IJFST155

International Journal of Food Science and Technology 1998, 33, 19–29 19

Chemical tainting of foods

Donald S. Mottram*
Department of Food Science and Technology, The University of Reading, PO Box 226, Whiteknights, Reading
RG6 6AP, UK

Summary Taints and off-flavours in food are a major cause of consumer rejection of the food prod-
uct, and consequently the occurrence of such flavour defects is of great concern also to
the manufacturer. Unacceptable flavours in foods may develop within the food through
chemical or microbial action on food components, or they may be inadvertently intro-
duced into the food during processing or storage, by absorption of chemicals from air-
borne, waterborne or packaging-related sources. The chemicals responsible for taints and
off-flavours are usually volatile organic compounds, which are frequently found at con-
centrations of less than 1 mg kg21, and cause flavour problems because of their low odour-
threshold values. This paper discusses the possible origins of off-flavours and taints in
foods, and describes some incidents in which food taints have been caused by chemical
contamination from the environment.
Keywords Catty odours, chlorophenols, food storage, off-flavour, oxidation, packaging, taint.

from the immediate financial costs resulting from

Introduction
having to dispose of a batch of tainted food, the
One of the most common reasons for consumer loss of consumer confidence in the product has
rejection of a food product is an unacceptable very important long-term consequences.
flavour, and every year the food industry receives In the past, when food processing was done on
complaints from consumers concerning off- a small scale, such problems could be dealt with
flavours or taints in fresh, processed and pack- in an ad hoc manner to the satisfaction of all par-
aged foods. Fortunately, many of these are ties involved. However, in the modern food
isolated incidents, but, on occasion, major prob- industry the large scale of production and the
lems are encountered, which may involve the loss country-wide distribution of products means that
of a day’s production or several freight-container a taint problem can have far-reaching repercus-
loads of packaged foods. In the modern food sions. In addition, over the past 40 years many
industry, such problems can involve substantial new synthetic chemicals have been introduced
financial loss to the company and there have been into the environment, and some of these have
cases where subsequent legal action by food com- resulted in the indirect contamination of foods
panies against the supplier of raw materials or with potent new classes of taints. Furthermore,
packaging or processing materials has resulted in today’s consumers have become more aware of
very large compensation payments. In most cases, quality in foods and have an increased expecta-
however, the blame cannot be attributed to third tion of consistency in all quality parameters. The
parties and the food company has to bear the food industry has consequently become much
costs. Flavour problems usually come to light as more sensitive to taint and off-flavour complaints
a result of consumers’ complaints. Thus, apart and will seek rapid identification and eradication
of the cause of the problem.
*Correspondent: Fax: 144 1189 310080; The food industry frequently turns to the spe-
e-mail: [email protected] cialized flavour research chemist to identify the

© 1998 Blackwell Science Ltd

20 Chemical tainting of foods D. S. Mottram

nature and source of taint problems. In many cases will be that much more difficult to achieve.
cases, however, the nature of the problem or the This paper discusses the possible origins of off-
offending chemical compounds have not been flavours and taints in foods, and describes some
reported in the scientific literature or trade press, incidents in which food taints have been the result
usually because the companies involved have, of chemical contamination from the environment.
understandably, no wish to draw attention to the The paper does not deal with taints involving the
occurrence of taints in its products. Prevention of action of microorganisms on food components or
tainting relies largely on awareness of potential their role in the generation of taint chemicals in
problems and thus wide dissemination of infor- the environment; this is the subject of another
mation would be of major benefit to the industry paper in the present issue (Whitfield, 1998).
overall. Although many laboratories around the
world are involved in the analysis of taints and
Taints and off-flavours and their
off-flavours, relatively few publish the results of
identification
their work. Fortunately, this was not the case in
the early 1970s, when Derek Land at the Food Essentially a taint or off-flavour in a food is any
Research Institute in Norwich identified flavour which is not normally associated with that
chlorophenols as the cause of disinfectant taints food. It is usually caused by trace amounts of
in biscuits (Griffiths & Land, 1973) and volatile organic compounds not normally present
chloroanisoles as the cause of musty taints in in the food. Although the terms ‘taint’ and ‘off-
chicken and eggs (Curtis et al., 1972; Curtis et al., flavour’ are often used synonymously, it is now
1974). These two classes of compounds have sub- common to use ‘off-flavour’ to describe an unac-
sequently turned into the most prolific causes of ceptable flavour which develops within the food
taints and have been encountered in many foods through chemical or microbial action on food
of different types. The flavour research group at components, whereas ‘taint’ is used for unaccept-
the Netherlands Organization for Applied able flavours arising from external contamination
Scientific Research (TNO) had previously associ- of the food.
ated musty taints with chloroanisoles (Engel Some of the unacceptable flavours most fre-
et al., 1966; Maarse et al., 1988), while Patterson quently encountered are described by the con-
identified a chlorophenol as the cause of disinfec- sumer as disinfectant, mouldy, musty, earthy,
tant taints in poultry meat (Patterson, 1972). faecal, metallic, fishy, painty and plastic-like.
These research groups were among the first to There have been several reviews on taints and off-
isolate and identify successfully trace quantities of flavours in recent years (Saxby, 1982; Whitfield,
compounds from the environment which caused 1986; Nijssen, 1991; Reineccius, 1991), including
taints in foods. Other taint compounds in foods an excellent book (Saxby, 1993a).
have subsequently been identified and reported by The compounds responsible for taints and
different researchers, but the largest contribution off-flavours are frequently found at concentra-
to scientific knowledge has been provided by tions of less than 1 mg kg21 (ppb) and cause
Whitfield and co-workers at CSIRO in Australia flavour problems because of their low odour-
through an extensive series of publications over threshold values (the minimum concentration at
the past 25 years. Without the early publications which a compound can be detected by the sense
by Land and others and the extensive coverage of of smell). At these concentrations, 1 mg of the
the area by Whitfield et al. it would be much compound would be sufficient to contaminate
more difficult to deal with problems which con- over 1000 kg of food. Some taint compounds are
tinue to arise in the industry today. In recent even more potent and have odour-threshold
years, there have been fewer publications, possi- values reported to be as low as 3 3 1025 mg kg21
bly reflecting the greater reluctance by food com- (Table 1).
panies to allow disclosure of such information. Identification and determination of such low
Prevention of taints depends on awareness of concentrations provides a major challenge to the
potential problem areas and, if incidents of new analytical chemist and requires sophisticated
taints remain unpublished, avoidance of further instrumental techniques. However, almost all the

International Journal of Food Science and Technology 1998, 33, 19–29 © 1998 Blackwell Science Ltd
 Chemical tainting of foods D. S. Mottram 21

Table 1 Odour-threshold values

Compound Threshold Reference
for the detection of some taint
(mg kg21)
and off-flavour compounds in
water
2,4,6-trichloroanisole 3 3 1025 Curtis et al. (1972)
2-chloro-6-methylphenol 8 3 1023 Griffiths & Land (1973)
2,3,4,6-tetrachloroanisole 4 3 1022 Curtis et al. (1972)
4-mercapto-4-methylpentan-2-one 1 3 1022 Reineccius (1991)
2-methylisoborneol 3 3 1022 Whitfield et al. (1983)
geosmin 5 3 1022 Murray et al. (1976)
1-(Z)5-octadien-3-one 5 3 1021 Swoboda & Peers (1977)
2,4,6-trichlorophenol 2 van Gemert & Nettenbreijer (1977)

compounds responsible for taints and off-flavours lipid hydroperoxides, which subsequently break
are volatile and the techniques used for their iso- down to give a complex mixture of volatile com-
lation are those which the flavour chemist pounds, many of which contain oxygen.
employs for the determination of the volatiles in Aldehydes, unsaturated ketones and unsaturated
foods which contribute to desirable aromas alcohols are the products of lipid autoxidation
(Maarse, 1993). Extraction from the food can be which are most widely reported as contributing to
achieved by distillation techniques (e.g. steam dis- off-flavours, primarily because they have low
tillation) or headspace concentration on porous odour-threshold values. Lipid oxidation can also
polymer adsorbents. Separation and identification be induced by enzymes, which give similar class-
requires combined gas chromatography (GC) and es of products, although, because very specific
mass spectrometry. The sensory evaluation of pathways are involved, off-flavours may be
components, as they elute from the GC column caused by specific compounds rather than the
by means of an odour-port, is essential in deter- mixture of compounds which is often responsible
mining which compound(s) in a volatile extract for autoxidation off-flavours. Milk and milk
are responsible for the taint. With the skilful use products are particularly susceptible to lipid-
of modern instrumental and sensory techniques, derived off-flavours. Examples are the production
the experienced analytical chemist can character- of 2-heptanone (Fig. 1a) and other alkanones in
ize most of the compounds responsible for off- UHT milk (Badings, 1991) and a metallic taint in
flavours and taints. However, even when the butter caused by 1,(Z)5-octadien-3-one (Fig. 1b)
chemical has been identified, tracking down the (Swoboda & Peers, 1977).
origins of the problem can be a lengthy and time- Lipolysis, especially that brought about by
consuming job, and the resulting case history enzymes, can also give rise to off-flavours due
often reads rather like a detective story. either to the release of short-chain fatty acids,
such as butanoic acid in milk, or to the enhanced
rate of autoxidation of free fatty acids compared
Sources of off-flavours
with those bound to lipids. The role of lipids in
One of the major sources of off-flavours, formed the formation of both desirable and undesirable
from food constituents, is the degradation of flavour has been well reviewed (Forss, 1972;
lipids. Although lipid breakdown is also an Grosch, 1982; Kochhar, 1993) and therefore will
important route to desirable flavours in foods,
lipid-derived off-flavours are often associated
with storage of foods rather than normal produc-
tion and cooking of fresh food. Lipid degradation
can occur through two routes: autoxidation and
enzymic action.
Autoxidation involves the unsaturated fatty
acid moieties of lipids. The mechanism involves Figure 1 The structures of (a) 2-heptanone and (b) 1,(Z)5-
free-radical reactions with the initial formation of octadien-3-one.

© 1998 Blackwell Science Ltd International Journal of Food Science and Technology 1998, 33, 19–29
22 Chemical tainting of foods D. S. Mottram

adipose tissue of older male pigs (Patterson,

1968a). Two other compounds, indole (Fig. 3b)
and 3-methylindole (skatole) (Fig. 3c), which are
metabolites of the amino acid tryptophan, have
also been implicated in boar taint (Hansson et al.,
Figure 2 The structures of (a) a-ionone and (b) b-ionone. 1980).
Other unacceptable flavours can arise in milk
and meat from animals fed on certain pastures.
not be discussed further here. Milk is particularly susceptible to such off-
Oxidation of other food components can also flavours because it has only a very mild flavour of
result in off-flavours. One example relates to a its own. Pasture-derived off-flavours can often be
floral off-flavour, which developed in carrots traced back to weeds. In Australia and New
stored in the presence of oxygen. This problem Zealand, peppercress (Lepidium hyssopifolium)
had been known for many years and was first and landcress (Coronopus didymus (L.) SM) are
investigated during World War II (Tomkins common weeds. The former caused skatole to
et al., 1944). In 1964, Land’s flavour group suc- accumulate in milk giving a faecal odour (Park,
cessfully identified a-ionone (Fig. 2a) and b- 1969), while the latter gave milk a burnt flavour,
ionone (Fig. 2b) as the compounds responsible which was shown to be due to benzylthiol and
for the characteristic aroma (Ayers et al., 1964). benzyl methyl sulfide (Park et al., 1969). Off-
All the compounds have odours reminiscent of flavours in milk and dairy products have been the
violets and are produced in the oxidative degra- subject of several reviews (Bassette et al., 1984;
dation of carotene. This elegant elucidation was Badings, 1991; Jeon, 1993; McSweeney et al.,
one of the first reported identifications of a trace 1997). The feeding of fish protein to meat ani-
volatile compound causing a taint or off-flavour. mals, especially pigs, can result in taints in the
Ionones provide important desirable flavour notes meat, possibly because of increased autoxidation
in some fruits, such as raspberries, but their asso- of the meat lipid. Diet was also shown to be
ciation with an off-flavour in the carrots demon- responsible for fishy taints in eggs (Pearson et al.,
strates that compounds which may contribute to 1983; Fenwick et al., 1984): a relationship
desirable flavours in some products may cause between the taint and trimethylamine was estab-
off-flavours in others. Another off-flavour associ- lished, the use of fish meal or rapeseed meal in the
ated with b-ionone was a hay-like flavour in dried poultry diets being shown to be the cause of the
skimmed milk fortified with vitamin A palmitate problem.
which had been added to compensate for vitamin Microbial spoilage of food very often leads to
lost during fat removal (Suyama et al., 1983). off-odours (see Whitfield, 1998), particularly in
Aspects of plant or animal metabolism can also meat where the highly objectionable spoilage
give rise to off-flavours. A prime example is pork odours associated with high bacterial counts ren-
from uncastrated male pigs, which can have a ders the meat unacceptable (Dainty et al., 1985;
characteristic and objectionable odour (boar Edwards & Dainty, 1987). The spoilage of fish is
taint), described as sweaty and urinous. A steroid, primarily the result of bacterial action, leading to
5-a-androst-16-en-3-one (Fig. 3a), has been the generation of trimethylamine from trimethy-
shown to be responsible. The compound is a lamine oxide, a natural component of fish muscle.
pheromone produced by the male pig as a sexual Less drastic microbial growth of bacteria, moulds
stimulant for the female, and accumulates in the or fungi on other foods, pre- or post-harvest, has

Figure 3 The structures of (a) 5-

a-androst-16-en-3-one, (b) indole
and (c) 3-methylindole (skatole).

International Journal of Food Science and Technology 1998, 33, 19–29 © 1998 Blackwell Science Ltd
 Chemical tainting of foods D. S. Mottram 23

Figure 5 The structure of 2-chloro-6-methyl-phenol.

Figure 4 The structures of (a) 2-acetylpyrroline and (b) 2-
acetyltetrahydropyridine.
separate taint incidents. In one paper, Griffiths &
Land (1973) showed that the compound was
led to a number of specific off-flavour problems responsible for a disinfectant taint in biscuits. The
(Goldenberg & Matheson, 1975). An interesting problem had occurred intermittently over a peri-
example is the formation of a mousy taint in wine od of 11 years with consumer complaints vari-
caused by the growth of a certain Lactobacillus. ously describing it as ‘disinfectant’, ‘antiseptic’
The compounds responsible have been identified and ‘soapy’ (Goldenberg & Matheson, 1975). All
as 2-acetylpyrroline (Fig. 4a) and 2-acetyltetrahy- obvious sources of the problem in the factory,
dropyridine (Fig. 4b) (Strauss & Heresztyn, 1984; such as water supply, oil applied to the machin-
Herderich et al., 1995). It is interesting to note ery and disinfectants used in the bakery, had been
that these two compounds are believed to be checked before airborne contamination was sus-
important in the desirable aroma of freshly baked pected and a potential link was made with two
bread (Schieberle & Grosch, 1987). agrochemical plants sited within a 5-mile radius
of the biscuit factory. By this time, Griffiths &
Land (1973) had been able to isolate trace
Taints caused by chemical contamination
amounts of 6-chloro-o-cresol from the biscuits
Taints, which have their origins in contamination and it was found that this compound was pro-
from outside sources, have caused many problems duced as a by-product in the manufacture of the
in recent years with costs to the food industry herbicide 4-chloro-2-methylphenoxyacetic acid.
amounting to hundreds of millions of pounds. The volatility of the compound was such that,
Such taints are usually introduced into the food when the wind was in a certain direction, trace
by absorption of chemicals from the environment quantities were carried towards the biscuit facto-
and may arise from airborne, waterborne or ry, where biscuits, with their relatively high fat
packaging-related sources. Exposure to such taint content, as they emerged from the oven would
compounds may involve the raw materials or present an excellent surface for sorption of air-
occur during processing, packaging, distribution borne volatiles. Furthermore, Griffiths & Land
or storage. The compounds may arise from syn- (1973) showed that 6-chloro-o-cresol had an
thetic compounds which come into contact with exceptionally low odour-threshold value of 8 3
the food, or they may be products of microbial 1023 mg kg21, which is over 10 000 times lower
action on natural or synthetic compounds. In than most other chlorophenols. More recently,
other instances, they have been shown to be pro- Whitfield (1986) reported a similar airborne con-
duced by the reaction of two or more different tamination by 6-chloro-o-cresol in empty drink
compounds within the food. Some examples are cans stored in a warehouse near to an agrochem-
discussed in the following sections. ical plant. These incidences clearly illustrate the
importance of careful siting of food processing
Phenolic taints plants and warehouses and, where necessary, the
Halogenated phenolic compounds are one of the installation of air purification systems.
most common causes of taints in foods. They give At about the same time as the biscuit taint was
taints described as ‘medicinal’ or ‘disinfectant’ being investigated, Patterson (1972) reported that
and they were first implicated in such problems in 6-chloro-o-cresol was responsible for a medicinal,
the early 1970s, when two papers were published disinfectant taint in chicken meat. The origin of
identifying 2-chloro-6-methylphenol (Fig. 5) the taint was the use of disinfectants containing
(commonly known as 6-chloro-o-cresol) in two 6-chloro-o-cresol in the food processing plant.

© 1998 Blackwell Science Ltd International Journal of Food Science and Technology 1998, 33, 19–29
24 Chemical tainting of foods D. S. Mottram

Many disinfectants are mixtures of phenols, (1993b) gives a number of examples of 6-chloro-
including chlorinated xylenols. They have distinc- o-cresol tainting, which have arisen from the mix-
tive odours, but not particularly low odour- ing of cresol with hypochlorite bleach, either as a
threshold values and, therefore, do not normally cleaning formulation or by inadvertent introduc-
have any strong, lingering odours. However, the tion of the two chemicals into water used in food
exception is 6-chloro-o-cresol with its unusually processing.
low odour-threshold value, and its use in disin- Traces of other chlorophenols, especially tri-,
fectants should be avoided for this reason. tetra- and pentachlorophenols (Fig. 6), have been
However, on occasion this compound has been regularly reported as contaminants in foods.
used as an ingredient of certain disinfectants Whitfield (1986) has provided an excellent
(mainly cheap, ‘black’ disinfectants); the use of overview of how chlorophenols may enter the
such products in close proximity to food process- food chain. They can arise from the reaction of
ing facilities has caused a number of tainting natural or synthetic phenols with chlorine, or
problems over the years (Mottram & Patterson, from direct contamination of the food with
1986), especially in meat, where some incidents chlorophenols.
have resulted in the loss of meat worth several The active ingredients in many fungicides and
hundred thousands of pounds. algicides are chlorophenols. Wood preservatives
In one notable episode, a quantity of inedible are often based on chlorophenols and any wood-
offal had been left at an abattoir over a hot week- based material in contact with food or water sup-
end and by Monday morning maggots had gained plies could introduce chlorophenols into the food
access to several meat-handling areas. To rectify (Parr et al., 1974). There have been several exam-
the problem, the affected areas were liberally ples of fibreboard, jute sacks or wood pallets
washed down and disinfected with a solution being the source of chlorophenols (Whitfield,
which contained a cheap, farm-grade disinfectant, 1983; Whitfield et al., 1984; Whitfield & Last,
unsuitable for use in premises handling food. 1986). Fibreboard and paper regenerated from
Work resumed, but later in the week complaints waste paper and board often contain relatively
were received from a large number of consumers high levels of chlorophenols, and the use of such
(400–500 in total) about disinfectant-like odour products for the direct packaging of raw materi-
and taste in minced meat and beefburgers pre- als or processed food should be avoided. In
pared at the abattoir. Analysis of the meat showed another example, contamination of canned veg-
that 6-chloro-o-cresol was responsible for the taint etables with chlorophenols occurred when con-
and its origin was traced to the cheap disinfectant denser water, from a refrigeration unit which
used to clean the abattoir. After cleaning of the contained an algicide, sucked back into the food
processing areas, sufficient of the offending com- processing water supply (Whitfield, 1983). Where
pound had remained to volatilize into the air and the contamination results from fungicides and
then to be adsorbed by the fat of the meat. In algicides, the chlorophenols found are usually a
another case, a drain cleaner and degreaser, used mixture of tri-, tetra- and penta-substituted deriv-
in a meat plant, contained 6-chloro-o-cresol and atives.
resulted in the contamination of meat and meat Another source of chlorophenols is from the
products throughout the processing plant. chlorination of phenol which readily gives 2,4,6-
Phenols can be easily chlorinated and Saxby trichlorophenol. In food processing plants, possi-

Figure 6 The structures of

(a) trichlorophenol,
(b) tetrachlorophenol and
(c) pentachlorophenol.

International Journal of Food Science and Technology 1998, 33, 19–29 © 1998 Blackwell Science Ltd
 Chemical tainting of foods D. S. Mottram 25

ble sources of chlorine are treated water supplies

and chlorine-based sterilizing agents, while there
are several sources of trace amounts of phenol
(e.g. plastic or resin fittings, paints or traces of
plant materials). Phenolic-based resins and paints,
used as protective coatings on storage tanks and
water filtration vessels, may serve as sources of
phenolics. In one case, the water in a storage tank
became contaminated with phenols from the Figure 7 The structures of (a) 4-bromo-2-chlorophenol
and (b) 2-bromo-4-methylphenol.
breakdown of the bonding resin of the fibreglass
lining. Subsequent use of hypochlorite to clean
the processing equipment resulted in residues of was demonstrated that the probable source of this
chlorophenols in the processing lines and conta- compound was the attack of active bromine on 4-
mination of the food (flour in this case) methylphenol which was present in the brine. The
(Whitfield, 1986). Another particularly interesting source of bromine was from the action of either
case involved the use of live steam for sterilization u.v. light or sodium hypochlorite on traces of
where ligninsulphonate in a boiler additive gave sodium bromide in the brine.
rise to traces of phenol (Whitfield, 1983). Bromophenols have been associated with
Chlorophenols are also formed in the bleaching flavour defects in fish and prawns (Whitfield
of wood pulp for paper manufacture, and et al., 1988; Whitfield et al., 1997). However, in
residues can remain in the product as well as the these situations they were not derived from syn-
effluent from paper mills (Whitfield & Last, thetic chemicals, but were biosynthesized by
1986). marine algae, polychaetes and other marine
Recently other halophenols have been shown microorganisms, which form part of the diet of
to cause chemical tainting of food. One case fish and crustacea (Whitfield et al., 1996;
involved a medicinal odour in a commercial cake Whitfield et al., 1997).
mix. None of the individual ingredients possessed Halophenols may cause disinfectant taints in
the odour, which was detected only in the cooked their own right, but many fungi and other
product. Investigations showed that iodocresol microorganisms convert these phenols to the
(iodomethylphenol, unspecified isomer) was corresponding anisoles, which are exceptionally
responsible for the odour and that it arose during potent odour compounds with odour-threshold
baking from the reaction of cresol, which was values many thousand times lower than those
present in a lemon flavouring used in the mix, of the halophenols (Table 1). The extremely
and iodine contained in iodized salt (Sevenants & low odour-threshold values for the haloanisoles
Sanders, 1984). This is an interesting example of mean that sub-threshold levels of chloro- or
how components within a product, which have no bromophenol contamination can give rise to
off-flavour on their own, can interact to give rise musty chloroanisole or bromoanisole taints.
to a taint. This cause of food taints, along with other
A chemical, fungicide taint was observed in musty, mouldy taints caused by other microbially
melons, which had been treated with the fungicide derived compounds, is discussed in detail by
profenofos (O-(4-bromo-2-chlorophenyl) O-ethyl Whitfield in another paper in this issue (Whitfield,
S-propyl phosphorothionate). No fungicide 1998).
residues were present in the melons, but the taint
was shown to be caused by 4-bromo-2-chlorophe- Catty taints
nol (Fig. 7a), which is a hydrolysis product of It is clear from the above examples that the con-
profenofos (Saez et al., 1991). tamination of food with compounds that cause
Another brominated phenol, 2-bromo-4- taints can arise from a complex series of events.
methylphenol (Fig. 7b), was identified as being Further complications arise when a food is
responsible for a chemical, phenolic taint in exposed to a safe, almost odourless compound,
brine-salted Gouda cheese (Mills et al., 1997). It which reacts with components of the food to

© 1998 Blackwell Science Ltd International Journal of Food Science and Technology 1998, 33, 19–29
26 Chemical tainting of foods D. S. Mottram

form an odoriferous derivative. for catty taints. Manufacturers now take great
An example of this is the compound 4-mercap- care to ensure that solvents containing mesityl
to-4-methylpentan-2-one (Fig. 8b), which has oxide are not used in lacquer formulations, and
been the source of several severe instances of this type of taint now rarely occurs.
catty odour in a variety of foods (Aylward et al.,
1967; Patterson & Rhodes, 1967; Patterson, Some other taints caused by chemical
1968b). The mercapto compound has a most contamination
objectionable odour resembling the urine of a Food packaging materials are one of the most
mature tomcat, as well as a very low odour frequent contributors to food taints (Goldenberg
threshold of 1022 mg kg21. It is readily produced & Matheson, 1975; Whitfield, 1986; Reineccius,
by the reaction of hydrogen sulfide with mesityl 1991). Some cases simply involve transfer of
oxide, 4-methylpent-3-en-2-one (Fig. 8). residual solvents used in the preparation of the
Hydrogen sulfide is present naturally in many packaging, from machinery or from printing ink
foods, especially meat, milk, cheese and vegeta- solvents. Others have been caused by traces of
bles, and thus a catty taint will occur in any such plastic monomer, such as styrene. As discussed
food which comes into contact with mesityl oxide. above, catty odours from mercapto-ketones have
A classic example of this occurred in meat car- been a particularly potent taint problem associat-
casses which had been stored in a recently paint- ed with the reaction of hydrogen sulfide in the
ed chillroom. The paint used was based on food with residues of ketonic solvents in the
polyurethane and had been left for sufficient time packaging. However, the most prolific taint com-
to eliminate residual paint odours. The chillroom pounds associated with packaging are the
was duly restocked with meat carcasses. On open- chloroanisoles, which arise from the fungal
ing the room after two days an obnoxious catty methylation of trace amounts of chlorophenols,
odour was evident on the carcasses and in the found as contaminants in wood, cardboard, fibre-
room. The paint was suspected and careful exam- board and paper (see above).
ination of the paint solvent showed the presence The compounds (E)-1,10-dimethyl-(E)-9-
of 0.4% mesityl oxide. None of the solvent com- decalol (geosmin) (Fig. 9a) and 2-methylisoborne-
ponents had low odour-threshold values and ol (Fig. 9b), which have earthy, musty flavours,
traces could not be detected by odour in the chill- are a common cause of taints in foods. They are
room. However, when the mesityl oxide impurity produced by microorganisms, in particular actin-
reacted with natural hydrogen sulfide in the meat, omycetes, and are found in soil (Buttery &
trace amounts of 4-mercapto-4-methylpentan-2- Garibaldi, 1976), from whence they can be trans-
one were formed (Patterson, 1969). The very low ferred to root vegetables. In some foods, such as
odour-threshold value of this compound resulted beetroot, such aromas are part of the characteris-
in the ready perception of the catty taint. tic flavour of the food, but in many other prod-
Similar catty taints have been found in a num- ucts such flavours are not acceptable. These
ber of different canned foods (Goldenberg & chemicals have low threshold values and are also
Matheson, 1975). In these cases the problem was known to be the cause of musty odours in water
caused by the solvents used for the lacquers supplies, which have been contaminated with
applied to the insides of the cans: these solvents actinomycetes or blue-green algae (Gerber, 1979).
contained trace amounts of mesityl oxide or sim- Large amounts of water are used in the food pro-
ilar ketones. In other incidents, traces of mesityl cessing industry, and consequently if the water
oxide in the solvent used in printing inks applied contains traces of these compounds there is a risk
to the packaging were believed to be responsible of tainting of food products. Buttery et al. (1976)

Figure 8 The reaction of

hydrogen sulfide with (a) 4-
methylpent-3-en-2-one to give (b)
4-mercapto-4-methylpentan-2-one.

International Journal of Food Science and Technology 1998, 33, 19–29 © 1998 Blackwell Science Ltd
 Chemical tainting of foods D. S. Mottram 27

Figure 9 The structures of (a) (E)-

1,10-dimethyl-(E)-9-decalol
(geosmin), (b) 2-methylisoborneol,
(c) 2-methylenebornane and
(d) 2-methyl-2-borene.

identified geosmin as a taint in navy beans and room (Goldenberg & Matheson, 1975).
suggested that actinomycetes could have been The materials used in the packaging of food,
responsible, either by the contamination of the both raw materials and finished product, are now
beans themselves or of the water supply used dur- the major source of off-flavours. Great care is
ing cultivation or processing. Later, Whitfield needed to minimize the risk of chlorophenol or
et al. (1983) reported that a musty odour in chloroanisole contamination through materials
canned champignons was primarily due to 2- used in packaging and distribution. Foods should
methylisoborneol and again implicated actino- not come into direct contact with fibre, wood or
mycetes and the water supply used in processing. recycled paper products. Wherever possible, poly-
These compounds are also responsible for earthy, mer-based films should be used as a barrier in
muddy flavours in fish (Whitfield, 1988). Two packaging materials, but even these will not nec-
dehydration products of 2-methylisoborneol, 2- essarily prevent adsorption of taints.
methylenebornane (Fig. 9c) and 2-methyl-2- The amount of an off-flavour compound
borene (Fig. 9d), have also been reported to required to cause tainting is extremely small, but
contribute to musty taints in fish (Martin et al., its financial consequences and loss of customer
1988). Other examples of taints associated with goodwill can be enormous. However, most taint
geosmin and 2-methylisoborneol, as well as other problems can be avoided by taking relatively sim-
taints originating in microbial activity, are dis- ple steps to ensure the control of chemicals in and
cussed in more detail in the review by Whitfield around food premises and the control of all mate-
(1998), published in this issue. rials coming into contact with the food.

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© 1998 Blackwell Science Ltd International Journal of Food Science and Technology 1998, 33, 19–29