LBF20406HO21: Difference between revisions

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(脂肪酸)

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Upper classes: LB LBF

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
	12(S)-HETE
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



	METHYL ESTER ; [ α ]X25 D =+1.50°(C=0.2, CHLOROFORM) Corey_EJ et al., [ α ]X22 D =+13°(C=1.5, ACETONE) Leblanc_Yet al.

	DIETHYL ETHER , ACETONE , BENZENE Leblanc_Yet 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.
	There are reports for various biological activities of 12(S)-hydroxy acid such as rat hypothalamic secretion of LH-RH, stimulated chemotactic activity of human eosinophils and neutrophils, stimulated migration of epidermal tumor cells and rat aortic smooth muscle cells, involvement in angiotension II-mediated aldosterone biosynthesis in human adrenal glomerulosa, and expression or activation of GpIIb/IIIa in tumor cells, but a general theory has not been established Yamamoto_S et al. Yoshimoto_T et al..


Spectral Information
Mass Spectra	METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) Just_Get al.
UV Spectra	METHYL ESTER ; λ MeOH max = 234nm Just_Get al.METHYL ESTER ; λ EtOH max = 237nm( ε 30500) Hamberg_Met al.
IR Spectra	NEAT : ν 3480b, 1710, 1460, 1400cm^-1 Leblanc_Yet al.
NMR Spectra	¹H-NMR(250MHz, ACETONE-D₆) ; δ 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) Leblanc_Yet al.. ¹³NMR(C₆D₆) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 Leblanc_Yet al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
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

@@ Line 8: / Line 8: @@
 |SysName=12 (S) -Hydoxy-5,8,10,14- (Z,E,Z,Z) -eicosatetraenoic acid
 |Common Name=&&12 (S) -Hydoxy-5,8,10,14- (Z,E,Z,Z) -eicosatetraenoic acid&&
-|Optical=METHYL ESTER ; [ alpha ]X^25_D =+1.50°(C=0.2, CHLOROFORM) [[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}}]], [ alpha ]X^22_D =+13°(C=1.5, ACETONE) [[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}}]]
+|Optical=METHYL ESTER ; [ alpha ]X^{25}_D =+1.50°(C=0.2, CHLOROFORM) [[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}}]], [ alpha ]X^{22}_D =+13°(C=1.5, ACETONE) [[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}}]]
 |Solubility=DIETHYL ETHER , ACETONE , BENZENE [[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}}]]
 |Mass Spectra=METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) [[Reference:Just_G:Wang_ZY:,J. Org. Chem.,1986,51,4796|{{RelationTable/GetFirstAuthor|Reference:Just_G:Wang_ZY:,J. Org. Chem.,1986,51,4796}}]]
-|UV Spectra=METHYL ESTER ;  lambda  ^M_m _a _x  = 234nm [[Reference:Just_G:Wang_ZY:,J. Org. Chem.,1986,51,4796|{{RelationTable/GetFirstAuthor|Reference:Just_G:Wang_ZY:,J. Org. Chem.,1986,51,4796}}]]METHYL ESTER ;  lambda  ^E_m _a _x  = 237nm( epsilon  30500) [[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}}]]
+|UV Spectra=METHYL ESTER ;  lambda  ^{MeOH}_{max} = 234nm [[Reference:Just_G:Wang_ZY:,J. Org. Chem.,1986,51,4796|{{RelationTable/GetFirstAuthor|Reference:Just_G:Wang_ZY:,J. Org. Chem.,1986,51,4796}}]]METHYL ESTER ;  lambda  ^{EtOH}_{max} = 237nm( epsilon  30500) [[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}}]]
-|IR Spectra=NEAT :  nu  3480b, 1710, 1460, 1400cm^- ^1  [[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}}]]
+|IR Spectra=NEAT :  nu  3480b, 1710, 1460, 1400cm^{-1} [[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=^1 H-NMR(250MHz, ACETONE-D_6 ) ;  delta  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}}]]. ^1 ^3 NMR(C_6 D_6 ) : 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=^1 H-NMR(250MHz, ACETONE-D_6 ) ;  delta  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}}]]. ^{13}NMR(C_6 D_6 ) : 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=
 |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}}

IDs and Links
LipidBank	XPR6102
LipidMaps	-
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF20406HO21

LBF20406HO21: Difference between revisions

Revision as of 19:00, 25 February 2010

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