_L et al. 1986
n.a. LBF20406HO22 See above. Yadagiri_P et al. 1986


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