LipidBank - Lipid peroxide

No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	PHYSICAL AND CHEMICAL PROPERTIES						SPECTRAL DATA					CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	MELTING POINT	BOILING POINT	DENSITY	REFRACTIVE INDEX	OPTICAL ROTATION	SOLUBILITY	UV SPECTRA	IR SPECTRA	NMR SPECTRA	MASS SPECTRA	OTHER SPECTRA	CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
1	No image		9-Hydroperoxy-10,12-Octadecadienoic Acid/9-Hydroperoxy-10,12-Octadecadienoate	OPO8001	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049)							Trans, cis isomer: l max=236nm, e =25900, trans, trans isomer: l max=233nm, e=28600 (Ref. 8001/8002/8003/8004/8005/8011)	Methyl ester: (Ref. 8001/8005/8006/8007/8008/8009/8010/8011): trans, cis isomer: 986 and 949cm^-¹, trans, trans isomer: 989cm^-¹, OOH group: 3550cm^-¹	¹H-NMR(Ref. 8001/8012), ¹H-NMR( after methanolyzation and reduction)(Ref. 8005/8017): 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)	GC/EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8012/8018/8013/8019/8014): 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) (Ref. 8020/8015/8016): m/e= 187[CH(OH)(CH2)7COOCH3], 158[(CH2)7COOCH3+H], 155[C(OH)-(CH)7CO]			Auto oxidation of methyllinoleate(Ref. 8021/8022/8023/8024/8025/8026/8027/8039/8028/8029/8030). Oxidation of methyl linoleate by singlet oxygen(Ref. 8022/8023/8025/8026/8027/8039/8030/8024). Oxidation of linoleic acid by lipoxygenase(Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036). Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
2	No image		13- Hydroperoxy-9,11-Octadecadienoic Acid/13- Hydroperoxy-9,11-Octadecadienoate	OPO8002	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048)							Trans , cis isomer: l max= 236nm, e= 26000, trans, trans isomer: l max= 233nm, e=28600 (025/027/028/029/036)	Methyl ester(Ref. 8001/8006/8007/8008/8009/8010/8011): cis, trans isomer: 986 and 949cm^-¹, trans, trans isomer: 989cm^-¹, OOH group: 3550cm^-¹	¹H-NMR (Ref. 8001/8012): C9-13 (5.45-6.53ppm), C13 (4.37ppm), J9-10= 11Hz (cis),J11-12=15Hz (trans) /¹H-NMR (after methanolyzation and reduction )(Ref. 8005/8017): cis, trans isomer : olefinic protons(5.91ppm), C8 (2.10ppm), C13(4.15ppm), trans, trans isomer: olefinic protons (5.41ppm), C8 (2.07ppm)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8012/8018/8019/8013/8014): m/e= 382[M], 292[M-HOTMS], 311[M-(CH2)4CH3] standard peak,225[M-(CH2)7COOCH3] / GC-EI-MS(after methylation, reduction and hydrogenation) (Ref. 8020/8015/8016): m/e= 243[CH(OH)(CH2)11COOCH3], 214[(CH2)11COOCH3+H], 211[C(OH(CH2)11CO)			Auto oxidation of methyl linoleate(Ref. 8029/8021/8022/8023/8024/8025/8026/8039/8028/8030). Oxidation of methyl linoleate by singlet oxygen(Ref. 8022/8023/8025/8026/8027/8030/8024). Oxidation of linoleic acid by lipoxygenase(Ref. 8023/8031/8032/8033/8034/8035/8037/8038/8036). Production mechanism (auto oxidation): bis-allylic hydrogen at C11.
3	No image		10-Hydroperoxy-8,12-Octadecadienoic Acid/10-Hydroperoxy-8,12-Octadecadienoate	OPO8003	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049)								After methanolyzation and reduction(Ref. 8091/8090): isolated double bond (3013-3010, 972-971cm^-¹)	¹H-NMR(after methanolyzation and reduction)(Ref. 8091): olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation)(Ref. 8090/8019): m/e= 271[SMTO=CH-CH=CH-(CH2)6COOCH3], GC-EI-MS (after methylation, reduction and hydrogenation)(Ref. 8020):m/e= 201[CH(OH)(CH2)8COOCH3], 172[(CH2)8COOCH3+H], 169[C(OH)(CH2)8CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)(Ref. 8090)			Oxidation of methyl linoleate by singlet oxygen(Ref. 8043/8044/8045/8046/8047/8048/8049).
4	No image		12-Hydroperoxy-9,13-Octadecadienoic Acid/12-Hydroperoxy-9,13-Octadecadienoate	OPO8004	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444		Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.(Ref. 8043/8044/8045/8046/8047/8048/8049)								After methanolyzation and reduction(Ref. 8091/8090): isolated double bond (3013-3010, 972-971cm^-¹)	¹H-NMR(after methanolyzation and reduction)(Ref. 8091): olefinic protons(5.55-5.59ppm), C10 (4.08-4.11ppm)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation)(Ref. 8090/8019): m/e= 185[SMTO=CH-CH=CH-(CH2)3CH3], GC-EI-MS (after methylation, reduction and hydrogenation)(Ref. 8020): m/e= 229[CH(OH)(CH2)10COOCH3], 200[(CH2)10COOCH3+H], 197[C(OH)(CH2)10CO] GC-EI-MS(after methylation, reduction, hydrogenation and trimethylsilylation)(Ref. 8090)			Oxidation of methyl linoleate by singlet oxygen(Ref. 8024/8022/8023/8025/8026/8027/8039/8030).
5	No image		8-Hydroperoxy-9,12-Octadecadienoic Acid	OPO8005	Tetsuyuki Kobayashi		C₁₈H₃₂O₄	312.444											¹H-NMR (after methanolyzation, reduction and 400MHz )(Ref. 8050): olefinic protons(5.91-5.51ppm), C8 (4.45ppm), C11(2.84ppm), C14(2.05ppm),J9-10= J12-13= 10.7Å }0.2Hz (cis)	GC-EI-MS(after methanolysis, reduction and trimethylsilylation) (Ref. 8050>: m/e= 292[M-HOTMS], 271[CH=CH-CH(OTMS)-(CH2)6COOCH3], 239[M-(CH2)6C00CH3], 173[SMTO=CH-(CH2)6COOCH3-TMS+H], 149[239-HOTMS] standard peak			A minor component of monohydroperoxide generated from linoleic acid or methyllinoleate by autooxidation(Ref. 8050/8051). A minor component of hydroperoxide generated from linoleic acid through oxidation by soy bean lipoxygenase (type-2)(Ref. 8050).				8-OOH and 14-OOH are known as small amount components of monohydroperoxidate from auto oxidation of linoleic acid and oxidation of soybean lipoxygenase(type-2). Their amount oes not change by temperature or addition of a-tocopherol(Ref. 8050).