LBF18206HP01: Difference between revisions

No edit summary
No edit summary
Line 9: Line 9:
|Common Name=&&9-Hydroperoxy-10,12-Octadecadienoic Acid&&9-Hydroperoxy-10,12-Octadecadienoate&&
|Common Name=&&9-Hydroperoxy-10,12-Octadecadienoic Acid&&9-Hydroperoxy-10,12-Octadecadienoate&&
|Mass Spectra=GC/EI-MS(after methanolysis, reduction and trimethylsilylation) [[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]][[Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31|{{RelationTable/GetFirstAuthor|Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31}}]][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961}}]][[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]]: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) [[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]][[Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28|{{RelationTable/GetFirstAuthor|Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28}}]][[Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392|{{RelationTable/GetFirstAuthor|Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392}}]]: m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]
|Mass Spectra=GC/EI-MS(after methanolysis, reduction and trimethylsilylation) [[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]][[Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31|{{RelationTable/GetFirstAuthor|Reference:Kleiman_R:Spencer_GF:,J. Am. Oil Chem. Soc.,1973,50,31}}]][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Bessler_TR:,Lipids,1979,14,961}}]][[Reference:Hamberg_M:,Lipids,1975,10,87|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:,Lipids,1975,10,87}}]]: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) [[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]][[Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28|{{RelationTable/GetFirstAuthor|Reference:Dolev_A:Rohwedder_WK:Dutton_HJ:,Lipids,1967,2,28}}]][[Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392|{{RelationTable/GetFirstAuthor|Reference:Zimmerman_DC:Vick_BA:,Lipids,1970,5,392}}]]: m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]
|UV Spectra=Trans, cis isomer: lambda max=236nm, epsilon =25900, trans, trans isomer: lambda max=233nm, epsilon=28600 [[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Bolland_JL:Koch_HP:,J. Chem. Soc.,1945,,445|{{RelationTable/GetFirstAuthor|Reference:Bolland_JL:Koch_HP:,J. Chem. Soc.,1945,,445}}]][[Reference:Lundberg_WO:Chipault_JR:,J. Am. Chem. Soc.,1947,69,833|{{RelationTable/GetFirstAuthor|Reference:Lundberg_WO:Chipault_JR:,J. Am. Chem. Soc.,1947,69,833}}]][[Reference:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109|{{RelationTable/GetFirstAuthor|Reference:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191}}]]
|UV Spectra=Trans, cis isomer: lambda max=236nm, epsilon =25900, trans, trans isomer: lambda max=233nm, epsilon =28600 [[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Bolland_JL:Koch_HP:,J. Chem. Soc.,1945,,445|{{RelationTable/GetFirstAuthor|Reference:Bolland_JL:Koch_HP:,J. Chem. Soc.,1945,,445}}]][[Reference:Lundberg_WO:Chipault_JR:,J. Am. Chem. Soc.,1947,69,833|{{RelationTable/GetFirstAuthor|Reference:Lundberg_WO:Chipault_JR:,J. Am. Chem. Soc.,1947,69,833}}]][[Reference:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109|{{RelationTable/GetFirstAuthor|Reference:Lundberg_WO:Chipault_JR:Hendrickson_NJ:,J. Am. Oil Chem. Soc.,1949,26,109}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191}}]]
|IR Spectra=Methyl ester: [[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447|{{RelationTable/GetFirstAuthor|Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447}}]][[Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61}}]][[Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263|{{RelationTable/GetFirstAuthor|Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]][[Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191}}]]: trans, cis isomer: 986 and 949cm^- ^1 , trans, trans isomer: 989cm^- ^1 , OOH group: 3550cm^- ^1  
|IR Spectra=Methyl ester: [[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447|{{RelationTable/GetFirstAuthor|Reference:Cannon_JA:Zilch_KT:Burket_SC:Dutton_HJ:,J. Am. Oil Chem. Soc.,1952,29,447}}]][[Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Lundberg_WO:Khan_NA:Tolberg_WE:Wheeler_DH:,J. Am. Oil Chem. Soc.,1953,30,61}}]][[Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263|{{RelationTable/GetFirstAuthor|Reference:Sephton_HH:Sutton_DA:,J. Am. Oil Chem. Soc.,1956,33,263}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]][[Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505|{{RelationTable/GetFirstAuthor|Reference:Privett_OS:Nickell_C:Lundberg_WO:Boyer_PD:,J. Am. Oil Chem. Soc.,1955,32,505}}]][[Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1972,7,191}}]]: trans, cis isomer: 986 and 949cm^- ^1 , trans, trans isomer: 989cm^- ^1 , OOH group: 3550cm^- ^1  
|NMR Spectra=^1 H-NMR[[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]], ^1 H-NMR( after methanolyzation and reduction)[[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]]: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
|NMR Spectra=^1 H-NMR[[Reference:Chan_HW:Levett_G:,Lipids,1977,12,99|{{RelationTable/GetFirstAuthor|Reference:Chan_HW:Levett_G:,Lipids,1977,12,99}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]], ^1 H-NMR( after methanolyzation and reduction)[[Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:,Lipids,1970,5,678}}]][[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]]: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)

Revision as of 14:00, 19 February 2010

LipidBank Top
(トップ)
Fatty acid
(脂肪酸)
Glycerolipid
(グリセロ脂質)
Sphingolipid
(スフィンゴ脂質)
Journals
(雑誌一覧)
How to edit
(ページの書き方)


Upper classes: LB LBF



9-Hydroperoxy-10,12-Octadecadienoic Acid
LBF18206HP01.png
Structural Information
9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate
  • 9-Hydroperoxy-10,12-Octadecadienoic Acid
  • 9-Hydroperoxy-10,12-Octadecadienoate
Formula C18H32O4
Exact Mass 312.23005951199997
Average Mass 312.44428
SMILES CCCCCC=CC=CC(OO)CCCCCCCC(O)=O
Physicochemical Information
Auto oxidation of methyllinoleate Frankel_EN Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.. Oxidation of methyl linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN Frankel_EN . Oxidation of linoleic acid by lipoxygenase Mathuo_M Wakabayashi_T . Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously. Logani_MK et al. Sevanian_A et al. Fujimoto_K
Spectral Information
Mass Spectra GC/EI-MS(after methanolysis, reduction and trimethylsilylation) Frankel_EN et al. KleimanRet al. Gardner_HW et al. Frankel_EN et al. HambergM: m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3], 225[M-(CH2)7COOCH3] standard peak/ GC-EI-MS(after methylation, reduction and hydrogenation) Chan_HWS DolevAet al. Zimmerman_DC et al.: m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]
UV Spectra Trans, cis isomer: λ max=236nm, ε =25900, trans, trans isomer: λ max=233nm, ε =28600 Chan_HW et al. Bolland_JL et al. Lundberg_WO et al. Lundberg_WO et al. Gardner_HW et al. Gardner_HW et al.
IR Spectra Methyl ester: Chan_HW et al. Gardner_HW et al. Cannon_JA et al. Privett_OS et al. Sephton_HH et al. Graveland_A_ Privett_OS et al. Gardner_HW et al.: trans, cis isomer: 986 and 949cm-1, trans, trans isomer: 989cm-1, OOH group: 3550cm-^1
NMR Spectra 1H-NMR Chan_HW et al. Frankel_EN et al., 1H-NMR( after methanolyzation and reduction) Gardner_HW et al. Neff_WE et al.: trans,cis isomer: C10-13 (5.42-6.48ppm), C14 (2.10-2.18ppm), C9(4.15ppm), J10-11= 15.4Hz(trans), J12-13= 10.8Hz (cis), trans, trans isomer: olefinic protons (5.41ppm), C14 (2.07ppm), C9 (4.20ppm)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18206HP01 See above. Bolland_JL et al. 1945
n.a. LBF18206HP01 See above. Cannon_JA et al. 1952
n.a. LBF18206HP01 See above. Chan_HW et al. 1977
n.a. LBF18206HP01 See above. Chan_HWS 1977
n.a. LBF18206HP01 See above. Chan_HWS et al. 1982
n.a. LBF18206HP01 See above. Dolev_A et al. 1967
n.a. LBF18206HP01 See above. Frankel_EN 1987
n.a. LBF18206HP01 See above. Frankel_EN 1980
n.a. LBF18206HP01 See above. Frankel_EN 1983
n.a. LBF18206HP01 See above. Frankel_EN 1984
n.a. LBF18206HP01 See above. Frankel_EN et al. 1979
n.a. LBF18206HP01 See above. Frankel_EN et al. 1977
n.a. LBF18206HP01 See above. Fujimoto_K 1986
n.a. LBF18206HP01 See above. Gardner_HW et al. 1974
n.a. LBF18206HP01 See above. Gardner_HW et al. 1970
n.a. LBF18206HP01 See above. Gardner_HW et al. 1972
n.a. LBF18206HP01 See above. Graveland_A_ 1970
n.a. LBF18206HP01 See above. Hamberg_M 1975
n.a. LBF18206HP01 See above. Kleiman_R et al. 1973
n.a. LBF18206HP01 See above. Logani_MK et al. 1980
n.a. LBF18206HP01 See above. Lundberg_WO et al. 1947
n.a. LBF18206HP01 See above. Lundberg_WO et al. 1949
n.a. LBF18206HP01 See above. Mathuo_M 1986
n.a. LBF18206HP01 See above. Neff_WE et al. 1978
n.a. LBF18206HP01 See above. Privett_OS et al. 1953
n.a. LBF18206HP01 See above. Privett_OS et al. 1955
n.a. LBF18206HP01 See above. Sephton_HH et al. 1956
n.a. LBF18206HP01 See above. Sevanian_A et al. 1985
n.a. LBF18206HP01 See above. Wakabayashi_T 1980
n.a. LBF18206HP01 See above. Zimmerman_DC et al. 1970