메뉴 건너뛰기




Volumn 93, Issue 4, 2016, Pages 467-478

1H-NMR Characterization of Epoxides Derived from Polyunsaturated Fatty Acids

Author keywords

1H NMR; Canola oil; Diepoxide; Fish oil; Lipid oxidation; Stereoisomer; Triepoxide

Indexed keywords

CHEMICAL SHIFT; DEGRADATION; EPOXIDATION; FISH; ISOMERS; STEREOCHEMISTRY;

EID: 84957938901     PISSN: 0003021X     EISSN: 15589331     Source Type: Journal    
DOI: 10.1007/s11746-016-2800-2     Document Type: Article
Times cited : (51)

References (39)
  • 1
    • 33645323216 scopus 로고    scopus 로고
    • Chemical modification of vegetable oils for lubricant applications
    • 1:CAS:528:DC%2BD28XislKnsLk%3D
    • Sharma BK, Adhvaryu A, Liu Z, Erhan SZ (2006) Chemical modification of vegetable oils for lubricant applications. J Am Oil Chem Soc 83:129-136
    • (2006) J Am Oil Chem Soc , vol.83 , pp. 129-136
    • Sharma, B.K.1    Adhvaryu, A.2    Liu, Z.3    Erhan, S.Z.4
  • 2
    • 49649084628 scopus 로고    scopus 로고
    • Epoxidation of canola oil with hydrogen peroxide catalyzed by acidic ion exchange resin
    • 1:CAS:528:DC%2BD1cXhtFeis7jM
    • Mungroo R, Pradhan NC, Goud VV, Dalai AK (2008) Epoxidation of canola oil with hydrogen peroxide catalyzed by acidic ion exchange resin. J Am Oil Chem Soc 85:887-896
    • (2008) J Am Oil Chem Soc , vol.85 , pp. 887-896
    • Mungroo, R.1    Pradhan, N.C.2    Goud, V.V.3    Dalai, A.K.4
  • 3
    • 84858169638 scopus 로고    scopus 로고
    • Thinking outside the classical chain reaction box of lipid oxidation
    • 1:CAS:528:DC%2BC38Xjs1Ohuro%3D
    • Schaich KM (2012) Thinking outside the classical chain reaction box of lipid oxidation. Lipid Technol 24:55-58
    • (2012) Lipid Technol , vol.24 , pp. 55-58
    • Schaich, K.M.1
  • 4
    • 80054089650 scopus 로고    scopus 로고
    • Free radical lipid peroxidation: Mechanisms and analysis
    • 1:CAS:528:DC%2BC3MXhtVOnsrvM
    • Yin H, Xu L, Porter NA (2011) Free radical lipid peroxidation: Mechanisms and analysis. Chem Rev 111:5944-5972
    • (2011) Chem Rev , vol.111 , pp. 5944-5972
    • Yin, H.1    Xu, L.2    Porter, N.A.3
  • 5
    • 0021534299 scopus 로고
    • Chemistry of free radical and singlet oxidation of lipids
    • 1:CAS:528:DyaL28XktVaht7g%3D
    • Frankel EN (1984) Chemistry of free radical and singlet oxidation of lipids. Prog Lipid Res 23:197-221
    • (1984) Prog Lipid Res , vol.23 , pp. 197-221
    • Frankel, E.N.1
  • 7
    • 0016313594 scopus 로고
    • Detection and analysis of epoxides with 4-(p-nitrobenzyl)-pyridine
    • 1:CAS:528:DyaE2MXkt1ajsLY%3D
    • Hammock LG, Hammock BD, Casida JE (1974) Detection and analysis of epoxides with 4-(p-nitrobenzyl)-pyridine. Bull Environ Contam Toxicol 12:759-764
    • (1974) Bull Environ Contam Toxicol , vol.12 , pp. 759-764
    • Hammock, L.G.1    Hammock, B.D.2    Casida, J.E.3
  • 8
    • 33846609438 scopus 로고    scopus 로고
    • Determination of epoxides by high-performance liquid chromatography following derivatization with N,N-diethyldithiocarbamate
    • 1:CAS:528:DC%2BD2sXht1Wiu78%3D
    • Dupard-Julien CL, Kandlakunta B, Uppu RM (2007) Determination of epoxides by high-performance liquid chromatography following derivatization with N,N-diethyldithiocarbamate. Anal Bioanal Chem 387:1027-1032
    • (2007) Anal Bioanal Chem , vol.387 , pp. 1027-1032
    • Dupard-Julien, C.L.1    Kandlakunta, B.2    Uppu, R.M.3
  • 9
    • 84897539603 scopus 로고    scopus 로고
    • Development and validation of a gas chromatography-flame ionization detection method for the determination of epoxy fatty acids in food matrices
    • 1:CAS:528:DC%2BC2cXjvVOgu7w%3D
    • Mubiru E, Shrestha K, Papastergiadis A, De Meulenaer B (2014) Development and validation of a gas chromatography-flame ionization detection method for the determination of epoxy fatty acids in food matrices. J Agric Food Chem 62:2982-2988
    • (2014) J Agric Food Chem , vol.62 , pp. 2982-2988
    • Mubiru, E.1    Shrestha, K.2    Papastergiadis, A.3    De Meulenaer, B.4
  • 10
    • 77952610399 scopus 로고    scopus 로고
    • 1H nuclear magnetic resonance in sunflower oil oxidized at 70 and 100 degrees C
    • 1:CAS:528:DC%2BC3cXlsV2ktro%3D
    • 1H nuclear magnetic resonance in sunflower oil oxidized at 70 and 100 degrees C. J Agric Food Chem 58:6234-6245
    • (2010) J Agric Food Chem , vol.58 , pp. 6234-6245
    • Goicoechea, E.1    Guillen, M.D.2
  • 11
    • 33645966854 scopus 로고    scopus 로고
    • Synthetic lubricant basestocks from epoxidized soybean oil and Guerbet alcohols
    • 1:CAS:528:DC%2BD28Xjs1yhsLs%3D
    • Hwang HS, Erhan SZ (2006) Synthetic lubricant basestocks from epoxidized soybean oil and Guerbet alcohols. Ind Crops Prod 23:311-317
    • (2006) Ind Crops Prod , vol.23 , pp. 311-317
    • Hwang, H.S.1    Erhan, S.Z.2
  • 13
    • 33845658605 scopus 로고    scopus 로고
    • Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil
    • 1:CAS:528:DC%2BD2sXislKh
    • Lathi P, Mattiasson B (2007) Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil. Appl Catal B 69:207-212
    • (2007) Appl Catal B , vol.69 , pp. 207-212
    • Lathi, P.1    Mattiasson, B.2
  • 14
    • 84901703672 scopus 로고    scopus 로고
    • Synthesis of epoxy jatropha oil and its evaluation for lubricant properties
    • 1:CAS:528:DC%2BC2cXpsVehtb4%3D
    • Sammaiah A, Padmaja KV, Prasad RB (2014) Synthesis of epoxy jatropha oil and its evaluation for lubricant properties. J Oleo Sci 63:637-643
    • (2014) J Oleo Sci , vol.63 , pp. 637-643
    • Sammaiah, A.1    Padmaja, K.V.2    Prasad, R.B.3
  • 17
    • 84961977322 scopus 로고    scopus 로고
    • Global Organization for EPA and DHA omega-3. GOED Voluntary Monograph Accessed Sept 2014
    • Global Organization for EPA and DHA omega-3. GOED Voluntary Monograph. http://www.goedomega3.com/index.php/files/download/155. Accessed Sept 2014
  • 18
    • 79952533641 scopus 로고    scopus 로고
    • Modeling the primary oxidation in commercial fish oil preparations
    • Sullivan JC, Budge SM, St-Onge M (2010) Modeling the primary oxidation in commercial fish oil preparations. Lipids 46:87-93
    • (2010) Lipids , vol.46 , pp. 87-93
    • Sullivan, J.C.1    Budge, S.M.2    St-Onge, M.3
  • 19
    • 84870064872 scopus 로고    scopus 로고
    • Monitoring the epoxidation of canola oil by non-aqueous reversed phase liquid chromatography/mass spectrometry for process optimization and control
    • 1:CAS:528:DC%2BC38XhsFCltrjP
    • Anuar ST, Zhao YY, Mugo SM, Curtis J (2012) Monitoring the epoxidation of canola oil by non-aqueous reversed phase liquid chromatography/mass spectrometry for process optimization and control. J Am Oil Chem Soc 89:1951-1960
    • (2012) J Am Oil Chem Soc , vol.89 , pp. 1951-1960
    • Anuar, S.T.1    Zhao, Y.Y.2    Mugo, S.M.3    Curtis, J.4
  • 20
    • 77954792401 scopus 로고    scopus 로고
    • Epoxidation of vegetable oils and fatty acids: Catalysts, methods and advantages
    • Mudhaffar B, Salimon J (2010) Epoxidation of vegetable oils and fatty acids: Catalysts, methods and advantages. J Appl Sci 10:1545-1553
    • (2010) J Appl Sci , vol.10 , pp. 1545-1553
    • Mudhaffar, B.1    Salimon, J.2
  • 21
    • 43849092155 scopus 로고    scopus 로고
    • Epoxidation of cottonseed oil by aqueous hydrogen peroxide catalysed by liquid inorganic acids
    • 1:CAS:528:DC%2BD1cXitlyqtb8%3D
    • Dinda S, Patwardhan AV, Goud VV, Pradhan N (2008) Epoxidation of cottonseed oil by aqueous hydrogen peroxide catalysed by liquid inorganic acids. Bioresour Technol 99:3737-3744
    • (2008) Bioresour Technol , vol.99 , pp. 3737-3744
    • Dinda, S.1    Patwardhan, A.V.2    Goud, V.V.3    Pradhan, N.4
  • 22
    • 54549097931 scopus 로고    scopus 로고
    • Quantitative determination of epoxy acids, keto acids and hydroxy acids formed in fats and oils at frying temperatures
    • 1:CAS:528:DC%2BD1cXhtlaqsLnJ
    • Marmesat S, Velasco J, Dobarganes MC (2008) Quantitative determination of epoxy acids, keto acids and hydroxy acids formed in fats and oils at frying temperatures. J Chromatogr A 1211:129-134
    • (2008) J Chromatogr A , vol.1211 , pp. 129-134
    • Marmesat, S.1    Velasco, J.2    Dobarganes, M.C.3
  • 24
    • 34250850751 scopus 로고    scopus 로고
    • Chemistry of deep-fat frying oils
    • Choe E, Min DB (2007) Chemistry of deep-fat frying oils. J Food Sci 72:77-86
    • (2007) J Food Sci , vol.72 , pp. 77-86
    • Choe, E.1    Min, D.B.2
  • 25
    • 0032166378 scopus 로고    scopus 로고
    • Determination of unsaturated fatty acid composition by high-resolution nuclear magnetic resonance spectroscopy
    • 1:CAS:528:DyaK1cXmsVKisr0%3D
    • Miyake Y, Yokomizo K, Matsuzaki N (1998) Determination of unsaturated fatty acid composition by high-resolution nuclear magnetic resonance spectroscopy. J Am Oil Chem Soc 75:1091-1094
    • (1998) J Am Oil Chem Soc , vol.75 , pp. 1091-1094
    • Miyake, Y.1    Yokomizo, K.2    Matsuzaki, N.3
  • 26
    • 33745478870 scopus 로고    scopus 로고
    • Assessment of epoxidized soy bean oil (ESBO) migrating into foods: Comparison with ESBO-like epoxy fatty acids in our normal diet
    • 1:CAS:528:DC%2BD28XmtVOltrY%3D
    • Fankhauser-Noti A, Fiselier K, Biedermann-Brem S, Grob K (2006) Assessment of epoxidized soy bean oil (ESBO) migrating into foods: Comparison with ESBO-like epoxy fatty acids in our normal diet. Food Chem Toxicol 44:1279-1286
    • (2006) Food Chem Toxicol , vol.44 , pp. 1279-1286
    • Fankhauser-Noti, A.1    Fiselier, K.2    Biedermann-Brem, S.3    Grob, K.4
  • 27
    • 0037448296 scopus 로고    scopus 로고
    • Epoxidation of fatty acids, fatty methyl esters, and alkenes by immobilized oat seed peroxygenase
    • 1:CAS:528:DC%2BD38XptlGju7k%3D
    • Piazza GJ, Nuñez A, Foglia TA (2003) Epoxidation of fatty acids, fatty methyl esters, and alkenes by immobilized oat seed peroxygenase. J Mol Catal B Enzym 21:143-151
    • (2003) J Mol Catal B Enzym , vol.21 , pp. 143-151
    • Piazza, G.J.1    Nuñez, A.2    Foglia, T.A.3
  • 28
    • 33845326123 scopus 로고    scopus 로고
    • Determination of epoxidized soy bean oil (ESBO) in oily foods by GC-FID or GC-MS analysis of the methyl diepoxy linoleate
    • 1:CAS:528:DC%2BD28Xht1Ogs7zL
    • Biedermann-Brem S, Biedermann M, Fankhauser-Noti A, Grob K, Helling R (2007) Determination of epoxidized soy bean oil (ESBO) in oily foods by GC-FID or GC-MS analysis of the methyl diepoxy linoleate. Eur Food Res Technol 224:309-314
    • (2007) Eur Food Res Technol , vol.224 , pp. 309-314
    • Biedermann-Brem, S.1    Biedermann, M.2    Fankhauser-Noti, A.3    Grob, K.4    Helling, R.5
  • 30
    • 0030836820 scopus 로고    scopus 로고
    • Mechanism of acid-catalyzed epoxidation of alkenes with peroxy acids
    • 1:CAS:528:DyaK2sXkvVSrsr0%3D
    • Bach RD, Canepa C, Winter JE, Blanchette PE (1997) Mechanism of acid-catalyzed epoxidation of alkenes with peroxy acids. J Org Chem 62:5191-5197
    • (1997) J Org Chem , vol.62 , pp. 5191-5197
    • Bach, R.D.1    Canepa, C.2    Winter, J.E.3    Blanchette, P.E.4
  • 31
    • 12844264705 scopus 로고    scopus 로고
    • 1H NMR and traditional methods for determining lipid oxidation of ethyl docosahexaenoate
    • 1:CAS:528:DC%2BD2MXhtVWksr0%3D
    • 1H NMR and traditional methods for determining lipid oxidation of ethyl docosahexaenoate. J Am Oil Chem Soc 81:1105-1110
    • (2004) J Am Oil Chem Soc , vol.81 , pp. 1105-1110
    • Falch, E.1    Anthonsen, H.W.2    Axelson, D.E.3    Aursand, M.4
  • 32
    • 0036199525 scopus 로고    scopus 로고
    • The conjugation and epoxidation of fish oil
    • 1:CAS:528:DC%2BD38XhvVegur8%3D
    • Marks DW, Larock RC (2002) The conjugation and epoxidation of fish oil. J Am Oil Chem Soc 79:65-68
    • (2002) J Am Oil Chem Soc , vol.79 , pp. 65-68
    • Marks, D.W.1    Larock, R.C.2
  • 34
    • 0013940725 scopus 로고
    • Epoxidation of methyl linoleate. II. The two isomers of methyl 9,10:12,13-diepoxystearate
    • 1:CAS:528:DyaF28XkvVWks7g%3D
    • Maerker G, Haeberer ET, Herb SF (1966) Epoxidation of methyl linoleate. II. The two isomers of methyl 9,10:12,13-diepoxystearate. J Am Oil Chem Soc 43:505-508
    • (1966) J Am Oil Chem Soc , vol.43 , pp. 505-508
    • Maerker, G.1    Haeberer, E.T.2    Herb, S.F.3
  • 35
    • 51249187614 scopus 로고
    • Determination of cis and trans in monoene and diene fatty esters by gas chromatography
    • 1:CAS:528:DyaE38XhsFWq
    • Emken EA (1971) Determination of cis and trans in monoene and diene fatty esters by gas chromatography. Lipids 6:686-687
    • (1971) Lipids , vol.6 , pp. 686-687
    • Emken, E.A.1
  • 37
    • 0035934430 scopus 로고    scopus 로고
    • Synthesis of thermoset plastics by Lewis acid initiated copolymerization of fish oil ethyl esters and alkenes
    • 1:CAS:528:DC%2BD3MXksFKju7c%3D
    • Marks DW, Li F, Pacha CM, Larock RC (2001) Synthesis of thermoset plastics by Lewis acid initiated copolymerization of fish oil ethyl esters and alkenes. J Appl Polym Sci 81:2001-2012
    • (2001) J Appl Polym Sci , vol.81 , pp. 2001-2012
    • Marks, D.W.1    Li, F.2    Pacha, C.M.3    Larock, R.C.4
  • 39
    • 34447640287 scopus 로고    scopus 로고
    • Lipid oxidation: Theoretical aspects
    • F. Shahidi (eds) Wiley Hoboken
    • Schaich KM (2005) Lipid oxidation: Theoretical aspects. In: Shahidi F (ed) Bailey's industrial oil and fat products. Wiley, Hoboken
    • (2005) Bailey's Industrial Oil and Fat Products
    • Schaich, K.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.