The Formation of Furfural Compounds in Selected Saccharide- and Polysaccharide-based Pharmaceutical Excipients

The acid hydrolysis of various selected saccharide- and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography–mass spectrometry and nuc...

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Published inJournal of pharmaceutical sciences Vol. 101; no. 5; pp. 1811 - 1820
Main Authors Douša, Michal, Gibala, Petr, Břicháč, Jiří, Havlíček, Jaroslav
Format Journal Article
LanguageEnglish
Published Hoboken Elsevier Inc 01.05.2012
Wiley Subscription Services, Inc., A Wiley Company
Elsevier
Wiley
American Pharmaceutical Association
Elsevier Limited
Subjects
5-hydroxymethyl furfural
analytical chemistry
Biological and medical sciences
Carbohydrates - chemistry
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Chromatography, High Pressure Liquid
Excipients
excipients degradation
formulation
Furaldehyde - chemical synthesis
General pharmacology
HPLC
Hydrogen-Ion Concentration
Hydrolysis
Kinetics
Life Sciences & Biomedicine
Limit of Detection
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Pharmaceutical Preparations - chemistry
Pharmaceutical technology. Pharmaceutical industry
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Physical Sciences
Polysaccharides - chemistry
Reproducibility of Results
Science & Technology
stability
Temperature
formulation
5-hydroxymethyl furfural
analytical chemistry
excipients
excipients degradation
HPLC
stability
DEXTROSE
JUICES
LIQUID-CHROMATOGRAPHIC DETERMINATION
5-HMF
D-FRUCTOSE
MUTAGENICITY
FURAN
5-hydroxymethylfurfural
DEGRADATION
HPLC DETERMINATION
CELLULOSE
Stability
Pharmaceutical technology
Vehicle(excipient)
HPLC chromatography
Degradation
5-hydroxymethyl-furfural
Formulation
Oside polymer
Carbohydrate
Polysaccharide
Physicochemical properties
Online AccessGet full text

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Abstract The acid hydrolysis of various selected saccharide- and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography–mass spectrometry and nuclear magnetic resonance techniques were employed to identify and fully characterize these unknown compounds. The degradation products were identified as [(5-formylfuran-2-yl)methoxy]acetic acid, 5-[(propan-2-yloxy)methyl]furan-2-carbaldehyde, along with the previously identified 5-(methoxymethyl)furan-2-carbaldehyde. On the basis of the identification of these degradation products, a reasonable mechanism for their formation can be proposed. Temperature and pH affect the hydrolysis rates of saccharides and polysaccharides, which in turn affects the rate of formation of furfural compounds. © 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101:1811–1820, 2012
AbstractList The acid hydrolysis of various selected saccharide-and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography-mass spectrometry and nuclear magnetic resonance techniques were employed to identify and fully characterize these unknown compounds. The degradation products were identified as [(5-formylfuran-2-yl)methoxy]acetic acid, 5-[(propan-2-yloxy)methyl]furan-2-carbaldehyde, along with the previously identified 5-(methoxymethyl) furan-2-carbaldehyde. On the basis of the identification of these degradation products, a reasonable mechanism for their formation can be proposed. Temperature and pH affect the hydrolysis rates of saccharides and polysaccharides, which in turn affects the rate of formation of furfural compounds. (C) 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101: 1811-1820, 2012
The acid hydrolysis of various selected saccharide- and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography-mass spectrometry and nuclear magnetic resonance techniques were employed to identify and fully characterize these unknown compounds. The degradation products were identified as [(5-formylfuran-2-yl)methoxy]acetic acid, 5-[(propan-2-yloxy)methyl]furan-2-carbaldehyde, along with the previously identified 5-(methoxymethyl)furan-2-carbaldehyde. On the basis of the identification of these degradation products, a reasonable mechanism for their formation can be proposed. Temperature and pH affect the hydrolysis rates of saccharides and polysaccharides, which in turn affects the rate of formation of furfural compounds.
The acid hydrolysis of various selected saccharide- and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography-mass spectrometry and nuclear magnetic resonance techniques were employed to identify and fully characterize these unknown compounds. The degradation products were identified as [(5-formylfuran-2-yl)methoxy]acetic acid, 5-[(propan-2-yloxy)methyl]furan-2-carbaldehyde, along with the previously identified 5-(methoxymethyl)furan-2-carbaldehyde. On the basis of the identification of these degradation products, a reasonable mechanism for their formation can be proposed. Temperature and pH affect the hydrolysis rates of saccharides and polysaccharides, which in turn affects the rate of formation of furfural compounds. © 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101:1811-1820, 2012 [PUBLICATION ABSTRACT]
The acid hydrolysis of various selected saccharide‐ and polysaccharide‐based pharmaceutical excipients under acid hydrolysis and the formation of degradation compounds were studied. New degradation products formed from these excipients were discovered. Liquid chromatography–mass spectrometry and nuclear magnetic resonance techniques were employed to identify and fully characterize these unknown compounds. The degradation products were identified as [(5‐formylfuran‐2‐yl)methoxy]acetic acid, 5‐[(propan‐2‐yloxy)methyl]furan‐2‐carbaldehyde, along with the previously identified 5‐(methoxymethyl)furan‐2‐carbaldehyde. On the basis of the identification of these degradation products, a reasonable mechanism for their formation can be proposed. Temperature and pH affect the hydrolysis rates of saccharides and polysaccharides, which in turn affects the rate of formation of furfural compounds. © 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101:1811–1820, 2012
Author Havlíček, Jaroslav
Douša, Michal
Gibala, Petr
Břicháč, Jiří
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  surname: Havlíček
  fullname: Havlíček, Jaroslav
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Issue 5
Keywords formulation
5-hydroxymethyl furfural
analytical chemistry
excipients
excipients degradation
HPLC
stability
DEXTROSE
JUICES
LIQUID-CHROMATOGRAPHIC DETERMINATION
5-HMF
D-FRUCTOSE
MUTAGENICITY
FURAN
5-hydroxymethylfurfural
DEGRADATION
HPLC DETERMINATION
CELLULOSE
Stability
Pharmaceutical technology
Vehicle(excipient)
HPLC chromatography
Degradation
5-hydroxymethyl-furfural
Formulation
Oside polymer
Carbohydrate
Polysaccharide
Physicochemical properties
Language English
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1990; 14
1987; 4
1997; 45
1999; 88
2007; 71
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2009; 57
1987; 41
2001
2006; 68
1980; 34
1973; 47
2002; 947
1977; 34
2010; 3
1998; 168
2005; 77
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1991; 39
1986; 51
1980; 63
1991; 32
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1995; 57
2002; 7
1993; 41
2009
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1988; 52
2002
1994; 83
1992; 33
2003; 32
1953; 1
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1993; 18
2000; 38
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2006; 45
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1995; 89
1988; 8
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2001; 917
2001; 39
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– volume: 7
  start-page: 313
  year: 1994
  ident: 10.1002/jps.23072_bb0150
  article-title: Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination
  publication-title: Chem Res Toxicol
  doi: 10.1021/tx00039a007
  contributor:
    fullname: Surh
– year: 2001
  ident: 10.1002/jps.23072_bb0235
– volume: 32
  start-page: 451
  year: 2003
  ident: 10.1002/jps.23072_bb0195
  article-title: Quantification of 5-HMF and dextrose in commercial aqueous dextrose solutions
  publication-title: J Pharm Biomed Anal
  doi: 10.1016/S0731-7085(03)00163-8
  contributor:
    fullname: Xu
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Snippet The acid hydrolysis of various selected saccharide- and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation...
The acid hydrolysis of various selected saccharide‐ and polysaccharide‐based pharmaceutical excipients under acid hydrolysis and the formation of degradation...
The acid hydrolysis of various selected saccharide-and polysaccharide-based pharmaceutical excipients under acid hydrolysis and the formation of degradation...
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SubjectTerms 5-hydroxymethyl furfural
analytical chemistry
Biological and medical sciences
Carbohydrates - chemistry
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Chromatography, High Pressure Liquid
Excipients
excipients degradation
formulation
Furaldehyde - chemical synthesis
General pharmacology
HPLC
Hydrogen-Ion Concentration
Hydrolysis
Kinetics
Life Sciences & Biomedicine
Limit of Detection
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Pharmaceutical Preparations - chemistry
Pharmaceutical technology. Pharmaceutical industry
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Physical Sciences
Polysaccharides - chemistry
Reproducibility of Results
Science & Technology
stability
Temperature
Title The Formation of Furfural Compounds in Selected Saccharide- and Polysaccharide-based Pharmaceutical Excipients
URI https://dx.doi.org/10.1002/jps.23072
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Volume 101
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