Furan in Foods

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Furans in foods
a b
Joseph A. Maga & Ira Katz
a
Professor, Department of Food Science and Nutrition, Colorado State University, Fort
Collins, Colorado
b
Director, Organoleptic Research, International Flavors and Fragrances, Union Beach, New
Jersey
Version of record first published: 29 Sep 2009
To cite this article: Joseph A. Maga & Ira Katz (1979): Furans in foods, C R C Critical Reviews in Food Science and Nutrition,
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May 1979 • 355
FURANS IN FOODS
Author: Joseph A. Maga

Department of Food Science and
Nutrition
Colorado State University
Fort Collins, Colorado
Referee: Ira Katz

Organoleptic Research
International Flavors and Fragrances
Union Beach, New Jersey
Downloaded by [Cornell University] at 11:25 20 July 2012
INTRODUCTION
Numerous classes of compounds that can significantly contribute to the sensory
properties of food have been identified. However, perhaps one of the most intriguing
is the furans. Their existence in foods has been known for quite some time, and their
basic formation pathway through carbohydrate thermal decomposition has been pos-
tulated for over a quarter of a century. However, their overall significance has only
begun to be appreciated by the food chemist.
Historically, they have represented a compound class that is difficult to investigate
for a number of reasons. First, certain furan derivatives are relatively unstable, and,
as such, identification can be difficult. Second, normally, small amounts are formed,
and thus isolation of sufficient quantities for confirmatory identification techniques
can be tedious. Third, most furans have rather low sensory thresholds, and problems
with instability and questions of purity have made absolute quantitation difficult.
Nevertheless, the flavor-patent literature would indicate that furans can be of primary
economic importance to the flavor industry.
Based on their unique properties, it is indeed surprising to this author that no exten-
sive furan review has recently appeared. Thus, the primary objectives of this review
are to list and discuss the major furans and food systems from which they have been
identified, report on the organoleptic properties of furans, and to outline and discuss
the reported and postulated formation pathways for this group of important food-
related compounds.
FOOD OCCURRENCES
As can be appreciated from Table 1, furans have been reported in a wide variety of
food systems, and it should be noted that not all foods listed have undergone extensive
heating. Thus, an individual consuming a normal diet can be expected to be exposed
to the sensory properties of furans.
356 CRC Critical Reviews in Food Science and Nutrition
TABLE 1
Food Systems from which Furan Derivatives Have Been Isolated
Beverages, nonalcoholic Peanuts

Cocoa Pecans
Coffee
Tea Oilseed products
Rapeseed protein
Beverage, alcoholic Sesame seed
Beer Soybeans, deep fat-fried
Rum Soybean oil
Wine Soy sauce
Soy protein
Fruifs
Arctic bramble Vegetables
Cloudberry Asparagus
Cranberry Broccoli
Grapes Cabbage
Mango Cauliflower
Orange Celery
Pineapple Leek
Tamarind Onion
Peppers
Meat and poultry products Potato products
Beef broth Baked
Beef fat Boiled
Mutton fat Chips
Boiled beef Dehydrated
Canned beef Raw
Canned beef stew Shallots
Roast beef Tomato
Cooked pork liver
Chicken broth Miscellaneous
Cooked chicken Ascorbic acid
Eggs Barley
Roast turkey Bread
Caramel
Milk products Cod
Butter culture Corn oil
Dry whole milk Fish protein concentrate
Nonfat dry milk Grape leaves
Dry whey Maple syrup
Casein Mentha species
Sodium caseinate Mushrooms
Popcorn
Nut products Rice
Almonds Rye crisp bread
Filberts Smoke
Macadamia Tuna oil
Licorice
At this point some of the major food systems from which furans have been identified
will be discussed.
Nonalcoholic Beverages
Cocoa has been one product from which an impressive list of furan derivatives have
been identified. The specific compounds are summarized in Table 2. 2-Acetylfuran
was the only furan type compound among the 62 compounds detected by Flament et
al.1 from a cocoa extract. They estimated that it represented 0.25% of the total volatile
May 1979 357
TABLE2
Furans Identified in Cocoa Products
Furan Ref.
2-Acetylfuran 1,2,3
Furfuryl alcohol 2,3
Tetrahydro-2-methylfuran 2
Tetrahydro-2-methyl-3(2H)-f uranone 2,3,4
2-FurfuraI 2
5-Methyl-2-furfural 2,3,4
Dihydro-2(3H)-furanone 2
3-Phenylfuran 3,4
2-Propionylfuran 3,4
5-Methyl-2-acetylfuran 3,4
Methyl furoate 3
Ethyl furoate 3
(-)-(2R),5R-frans-2-vinyl-2-methyI-5-(l'-Hydroxy- 3
1 -methylethyl-)tetrahydrofuran
( + )-(2R,5S)-c/s-2-vinyl-2-methyl-5-(r-hydroxy-l'- 3
methylethyl-)tetrahydrofuran
2-(2'-furyl)-pyrazine 5
2-Methyl-5-(2'-furyl)-pyrazine 5
2-(2'-Furyl-5'-methyl)-5(6)-raethyl pyrazine 5
2-(2'-Furyl-3'(4'),5'-dimethyl)-5(6)-methylpyrazine 5
fraction isolated, van Praag et al.2 added to the list of furans found to be associated
with cocoa. They found furfuryl alcohol associated with the basic volatile fraction.
Most recently, Vitzthum et al. 5 identified a series of furan-pyrazine-based compounds
from the basic fraction of roasted cocoa volatiles.
Coffee represents another food system that has been shown to contain numerous
furans. In fact, as seen in Table 3, more furan-based compounds have been identified
in coffee than in any other food. Merritt et al.' reported that furans represented ap-
proximately 6.5% of the volatiles detected in coffee. However, only approximately 20
compounds were reported to be present in coffee when their work was published. Con-
trasted to this early report, studies just a few years later, typical of which was that of
Stoffelsma et al.,16 identified over 150 volatiles in coffee with the number of specific
furans identified approaching 30. Undoubtedly, the most impressive listing of furans
in coffee was the study reported by Vitzthum and Werkhoff21 in which 50 such com-
pounds were identified in the neutral fraction of roasted-coffee volatiles.
As seen from Table 4, the number of furans identified in tea has not been numerous.
However, it should be noted that furans have been found in both green and roasted
teas. Yamanishi et al." demonstrated that furan content was generally higher after
roasting tea, as compared to green tea. The only exception was the level of 5-methyl-
furfural, which was found to-be lower after roasting.
Alcoholic Beverages
As seen in Table 5, furans have been identified in various alcoholic beverages. In
the case of wine, Bertuccioli and Viani" concluded that 2-ethoxymethylfuran is only
present in aged wines. This assumption apparently is based on the fact that the com-
pound in question was not found in a 1973-vintage Italian varietal wine, but was de-
tected in a similar wine made in 1966. Further investigations are suggested to further
verify this observation.
TABLE3
Furans Identified in Coffee
Furan Ref.
Furan 6,9,16,19,20
2-Methylfuran 7,9,16,19,20
3-MethyIfuran 12
2,5-DimethyIfuran 8,9,16,19,21
2-Ethylfuran 12,21
2-PropyIfuran 9,21
2-ButyIfuran 9,21
2-PentyIfuran 13,21
2-Acetylfuran 11,16,19,21
2-PropionyIfuran 16,21
5-Methylfuran 11,16,19
5-MethyI-2-acetylfuran 10,13,19,21
5-MethyI-2-propionylfuran 16
2-Butylfuran 13,16,21
1 -{2'-Furyl)-2-propanone 11,16
1 -<2'-Furyl)-2-butanone 13,16
H2'-Furyl)-3-butanone 13
Benzofuran 13,21
2-Methylbenzofuran 13,21
3-PhenyIfuran 15,16,21
Furfuryl alcohol 11,16,19,20,21

5-Methyl-2-methylfurfurylsulfide 13,15
Furfurylmethylether 13,16,21
Methyl furoate 10,11,16,21
Ethyl furoate 16,21
Propyl furoate 13,16

Butyl furoate 13
Isobutyl furoate 13
Isopentyl furoate 13
2-Methylbutyl furoate 16
Dimethyl furoate 13
Difurfurylether 15,16,21
5-Methyldifurfuryl ether 13,15
Furfurylmercaptan 12,21
Furfurytaethylsulfide 10,16,19,21
Thioethyl furoate 13,15

Difurfurylsulfide 13,15
Furfural 11,16,19,20,21
l-(5'-Methyl-2'-furyl)-2-propanone 13
H5'-Methyl-2'-furyl)-2-butanone 13,16
H2'-Methyl-2'-furyI)-3-butanone 13
3-{2'-Furyl)-propenal 16
l-(2'-FuryI)-propane-l ,2-dione 10,13,19
l-(2'-Furyl)-butane-l ,2-dione 10,13,19
H5'-Methyl-2'-furyl)-propane-l,2-dione 10,13,19
K5'-Methyl-2'-furyl)-butane-l,2-dione 13
Methylthio furoate 13,15
5-Methyl-2-furfurylnitrile 13
2,2'-Difuryl 13,15,21
2,2'-DifurfuryImethane 10,16,19,21
May 1979 359
TABLE 3 (continued)
Furans Identified in Coffee
Furan Ref.
5-MethyI-2-furyI-2'-furfurylmethane 13,15
Bis-(5-methyl-2-furyl)-methane 13,15
4-(2'-FuryI)-3-butene-2-one 16
2-Furfuryloxyacetone 16,17
2-Furylacetone 21
2-Isobutylfuran 16
3-{2'-FuryI)propanal 16
Tetrahydrofuran 12,16,17
2-MethyItetrahydrofuran 11,16,17
2-Acetyltetrahydrofuran 18
2-Isopropenyl-5-vinyl-5-methyl tetrahydrofuran 13,15

2,3-Dihydrobenzofuran 13,21
2-Methyltetrahydrofuran-3-one 16,19,20,21
2,4,5-Trimethyl-3(2H)-furanone 14
2,5-Dimethyl-3(2H)-furanone 18,21
(-)-(2R),5R£rans-2-vinyl-2-methyl-5-(l'-hydroxy-l- 16,18
( + )-(2R,5S)-c/s-2-vinyl-2-methyl-5-(r-hydroxy-l'- 13,15
4-(2 -Furyl)-but-3-en-2-one 17
2-(2'-Furyl)-pyrazine 18
2-Furfuryl formate 19
2-Furfuryl acetate 19,20

N-Furfuryl-2-pyrrole 19
2-Vinylfuran 21
2-Vinyl-5-methylfuran 21
2-Vinyl-3-methylfuran 21
2-VinyI-4-methylfuran 21
2-Vinyl-3,5-dimethylfuran 21
2-Vinyl-4,5-dimethylfuran 21
2-Propenylfuran 21
2-Methyl-5-propenylfuran 21
2-Isobutenylfuran 21
2-Methyl-5-isopropylfuran 21
2,3,5-Trimethylfuran 21
2-IsopropyIfuran 21
2-Furfuryl formate 21
2-Furfuryl acetate 21
2-Furfuryl propionate 21
5-Methylfuran 21
4-(2'-Furyl-5 '-methyl)-butan-2-one 21
3-(2'-Furyl-5'-methyl)-popan-2-one 21
4-(2'-FuryI)-butan-2-one 21
5-Hydroxymethylfurfural 21
5-Methylfurfuryl Alcohol 21
4-(2'-Furyl)-butan-3-one 21
2-Furyl-(2'-methyI-5'-furyl)methane 21
2-Furfuryl-2'-methylbutyrate 21
TABLE4
Furans Identified in Tea
Furan Ref.
2-Pentylfuran 22
Furfural 22
2-Acetylfuran 22,171
5-Methyl furfural 22
Furfuryl alcohol 22
2-(2'-Furyl)-5-(or Qmethylpyrazine 22
(-)-(2R),5R-trans-2-vinyl-2-methyl-5-(r-Hydroxy- 20,22
1 -methylethyl-)tetrahydrofuran
(+)-(2R,5S)-4S-2-vinyl-2-methyl-5-(l '-hydroxy-1'- 20,22
TABLE5
Furans Identified in Alcoholic Beverages
Product Furan Re
German wines Ethyl-2-furoate 23

Tokaj Aszu wines 2-Furfural 24
5-Methyl-2-furfural 24
Ethyl-2-furoate 24
( + )-(2R,5S)-4S-2-vinyl-2-methyl-5-(l'-Hydroxy-l '- 24
Rubesco Italian wines Ethyl-2-furoate 25
2-Ethoxymethylfuran 25
French Flor sherry 4,5-DimethyItetrahydrofuran-2,3-dione 26
Rum 2-Furancarboxylic acid 149
3-Furancarboxylic acid 149
Furfural 149
5-Methylfurfural 149
2-Acetylfuran 149
2-Methyl-3-tetrahydrofuranone 149
2-Methylfuran 149
Beer 2-Furanmethanol 167
Furfural 167
2-Acetylfuran 167
Dihydro-2(3H)-furanone 167
Dihydro-5-methyl-2(3H)-furanone 167
Approximately 200 compounds were detected by Liebich et al.149 from Jamaica rum.
Among these were the 7 compounds in Table 6.
A series of 6 furans shown in Table 5 have been isolated from an English beer com-
posed of 75% malted barley, 20% corn syrup, and 5% lightly roasted barley.167
Fruits
The types of fruits from which furans have been identified has not been extensive,
but, as seen in Table 7, some unique furans can be present. In fact in some fruits,
furans make up the major volatile composition. A prime example would be the arctic
bramble (Tables 8 and 9). Since mesifurane is directly associated with arctic-bramble
flavor, Kallio34 has followed its level relative to berry ripeness. In green fruit, it ac-
counted for only 0.2% of the volatile aroma compounds, while in ripe berries its pro-
May 1979 361
TABLE6
Furan Concentrations Found in Rum14*
Compound Concentration (ppm)
2-Furancarboxylic acid 0.4

3-Furancarboxylic acid 0.3
Furfural 25
5-Methylfurfural 1.2
Acetylfuran 1.2
2-Methylfuran 0.05
TABLE 7
Furans Identified in Fruits
Fruit Furan Ref.
Arctic bramble (-)-(2R),5R-taMs-2-vinyl-2-methyl-5-(l'-hydroxy-l- 35,37

( + )-(2R,5S)-cw-2-vinyl-2-methyl-5-<l'-hydroxy-r- 35
2,5-Dimethyl-4-methoxy-2,3-dihydro-3-furanone 35,37
2,5-Dimethyl-4-hydroxy-2,3-dihydro-3-furanone 35
Cloudberry (-)-(2R),5R-tfans-2-vinyl-2-methyI-5-<r-hydroxy-l- 34
( + )-(2R,5S)-c/5-2-vinyl-2-methyl-5-(l'-hydroxy-r- 34
2 Furfural 34
5-Methylfurfural 34
Grapes 2-Pentylfuran 28
2-Vinyl-2-methyltetrahydrofuran-5-one 28
(-)-(2R),5R-tt2/w-2-vinyl-2-methyl-5-<l'-hydroxy-l- 28
( + )-(2R,5S)-c/s-2-vinyl-2-methyl-5(l'-hydroxy-r- 28
Mango 2-Furfural 38
2-Acetylfuran . 38
5-Methylfurfural 38
2,5-Dimethyl-2-H-furan-3-one 38
2,5-Dimethyl-4-methoxy-2-H-furan-3-one 38
(-)-(2R), 5 R-frans-2-vinyl-2-methyl-5-{ 1 '-hydroxy-1 - 38
(+)-(2R,5S)-cw-2-vinyl-2-methyl-5-(r-Hydroxy-l- 38
Orange powder 2-Furfural 29,142

5-Methyl-2-furfural 29,142
2-Hydroxyacetylfuran 29,142
Hydroxymethylfurfural 29,142
4-Hydroxy-2-hydroxymethyl-5-methyl-3(2H)-fura- 29
none
Orange juice 2-Furfural 30

2-Hydroxyacetylfuran 30
2,5-Dimethyl-4-hydroxy-3(2H)-furanone 30
TABLE 7 (continued)
Furans Identified in Fruits
Fruit Furan Ref.
Orange flavored drink Hydroxymethylfurfural 33

Hydroxyacetylfuran 33
Pineapple
Tamarind
2-Furfural 32
2-Acetylfuran 32
5-Methylfurfural 32
(-M2R),5R-frans-2-vinyl-2-methyl-5-(r-hydroxy-l- 32
( + )-(2R,5S)-cw-2-vinyl-2-methyl-5-(l'-hydroxy-r- 32
Raspberry + arctic bramble hy- 2-Furfural 37
brid
2,5-Dimethyl-4-methoxy-2,3-dihydro-3-furanone 37
(-)-(2R),5R-(rans-2-vinyl-2-methyl-5-(l'-hydroxy-I- 37
(+)-(2R,5S)-CK-2-vinyl-2-methyl-5(r-hydroxy-r- 37
Cranberry Furfural 172-174

2-Pentylfuran 172,173
2-Butylfuran 173
Dibenzofuran 173
Linalool oxide 173
c/s-Linalool oxide 173
trans-Linalool oxide 173
TABLE 8
Furan Composition and Content of Arctic Bramble Juice"
Compound Total aroma concentrate {%)
Trans-linalool oxide 0.45

Cis-linalool oxide 0.50
2,5-Dimethyl-4-methoxy-2,3- 32
dihydro-3-furanone
2,5-Dimethyl-4-hydroxy-2,3- Trace
dihydro-3-furanone
TABLE 9
Mesifurane Levels in Arctic Bramble as Influenced by Location

and Year of Harvest"
Location Year of Harvest Mesifurane Level (ppm)
Mikkeli, Finland 1973 18

Mikkeli, Finland 1974 11
Maaninka, Finland 1972 12
Lumijoki, Finland 1973 7
May 1979 363
portion was 20%, and in overripe fruit it accounted for approximately 30% of the
total volatiles.
Cloudberries have been reported to contain minor amounts of the four furans listed
in Table 7.
German-type wine grapes have been reported to contain furans.28 However, data
relative to amounts, differences between varieties, and the influence of the year of
harvest were not presented, although the report indicated that these factors were con-
sidered in the study.
Canned mango has also been reported to contain furans.3* However, one could pos-
tulate that certain furans in question could have resulted from added carbohydrate
used in the canning process.
The only citrus-based product which has been reported to contain furans are dehy-
drated or canned orange products. Theoretically, furans are also present in other citrus
products that are processed in a similar manner. Tatum et al." detected approximately
36 compounds associated with the volatiles of orange powder that had been stored at
37°C for 2 months. A total of seven furans were among the 19 compounds identified.
A control sample of orange powder was stored at -20°C, and only two compounds,
neither of which were furans, were identified. Similar furans were reported by Tatum
et al.30 to be present in canned single-strength orange juice that had been stored at
35°C for 12 weeks. Shaw and Berry33 have shown that furans can be detected in or-
ange-based products after as little as three weeks storage at 38°C. Shaw et al." 2 re-
ported finding 14 ppm 5-hydroxymethyl-furfural in stored, dehydrated, orange juice.
Rodin et al.31 was the first to report that 2,5-dimethyl-4-hydroxy-3 (2H)-furanone
was a volatile constituent of pineapple.
A series of five furans were among the 61 compounds identified in tamarind by Lee
et al.32 Their sensory properties, which will be discussed later, indicated that furans
contributed significantly to the aroma of tamarind.
Hybrids of raspberry and arctic bramble have also been shown to contain volatile
furans.37
Meat and Poultry Products

Interestingly, recent research relative to furans has been due primarily to numerous
reports that furans can significantly contribute to meat flavor. It is also interesting to
note that meat flavor has been one of the last frontiers of the flavor chemist. In any
event, a rather homogenous group of furans have been identified to date in meat and
poultry products. These are summarized in Table 10.
One report has appeared53 in which 2,5-dimethylfuran at a level of 0.13 relative
percentage abundance was among the 115 compounds identified in heated hen's egg.
A rather limited number of furans have been isolated from cooked chicken,39-4043
while only pentylfuran has been identified in chicken broth.46
Roast turkey represents another poultry product in which furans have been found.55
However, it would appear that diet can influence furan composition. All of the furans
were identified in a basel diet supplemented with 2% tuna oil, whereas only 2-pentyl-
furan was found in a diet supplemented with 4% beef fat.
A total of 23 furans were among the 179 compounds identified in pressure-cooked
pork liver.49 They represented approximately 28% of the volatiles measured. To date,
this represents the largest number of furans reported in a meat source.
Beef fat that had been heated at 145°C for 10 min was reported to contain furfuryl
alcohol as the only furan derivative.44
A series of alkylfurans was reported by Liebich et al.45 in roast beef. Roasting was
at a temperature of 163°F for approximately 130 min. Furan levels as influenced by
beef cooking method have been reported,57 and it appeared that with roasting up to
TABLE 10
Furans Identified in Meat and Poultry Products
Food Furan Ref.
Eggs 2,5-Dimethylfuran 53
Roast Turkey 2-Pentylfuran • 55

Methylpentylfuran 55
Heptylfuran 55
Methylheptylfuran 55
Octylfuran 55
Chicken Broth Pentylfuran 46
Cooked Chicken 2-Methylfuran 39

2-Ethylfuran 39,43
2-Propylfuran 39
2-Butylfuran 39
2-Pentylfuran 39,43
2-Hexylfuran 39
2-Heptylfuran 39
Furan 40
Tetrahydrofuran 40
Cooked Pork Liver 2-Methylfuran 49

2-Ethylfuran 49
2-Butylfuran 49
2-Pentylfuran 49
2-Furfural 49
Furfuryl alcohol 49
2-Acetylfuran 49
Propionylfuran 49
Furfuryl methyl ketone 49
2-Methyltetrahydrofuran-3-one 49
Furfuryl formate 49
Furfuryl acetate 49
Furfuryl propionate 49
Furfuryl butyrate 49
Furfuryl pentanoate 49
Furfuryl hexanoate 49
Ethyl furoate 49
Ethyl furfuryl ether 49
Furfuryl ether 49
2,2'-Methylenedifuran 49
5-Methylenedifuran 49
5-Methyl-2,2'-methylenedifuran 49
2 (or 3)-Phenylfuran 49
Furfuryl methyl sulfide 49
Furfuryl methyl disulfide 49
(2-Furyl)-pyrazine 49
2-(2-Furyl)-5 (or 6)-methylpyrazine 49
Heated Beef Fat Furfuryl alcohol 44

May 1979 365
TABLE 10 (continued)
Furans Identified in Meat and Poultry Products
Food Furan Ref.
Roast Beef 2-Pentylfuran 45

2-MethyIfuran 57
2-Hexylfuran 45
2-Heptylfuran 45
2-Octylfuran 45
Beef Broth 4-Hydroxy-5-methyl-3(2H)-furanone 41,42

4-Hydroxy-2,5-dimethyl-3(2H)-furanone 41
Boiled Beef 2-MethyItetrahydrofuran-3-one 47,58
5-Thiomethylfuran 47,59
2-Pentylfuran 47,54,58,59,60
2-Methylfuran 54, 57,60
2-Ethylfuran 54,60
2-Acetylfuran 58
5-Methyl-2-acetylfuran 58
2-Furfural 58
5-Trimethylfurfural 58
Canned Beef Furan 48,51,56

2-Methylfuran 48,56
2-Ethylfuran 50,51,56
2-Propylfuran 48,56
2-Butylfuran 48,56
2-Pentylfuran 48,51,52,56,59
2-Hexylfuran 48
3-Methylfuran 48,56
2,5-DimethyIfuran 48
2-MethyI-5-ethylfuran 48,56
2-Furfural 52,59
5-MethyI-2-furfuraI 52,59
2-Acetylfuran 52,59
5-Methyl-2-acetylfuran 52,59
2-Methyl-propenyl-furan 48
two hrs furan content approximately doubled, whereas with boiling for the same time
period, furan content tripled. However, relative to other volatile compound classes
identified, the relative percentage of furans decreased with roasting and increased with
boiling as influenced by time. However, it should be noted that in this study57 effective
gas-chromatographic peak separation was not achieved for certain of the furan deriv-
atives used in arriving at the conclusion cited above.
MacLeod and Coppock" also compared the levels of various volatiles in boiled beef
as influenced by either conventional or microwave cookery. In general, they found
that conventional boiling of beef resulted in greater levels of furans than microwave
boiling. Again, incomplete peak separations make some of their conclusions somewhat
questionable. The major furan identified in boiled beef by Hirai et al/ 7 was 2-pentyl-
furan. The effect of aging on the level of volatiles isolated from boiled beef has been
reported.40 Beef was aged up to 4 weeks with samples boiled at weekly intervals. The
authors concluded that furan levels were fairly constant in boiled meat that had been
aged up to 3 weeks but that furan levels approximately doubled in boiled beef that
had previously been aged 4 weeks.
The concept that certain furan derivatives could serve as meat-flavor precursors was
investigated by Tonsbeek et al. 4142 They reported that 4-hydroxy-5-methyl-3(2H)-fur-
anone was a key compound relative to beef flavor.
Several groups have also investigated the volatiles associated with canned beef prod-
ucts. 4 8 5 0 ' 5 2 "" In an extensive study by Persson and von Sydow,48 numerous com-
pounds were identified in canned beef, and their absolute concentrations measured.
Data for the furans in this study are summarized in Table 11, and, as can be seen,
furan was the compound present in the highest concentration.
In addition, they evaluated different canned beef formulations and processing times.
Data relative to certain furans are shown in Table 12. As can be seen, the addition of
fat greatly enhanced furan levels, while increased heating time increased furan-deriva-
tive levels up to a maximum level before leveling off or decreased levels occurred.
Additional processing aspects were reported in another study.50 For example, 2-ethyl-
furan level was one of the compounds measured as influenced by retort temperature.
As temperature increased from 115° to 121° and finally 131°C, its level decreased from
TABLE 11
Furan Compositiont ana content in (
Compound Absolute
Absc Concentration (ppb)
Furan >50
2-MethyIfuran 61
2-PropyIfuran Trace
2-Butylfuran Trace
2-Pentylfuran 4.7
2-Hexylfuran 0.2
3-Methylfuran 0.2
2,5-Dimcthylfuran 25
2-Methyl-5-ethylfuran 22
A furyl ketone (mol wt, 152) 0.1
A furyl derivative (mol wt, 124) Trace
A furyl derivative (mol wt, 122) Trace
TABLE 12
Effect of Canned Beef Formulation and Processing Time on Furan Levels4*
Absolute concentration (ppb)

Processing Time
Formulation (minatl21°C) Furan 2-Methylfuran 2-Pentylfuran
79.3% Beef, 20% H,0,0.7% NaCl 15 930 9.2 2.6

30 750 61 4.7
45 760 82 8.7
60 960 150 7.6
75 870 130 8.1
66.3% Beef, 13% fat, 20% H 2 O, 30 3700 100 3.0
0.7% NaCl
74.3% Beef, 5% carbohydrate, 20% 30 670 89 5.0
H,0,0.7% NaCl
61.3% Beef, 13% fat, 5% carbohy- 15 2800 76 0.7
drate, 20% H,0,0.7% NaCl 30 3900 110 1.6
45 3700 120 3.0
60 980 110 2.2
75 1400 140 3.8
May 1979 367
180 to 120 to 89 ppb, respectively. In another portion of their study, canned beef was
heated in cans with and without lids, with the latter process simulating aseptic canning.
In most formulations evaluated, 2-ethylfuran levels were found to be lower in the asep-
tically canned products. They also investigated the effect of storage time after process-
ing on the headspace-gas composition of canned beef, and, as seen in Table 13, 2-
ethylfuran levels seemed to increase with storage up to 12 months and then to fall to a
level at 18 months that was lower than the original concentration. In another study,
Peterson et al." reported that 2-furfural and 2-acetylfuran were the major furans in
canned beef stew. However it should be noted that the product used in this study
contained potatoes, carrots, starch, wheat flour, and caramel coloring.
Recently Qvist et al." reported upon the volatiles and levels associated with canned
beef stew that had increasing levels of soy or rapeseed protein added. The portion of
their data relative to furans is summarized in Table 14. As can be seen, the addition
of protein did influence furan concentrations. Also, furan level was influenced by pro-
tein type especially for 2-methyl- and 2-ethylfurans at 40% protein addition.
Recently, Caporaso et al.177 reported 2-pentylfuran to be present in s.c. mutton fat.
MUk Products
Furfural was originally identified by Parks and Patton" in dry whole milk, and it
has been found by other researchers in dehydrated dairy products. As seen in Table
15, a rather extensive list of furans has been found in whey powders. Most shown have
been found in whey powder that had undergone nonenzymatic browning. In the case
of nonfat dry milk, product was used that was 2 years old in an effort to identify
compounds that were contributing to stale flavor." Likewise, stored casein was inves-
tigated,150 and was found to contain approximately 1.4% each of furfural, methylfur-
fural, and methyl furyl ketone relative to the total volatiles isolated. The author is not
aware of any studies reporting on the occurrence of furans in cheese products.
TABLE 13
Effect of Storage Time on 2-Ethylfuran Levels in Canned

Beef"
Storage time (months at 2 0 ° Q Concentration (ppb)
0 250
6 290
12 330
18 160
TABLE 14
Furan Levels (ppb) in Canned Beef Containing Varying Levels of Soy and Rapeseed Protein*4
% Added soy *i* Added rapeseed
Furan 0 5 10 20 30 40 0 5 10 20 30 40
2-MethyIfuran 98 110 130 200 170 390 98 92 96 110 140 130

2-Ethylfuran 130 150 160 150 150 180 130 68 92 150 260 320
2-Propylfuran 0.2 0.3 0.3 0.5 0.6 1.0 0.2 0.2 0.3 0.7 1.5 2.0
2-Butylfuran 1.0 1.6 1.7 2.2 3.0 3.6 1.0 1.2 1.8 1.8 3.9 4.9
2-Pentylfuran 6.3 15 14 23 27 70 6.3 5.2 7.9 17 37 50
3-Methylfuran 2.7 4.7 4.6 3.5 8.7 8.7 2.7 4.8 3.7 2.0 3.6 5.5
2-Methyl-5- 0.7 0.7 0.8 0.8 1.3 1.9 0.7 1.0 0.9 1.7 2.5 2.7
ethylfuran
TABLE 15
Furans Identified in Milk Products
Milk Product Furan Ref.
Dry whole milk 2-Furfural 61
Butter culture 2-Furfural 62

Furfuryl alcohol 62
2-Furfuryl acetate 62
Whey powder 2-Furfural 63

Furfuryl formate 63
2-Acetylfuran 63,64
Furfurylmethyl ketone 63
Furfuryl acetate 63
Benzofuran 63
2-Propionylfuran 63,64
2,2'-Bifuran 63
Furfuryl propionate 63
2,2'-Difurylmethane 63
2-Methylbenzofuran 63
5-Methyl-2-furfuryl alcohol 63
Difurfuryl ether 63
[2-Furyl-(2'-methyl-5'-furyl)]methane 63
Furfuryl butyrate 63
1 -{2'-Furyl)-propane-1,2-dione 63
2-Furylhydroxymethyl ketone 63
5-(2'-Furfuryl)-2-furfural 63
2-Methyl-5-furfuryl-2'-furfuryl ether 63
2-Methyl-5-(5'-methyl-2'-furfuryl) furan 63
5-(5'-Methyl-2'-furfuryl)-2-furfural 63
5-Hydroxymethyl-2-furfural 63
2-[2'-Furfuryl]-5-[2'-furfuryl] furan 63
Stale nonfat dry milk 2-Furfural 65

2-Acetylfuran 65
2-Furfuryl butyrate 65
2-Furfuryl valerate 65
Sodium caseinate Furan 77

2-Methylfuran 77
2-Ethylfuran 77
2-Propylfuran 77
2-Butylfuran 77
2-Pentylfuran 77
2-Hexylfuran 77
3-Methylfuran 77
2,5-Dimethylfuran 77
2-Methyl-5-propylfuran 77
2-Pronenvlfuran 77
May 1979 369
Furans Identified in Milk Products
Milk Product Furan Ref
Casein Furfural 150

Methylfurfural 150
Methyl furyl ketone 150
Furfural alcohol 150
Nut Products
Furans have been reported to be present in the five roasted nut varieties listed in
Table 16. Interestingly, none of the investigators reported absolute or relative amounts
present, nor have formation rates during roasting been reported.
Oilseed Products
Several different oilseeds have been reported to contain furans among their volatiles.
The products and corresponding furans are summarized in Table 17.
Qvist and von Sydow78 analyzed the volatile compounds associated with heated and
unheated rapeseed protein. Data specific to furans identified in this study are shown
in Table 18. As seen, numerous furans appeared as the result of heating in water at
121 °C, and for all furans higher levels were found in the heated product.
Manley et al.76 identified two furylpyrazine derivatives in the volatile, basic fraction
of roasted sesame seed, while 5-methylfurfural was found in the neutral volatile frac-
tion.
Numerous furans have been identified in various soy products. For example, Wilk-
ens and Lin75 found several furans among the 33 compounds identified from deep-fat-
fried soybeans, including a relatively large amount of 2,3-dihydrobenzofuran. The
furan 2-pentylfuran has been associated by one research group as being primarily re-
sponsible for the flavor of reverted soybean oil.152153 Several furans were among the
50 volatiles identified in soy sauce.7' Furans have also been reported to be present in
the acidic, neutral, and basic volatile fractions isolated from hydrolyzed soy
protein.73-74 As seen in Table 19, the heating of soy also results in increased furan
levels.77
Vegetables
Relatively few furan derivatives have been found in vegetables, but the types of
vegetables from which they have been isolated and identified is quite varied (see Table
20).
TressI et al.80 found more than 100 volatiles in cooked asparagus, including 6 furans.
Among these, furfuryl alcohol was estimated to be present at a level of 350 ppb and
2-pentylfuran at a level of 165 ppb, while the other four furans were only detectable
in trace quantities.
To date, 2-pentylfuran is the only furan reported to be present in cooked cabbage,
broccoli, and cauliflower.81
Essentially, the same furan derivatives have been found in all Allium species, such
as leeks, onions, and shallots.
Furfural is the most common furan derivative found in tomatoes.27-90-"'95
Buttery et al.89 have identified furfural and 2-pentylfuran among the constituents of
steam-volatile bell-pepper oil. They also clearly demonstrated that the relative percent-
age found can vary dramatically dependent upon the isolation procedure. For example,
using vacuum-isolation techniques, 0.3% furfural and 1% 2-pentylfuran were found.
TABLE 16
Furans Identified in Nut Products
Nut Furan Ref.
Peanuts 1 -Furf urylpyrrole 66,67

2-Pentylfuran 66
3-Phenylfuran 66,67
2-Furfural 66,67
5-Methylfurfural 66,67
Furyl methyl ketone 66
Furfuryl alcohol acetate 66
Methyl furoate 66
Ethyl furoate 66
Methyl-5-Methylfuryl ketone 66
c-Methylfuranacrolein 66
67
2-Acetylfuran
2-Amylfuran 67
Filberts 2-Furfural 68, 69

5-Methylfuran 68.69
2-Acetylfuran 68.69
2-Pentylfuran 68,69
JV-Furfurylpyrrole 68,69
(2'-Furyl) pyrazine 69
Furan 69
2-Methylfuran 69
2-Ethylfuran 69
2-Butylfuran 69
Phenylfuran 69
• 2-Hexylfuran 69
2-Heptylfuran 69
2-OctyIfuran 69
Dimethylfuran 69
2-Vinylfuran 69
Furfural acetate 69
Methyl furoate 69
Pecans 2-Furfural 70
Almonds 5-Methylfurfural 71
Macadamia Methylfuran 72
2-Pentylfuran 72
2-Furfural 72
2-MethyItetrahydrofuran-3-one 72
May 1979 371
TABLE 17
Furans Identified in Oilseed Products
Oilseed Product Furan Ref.
Hydrolyzed soy protein 2-Furoic acid 73

Furan 73
Furfural 73
2-Furfuryl methyl ketone 73
Acetyl-2-propionyl-5-furan 73
Deep fat-fried soybeans Furfural 75

5-Methylfurfural 75
Furfuryl alcohol 75
2,3-Dihydrobenzofuran 75
Sesame seed 2(2'-FuryI)-pyrazine 76

2(2'-Furyl)-3-methylpyrazine 76
5-Methylfurfural 76
Soy protein isolate Furan 77

2-Methylfuran 77
2-Ethylfuran 77
2-Propylfuran 77
2-Butylfuran 77
2-Pentylfuran 77
2-Hexylfuran 77
3-Methylfuran 77
2-MethyI-5-propylfuran 77
2-Methyl-5-pentylfuran 77
2-Methyltetrahydrofuran 77
2-Propenylfuran 77
Rapeseed protein Furan 78

2-Methylfuran 78
2-Ethylfuran 78
2-Propylfuran 78
2-Butylfuran 78
2-Pentylfuran 78
3-Methylfuran 78
2-Methyl-5-propylfuran 78
2-Methyltetrahydrofuran 78
2-Vinylfuran 78
Butenylfuran 78
Soy sauce Furfural 79

2-Acetylfuran 79
Furfuryl acetate 79
Furfuryl alcohol 79
Soybean oil 2-Pentylfuran 152,15

TABLE 18
FUran Concentrations Associated with Unheated and

Heated Rapeseed Protein7'
Concentration (ppb)
Furan Unheated Heated
Furan 330
2-Methylfuran 27 440
2-Ethylfuran 13 1370
2-Propylfuran 30
2-Butylfuran 1.2 32
2-Pentylfuran 13 340
3-Methylfuran 0.5 17
2,5-DimethyIfuran Trace
2-Methyl-5-propyIfuran 16
2-Methyltetrahydrofuran 0.5
2-Vinylfuran Trace
A butenylfuran 0.4 12
A butenylfuran 23
TABLE 19
Furan Levels as Influenced by Heating Soy Protein"
Concentration (ppb)
Furan 370
2-Methylfuran 14 310
2-Ethylfuran 130 4000
2-Propylfuran 1.5 57
2-Butylfuran 14 125
2-Pentylfuran 95 2700
2-Hexylfuran — 0.2
2,5-Dimethylfuran — 31
2-MethyI-5-ethylfuran 2.3 54
2-Methyl-5-propyIfuran 0.9 12
2-MethyI-5-pentylfuran 0.1 1.4
2-Methyltetrahydrofuran — 30
2-Propenylfuran 0.2 1.7
However, when atmospheric-isolation techniques were employed, their levels had in-
creased to 1 and 4%, respectively.
Various potato products have been shown to contain furans. However, the types of
furans identified are not very extensive.
Miscellaneous Food Systems

As seen in Table 21, there is a wide variety of miscellaneous food systems in which
furans have been identified.
Furans have been reported to be the major thermal decomposition products of as-
corbic acid. Of the 15 compounds identified in such a reaction, 10 were furans." 7
Furans are among the volatiles isolated from roasted barley.101"104 Several bread
products have also been shown to contain furans. In the case of rye crispbread, furans
May 1979 373
TABLE20
Furans Identified in Vegetables
Vegetable Furan Ref.
Asparagus 2-Furfural 80
Furfuryl alcohol 80
2-Acetylfuran 80
2-Ethylfuran 80
2-Pentylfuran 80
Broccoli 2-Pentylfuran 81
Cabbage 2-Pentylfuran 81
Carrot Oil 2-Furfural 82
Cauliflower 2-Pentylfuran 81
Celery 2-Furfural 83
Leek 2-Furfural 84
Furfuryl alcohol 84
2-Ethylfuran 84
2,3-Dihydro-2-n-hexyl-5-methyl-furan-3-one 84,85
2,3-Dihydro-2-n-octyl-5-methyl-furan-3-one 84,85
Onion Dimethylfuran 87
2,3-Dihydro-2-n-hexyl-5-methyl-furan-3-one 86,87
2,3-Dihydro-2-n-octyl-5-methyl-furan-3-one 86
Peppers 2-Furfural 89
2-Pentylfuran 89
Shallots 2,3-Dihydro-2-n-hexyl-5-methyl-furan-3-one 88
2,3-Dihydro-2-n-octyl-5-methyl-furan-3-one 88
Tomato 2-Furfural 27,90,92—95

2-Ethylfuran 91
2-Pentylfuran 95
2-Acetylfuran 95
5-Methylfurfural 95
Potato, baked 2-Furfural 100

2-Acetylfuran 96
2-Pentylfuran 96
Potato, cooked 2-Furfural 99

2-Ethylfuran 99
2-Pentylfuran 99
2-Methylfuran 97
3-Methylfuran 97
2-Butylfuran 97
2-Hexylfuran 97
Potato chips 2-Furfural 98,125

2-Methylfuran 98
Potato, dehydrated Furfural 151
TABLE 21
Furans Identified in Miscellaneous Food Systems
Food Furan Ref.
Barley Furfural 101,103

Acetylfuran 104
Rye crispbread Furfural 105

5-MethyI-2-furfural 105
2-Pentylfuran 105
Furfuryl methyl ketone 105
2-Acetyl-5-methylfuran 105
2-Propionylfuran 105
Furfuryl alcohol 105
Difurfuryl ether 105
Furfuryl formate 105
Furfuryl acetate 105
1 -(2-Furyl) 1,2-propandione 105

1 -(2-Furyl) 1,2-butandione 105
1 -(5-Methyl-2-furyl)-1,2-propandione 105
l-Furfuryl-2-formylpyrroIe 105
Bread vapor Furfural 106
Bread Furfural 107—111,113,114,168

Hydroxymethylfurfural 109,111,114,168
Furan 112
2-Methylfuran 112,168
Pentylfuran 113,168
Ethyl furfuryl ether 113,168
Dihydro-2-methyl-2(2H)-furanone 113,168
3-Furfural 113
2-Methyl-5(or 6)-(2'-furyl)-pyrazine 168
2-Furoic acid 168
2,2'-Difurfuryl ether 168
l-(2'-Methyl-5'-furyl)-propan-l,2-dione 168
2-Acetyl-3-hydroxyfuran 168
2-Propionylfuran 168
Furfuryl formate 113,168
2,5-Dimethyl-3(2H)-furanone 113
Furfuryl acetate 113
1 (2-Furyl)-2-propanone 113
5-Methyl-2-furfural 113,114,168
1 (2-Furyl)-1,2-propanedione 113,168
2-Fonnyl-N-furfuryI-pyrroIe 168
l-Furfurylpyrrole 113,168
Cod Furfural 115,176

Propylfuran 115,176
Dimethylfuran 115,176
May 1979 375
Food Furan Ref.

Tuna Oil 2-Pentylfuran 116
2-Hexylfuran 116
Methylheptylfuran 116
Fish Protein Concentrate Furan 77

2-Methylfuran 77
2-Ethylfuran 77
2-Propylfuran 77
2-Hexylfuran 77
3-Methylfuran 77
2-Propenylfuran 77
Grape leaves Furfural 117

(-)-(2R),5R-fran5-2-vinyl-2-methyl-5-(l'-hydroxy-l- 117
(+ )-(2R,5S)-4S-2-vinyl-2-methyl-5-(r-hydroxy-l- 117
Mentha species Menthofuran 118
Dried Mushroom 2-Methyltetrahydrofuran-3-one 119 .

Furfural 119
2-Acetylfufan 119
2-AcetyI-5-methylfuran 119
Furfurylraethanol 119
Popcorn Furfural 120

2-Pentylfuran 120
2-Acetylfuran 120
(5-Methyl-2-furyl)-(2-furyl)-methane 120
5-Methyl-2 acetylfuran 120
Bis-(5-methyl-2-furyl)-methane 120
JV-Furfuryl pyrrole 120
4-Hydroxy-2,5-dimethyl-3(2H)-furanone 120
JV-Furfuryl pyrrole-2-aldehyde 120
Rice 2,5-Dimethylfuran 121

2-Butylfuran 121
2;Acetylfuran 121
2-Pentylfuran 121
Wood smoke Furan 122

Furfural 123,124
2-Furyl methyl ketone 124
5-Hydroxymethyl-2-furfuraI 124
Food Furan Ref.

Corn oil 2-PentyIfuran 154
Caramel Furan 155

2-Methylfuran 155
Maple syrup Furfural 156

Hydroxy methylfurfural 156,170
"Pineapple furanone" 156
"A furanone" 156
Ascorbic acid Furfural 157

2-Acetylfuran 157
2,2'-Difurylmethane 157
2-Hydroxyacetylfuran 157
2,5-Dihydrofuroic acid 157

Deoxyfuroin 157
Furoin 157
Furil 157
represented approximately 17% of the total volatiles isolated, with furfuryl alcohol
being the major furan.105 A rather extensive group of furans have also been isolated
in white bread"3 and white-bread crust."8
Several fishery products have also been found to contain furans. These include cold-
stored cod, tuna oil, and fish-protein concentrate. In the case of the latter product, it
has been demonstrated that heating results in increased levels of furans. As seen in
Table 22,2-ethylfuran is the predominant furan in heated fish-protein concentrate.
Corn oil and soy oil have been shown to contain 2-pentylfuran, but its presence has
not been detected in cottonseed oil.
Popcorn is another food item where furans have been found.120
Bullard and Holquin121 have reported that unprocessed rice contains furans. Five
such compounds were among the 73 identified.
As seen in Table 23, heating maple syrup for varying lengths of time results in in-
creased furan levels.
Approximately one third of the 51 volatile compounds recently identified in licorice
(Table 24) were furans.178
SENSORY PROPERTIES
The primary interest in furans to the food chemist is their sensory properties, and,
thus, numerous investigators have reported upon this interesting area. As with most
flavoring compounds, both pleasant and objectionable properties have been reported.
Factors such as usage level, degree of purity, and synergistic effects are governing
factors. Another problem, which is common to most early flavor-chemistry work, is
the fact that vague terminology was used to describe the organoleptic properties of
synthesized compounds. Thus, what one researcher described as pleasant, another in-
vestigator may have judged to be objectionable. In any event, at this point an attempt
shall be made to review published sensory data relative to furans.
Evans et al. 1 " attempted to determine the odor thresholds of various flavoring-com-
pound classes which were added to bland cottonseed oil. They defined odor threshold
May 1979 377
TABLE 22
Furan Levels as Influenced by Heating Fish Protein

Concentrate"
Concentration (ppb)
Furan Trace 120

2-Methylfuran 12 52
2-Ethylfuran 3.6 710
2-Propylfuran — 1.9
2-Hexylfuran — 1.6
3-Methylfuran — 0.2
2,5-Dimethylfuran — Trace
2-Methyl-5-ethylfuran 0.3 6.9
2-Propenylfuran — 2.1
TABLE 23
Influence of Heating Time on Furan Levels (Peak Height)

in Maple Syrup 1 "
Heating Time (Hr)
Furan 0 1.5 4.0
Furfural _ 7.5 31
Pineapple furanone 8.5 36 66
A furanone 2.0 71 300
Hydroxymethylfurfural 8.5 30 77
TABLE 24
Furans Identified in Licorice1"
Furfural Furfuryl formate

Furfuryl alcohol Furfuryl acetate
5-Methyl-3-hydrofuran-2-one Furfuryl propionate
2-Methyl-2-tetrahydrofuran-3-one Furfuryl butyrate
2-Acetylfuran
2,2-Difurylmethane
5-Methylfural 2,2-Difurylm ethane
Dihydrobenzofuran 2,2-Difurylmethane
2-Acetyl-5-methylfuran Difurfuryl ether
1 -(2-Furyl)-2-propanone 1 -Furfuryl-2-formylpyrrole
Furyl ethyl ketone l-Furfuryl-2-acetylpyrrole
2,4-Difurfurylfuran
l-(5-Methyl-2-furyl)l,2-propanedione
as the concentration at which 50% of their 15 to 18 member panel could detect an

odor difference from a control. Varying concentrations of the compounds in question
were added to 7.5 ml of freshly deodorized cottonseed salad oil. Sampling was done
in 150 ml beakers covered with watch glasses. The samples were presented to the panel
after being warmed to 55°C, which would make the furans in question quite volatile.
Odor thresholds obtained by this technique for a number of substituted furans are
shown in Table 25. As can be seen, 2-vinylfuran had the lowest odor threshold of the
furans evaluated. Due to reports that 2-pentylfuran was responsible for the reverted
378. CRC Critical Reviews in Food Science and Nutrition
TABLE 25
Furan Odor Thresholds in Cottonseed Oil11
Furan Odor threshold (ppm)
2-Methylfuran 27
2-Ethylfuran 8
2-Propylfuran 6
2-Butylfuran 10
2-Pentylfuran 2
2-Vinylfuran 1
TABLE26
Flavor Responses to Increasing Levels of 2-Pentylfuran in Cot-

tonseed Oil 1 "
Concentration added (ppm) Resulting flavor sensation
0 Buttery
1 Buttery, beany
5 Buttery, rancid
8 Rancid, buttery
20 Grassy, rancid
flavor of soybean oil, Evans et al.127 added increasing amounts of this compound to
cottonseed oil, and recorded the resulting flavor responses. These data are summarized
in Table 26, and from these, the authors concluded that 2-pentylfuran is not unique
to aged soybean oil because its addition to cottonseed oil produced similar organoleptic
responses.
Shaw et al.M2 investigated the taste thresholds of known orange-juice storage prod-
ucts, including furans, using dehydrated orange-juice crystals which were reconstituted
to single-strength juice. Taste thresholds for furans are shown in Table 27. Based on
their measured thresholds, the authors concluded that furans did not significantly con-
tribute to off-flavor in dehydrated orange juice.
Based on the volatiles found in tamarind, Lee et al.32 concluded that furans contrib-
ute significantly to its overall aroma. Specific furans mentioned included cis and trans
linalool oxides, 2-acetylfuran, furfural, and 5-methylfurfural.
Persson and von Sydow31 attempted to relate sensory and chemical data obtained
from the volatiles associated with canned beef to regression model analysis. Three
furans were among the 23 compounds chosen for the models. However, no major
contribution from furans was found using this technique.
Qvist et al.54 attempted to correlate gas chromatographic and sensory data obtained
from canned-beef studies by using stepwise discriminant analysis. Furans were among
the classes of compounds evaluated. The sensory terms cardboard-like and wet wool
were significantly correlated to compound groups including 2-methylfuran, 2-pentyl-
furan, and 2-butylfuran. In general, furans were also found to be associated with sen-
sory terms such as wort-like, hay-like, musty, cooked meat, and retort off-flavor.
Although noted for thier sensory properties, relatively few furan odor thresholds
have been reported in the general scientific literature. Data compiled in Table 28, which
does not include any of the flavor-patent literature, reinforces this observation. It is
apparent that wide discrepancies in values are present in the literature. But, in any
event, most odor-threshold values for furans are in the low ppm range. The recording
and reporting of accurate furan odor thresholds represents an area of flavor research
that deserves attention.
May 1979 379
TABLE 27
Taste Thresholds for Furans in Dehydrated Orange

Juice"1
Furan Taste threshold (ppm)
Furfuryl alcohol 30
Furfural 80
2-Acetylfuran 110
2-Hydroxyacetylfuran >200
5-Hydroxymethylfuran >200
TABLE28
Reported Odor Thresholds For Furans
Odor threshold
Compound (ppm in HjO) Ref.
Furan 4.5 78
27.0 77
2-Ethylfuran 8.0 77,78
2-Propylfuran 6.0 77,78
2-Butylfuran 10.0 77,78
2-Pentylfuran 2.0 77,78
0.006 89,95
Furfural 3.0 95,125,126
Cepanone 1.0 86
Norcepanone 0.5—1.0 86
2,5-Dimethyl-4-methoxy-3(2H)-furanone 0.00003 126
2,5-Dimethyl-4-hydroxy-3(2H)-furanone 0.00004 126
The rather primitive state relative to furan sensory-descriptive terminology can be

appreciated by viewing the descriptive phrases reported in the literature for furans in
Table 29. Undoubtedly, some of the contrasting terms reported for theoretically the
same furan is due to the concentration of the compound evaluated. In any event, the
wide range of sensory properties that furans possess is quite apparent.
A general measure of the sensory value of certain flavor-compound classes can be
obtained by noting the preponderance of such compounds that are commonly used by
the flavoring industry. In the case of furans, the list is quite extensive (Table 30). The
potency of furans can also be appreciated by noting that usage levels are normally
quite low.
The gas chromatograph has unquestionably been a valuable tool to the flavor chem-
ist. However, there is one major limitation that some investigators sometimes forget.
Certain furans can be unstable at room temperature, and yet, with gas chromatogra-
phy, injection-port temperatures many times higher than room temperature are com-
monly employed. Thus, the odor sensations that are described during emission from a
gas-chromatographic splitter may not be actually coming from the compounds in-
jected. Thus, the reported occurrence of certain furans as determined by gas chroma-
tography may be erroneous.
FORMATION PATHWAYS
Based upon the literature, it can be concluded that the vast majority of furans that
are found in our food supply are derived from the thermal degradation and rearrange-
TABLE 29
Organoleptic Descriptions Reported for Various Furans
Compound Description Ref.
Furan Sickly, nasty smelling 48

Ethereal 166
2-Methylfuran Sickly 48
Ethereal 166
2-Ethylfuran Powerful, burnt, sweet, coffeelike 169
2-Pentylfuran Beany, grassy 154

Licorice 127
Green, pungent, sweet 48
Fruity 169
2-Acetylfuran ' Powerful, balsamic, sweet 169

Burning, sweetish taste 166
Tobacco-like 147
Balsamic, cinnamic 32
"Oxygenated furans' Retort flavor 52
Furfural Rotten 84
Sweet, caramellike flavor 32
Sharp 29
Penetrating odor 169
Sweet, breadlike 147
Sweet taste 166
Furfuryl alcohol Bitter taste 166

Coconut 29
Burnt potato 84
5-Methylfurfural Sweet, caramellike flavor 32

Sharp,grape 29
Sweet, spicy, warm odor 169
c/s-Linalool Rosy aroma 32
(ran-Linalool Rosy aroma 32

4-Hydroxy-5-methyl-3(2H)-furanone Roasted chicory root 41
4-Hydroxy-2,5-dimethyl-3(2H)-furanone Caramel odor 41
Pineapplelike 30
Burnt pineapple 31
Fragrant, fruity, caramel 166
Floral, sickly, sweet, fruity 126
4-Hydroxy-2-hydroxymethyl-5-methyl- Charred sugar 29

3(2H)-furanone
4-Methoxy-2,5-dimethyl-3(2H)-furanone Sweet, herbal, arctic bramble 126
4,5-Dimethyltetrahydrofuran-2,3-dione Sherry 26
2-(Ethoxymethyl)-furan Fruity, aromatic, pungent 25
2,5-Dimethylfuran Pungent 53
Furil Mild, sweet 147
2-Furoic acid Stinging aroma, sour taste 166
2-Furfurylfuran Caramellic 147
Difurylethylene Fatty 147
2-Furylmethanethiol Coffeelike, unpleasant 147, 169

Difurfuryl sulfide Toasted 147
2-Furfuryl disulfide Roasted, powerful, repulsive sulfide, 169
unpleasant
May 1979 381
Organoleptic Descriptions Reported for Various Furans
Compound Description Ref.
2,5-Diethyltetrahydrofuran Sweet, herbaceous, caramellic odor 169

2-Methyl-5-thiomethylfuran Fruity, sulfurated 169
o-Furyl cyanide Sweet, pungent 147

5-Hydroxymethyl-2-furfural Bitter, astringent taste 166
2-Furyl hydroxymethyl ketone Burning, sweetish taste 166
2-Ethylfuryl ketone Sweet 84
Methyl furoate Pleasant, fruity, mushroom, fungus, to- 169
bacco
Ethyl-2-furanpropionate Camomile 169

(2-Furyl)-2-propanone Radish 169
Isoamyl-2-furanbutyrate Sweet, buttery, fruity 169
Isoamyl-2-furanpropionate Sweet, green, floral 169
Isobutyl-2-furanpropionate Fruity, winey, brandylike 169
Tetrahydrofurfuryl acetate Faint, fruity, ethereal 169

Tetrahydrofurfuryl alcohol Faint, warm, oily 169
Tetrahydrofurfuryl butyrate Sweet, apricot, pineapple 169
Tetrahydrofurfuryl cinnamate Sweet, balmy, Vi-ous 169
2-Methyl-3 or 5 or 6-furfuryl thiopyrazine Roasted, coffeelike 169
2-Methyl-3-furanthiol Roasted meat 128, 169

Menthofuran Menthol 169
2-Hexyl-4-acetoxytetrahydrofuran Sweet, floral, fruity 169
2,3-Dihydro-2-Af-hexyl-5-methyIfuran-3-one Rubbery 84
2,3-2-JV-octyl-5-methylfuran-3-one Onion, irritating 84
Cepanone Fatty, waxy, meaty, burnt, musty 86

Norcepanone Fatty, waxy, meaty, burnt, musty 86
4-Mercapto-2-methylfuran Green, meaty, herbaceous 136
3-Mercapto-2-methyl-4,5-dihydrofuran Roasted meat 136
4-Mercapto-3-oxotetrahydrofuran Green, meaty 136
4-Mercapto-5-methyl-3-oxotetrahydrofuran Meaty 136

3-Hydroxy-2-methyltetrahydrofuran Fatty 136
2,5-Dimethyl-3-furanthiol Roasted meat 128
5-Methyl-2-furanthiol Burnt, sulfury 128
B/s(2-methyl-3-furyl) disulfide Cooked meat aroma 128
Bjs(2,5-dimethyl-3-furyl) disulfide Meaty 128

Bis(2,5-dimethyl-3-furyl) sulfide Bloody aroma, boiled meat taste 128
Bis(5-methyl-2-furyl) disulfide Chemical, rubbery 128
B/s(2-methyl-3-furyl) trisulfide Brothy 128
B/s(2-methyl-3-furyl)tetrasulfide Braised beef aroma and taste 128
ment of organic compounds with primary emphasis being placed on carbohydrates.

The classical reviews by Hodge165166 still serve as the backbone for the understanding
of nonenzymatic browning chemistry. At this point, certain of the model-system stud-
ies relative to furan formation will be discussed.
As mentioned above, carbohydrates have been proposed to be the primary source
of furans with most of the earlier work being summarized by Fagerson.12' Greenwood
et al.158 pyrolyzed a series of carbohydrates of 300°C in the presence of nitrogen, and
found 2-methylfuran to be the major decomposition product of sucrose, while furan
was predominant in cellulose and starch.
TABLE 30
FEMA Listed Furans and Their Usage Levels in Various Products'**
Usage level
Furan Fema No. Product (ppm)
2,5-DimethyI-3-acetylfuran 3391 Nonalcoholic beverages 1.0

Ice cream 0.6
Candy 1.5
Baked goods 2.0
Gelatins and puddings 1.5
Meat sauces, soups 1.0
2-Acetylfuran 3163 Baked goods 20.0

Condiments 20.0
Meats, meat sauces 20.0
Soups 20.0
B«(2-furfuryl) disulfide 3257 Nonalcoholic beverages 3.0

Ice cream 3.0
Candy 3.0
Baked goods 3.0
Chewing gum 3.0
Condiments, pickles 3.0
Difurfuryl ether 3337 Baked goods 1.0

Difurfuryl sulfide 3258 Nonalcoholic beverages 5.0

Ice cream 5.0
Candy 5.0
Baked goods 5.0
Chewing gum 5.0
Condiments 5.0
Bis(2-Methyl-3-furyl) disulfide 3259 Baked goods 0.1

Ethyl-2-furanpropionate 2435 Nonalcoholic beverages 1.6

Ice cream 1.6
Candy 5.6
* Baked goods 7.5
5-Ethyl-3-hydroxy-4-methyl-2(5H)-furanone 3153 Candy 1.0

Baked goods 1.0
2-Formylbenzofuran 3128 Ice cream 10.0

Candy 10.0
Baked goods 20.0
2-Furanmethanethiol formate 3158 Nonalcoholic beverages 1.0

Ice cream 1.0
Candy 1.0
May 1979 383
FEMA Listed Furans and Their Usage Levels in Various Products"
Usage level
Furfural 2489 Nonalcoholic beverages 4.0
Alcoholic beverages 10.0
Icecream 13.0
Candy 12.0
Baked goods 17.0
Chewing gum 45.0
Syrups 30.0
oooooooo
2-Furfuryl disulfide 3146 Nonalcoholic beverages
Icecream
Candy
Baked goods
Gelatins and puddings
Chewing gum
Condiments
Meat sauces, soups
Furfuryl isopropyl sulfide 3161 Nonalcoholic beverages 0.5

Icecream 0.5
Candy 0.5
Baked goods 0.5
Furfuryl isovalerate 3283 Nonalcoholic beverages 5.0

Ice cream 5.0
Candy 10.0
Furfuryl mercaptan 2493 Nonalcoholic beverages 0.5

Ice cream 0.8
Candy 2.0
Baked goods 2.1
Icings 0.5
Furfuryl methyl ether 3159 Nonalcoholic beverages 2.0

Candy 2.0
Sauces 2.0
Furfuryl methyl sulfide 3160 Nonalcoholic beverages 1.0

Ice cream 1.0
Candy 1.0
o-Furfuryl caprylate 3396 Baked goods 4.0

Margarine 2.0
Snacks 10.0 .
o-Furfuryl pentanoate 3397 Nonalcoholic beverages 1.5

Candy 3.0
FEMA Listed Furans and Their Usage Levels in Various Products"

Usage level
Fema No. Product (ppm)
Furan
3346 Nonalcoholic beverages 0.5
Furfuryl propionate 0.5
Ice cream
Candy 1.0
Baked goods 1.0
Chewing gum 1.0
Cereals 1.0

N-Furf uryl pyrrole
Ice cream 2.0
Candy 2.0
Baked goods 2.0
Cereals 2.0
2070 Nonalcoholic beverages 0.03—5.0

Isoamyl-2- f uranbutyrate
Ice cream 2.8
Candy 6.0
Baked goods 0.5—8.0
2071 Nonalcoholic beverages 0.02—0.3

Isoamyl-2-furanpropionate
Ice cream 0.3—0.7
Candy 1.6—3.6

Isobutyl-2-furanprOpionate
Ice cream 14.0
Candy 17.0
Baked goods 21.0
Gelatins and puddings 4.0—30.0
Chewing gum 12.0
Icings 20.0

Menthofuran
Ice cream 10.0
Candy 10.0
3188 Baked goods 0.3

2-Methyl-3-furanthiol
Condiments 0.3

5-Methylfurfural
Ice cream 0.1
Candy 0.03—0.1
Baked goods 0.03

Methyl furfuryl disulfide
Ice cream 1.0

Furfuryl thioacetate
Ice cream 1.0
Candy 1.5
May 1979 385
FEMA Listed Furans and Their Usage Levels in Various Products'"
Usage level
Furfuryl thiopropionate 3347 Nonalcoholic beverages 1.0

Ice cream 1.0
Candy 1.0
Baked goods 1.0
(2-Furyl)-2-propanone 2496 Ice cream 5.0

Candy 3.8—20.0
3-Heptyl-5-methyl-2(3H)-furanone 3350 Baked goods 1.5

Dairy products 1.5
2-Heptylfuran 3401 Nonalcoholic beverages 0.02

Ice cream 0.02

Baked goods 0.06
Chewing gum 0.06
2-Hexyl-4-acetoxytetrahydrofuran 2566 Nonalcoholic beverages 1.0

Ice cream 3.0
Candy 3.0
Baked goods 3.0
4-Hydroxy-2,5-dimethyl-3(2H)-furanone 3174 Ice cream 5.0

Candy 10.0
Baked goods 10.0
Candy 2.0
Baked goods 2.0
2-Methyl-3 or 5 or 6-furfuryl thiopyrazine 3189 Nonalcoholic beverages 1.0

Ice cream 1.0
Baked goods 1.0
Condiments 1.0
Sauces 1.0
Methyl furoate 2703 Nonalcoholic beverages 0.6

Ice cream 0.06—1.3
Candy 0.7
Condiments 0.02
3-(5-Methyl-2-furyl) butanal 3307 Nonalcoholic beverages 0.1

Ice cream 0.4
Candy 1.2
Chewing gum 2.5
Protein foods 0.1
2-MethyItetrahydrofuran-3-one 3373 Nonalcoholic beverages 10.0

Ice cream 10.0
Candy 10.0
Baked goods 10.0
FEMA Listed Furans and Their Usage Levels in Various Products'"
Usage level
Furan Fetna No. Product (ppm)
2-Methyltetrahydrofuran-3-one (continued) 3373 Chewing gum 10.0

Meat sauces, soup 10.0
Cereals 10.0
Methyl thiofuroate 3311 Nonalcoholic beverages 3.0

Ice cream 3.0
Candy 3.0
Baked goods 5.0
Condiments 3.0
Meat, soups 3.0
2-Methyl-5-thiomethylfuran 3366 Baked goods 1.5

2-Pentylfuran 3317 Nonalcoholic beverages 3.0

Candy 3.0
Baked goods 3.0
Cereals 3.0
Pentyl-2-furyl ketone 3418 Nonalcoholic beverages 0.05

Ice cream 0.05
Baked goods 0.15
Chewing gum 0.15
Tetrahydrofurfuryl acetate 3055 Nonalcoholic beverages 1.3—2.0

Ice cream 8.0
Candy 1.0—20.0
Tetrahydrofurfuryl alcohol 3056 Nonalcoholic beverages 0.03—14.0

Ice cream 0.03
Candy 0.03—18.0
Baked goods 0.04
Tetrahydrofurfuryl butyrate 3057 Nonalcoholic beverages 0.9

Ice cream 6.0
Candy 15.0
Baked goods 15.0
Tetrahydrofurfuryl cinnamate 3320 Nonalcoholic beverages 20.0

Ice cream 20.0
Baked goods 20.0
Tetrahydrofurfuryl propionate 3058 Nonalcoholic beverages 1.3—2.0

Ice cream 8.0
Candy 1.0—20.0
3,3'-Tetrathio-6/i(2-rnethylfuran) 3260 Baked goods 0.1

Condiments, pickles. 0.1
Cereals 0.1
May 1979 387
FEMA Listed Furans and Their Usage Levels in Various Products1*
Usage level
2,2'-(Thiodimethylene)-difuran 3238 Nonalcoholic beverages
b b b b
Icecream
Candy
Baked goods
Gelatins and puddings
b b b b
Chewing gum
Condiments
Meat sauces, soups
B/s-(2,5-dimethyl-3-furyl)disuIfide 3476 Baked goods 0.1

2,5-Dimethyl-3-thiofuroylfuran 3481 Baked goods 0.2

2,5-Dimethyl-3-thioisovalerylfuran 3482 Baked goods 0 .2

Meat sauces, soups 0 .2
As seen in Table 31, in a bread system added sucrose level has been correlated with
resulting furfural amounts in bread crust, and, thus, it was proposed that furfural
could significantly contribute to bread flavor. However, the same researchers also
demonstrated (Table 32) that furfural levels decreased with storage time. Unwrapped
bread had a significantly lower level than wrapped bread. Apparently, most of the loss
occurred during the first day.
One of the most extensive studies relative to carbohydrate degradation was reported
by Heyns et al.140 They identified 56 volatiles from glucose that had been heated at
300°C, including the 23 furans listed in Table 33. It was their observation that the
vinylfurans formed during the early stages of pyrolysis. They also identified furan-
based compounds having more than six carbon atoms, thus suggesting that they were
formed from the fragmentation of glucose polymers.
The role of heating specific sugars and amino acids together on resulting furan levels
was reported by Langner and Tobins.1" As seen in Table 34, overall, lactose was more
active than glucose in forming furans. However, no clearcut conclusions could be made
relative to amino acid reactivity. It should be noted that in this study sugar and amino
acid levels were -iOt constant, in that 9% glucose was used while 15% lactose was
employed. Likewise, 1M of glycine, but only 0.5M of lysine and valine, were reacted.
Walter and Fagerson1" also heated glucose, and identified the resulting volatiles.
Gas chromatography revealed approximately 100 compounds, including the furan
summarized in Table 35. They also postulated that seven-carbon furan compounds
could result from glucose polymer fragmentation or by the reaction of intermediate
compounds. An example of this latter mechanism would be the formation of l-(2'-
furyl)-propane-l ,2-dione from acetic acid and furfural.
Fructose degradation relative to furan formation has also been reported.164 How-
ever, only 15 compounds were identified, including the furans shown in Table 36.
A study by Heyns and Klier1*3 evaluated the influence of glucose pyrolysis tempera-
ture on relative volatile-compound formation, and, as seen in Table 37, a temperature
of 300°C was achieved before furans were detected. In some cases, temperatures as
high as 450°C were required. Interestingly, relative furan levels were not found to
TABLE 31 TABLE 32
Effect of Sucrose Concentration on Fur- Influence of Bread Storage and Wrapping on the
fural Level in Bread Crust10* Furfural Content of Bread Crust10*
Vo Sucrose Furfural (mg/lOOg) Furfural Level (mg/lOOg)
4 0.325 Storage time (days) Unwrapped Wrapped

5 0.338
6 0.350 1 0.13 0.23
7 0.386 2 0.04 0.11
8 0.435 3 0.10 0.17
5 0.07 0.17
7 0.04 0.14
TABLE 33
Furans Identified from Thermal Degradation of Glucose"*
Furan 2,5-Diethylfuran
2-Methylfuran Cw-2-propenylfuran
3-Methylfuran Traos-2-propenylfuran
2-EthyIfuran 3-Furfural
2,5-Dimethylfuran Cis-2-methyl-5-propenylfuran
2-Vinylfuran 2-Furfural
2-Propylfuran 7Jrans-2-methyl-5-propenylfuran
2-Methyl-5-ethylfuran 2-Methyl-3-(2-furyI)-2-propene
2,3,5-Trimethylfuran 2-Acetylfuran
2-Methyl-5-isopropyIfuran 2,3-Benzofuran
2-MethyI-5-vinylfuran 5-Methylfurfural
2-Methyl-S-propylfuran
increase with temperature. In this same study, the thermal degradation products of
other carbohydrates were investigated relative to temperature. As seen in Table 38,
furans were found in all products, with relative amounts generally increasing with tem-
perature.
The role of an Amadori compound in the further thermal formation of other com-
pounds was reported by Mills et al.130 A total of 15 compounds, including the four
furans shown in Table 39, were identified with 1-deoxy-l-pideridino-D-fructose was
pyrolyzed. Likewise, other intermediates can serve as furan sources.
Jurch and Tatum175 refluxed methylamine, acetic acid, and glucose in water for 2
hr, and identified 13 compounds, including the five furans shown in Table 40.
Ferretti's group139140 have extensively investigated lactose-casein-model browning
systems, resulting in the furans listed in Tables 41 and 42. They postulated that many
of the furans resulted from interaction of degradation intermediates.
The volatile products resulting from the roasting of alanine and glucose at 250°C
have resulted in the identification of numerous compounds, including the five furans
in Table 43. Intermediate reactions, such as that between alkyl furans and pyrroles,
were postulated. They found 5-methyl-2-furfurylaldehyde to be the most predominant
volatile.
Kato et al.138 have also thermally reacted amino acids with glucose and related com-
pounds. They were specifically interested in sulfur-containing amino acids, and, as
seen in Table 44, a small, but characteristic, group of furans were identified.
Furans resulting from cysteine and xylose (Table 45) and from rhamnose and alanine
(Table 46) have also been reported. Severin and Seilmeter132 have also investigated
xylose alone. Thermal breakdown of higher perpenes has also been proposed as a furan
formation pathway."
TABLE 34
Furan Amounts (Relative GLC Peak Area) from Different Sugar-Amino Acid Mixtures'"
Glucose- Glucose- Glucose- Glucose- Lactose- Lactose- Lactose- Lactose-

Furan Glucose glysine lysine valine casein Lactose glycine Iysine valine casein
2-Furfural 3.81 1.63 8.73 1.11 3.10 2.52 7.82 5.89 8.29 0.22
2-Acetylfuran 4.51 9.31 10.00 6.98 14.70 7.87 5.57 0.44
5-Methyl-2-furfural 0.65 3.02 0.63 0.97 1.51 6.09 7.45 1.23
TABLE35 TABLE 36
Furans Identified in the Volatile Fraction of Heated Glucose1" Furans Isolated from Base-Catalyzed Fructose Degradation"4
Furan 3-Furaldehyde Furfuryl alcohol

2-Methylfuran 5-Metbyl-2-furaldehyde 5-Methyl-2-furfuryl alcohol
2-PropyIfuran 5-Methyl-2-acetylfuran 2,5-Dimethyl-4-hydroxy-3(2H)-furanone
2-Furaldehyde 1 -(2'-FuryI)-propane-l ,2-dione 4-Hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone
2-Acetylfuran Methylfuroic acid
TABLE 37
Influence of D-Glucose Pyrolysis Temperature on Relative Amounts of Fur-

ans Formed 10
Temperature (°
Furan 250 300 350 400 450
Furan
2-Methylfuran
2,5-Dimethylfuran
2-Vinylfuran
Furfural
5-Methylfurfural
TABLE 38
Furan Formation Amounts as Influenced by Heating Various Carbohydrates to Elevated Temperatures1"
Glyceraldehyde D-Erythrose Pentosans, hexoses Polysaccharide
Furan 400°F 450°F 400°F 450°F 400°F 450°F 400°F 450°F
Furan + ++ +++ +++ ++ +++ ++ +++
2-Methylfuran - + + ++ ++ +++ ++ ++
2,5-Dimethylfuran - — — + + ++ — +
2-Vinylfuran - - + + + + + + +
2-Methyl-5-vinylfuran - - + + + + - +
Furfural - + +++ +++ ++++ ++++ + +++ + +++
5-MethyIfurfural - - + + + + + +
TABLE 39 TABLE 40
Furans Identified from the Pyrolysis of 1- Furans Formed from the Heating of D-
Deoxy-1 -Piperidino-D-Fructose1" Glucose, Acetic Acid, and Methyl-
amine1"
2-Acetyl-3-piperidinofuran
2-Acetyl-3-piperidino-4,5-dihydrofuran 5-Methyl-2-furufryl acetate
4-Hydroxy-2,5-dimethyl-3(2H)-furanone 2,5-Dimethyl-4-hydroxy-3(2H)-furanone
2,5-Dimethyl-3-piperidinofuran 5-Hydroxymethyl-2-furfuraIdehyde
Furfuryl alcohol
5-Methyl-2-furfuryl alcohol
TABLE 41
Furans Isolated from a Lactose-Casein Browning System1"1'*1
Furan 5-Hydroxymethyl-2-furaldehyde
2-Methylfuran 5-(2'-Furfuryl)-2-Furfuryl alcohol
2-Furfuryl methyl sulfide 2-(2'-Furfuryl)-5-(2'-furfuryl)-furan
Furfuryl acetate 5-Methyl-2-furaldehyde
5-Methyl-2-acetylfuran Furfuryl alcohol
2-Propionylfuran
2-Acetylfuran 2,2'-Difurylmethane
2-FurfuryI methyl ketone [2-Furyl-(2'-methyl-5'-furyl]-methane
2-Methyltetrahydrofuran-3-one 2-Furoic acid
2-Furaldehyde 2,2'-Bifuran
2-Furfuryl formate l-(2'FuryI)-2-butanone
2-Methylbenzofuran 2-Furfurylvinylacrylate
5-Methyl-2-propionylfuran 1-<2'-Furyl)-3-butanone
Difurfuryl ether 2-MethyI-5-(5'-methyl-2'-furfuryl)-furan
5-(2'-Furfuryl)-2-furaldehyde
A specific furan that has received widespread attention is 4-hydroxy-5-methyl-3(2H)-

furanone. This is due to the fa.ct that it has been associated with meat flavor. 42 ' 33 " 4
It was concluded42 that this compound results from a reaction between ribose-5-phos-
phate and either pyrrolidone carboxylic acid or taurine. However, the same compound
can also result from 1-deoxy-l-dibenzylamino-D-fructuronic add."'-'" In addition, the
compound has been used as a starting compound in the formation of a wide variety
of furans such as those shown in Table 47.
An important consideration in pathway chemistry is the stability of certain interme-
diates, as well as some of the end products. Thus, it is entirely possible that some
May 1979 391
TABLE 42 TABLE 43
Furans Identified in a Mr-Formyl-L-Lys- Furans Isolated from Roasting DL a-

ine-D-Lactose Browning System"1 Aianine with D-Glucose"'
2-Furaldehyde 2-Acetylfuran
2-Furfuryl formate 2-Furaldehyde
2-Acetylfuran 2-Acetyl-5-methylfuran
2-Furfuryl acetate 5-Methyl-2-furfurylalcohol
5-MethyI-2-furaldehyde 1 -(5'-Methyl-2'-furf uryl)-pyrrole
2,2'-Difurylmethane
Furfuryl alcohol
5-Methyl-(2-furyl)-(2'-furyl)-methane
Difurfurylether
5-Hydroxymethyl-2-furaldehyde
TABLE 44
Furans Isolated from the Heating of Sulfur-Containing Amino Adds with Glucose
and/or Pyruvaldehyde1"
Cystine + glucose Cystine + pyruvaldehyde Cysteine + glucose
Furfural 5-Methylfurfural 2-Acetylfuran

2-Methyl-5-ethylfuran 2,5-Dimethyl-3-ethylfuran 2-AcetyI-5-methylfuran
5-Methylfurfural 2-Furoic acid
Furfuryl alcohol
TABLE 45
Furans Identified in HVP-Xylose- and Xylose-Cysteine

Model Systems"3
HVP-Xylose-Cysteine Xylose-Cysteine
Furfuryl methyl sulfide Furfuryl mercaptan

2-Methyl-5-thiomethylfuran
TABLE46
Furans Identified in Acidic Hexose-Amino-Acid Reactions144
Reactants
Furan Fructose-alanine Fructose-y-aminobutyic Rhamnose-

acid alanine
Acetylfuran 0.71' 0.13 _

2,5-Dimethyl-4-hydroxy-3(2H)-furanone — 11.10
Furfural 1.45 .4.42
Furfuryl alcohol 0.24 0.11
Hydroxyacetylfuran 3.49 1.76
Hydroxymethylfurfural 91.45 82.71
5-Methylfurfural 0.39 1.49 87.28
GLC peak area % of ether-soluble products.

important intermediates will never be isolated and, therefore, the complete step-by-
step process can never be fully proven. For example, 2,5-dimethyl-4-hydroxy-2,3-di-
hydrofuran-3-one has been reported to be unstable.1"
Recently, Shibamoto and Russell"15146 have reported on the compounds formed by
the heating of glucose, hydrogen sulfide, and ammonia. Resulting furans are listed in
Table 48. In the latter study, the authors reported that when small amounts of ammo-
nia were used in the starting-reaction mixture, a large relative percentage of furans
was formed and the resulting odor resembled rare cooked meat. When a larger amount
of ammonia was used, resulting furan levels decreased, and the product had a nutty
or burnt aroma.
Shibamoto147 expanded on his earlier work by investigating the volatiles produced
by reacting furfural, hydrogen sulfide, and ammonia. A total of 17 compounds were
identified, including the furans shown in Table 49. The most abundant furans identi-
fied were difurylethylene and furil, which are believed to be self-condensation products
of furfural.
Thermal degradation of certain vitamins can also serve as a pathway for furan for-
mation. For example, Tatum et al.157 found the furans listed in Table 50 to be the
primary end products of ascorbic acid degradation. Furans as the result of dehydroas-
corbic acid degradation have also been reported (Table 51). The authors also evaluated
the effect of pH on furan formation rates, and, as seen in Table 52, certain furan
levels, especially 2-furfuraldehyde and 2-furan carboylic acid, were dramatically influ-
enced by pH. However, as seen in Table 53, except for 2-furancarboxylic acid, oxygen
had little influence on furan formation rates. Schutte179 has also reviewed the possibil-
ity that thiamin can thermally degrade to yield 2-thiomethyl-5-methylfuran.
TABLE 47 TABLE 48
Furans Formed from the Reaction of 4-Hydroxy- Furans Identified in a D-Glucose-Hydro-

S-Methyl-3 (2H)-Furanone with Hydrogen Sul- gen Sulfide-Ammonia Model System14114*
fide 1 "
Furfural
4-Mercapto-2-methylfuran Methyl furfuryl sulfide
3-Mercapto-2-methyl-4,5-dihydrofuran 2-Acetylfuran
3-Hydroxy-2-methyltetrahydrofuran (Furyl-2)-1 -propanone-2
4-Mercapto-3-oxotetrahydrofuran Methyl-2-ethyl furyl sulfide
4-Mercapto-5-methyl-3-oxotetrahydrofuran Methyl thiofuroate
5-Methylfurfural
Ethyl-2-furyl ketone
2-Furylmethanethiol
Furfuryl alcohol
TABLE 50
TABLE 49
Furans Isolated from Ascorbic Acid Deg-
Furans Identified from a Furfural-Hydro- radation1"
gen Sulfide-Ammonia Mixture14'
Furfural
Furfural 2-Acetylfuran
Furfuryl alcohol 2,2'-Difurylmethane
2-Furylmethanethiol Furfuryl alcohol
2-Acetylfuran 2-Hydroxyacetylfuran
Difurylethylene 2,5-Dihydrofuroic acid
2-Furfurylfuran Deoxyfuroin
N-FurfuryI-2-aminofuran 2-Furoic acid
Difurfuryl sulfide Furoin
Furyl furfuryl ketone Furil
May 1979 393
TABLE 51
Furans Identified as Degradation Prod-

ucts of L Dehydroascorbic Add 1 4 '
2-FuraIdehyde
2-Acetylfuran
2-Furfuryl alcohol
4-Hydroxy-5-methyl-3 (2H)-furanone
2,2'-Hydroxyacetylfuran
2,5-Dihydro-2-furancarboxylicacid
Deoxyfuroin
2-Furancarboxylic acid
Furoin
Furil
TABLE52
Furan Concentrations Derived After Refluxing L-Dehydroascorbic Acid for 3

Hr at Various p H V "
PH
Furan 2 4 6 8
2-Furaldehyde 1410- 162 35.1 5.12

2-Acetylfuran 185 71.5 111 149
2-Furancarboxylic acid 955 63.0 23.4 5.66
4-Hydroxy-5-methyl-3 (2H)-furanone 0.970 7.52 11.2 17.5
• Mol//.
TABLE 53
Influence of Oxygen and pH on Furan Content After Holding L-Dehyroascorbic

Acidfor200hrat25°C'«
PH
Furan Oxygen 2 4 6 8
2-Furaldehyde + 52.8- 4.16 0.546

- 53.1 5.20 0.174 —
2-Acetylfuran + 18.2 2.18 14.8 9.31
- 14.8 2.95 5.68 5.90
2-Furancarboxylic acid + 1940 698 8.03 4.01
_ 51.5 10.7
Mol/i.
All of the above discussion has been concerned with thermal formation pathways,
and in closing, it should be noted that nature has also provided for biogenic pathways
for certain furans.118
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Furan in Foods

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Furan in Foods

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C R C Critical Reviews in Food Science and Nutrition

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Author: Joseph A. Maga

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Food Systems from which Furan Derivatives Have Been Isolated

Beverages, nonalcoholic Peanuts

Furans Identified in Cocoa Products

Furans Identified in Coffee

Furfuryl alcohol 11,16,19,20,21

Propyl furoate 13,16

Thioethyl furoate 13,15

Furans Identified in Coffee

2-Isopropenyl-5-vinyl-5-methyl tetrahydrofuran 13,15

2-Furfuryl acetate 19,20

Furans Identified in Tea

Furans Identified in Alcoholic Beverages

German wines Ethyl-2-furoate 23

Furan Concentrations Found in Rum14*

Compound Concentration (ppm)

2-Furancarboxylic acid 0.4

Furans Identified in Fruits

Fruit Furan Ref.

Arctic bramble (-)-(2R),5R-taMs-2-vinyl-2-methyl-5-(l'-hydroxy-l- 35,37

Orange powder 2-Furfural 29,142

Orange juice 2-Furfural 30

Furans Identified in Fruits

Fruit Furan Ref.

Orange flavored drink Hydroxymethylfurfural 33

Cranberry Furfural 172-174

Furan Composition and Content of Arctic Bramble Juice"

Compound Total aroma concentrate {%)

Trans-linalool oxide 0.45

Mesifurane Levels in Arctic Bramble as Influenced by Location

Location Year of Harvest Mesifurane Level (ppm)

Mikkeli, Finland 1973 18

Meat and Poultry Products

Furans Identified in Meat and Poultry Products

Food Furan Ref.

Roast Turkey 2-Pentylfuran • 55

Chicken Broth Pentylfuran 46

Cooked Chicken 2-Methylfuran 39

Cooked Pork Liver 2-Methylfuran 49

Heated Beef Fat Furfuryl alcohol 44

Furans Identified in Meat and Poultry Products

Food Furan Ref.

Roast Beef 2-Pentylfuran 45

Beef Broth 4-Hydroxy-5-methyl-3(2H)-furanone 41,42

Canned Beef Furan 48,51,56

Furan Compositiont ana content in (

Effect of Canned Beef Formulation and Processing Time on Furan Levels4*

Absolute concentration (ppb)

79.3% Beef, 20% H,0,0.7% NaCl 15 930 9.2 2.6

Effect of Storage Time on 2-Ethylfuran Levels in Canned

Storage time (months at 2 0 ° Q Concentration (ppb)

% Added soy *i* Added rapeseed

2-MethyIfuran 98 110 130 200 170 390 98 92 96 110 140 130

Furans Identified in Milk Products

% Added soy i Added rapeseed