Analysis of 5-hydroxymethylfurfural in foods by gas chromatography–mass spectrometry

Teixidó, Elisabet; Santos, F.J.; Puignou, L.; Galcerán, M.T.

doi:10.1016/j.chroma.2006.09.023

Cited by 121 publications

(79 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The products were liquid/liquid-extracted using methyl-t-butyl ether. The extracts were dried with Na 2 SO 4 to remove water traces, evaporated in a rotary evaporator, and derivatized using bis (trimethylsilyl)trifluoroacetamide, at 25°C for 15 min [34]. A gas chromatograph equipped with an HP-5MS column (Agilent, Santa Clara, CA, USA; 30 m 9 0.25 mm internal diameter; 0.25 lm film thickness) coupled to a quadrupole mass detector was used.…”

Section: Gc-ms Analysesmentioning

confidence: 99%

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

Ferreira²,

et al. 2015

View full text Add to dashboard Cite

Oxidative conversion of 5-hydroxymethylfurfural (HMF) is of biotechnological interest for the production of renewable (lignocellulose-based) platform chemicals, such as 2,5-furandicarboxylic acid (FDCA). To the best of our knowledge, the ability of fungal aryl-alcohol oxidase (AAO) to oxidize HMF is reported here for the first time, resulting in almost complete conversion into 2,5-formylfurancarboxylic acid (FFCA) in a few hours. The reaction starts with alcohol oxidation, yielding 2,5-diformylfuran (DFF), which is rapidly converted into FFCA by carbonyl oxidation, most probably without leaving the enzyme active site. This agrees with the similar catalytic efficiencies of the enzyme with respect to oxidization of HMF and DFF, and its very low activity on 2,5-hydroxymethylfurancarboxylic acid (which was not detected by GC-MS). However, AAO was found to be unable to directly oxidize the carbonyl group in FFCA, and only modest amounts of FDCA are formed from HMF (most probably by chemical oxidation of FFCA by the H 2 O 2 previously generated by AAO). As aldehyde oxidation by AAO proceeds via the corresponding geminal diols (aldehyde hydrates), the various carbonyl oxidation rates may be related to the low degree of hydration of FFCA compared with DFF. The conversion of HMF was completed by introducing a fungal unspecific heme peroxygenase that uses the H 2 O 2 generated by AAO to transform FFCA into FDCA, albeit more slowly than the previous AAO reactions. By adding this peroxygenase when FFCA production by AAO has been completed, transformation of HMF into FDCA may be achieved in a reaction cascade in which O 2 is the only co-substrate required, and water is the only byproduct formed.

show abstract

Section: Gc-ms Analysesmentioning

confidence: 99%

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

Ferreira²,

et al. 2015

View full text Add to dashboard Cite

show abstract

“…At present, additional naturally occurring substances such as 5-(hydroxymethyl)-2-furfual (HMF) and related compounds, which are formed from hexoses in acidic media, are being evaluated for their potential human genotoxicity. In particular, high levels of HMF have been quantified in honeys, caramel products, plum-derived products, coffee and balsamic vinegars (Glatt & Sommer, 2006;Teixidó et al, 2006). Some examples of relatively abundant cooking mutagens among the types listed above, are the nitrosamine NMDA (Nnitrosodimethylamine); the polycyclic aromatic hydrocarbon BPA (benzo[a]pyrene); the heterocyclic aromatic amine PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine); HMF; furan and acrylamide, shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

Food Borne Carcinogens: A Dead End?

Busquets¹

2012

Carcinogen

View full text Add to dashboard Cite

“…A ldehydes, as products of the lipid peroxidation reactions and various atmospheric processes, are often detected in biological and environmental matrices [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. Derivatization of aldehydes is typically employed before the analysis to improve chromatographic separation and detection limits [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15].…”

mentioning

confidence: 99%

Detection limits of electron and electron capture negative ionization-mass spectrometry for aldehydes derivatized with o-(2,3,4,5,6-pentafluorobenzyl)-hydroxylamine hydrochloride

Beránek

Muggli

Kubátová

2010

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

In contrast to common expectations, the differences in limits of detection (LODs) between electron capture negative ionization (ECNI) and electron ionization (EI) mass spectrometry (MS) were found to be insignificant for a wide range of aldehydes derivatized with o- (2,3,4,5,6-pentafluorobenzyl)-hydroxylamine hydrochloride. Comparison of the two ionization methods based on LOD confidence intervals revealed that a traditional presentation of the LOD or limit of quantitation (LOQ) as a single value may over/underestimate the significance of obtained results. LODs were between 20 and 150 pg injected for the majority of tested derivatized carbonyls using both ionization methods. ECNI-MS improved LODs by ϳ10-to 20-fold only for two derivatized aldehydes, 4-hydroxybenzaldehyde and 5-(hydroxymethyl)furfural. Selectivity of ECNI did not appear to be beneficial when analyzing a wood smoke particulate matter (WS-PM) extract, possibly because the majority of interferences were removed during sample preparation (i.e., liquid-liquid extraction). The impact of four different data acquisition modes of transmission quadrupole (TQ)-MS on LODs and their precisions was also investigated. As expected, LODs in the selected ion monitoring (SIM) were ϳtwo to four times lower than those obtained using total ion current (TIC) mode. More importantly, TQ-MS in the selected ion-total ion (SITI) mode (i.e., acquiring SIM and TIC data in a single analysis) provided signal-to-noise ratios and precisions, which were comparable to SIM alone. (J Am Soc Mass Spectrom 2010, 21, 592-602)

show abstract

Analysis of 5-hydroxymethylfurfural in foods by gas chromatography–mass spectrometry

Cited by 121 publications

References 34 publications

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

Food Borne Carcinogens: A Dead End?

Detection limits of electron and electron capture negative ionization-mass spectrometry for aldehydes derivatized with o-(2,3,4,5,6-pentafluorobenzyl)-hydroxylamine hydrochloride

Contact Info

Product

Resources

About