E. T. Contis et al.

(Editors)
Food Flavors: Formation, Analysis and Packaging Influences
1998 Elsevier Science B.V. 187

Sensory characteristics of chemical compounds potentially associated

with smoky aroma in foods

D. H. Chambers^ E. Chambers IV^ L. M. Seitz^ D. B. Sauer^ K. Robinson^ and

A.A. Allison^

^The Sensory Analysis Center, Department of Foods and Nutrition, Kansas State
University, Justin Hall, Manhattan, KS, 66506-1407, United States of America

^Grain Marketing and Production Research Center, United States Department of

Agriculture, Agricultural Research Service, 1515 College Avenue, Manhattan, KS,
66502. Mention of firm names or trade products does not constitute endorsement
by the U. S. Department of Agriculture over others not mentioned.

Abstract
Smoky aroma can either enhance sensory quality of foods (e.g. meat or
cheese) or be detrimental to the product (e.g. raw or processed grains and grain
products). Twenty-one chemical compounds suggested from the literature or from
gas chromatographic headspace analysis of raw grains as potentially responsible for
smoky aroma were studied. Five highly trained sensory panelists smelled each
compound dissolved in propylene glycol (if soluble) at a dilution of 5,000 to 20,000
ppm depending on the aroma strength of the compound. Approximately 60% of the
compounds were found to have some smoke character, although the intensity of
smokiness often was low. Some compounds such as benzyl disulfide and
3,7-dimethyl-6-octenoic acid were predominately smoky, but had other aroma
characteristics that were lower in intensity. Most compounds had other aroma
characteristics that were more intense than smoke (e.g. 2-ethylpyridine) and some
compounds, such as 1-methylpyrrole were not smoky at all.

1. INTRODUCTION
Smoke has been used as a preservation method for over 90,000 years (1). But
in the modern "refrigeration" era, smoked foodstuffs, such as meat, fish, and cheese
are demanded by consumers not for their preserved states, but for their unique and
characteristic flavor, including smoky flavor. Because of this demand, smoked
products retain their success with consumers. However, smokiness is not always
a positive characteristic. Undesirable smoke flavors in grain have been identified
by Smith et al. (2), who referenced carvacrol to describe the smoke/ash flavor found
in grains such as corn, sorghum, and soybeans. The grains had a characteristic
described as a "black, charred aromatic, associated with ground-in residue of
unwashed ashtrays."
Although the number of chemical components that could result in smokiness
is a continuous source of debate, over 200 compounds have been identified in smoke
(3). There may be as many as 500 compounds (or more) that are linked to smoke
flavor (4). Generally, smoke-related compounds can be placed into six categories:
carbonyls, organic acids, phenols, organic bases, alcohols, and hydrocarbons, which
include the potentially carcinogenic polycyclic aromatics (3,5).
The phenolic fraction often has been cited as the main source of flavor and
aroma in smoke and smoked products (3, 6, 7). The phenol fraction is complex,
consisting of at least 30 components with both carbonyl and phenolic functional
groups (8). Phenolic esters, such as guaiacol (2-methoxyphenol) and syringol (2,6-
dimethoxyphenol) and their derivatives, can be formed from the pyrolysis of lignin,
which constitutes almost 25% of wood (1,4,9). The amount of phenolic compounds
present in smoke varies with wood variety (1,10), recovery technique (8), and smoke
generation methods (11).
Bratzler et al. (6) correlated phenolic content to overall smoke intensity in
bologna, concluding that the phenols had a greater contribution to smoke flavor
than either the carbonyl or acid components. Lantz and Vaisey (10) also concluded
that phenols had the greatest effect on smoke flavor in smoked Whitefish. Other
researchers have reached similar conclusions (3).
Three major phenolic compounds have been examined extensively and have
been described sensorially by researchers because of their influence on overall
smoke flavor: guaiacol (2-methoxyphenol), 4-methylguaiacol (creosol), and 2,6-
dimethoxyphenol (syringol) (1,9,12). Guaiacol, found predominantly from softwood
smoke, has smoky, aromatic, sharp, sweet, phenolish, spicy and smoked-sausage-
like odors and flavors (1,4,7,9). Creosol has been described as sweet, vanilla-like,
fruity, cinnamon, smoky, sharp, caramel-like, and burnt (1,7,9). Syringol was
described similarly to guaiacol as smoky, spicy, smoked-sausage-like, sharp, sweet,
phenolish, smoky, whiskey, dry, and sharp (1,7). Other phenolic compounds also
have been evaluated sensorially by Baltes et al. (1) including eugenol (4-allyl-2-
methoxyphenol), o-cresol, and dimethylphenol.
Eugenol is an example of a phenol that has been found in both smoke and
traditionally non-smoked products such as spices and grains. Phenol, cresol,
eugenol, and guaiacol are found in cinnamon. Cloves, marjoram, nutmeg, and
pepper also are spices with eugenol (1).
Early research showed that carbonyl compounds also have been found to
contain flavor characteristics, but are more likely to contribute to the smoky brown
color that is characteristic of smoked products (13). Kim et al. (7) found that
carbonyl and lactone components in addition to phenolic compounds were important
flavor components, though carbonyl compounds such as 2-cyclopentenone and 2-
methyl-2-cyclopentenone had a grassy, bitter odor. The authors also found that
alkyl substituted 1,2-cyclopentadione and 2-buterolide (internal lactone from 4-
hydroxy-2-butenoic acid) homologues (non-carbonyl neutral fraction) had
considerable sweet, burnt and caramel-like flavors, possibly showing smoky flavors
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contributed by non-phenolic compounds (7). In addition, research by Maga and

Fapojuwo (14) showed that the carbonyl fraction is the primary contributor to the
smoke aroma for most woods and recommended that because of the potential health
hazards, phenolic compounds might be removed from smoke sources without
eliminating smoke aroma intensity.
Toth and Potthast (4) indicated that a number of carcinogenic polycyclic
aromatic hydrocarbons (PAH) have been identified in smoke condensates and
smoked foods. However, in commercial liquid smoke, a purified phenolic fraction
can be produced without PAHs.
Many researchers have used vocabulary describing potentially smoky
chemicals, but the descriptors are poorly defined and may not represent smoky
aromas at all (1,7). Profiles provided by Dravnieks (15) gave a wider variety of
smoke related descriptors, but did not define the words. Work in our laboratories
on meat, cheese, grains, and other products has led us to believe "smoky" is not an
individual characteristic but is comprised of various smoky odor/flavors. Because
smoke flavor and aroma compounds have been found in foods other than smoked
meat and cheese products, further investigation into the sensory properties of
potentially smoky chemicals is needed.
Therefore, the objective of this study was to determine the sensory properties
of a variety of chemical compounds that potentially had a smoky or smoke related
character.

2. MATERIALS AND METHODS

2.1 Compounds
The compounds selected for this study were chosen because of their citing
frequency, because they had been described using smoky related terms (15), or
because they had been found in the headspace of smoky grains. Availability also
was taken into account. Compounds known to be toxic were excluded from this
study. The chemicals examined were: ethyl 3-hydroxyhexanoate; guaiacyl
phenylacetate; methylcyclopentenolone; 1-methylpyrrole; 2-ethylhexanoic acid; 3,7-
dimethyl-6-octenoic acid; furfuryl mercaptan; 1,2 cyclohexanedione; cyclohexanol;
2,6-dimethoxyphenol; 4-ethylguaiacol; D-xylose; benzyl disulfide; thymol; guaiacol;
carvacrol; amylbenzene; 2-methylbenzofuran; 2,3-benzofuran; 2-ethylp5n:idine; and
1-phenyl hexane (hexylbenzene).

2.2 Dilutions
All chemicals were dispersed in propylene glycol. Typically, the
concentrations were 20,000 ppm, 10,000 ppm and 5,000ppm, although other levels
were used. The determination of the level tested was made by serially diluting the
chemical and having the sensory panelists determine if the dilution was smoky.
The highest level of compound that was reasonably, but not overwhelmingly, smoky
was used. If no level was smoky, a concentration that represented the odor
character of the material was used. The propylene glycol solutions were stored in
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120 ml glass bottles with Teflon covered lids. Prior to testing, a fragrance testing
strip was dipped to the depth of 3mm in the chemical solution and then carefully
placed in a 20 ml coded, capped glass tube.

2.3 Testing Procedure

The chemicals were profiled for odor by a highly trained descriptive panel
consisting of 5 female panelists with a broad background of experience in odor
description. All panelists had completed 120 hours of sensory descriptive training,
a 40 hour apprenticeship to check their performance, and then had over 2,000 hours
of testing experience.
Each chemical sample was presented monadically, with a three digit code, in
random order. Each panelist removed the fragrance strip and waved it directly
underneath her nose twice while taking quick, sharp sniffs.
Each panelist evaluated the odor description of the compound, using
descriptors determined in preliminary evaluations of the compounds and previous
experience with smoky foods. An intensity was given to each characteristic from 1
(just recognizable) to 15 (extremely intense).
After scoring, panelists discussed the characteristics and intensities for the
compound and a consensus score was determined. Most compounds had to be
smelled multiple times, although no compound was sniffed more than two times in
a single session. Approximately 20 min elapsed between sniffing different
compounds to reduce carryover. The panelists were instructed to stop testing
anytime they believed carryover from one compound to another could not be
avoided. Fresh air and sniffs of distilled lime oil, which seemed to ameliorate odor
carryover of the chemicals, was used to cleanse the nasal passages between
samples.

3. RESULTS AND DISCUSSION

Table 1 lists the chemicals that were associated with smoky characteristics
in the literature, but were not found to be smoky in this research. No particular
chemical class of compounds was not smoky; compounds from many chemical
classses were tested that the panel found not to be smoky. Commonly, the non-
smokey compounds exhibited sweet, fruity, medicinal characteristics that
potentially could be related to smoky odors in the presence of other compounds.
Some of these same odor notes were found in smoky compounds. However, in these
chemicals the *T3lend" did not provide any overall smokiness.
Many smoky related terms were found to describe the odor properties of these
chemicals. Table 2 gives those terms that were found to contribute to the distinctive
smoky character in the compounds tested. On the surface, many of the odor notes
do not have an obvious smokiness. However, they were part of the smoky character
of the chemical and provide the uniqueness to the smoke character in many of these
compounds. The smokiness of the compounds tested was not simply "smoky," but
was represented by many "types" of smoky characters, all of which had an
underl5dng smokiness.
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Table 1
Chemicals that did not exhibit smoky characteristics
Chemical Characteristics
ethyl 3-hydroxyhexanoate Sweet, Anise, Almond, Citrus Peel
methyl cyclopentenolone (also Sweet, Maple, Caramelized, Woody
containing some keto-
tautomer)
guaiacyl phenylacetate Sweet, Medicinal, Brown/Spicy
1-methylpyrrole Petroleum, Chemical, Pungent, Sulfur
amylbenzene Anise, Heated Vegetable Oil, Citrus Peel
2,3-benzofuran Shoe Glue, Ether
1-phenyl hexane Floral, Anise, Heated Vegetable Oil, Weedy
2-methylbenzofuran Mothball, Resinous, Medicinal

Table 2
Smoky related sensory terminology found in the chemical profiles
Sensory Term Description
Ashy dry, dusty, burnt, charred
Brown spice sweet, dark brown spices
Burnt sharp, acrid, charred
Burnt Sugar dark brown, caramelized
Clove sweet, brown spice, minty, alcohol
Creosote tar-like
Cured preserved meat, sweet
Maple brown sweet, caramelized, woody, vanilla
Sulphur pungent, rotten egg-like, sewer gas
Woody bark-like

Table 3 lists chemicals that were associated with smoky odor. A profile for
each chemical is shown and in most cases the "smoky" character of the compound
is less intense than some other sensory attributes of the chemical. For example,
3,7-dimethyl-6-octenoic acid is more waxy and fruity than smoky. Similarly,
cyclohexanol is more resinous and medicinal than woody-smoky.
Some compounds, like 4-ethyl guaiacol, had moderate smoke characteristics
and also had other notes that would contribute additional odors to foods it might be
present in. In foods containing these compounds it may be that only low smoky
odors are noted (or desired) in those food classes. However, other smoky compounds
also may be present and may boost the smoke character of compounds such as
guaiacol.
A few chemicals, such as 2,6-dimethoxyphenol and benzyl disulfide, are
essentially nothing but smoky. Those two compounds illustrate the differences
noted in smoky odors. The dimethoxyphenol compound gave a sweet, woody, burnt
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smokiness, but the benzyl disulfide was predominantly a burnt, ashy smoke. Based
on this data, it would be difficult to interchange the two compounds, although both
are smoky. Similarly, although one of those compounds might provide a positive
flavor character to a specific food class, it could result in a negative odor or flavor
property to another food class.
Table 3
Aroma profiles with sensory descriptors and intensities for smoky related
chemicals studied.
2-ethylhexanoic acid 3,7-dimethyl-6-octenoic acid
Smoke - 1.5 Smoke - 3.0
Ether - 5.5 Waxy - 6.0
Alcohol - 5.0 Ashy - 4.0
Ashy - 3.0 Fruity/pineapple - 3.5
Sweet - 2.0 Metallic - 2.5
Sweet - 2.5
furfuryl mercaptan 2-ethylpyridine
Smoke - 4.5 Smoke - 2.0
Skunky - 9.0 Weedy - 12.0
Pungent - 8.0 Chemical - 10.0
Sulfur - 2.0
1,2 cyclohexanedione (containing cyclohexanol
some enol-tautomer) Sweet - 2.0
Smoke - 3.0 Smoky/Burnt/Spicy - 2.0
Burnt Sugar - 6.0 Resinous - 6.0
Sweet - 5.0 Medicinal - 4.0
Celery - 4.5 Woody - 3.5
Maple - 3.5 Alcohol - 3.0
2,6 -dimethoxyphenol d-xylose
Smoke - 4.5 Smoke - 2.0
Cured - 4.5 Sulfur - 4.5
Woody - 3.5 Wet Wool - 5.5
Sweet - 3.5 Sweet -1.0
Burnt/Spice - 3.0
4-ethylguaiacol benzyl disulfide
Smoke - 5.0 Smoke - 3.5
Clove - 8.5 Sulfur - 3.5
Sweet - 6.5 Burnt - 4.5
Medicinal - 6.5 Ashy - 4.0
Brown/Spicy - 6.0
Woody - 4.0
Pungent
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Table 3. Cont.
thymol (2-isopropyl-5- guaiacol (2-niethoxyphenol)
methylphenol) Smoke - 1.5
Smoke - 2.5 Clove - 5.0
Pencil Shavings - 6.0 Medicinal - 5.5
Woody - 4.5 Brown/Spice - 3.0
Rubbery - 4.0 Cured - 2.0
c a r v a c r o l (5-isopropyl-2-
methylphenol)
Smoke - 3.0
Creosote - 3.5
Chemical - 3.0
Smoke/Ashy - 3/5
Pungent - 2.5
Scale: 1 - just recognizable to 15 - extremely intense

4. CONCLUSIONS

Some compounds previously thought to be associated with smoky odors are

not smoky by themselves, at levels examined in this study. Many smoky
compounds had different types of smoky characteristics indicating they may impart
a unique "smoky" character that may be difficult to duplicate using other chemicals.
Smoky compounds also may contribute other odor properties to the food products
in which they are present.

5. REFERENCES
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And Beverages - Ch. 1. Academic Press, Inc., NY, 1981.
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3. H. Daun, Food Technol. 41 (5) (1979) 66.
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194

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Acknowledgment: This research was funded, in part, by USDA grant #58-5430-5-

124, "Grain Odor"