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Abstract:

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.

Registro:

Documento: Artículo
Título: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
Autor:Tarzi, O.I.; Nonami, H.; Erra-Balsells, R.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón II, 3P, 1428-Buenos Aires, Argentina
Plant Biophysics/Biochemistry Research Laboratory, Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama 790-8566, Japan
Palabras clave: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
Año:2009
Volumen:44
Número:2
Página de inicio:260
Página de fin:277
DOI: http://dx.doi.org/10.1002/jms.1506
Título revista:Journal of Mass Spectrometry
Título revista abreviado:J. Mass Spectrom.
ISSN:10765174
CODEN:JMSPF
CAS:alpha cyano 4 hydroxycinnamic acid, 28166-41-8; carbon dioxide, 124-38-9, 58561-67-4; crystallin, 11046-99-4; gentisic acid, 490-79-9; harman, 486-84-0; perchlorate, 14797-73-0; sinapic acid, 530-59-6; 2,4,6-trihydroxyacetophenone; 2,5-dihydroxybenzoic acid, 490-79-9; Acetophenones; alpha-cyano-4-hydroxycinnamate, 28166-41-8; Coumaric Acids; Gentisates; harman, 486-84-0; Harmine, 442-51-3; norharman, 244-63-3; sinapinic acid, 530-59-6
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v44_n2_p260_Tarzi

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Citas:

---------- APA ----------
Tarzi, O.I., Nonami, H. & Erra-Balsells, R. (2009) . 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. Journal of Mass Spectrometry, 44(2), 260-277.
http://dx.doi.org/10.1002/jms.1506
---------- CHICAGO ----------
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" . Journal of Mass Spectrometry 44, no. 2 (2009) : 260-277.
http://dx.doi.org/10.1002/jms.1506
---------- MLA ----------
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" . Journal of Mass Spectrometry, vol. 44, no. 2, 2009, pp. 260-277.
http://dx.doi.org/10.1002/jms.1506
---------- VANCOUVER ----------
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. J. Mass Spectrom. 2009;44(2):260-277.
http://dx.doi.org/10.1002/jms.1506