Food Chemistry 129 (2011) 546–550

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Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Analytical Methods

Thermal decomposition of vitamin C: An evolved gas analysision attachment

mass spectrometry study
Márta Juhász, Yuki Kitahara, Toshihiro Fujii ⇑
Department of Chemistry, Faculty of Sciences and Engineering, Meisei University, Hodokubo 2-1-1, Hino, Tokyo 191-8506, Japan

a r t i c l e i n f o a b s t r a c t

Article history: Evolved gas analysision attachment mass spectrometry (EGAIAMS) was utilised to study the real-time
Received 18 February 2011 non-isothermal decomposition of vitamin C. Dehydro-L-ascorbic acid, which has until this study been
Received in revised form 20 April 2011 undetectable from the solid phase degradation of vitamin C, was observed as a decomposition product.
Accepted 22 April 2011
While it is an important compound because it possesses some biological activity, dehydro-L-ascorbic acid
Available online 30 April 2011
is difficult to measure due to its chemical instability. In the present study using EGAIAMS, we were able
to detect dehydro-L-ascorbic acid from the thermal degradation of vitamin C. Our EGAIAMS results
Keywords:
obtained from the thermal decomposition of vitamin C were compared with a previous study employing
L-Ascorbic acid
Dehydro-L-ascorbic acid
pyrolysis-gas chromatographymass spectrometry (Pyr-GCMS). The observed quantitative and qualita-
Ion attachment mass spectrometry tive differences of the pyrolysis products obtained by the two techniques (EGAIAMS vs. Pyr-GC–MS) are
Decomposition in part due to the difference in transportation time of the products out of the pyrolysis chamber.
Pyrolysis products Ó 2011 Elsevier Ltd. All rights reserved.
Li+ attachment

1. Introduction
Vitamin C, also called L-ascorbic acid, is a water-soluble nutrient
that serves a predominantly protective role in the body. Vitamin C
is used in the pharmaceutical and food industry as an antioxidant
to maintain the health and prolong the shelf life of foodstuffs. Vita-
min C is a sensitive molecule and exposure to oxygen, metals,
humidity, light, pH, and temperature leads to its degradation. Iden-
tification and understanding of the degradation products of
vitamin C and the mechanisms through which the products are
formed is important information for determining optimal storage
and processing conditions for vitamin C-containing foodstuffs.
Interest in the thermal degradation processes of vitamin C is of
particular importance as most foodstuffs, including those con-
taining vitamin C, are subjected to thermal treatment during
processing, storage, and preparation (Cruz, Vieira, & Silva, 2008;
Dhuique-Mayer et al., 2007; Karhan, Aksu, Tetik, & Turhan, 2004;
Nisha, Singhal, & Pandit, 2004).
Thermal decomposition of solid vitamin C has been studied pre-
viously by Vernin et al. using pyrolysis-gas chromatographymass
spectrometry (Pyr-GCMS) (Vernin, Chakib, Rogacheva, Obretenov,
& Párkányi, 1998). After the vitamin C was pyrolysed at 300 °C, the
volatile degradation products were transferred to a GCMS for anal-
ysis. Vernin et al. reported that under vitamin C pyrolysis conditions,
mainly furan-related compounds and a,b-unsaturated cyclic
⇑ Corresponding author. Tel./fax: +81 42 591 5595.
E-mail address: fujii@chem.meisei-u.ac.jp (T. Fujii).
ketones are formed. Furfural was found to be the major product
and two formation pathways for this product were postulated (Ver-
nin et al., 1998).
Pyr-GCMS, where the pyrolysis products are separated by gas
chromatography and analysed by mass spectrometry, is a conven-
tional method for the thermal degradation studies of volatile
compounds. Applications of the Pyr-GCMS technique include
quality- and quantity-control analysis and screening of various
materials, such as polymers (Tsuge & Ohtani, 2002) and drugs
and their metabolites (Nishikawa, Bell, Kraner, & Callery, 2009;
Shen, Carter, Brereton, & Eckers, 2003; Slack & Irwin, 1977). Some
disadvantages of the Pyr-GCMS technique are: (1) only the vola-
tile products or those which can be made volatile can be detected,
(2) time-resolved thermal degradation of target compounds is not
possible, and (3) primary pyrolysis products formed in the pyroly-
ser might be not be detected, due to rearrangement, degradation,
or remaining on the GC column.
Motivated to develop an efficient method for the rapid identifi-
cation of species in chemical processes (Fujii, 1992, 1997, 1998,
2007; Sablier & Fujii, 2002) proposed and developed a novel
technique employing soft ionisation Li+ attachment coupled with
a mass spectrometer (Li+IAMS). The technique has been extensively
tested, optimised, and shown to have high efficacy and sensitivity.
One of the greatest advantages of the Li+IAMS technique is the
ability to directly analyse gaseous compounds, since Li+IAMS pro-
vides mass spectra of only quasi-molecular ions formed by Li+
attachment to any chemical species, including free radicals. An
evolved gas analysis (EGA) system has been coupled to an Li+IAMS

0308-8146/$ - see front matter Ó 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.foodchem.2011.04.056
 M. Juhász et al. / Food Chemistry 129 (2011) 546–550 547

(EGAIAMS), and the method works well for nonvolatile, untreated,

and complex samples, such as polyethylene polymers (Takahashi,
Tsukagoshi, Kitahara, Juhász, & Fujii, 2010). The simplicity of the
IA spectrum permits the analysis of mixtures whose spectra are dif-
ficult to interpret using the electron impact (EI) mode of operation.
With the EGAIAMS technique, temperature-programmed decom-
position of a number of solid materials can be studied in detail by
directly detecting any chemical species in real time and in situ.
Pyrolysis is achieved in ca. 40 Pa vacuum, and therefore the thermal
decomposition products formed can be easily volatilised. At the
same time, the pyrolysis process takes place close to the Li+ ion
emitter, which ensures the immediate formation of Li+ adducts.
These features of the EGAIAMS technique, along with fast
detection and the absence of the molecular collisions reducing
the occurrence of secondary reactions, ensures almost exclusively
primary thermal decomposition products formed from the target
Fig. 1. Total ion chromatogram (TIC) of vitamin C obtained in total ion monitoring
molecule are detected. Furthermore, EGAIAMS requires only a
mode at a heating rate of 128 °C min1 in the temperature range of 25–300 °C
small amount of sample (0.1–1 mg), and no sample preparation (Inset). Ion attachment mass spectrum of vitamin C heated to 150–230 °C at
or derivatisation is required. The integration of EGA and IAMS 128 °C min1. Peak assignments are provided in Table 1. The intensities of the mass
produces a method having specificity, high sensitivity, rapid peaks were normalised to 100% for the peak representing the main thermal
response, and low detection limits. decomposition product (m/z 181, dehydro-L-ascorbic acid).

In this work, the EGAIAMS technique was used to study the

thermal decomposition of solid vitamin C and dynamically monitor
the complex pyrolysis process. Furthermore, we compared the
EGAIAMS results obtained from the thermal decomposition of
vitamin C with the Pyr-GCMS results reported previously. In
addition, explanations are provided for the differences in the out-
comes obtained by the two methods for the pyrolysis of vitamin C.
2. Materials and methods
2.1. Sample
Solid vitamin C (C6H8O6; MW 176.12 g mol1; m.p. 190194 °C)
was purchased from Sigma-Aldrich Co., Tokyo (purity P99.0%) and
was used as received without pretreatment.
2.2. Apparatus
Measurements were carried out on an Li+ attachment mass
spectrometer (Fujii, 2007; Takahashi et al., 2010). The quadrupole
mass analyser had a mass range up to 400 Da. The solid sample
was introduced to the reaction chamber, containing the Li+ emitter
and repeller, via a heatable direct insertion probe (DIP). EGAMS
analysis was carried out with 0.1 mg of the sample, which was
heated from 25 to 300 °C with a heating rate of 128 °C min1.
The molecular species (neutral molecules or radicals) attached to
the Li+ and produced the corresponding [M+Li]+ adducts. IAMS
mass spectra were recorded continuously during the sample heat-
ing with a scanning speed of 1 scan/s. Selected ion monitoring
(SIM) for various adducts was also conducted at the same temper-
ature program as described above.
3. Results and discussion
3.1. Mass spectrum of thermal decomposition
From the total ion chromatogram (TIC) of vitamin C obtained in
total ion monitoring mode at a heating rate of 128 °C min1 in the
temperature range of 25–300 °C (left inset of Fig. 1), we observed
that the vitamin C samples yielded the bulk of gaseous emissions
within the temperature range of 150–230 °C.
The IAMS mass spectra recorded within a temperature range of
150–230 °C were combined into a single mass spectrum (Fig. 1).
The mass spectra obtained with the Li+IAMS technique contained
quasi-molecular ions (formed by Li+ attachment) of products
formed from the thermal decomposition of vitamin C. Molecules
of the sample that evaporated in molecular form were also present.
The intensities of the peaks were normalised to 100% for the peak
representing the main thermal decomposition product (m/z 181,
dehydro-L-ascorbic acid).
In the IAMS mass spectrum, the presence of the peak with m/z
183 indicates that IAMS is a suitable technique for the detection
of the parent vitamin C molecule. The large intensity of this peak
shows that the some of the vitamin C vaporised in molecular form.
Peaks of the twelve most abundant decomposition products are
numbered in the IAMS spectrum in Fig. 1. The mass peak at m/z
181 in the IAMS spectrum is the most abundant pyrolysis product,
dehydro-L-ascorbic acid, having a molecular mass of 174. The other
degradation product peaks were substantially less abundant.
The 12 mass spectral peaks were assigned (Table 1) and their
relative intensities were determined. Since the validity of identifi-
cation of the mass spectral peaks is based principally on the mass
to charge ratio, there can be some uncertainty in the assignment of
some of the species. Therefore, the peak assignments in the present
study were confirmed by referring to a previous study on pyrolysis
products detected by Pyr-GCMS in the thermal degradation of
vitamin C (Vernin et al., 1998).
Under EGAIAMS conditions, the main decomposition product
is dehydro-L-ascorbic acid, which we detected for the first time
from thermal degradation of solid vitamin C. Dehydro-L-ascorbic
acid, which readily forms from vitamin C, is an important com-
pound as a dietary supplement, cosmetic ingredient, and pharma-
ceutical agent (Olson, Israel, & Boyd, 2001; Urs, Rama, & Dunleavy,
1974). It is also well-known that dehydro-L-ascorbic acid possesses
some vitamin C activity (Masaru et al., 2008; Megumi, Tadao, &
Nobuhiko, 1986; Ogiri et al., 2002). However, dehydro-L-ascorbic
acid is difficult to measure, due to its chemical instability. For
example, the expected formation of dehydro-L-ascorbic acid could
not be confirmed under the moisture-induced decomposition of
vitamin C made by Shephard, Nichols, and Braithwaite (1999a).
Although dehydro-L-ascorbic acid may have been formed in the
study, it was not detectable (Shephard, Nichols, & Braithwaite,
1999b; Shephard et al., 1999a). Shephard et al. explained the
apparent absence of dehydro-L-ascorbic acid by noting its chemical
instability. It was concluded that the ring in dehydro-L-ascorbic
acid rapidly opened and produced 2,3-diketogulonic acid, which
then underwent further reaction (Shephard et al., 1999b). In the
548 M. Juhász et al. / Food Chemistry 129 (2011) 546–550

Table 1
Decomposition products (structures and intensities of products) from thermal degradation of vitamin C obtained by EGAIAMS in this study and by PyrGCMS in a previously
reported study (Vernin et al., 1998). Decomposition products belonging to the 12 most abundant peaks in the IAMS spectrum are reported.

Peak numbera Molecular mass Productsb Intensity (%) of pyrolysis products

EGALi+IAMS PyrGCMS
(1) 60 Hydroxyacetaldehyde, ethenediol 4.8 N.D.
(2) 84 4,5-Dehydro-c-butyrolactone 7.1 Small
(3) 86 Butanedione 4.9 Small
(4) 96 Furfural 2.6 100,
2(or 3)-Methyl-2-cyclopenten-1-one Small,
4-Methyl-2-cyclopenten-1-one Small,
2-Cyclohexen-1-one Small
(5) 98 C5H6O2c, 3.2 Small,
2-Hydroxy-2-cyclopenten-1-one Small
(6) 100 2-Methyltetrahydrofuran-3-one 4.0 Small
110 2-Acetylfuran N.D. Small
(7) 112 Furoic acid 11.4 11.4,
2-Hydroxy-2-cyclohexen-1-one 14.3,
2-Hydroxy-3-methyl-2-cyclopenten-1-one Small
(8) 114 Methyl ketonec, 3.0 Small,
C6H10O2c, Small,
[M – (H2O + CO2)]c N.D.
122 A furoyl derivative N.D. Small
126 2-Hydroxy-3-ethyl-2-cyclopenten-1-one N.D. Small
(9) 128 [M(2H + H2O + CO)]c 2.8 N.D.
(10) 130 [M(2H + CO2)]c, 8.0 N.D.
[M(H2O + CO)]c
140 1-(2-Furyl)-2-hydroxy-1-propanone N.D. Small
(11) 158 3,6-Dihydroxy-6,6a-dihydrofuro[3,2-b]furan-2(5H)-one [MH2O] 1.8 N.D.
162 2-Furoylfuran N.D. Small
(12) 174 Dehydro-L-ascorbic acid [M2H] 100.0 N.D.

M, vitamin C.; N.D., not detected.

a
Peak numbers in the IAMS mass spectrum (Fig. 1).
b
In the IAMS mass spectrum, the compounds are present at the corresponding m/z values in the form of lithium adducts.
c
Structural formula is not known.

present work, we were able to confirm the formation and presence thermal degradation of vitamin C in the previous Pyr-GCMS
of the unstable, short-lived dehydro-L-ascorbic acid compound. study (Vernin et al., 1998) were not formed using the EGAIAMS
In addition, products with molecular masses of 158, 130, 128, technique.
and 60 were also formed and detected for the first time from the To further investigate the differences among the products ob-
thermal decomposition of vitamin C. Degradation products with tained by the two techniques, we chose four molecular masses
molecular masses of 114, 112, 110, 100, 98, 96, 86, and 84 have and compared the intensities of these products obtained from
been described previously by Vernin et al. in studies wherein vita- the two techniques (Fig. 2). Two of the four molecular masses rep-
min C was pyrolysed at 300 °C (Vernin et al., 1998). Since resent the most abundant peaks in Pyr-GCMS (Vernin et al.,
[MH2O], [MCO2], H2O, and CO2 species were detected, though 1998), whereas the other two molecular masses correspond to
the last three species with smaller abundances, in addition to the the most abundant peaks in the EGAIAMS system.
products obtained and identified in the Pyr-GCMS measurement
(Vernin et al., 1998), we identified the species having a molecular
mass of 114 as [M(H2O + CO2)], where M represents the vitamin
C molecule. For the [M(H2O + CO2)] species, two postulated
structures  4,5-dihydro-4-hydroxy-2-furancarboxaldehyde and
3,4-dideoxypentos-3-enulose  can be given. 3,4-Dideoxypentos-
3-enulose was described as an intermediate for furfural formation
from thermal degradation of vitamin C (Vernin et al., 1998).

3.2. Comparison with Pyr-GCMS results

Thermal decomposition of vitamin C at 300 °C was investigated

previously by Pyr-GCMS (Vernin et al., 1998). The results from
the present work using the EGAIAMS technique show both quan-
titative and qualitative differences from those of the previous
study (Vernin et al., 1998). Many of the degradation products
formed in the EGAIAMS study (Table 1) agree with those previ-
ously detected by Pyr-GCMS (Vernin et al., 1998). However, the
relative abundances of the decomposition products are very differ- Fig. 2. Comparison bar graph showing the intensities of the two most abundant
molecular masses obtained from thermal decomposition of vitamin C by EGAIAMS
ent. The EGAIAMS method allowed for the detection of new ther- (h) in this study and the two most abundant molecular masses obtained from
mal degradation products, in addition to the common pyrolysis thermal decomposition of vitamin C by Pyr-GCMS ( ) in reference 5. Assignments
products obtained with both methods. Some products from the of these molecular masses are given in Table 1.
 M. Juhász et al. / Food Chemistry 129 (2011) 546–550
3.2.1. Quantitative differences between the results obtained by
EGAIAMS vs. Pyr-GCMS
The largest quantitative difference can be seen in the amount of
decomposition product detected at a molecular mass of 96 (Fig. 2).
A molecular mass of 96 includes the pyrolysis products furfural, 2
(or 3)-methyl-2-cyclopenten-1-one, 4-methyl-2-cyclopenten-1-
one, and 2-cyclohexen-1-one. Formation of these products,
particularly the formation of furfural, was far more intense using
the Pyr-GCMS technique than the EGAIAMS technique. Furfural
was found to be the major product of vitamin C pyrolysis at 300 °C
in the Pyr-GCMS experiment (Vernin et al., 1998). In the Pyr-
GCMS system, the transportation time out of the hot zone (i.e.,
out of the pyrolysis chamber) for the pyrolysis products is longer
than in the EGAIAMS system. In the Pyr-GCMS technique, the
transportation time out of the hot zone is in the order of seconds.
Hence, in Pyr-GCMS experiments, secondary reactions of the pri-
mary pyrolysis products can occur before the products enter the
GC column. In the EGAIAMS system, the pyrolysis products are
created, ionised, and detected as soon as they are formed. The short
pyrolysis product transportation time, which is in the order of mil-
liseconds from the ion source to the emitter, reduces the occur-
rence of secondary reactions (Montaudo, Puglisi, Blazsó, Kishore,
& Ganesh, 1994).
Three different products (furoic acid, 2-hydroxy-2-cyclohexen-
1-one, and 2-hydroxy-3-methyl-2-cyclopenten-1-one) were
formed from vitamin C decomposition and have the same molecu-
lar mass of 112. In the Pyr-GCMS system, these products
accounted for 25.7% of the total intensity, whereas they accounted
for only 11.4% of the intensity in the EGAIAMS study. The differ-
ences in the intensities of these products detected by the two
methods can be explained again by the transportation time, which
differed between the two techniques.
3.2.2. Qualitative differences between the results obtained by
EGAIAMS vs. Pyr-GCMS
Under EGAIAMS conditions, some products were detected for
the first time. The most abundant was dehydro-L-ascorbic acid.
This product was undetected in the Pyr-GCMS study of Vernin
et al. (1998) because dehydro-L-ascorbic acid is a reactive species
and was not stable enough to be observed with those authors’
experimental setup. With the EGAIAMS system, however, the
detection of the formed species is achieved in short time, allowing
for observation of the dehydro-L-ascorbic acid product.
In the EGAIAMS system we detected a species with molecular
mass of 130 as the second most intense peak in the mass spectrum.
We have currently assigned this peak to both [M(2H+CO2)] and
[M(H2O+CO)]. These products are assumed to have been formed
by the mechanisms presented below, where M represents vitamin
C:
M ! ðM  2HÞ þ 2H
ðM  2HÞ ! ½ðM  2HÞ  CO2  þ CO2 ð1Þ
M ! ðM  H2 OÞ þ H2 O
ðM  H2 OÞ ! ½ðM  H2 OÞ  CO þ CO ð2Þ
The occurrence of these reactions is consistent with the fact that
we observed both (M2H) and (MH2O) species in the present
study. Further supporting evidence is that we have observed
H2OLi+ and CO2Li+ with low intensity (not shown in Fig. 1). In
contrast, neither (M2H) nor (MH2O) species were observed un-
der the Pyr-GCMS conditions (Vernin et al., 1998), indicating that
these and the final products with a molecular mass of 130 were not
formed in that study. As an alternative explanation, (M2H) and
(MH2O) species might have formed under Pyr-GCMS conditions
549
(Vernin et al., 1998) but then rapidly reacted according to other
mechanisms to yield final products with molecular masses differ-
ent from 130.
4. Concluding remarks
We used the EGAIAMS technique to study the thermal degra-
dation of solid vitamin C and compared our results with those
obtained in a similar study on thermal decomposition of vitamin
C using Pyr-GCMS. Significant differences between the two tech-
niques, in terms of products and relative amounts of products
formed, were found. A major difference between the two tech-
niques was determined to be the transportation time of the pyro-
lysis products out of the pyrolysis chamber (or hot zone). In the
EGAIAMS technique, the transportation time out of the hot zone
for the compounds formed is significantly shorter than in Pyr-
GCMS, which reduces the occurrence of secondary reactions of
the primary pyrolysis products. Some decomposition products
formed in the EGAIAMS system were not detected in the previous
Pyr-GCMS study and thus were detected here for the first time.
The main degradation product detected from EGAIAMS was
dehydro-L-ascorbic acid, which prior to this study was undetect-
able from the decomposition of solid vitamin C.
Acknowledgement
M.J. thanks the Japan Society for the Promotion of Science (JSPS)
for a JSPS Fellowship (P09706).
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