The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane
The thermal stability of several commonly used crystalline matrix-assisted ultraviolet laser desorption/ionization mass spectrometry (UV-MALDI-MS) matrices, 2,5-dihydroxybenzoic acid (gentisic acid; GA), 2,4,6- trihydroxyacetophenone (THA), α-cyano-4-hydroxycinnamic acid (CHC), 3,5-dimethoxy-4-hydro...
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todo:paper_10765174_v44_n2_p260_Tarzi2023-10-03T16:03:23Z The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane Tarzi, O.I. Nonami, H. Erra-Balsells, R. Matrix Melting point Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Absorption spectroscopy Acids Chromatographic analysis Desorption Electrospray ionization Emission spectroscopy Ethylene High performance liquid chromatography Holmium Inductively coupled plasma Ionization Magnetic resonance Mass spectrometers Mass spectrometry Melting Negative ions Nuclear magnetic resonance Nuclear magnetic resonance spectroscopy Simulated annealing Spectrometers Spectrometry Spectrum analysis Stability Steelmaking Thermochemistry Thermodynamic stability Thin layer chromatography Unmanned aerial vehicles (UAV) Matrix Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Melting point acetophenone derivative alpha cyano 4 hydroxycinnamic acid carbon dioxide crystallin gentisic acid harman perchlorate sinapic acid article chemical analysis chemical structure decarboxylation electrospray mass spectrometry fluorescence isomerization macromolecule matrix assisted laser desorption ionization time of flight mass spectrometry melting point priority journal proton nuclear magnetic resonance temperature sensitivity thermostability thin layer chromatography time of flight mass spectrometry ultraviolet radiation ultraviolet spectroscopy Acetophenones Coumaric Acids Gentisates Harmine Hot Temperature Magnetic Resonance Spectroscopy Phase Transition Photochemistry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization The thermal stability of several commonly used crystalline matrix-assisted ultraviolet laser desorption/ionization mass spectrometry (UV-MALDI-MS) matrices, 2,5-dihydroxybenzoic acid (gentisic acid; GA), 2,4,6- trihydroxyacetophenone (THA), α-cyano-4-hydroxycinnamic acid (CHC), 3,5-dimethoxy-4-hydroxycinnamic acid (sinapinic acid; SA), 9H-pirido[3,4-b] indole (nor-harmane; nor-Ho), 1-methyl-9H-pirido[3,4-b]indole (harmane; Ho), perchlorate of nor-harmanonium ([nor-Ho + H]+) and perchlorate of harmanonium ([Ho + H]+) was studied by heating them at their melting point and characterizing the remaining material by using different MS techniques [electron ionization mass spectrometry (EI-MS), ultraviolet laserdesorption/ionization-time-of-flight-mass spectrometry (UV-LDI-TOF-MS) and electrospray ionization-time-of-flight-mass spectrometry (ESI-TOF-MS)] as well as by thin layer chromatography analysis (TLC), electronic spectroscopy (UV-absorption, fluorescence emission and excitation spectroscopy) and 1H nuclear magnetic resonance spectroscopy (1H-NMR). In general, all compounds, except for CHC and SA, remained unchanged after fusion. CHC showed loss of CO2, yielding the trans-/cis-4- hydroxyphenylacrilonitrile mixture. This mixture was unambiguously characterized by MS and 1H-NMR spectroscopy, and its sublimation capability was demonstrated. These results explain the well-known cluster formation, fading (vanishing) and further recovering of CHC when used as a matrix in UV-MALDI-MS. Commercial SA (SA 98%; trans-SA/cis-SA 5:1) showed mainly cis- to-trans thermal isomerization and, with very poor yield, loss of CO2, yielding (3′,5′-dimethoxy-4′-hydroxyphenyl)-1-ethene as the decarboxilated product. These thermal conversions would not drastically affect its behavior as a UV-MALDI matrix as happens in the case of CHC. Complementary studies of the photochemical stability of these matrices in solid state were also conducted. Copyright © 2008 John Wiley & Sons, Ltd. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_10765174_v44_n2_p260_Tarzi |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Matrix Melting point Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Absorption spectroscopy Acids Chromatographic analysis Desorption Electrospray ionization Emission spectroscopy Ethylene High performance liquid chromatography Holmium Inductively coupled plasma Ionization Magnetic resonance Mass spectrometers Mass spectrometry Melting Negative ions Nuclear magnetic resonance Nuclear magnetic resonance spectroscopy Simulated annealing Spectrometers Spectrometry Spectrum analysis Stability Steelmaking Thermochemistry Thermodynamic stability Thin layer chromatography Unmanned aerial vehicles (UAV) Matrix Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Melting point acetophenone derivative alpha cyano 4 hydroxycinnamic acid carbon dioxide crystallin gentisic acid harman perchlorate sinapic acid article chemical analysis chemical structure decarboxylation electrospray mass spectrometry fluorescence isomerization macromolecule matrix assisted laser desorption ionization time of flight mass spectrometry melting point priority journal proton nuclear magnetic resonance temperature sensitivity thermostability thin layer chromatography time of flight mass spectrometry ultraviolet radiation ultraviolet spectroscopy Acetophenones Coumaric Acids Gentisates Harmine Hot Temperature Magnetic Resonance Spectroscopy Phase Transition Photochemistry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization |
| spellingShingle |
Matrix Melting point Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Absorption spectroscopy Acids Chromatographic analysis Desorption Electrospray ionization Emission spectroscopy Ethylene High performance liquid chromatography Holmium Inductively coupled plasma Ionization Magnetic resonance Mass spectrometers Mass spectrometry Melting Negative ions Nuclear magnetic resonance Nuclear magnetic resonance spectroscopy Simulated annealing Spectrometers Spectrometry Spectrum analysis Stability Steelmaking Thermochemistry Thermodynamic stability Thin layer chromatography Unmanned aerial vehicles (UAV) Matrix Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Melting point acetophenone derivative alpha cyano 4 hydroxycinnamic acid carbon dioxide crystallin gentisic acid harman perchlorate sinapic acid article chemical analysis chemical structure decarboxylation electrospray mass spectrometry fluorescence isomerization macromolecule matrix assisted laser desorption ionization time of flight mass spectrometry melting point priority journal proton nuclear magnetic resonance temperature sensitivity thermostability thin layer chromatography time of flight mass spectrometry ultraviolet radiation ultraviolet spectroscopy Acetophenones Coumaric Acids Gentisates Harmine Hot Temperature Magnetic Resonance Spectroscopy Phase Transition Photochemistry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Tarzi, O.I. Nonami, H. Erra-Balsells, R. The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| topic_facet |
Matrix Melting point Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Absorption spectroscopy Acids Chromatographic analysis Desorption Electrospray ionization Emission spectroscopy Ethylene High performance liquid chromatography Holmium Inductively coupled plasma Ionization Magnetic resonance Mass spectrometers Mass spectrometry Melting Negative ions Nuclear magnetic resonance Nuclear magnetic resonance spectroscopy Simulated annealing Spectrometers Spectrometry Spectrum analysis Stability Steelmaking Thermochemistry Thermodynamic stability Thin layer chromatography Unmanned aerial vehicles (UAV) Matrix Photochemical stability Thermal stability UV-LDI-MS UV-MALDI-MS Melting point acetophenone derivative alpha cyano 4 hydroxycinnamic acid carbon dioxide crystallin gentisic acid harman perchlorate sinapic acid article chemical analysis chemical structure decarboxylation electrospray mass spectrometry fluorescence isomerization macromolecule matrix assisted laser desorption ionization time of flight mass spectrometry melting point priority journal proton nuclear magnetic resonance temperature sensitivity thermostability thin layer chromatography time of flight mass spectrometry ultraviolet radiation ultraviolet spectroscopy Acetophenones Coumaric Acids Gentisates Harmine Hot Temperature Magnetic Resonance Spectroscopy Phase Transition Photochemistry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization |
| description |
The thermal stability of several commonly used crystalline matrix-assisted ultraviolet laser desorption/ionization mass spectrometry (UV-MALDI-MS) matrices, 2,5-dihydroxybenzoic acid (gentisic acid; GA), 2,4,6- trihydroxyacetophenone (THA), α-cyano-4-hydroxycinnamic acid (CHC), 3,5-dimethoxy-4-hydroxycinnamic acid (sinapinic acid; SA), 9H-pirido[3,4-b] indole (nor-harmane; nor-Ho), 1-methyl-9H-pirido[3,4-b]indole (harmane; Ho), perchlorate of nor-harmanonium ([nor-Ho + H]+) and perchlorate of harmanonium ([Ho + H]+) was studied by heating them at their melting point and characterizing the remaining material by using different MS techniques [electron ionization mass spectrometry (EI-MS), ultraviolet laserdesorption/ionization-time-of-flight-mass spectrometry (UV-LDI-TOF-MS) and electrospray ionization-time-of-flight-mass spectrometry (ESI-TOF-MS)] as well as by thin layer chromatography analysis (TLC), electronic spectroscopy (UV-absorption, fluorescence emission and excitation spectroscopy) and 1H nuclear magnetic resonance spectroscopy (1H-NMR). In general, all compounds, except for CHC and SA, remained unchanged after fusion. CHC showed loss of CO2, yielding the trans-/cis-4- hydroxyphenylacrilonitrile mixture. This mixture was unambiguously characterized by MS and 1H-NMR spectroscopy, and its sublimation capability was demonstrated. These results explain the well-known cluster formation, fading (vanishing) and further recovering of CHC when used as a matrix in UV-MALDI-MS. Commercial SA (SA 98%; trans-SA/cis-SA 5:1) showed mainly cis- to-trans thermal isomerization and, with very poor yield, loss of CO2, yielding (3′,5′-dimethoxy-4′-hydroxyphenyl)-1-ethene as the decarboxilated product. These thermal conversions would not drastically affect its behavior as a UV-MALDI matrix as happens in the case of CHC. Complementary studies of the photochemical stability of these matrices in solid state were also conducted. Copyright © 2008 John Wiley & Sons, Ltd. |
| format |
JOUR |
| author |
Tarzi, O.I. Nonami, H. Erra-Balsells, R. |
| author_facet |
Tarzi, O.I. Nonami, H. Erra-Balsells, R. |
| author_sort |
Tarzi, O.I. |
| title |
The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| title_short |
The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| title_full |
The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| title_fullStr |
The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| title_full_unstemmed |
The effect of temperature on the stability of compounds used as UV-MALDI-MS matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| title_sort |
effect of temperature on the stability of compounds used as uv-maldi-ms matrix: 2,5-dihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, α-cyano-4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, nor-harmane and harmane |
| url |
http://hdl.handle.net/20.500.12110/paper_10765174_v44_n2_p260_Tarzi |
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