FLAVOUR AND FRAGRANCE JOURNAL Flavour Fragr. J.

2007; 22: 395400 Published online 2 May 2007 in Wiley InterScience (www.interscience.wiley.com) DOI: 10.1002/ffj.1811

AROMA VOLATILES OF TOMATOES AND TOMATO PRODUCTS 395

Aroma volatiles of tomatoes and tomato products evaluated by solid-phase microextraction

K. Markovi0,1* N. Vahi0,1 K. Kovaevi0 Gani02 and M. Banovi02
1

University of Zagreb, Faculty of Food Technology and Biotechnology, Department of Food Quality Control and Nutrition, 10 000 Zagreb, Croatia University of Zagreb, Faculty of Food Technology and Biotechnology, Department of Food Technology Engineering, 10 000 Zagreb, Croatia

Received 7 June 2006; Revised 30 August 2006; Accepted 1 March 2007

ABSTRACT: Solid-phase microextraction (SPME) was examined to investigate volatiles in tomatoes and tomato products. Aroma volatiles and differences in volatile composition of different varieties of fresh tomatoes and several commercial tomato products, such as tomato juice, tomato puree, tomato paste and canned diced tomatoes, were analysed by a manual headspace SPME technique coupled with gas chromatography (GCFID and GCMS). Fresh and processed tomato aroma was composed of terpenes and lactones, esters, carbonyls and alcohols, sulphur compounds, free acids and oxygencontaining heterocyclic compounds. In most samples of processed tomatoes, lower relative concentrations of volatiles than in fresh tomato samples were determined, but in some cases (especially in samples of tomato juice) higher concentrations were observed. The most important difference between fresh tomato and processed tomato aroma was the almost complete loss of cis-3-hexenal and the presence of furfural in tomato products. On the basis of the aromatic proles obtained by GC analysis, relationships between fresh and processed tomato samples were obtained, using multivariate PCA statistical analysis. Copyright 2007 John Wiley & Sons, Ltd. KEY WORDS: aroma volatiles; solid-phase microextraction; tomatoes; tomato products

Introduction
The nutritional importance of fresh tomatoes and tomato products is now well-known.1 Flavour and aroma are essential parameters of quality in tomatoes.2 The chemistry of tomato avour is not well understood, despite considerable literature on the topic.3 Characteristic tomato avour results from taste components, aromatic volatiles and a complex interaction between them.4 Of the over 400 volatile compounds determined in tomatoes, only a limited number are considered essential to the aromatic component of tomato avour.5 Volatiles in fresh tomatoes and leaves are formed from lipids, carotenoids, amino acids, terpenoids (C10 and C15), lignin and other sources.6 Research with many other foods indicates that only a very small fraction of the volatile compounds occur in concentrations above their odour thresholds and, thus, are actually contributors to the aroma of food.7 The pleasant sweet-sour taste of tomatoes is mainly due to their sugars (primarily the reducing sugars, glucose and fructose)

* Correspondence to: K. Markovib, Department of Food Quality Control and Nutrition, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottieva 6, 10 000 Zagreb, Croatia. E-mail: kmarkov@pbf.hr Contract/grant sponsor: Ministry of Science, Education and Sports, Republic of Croatia; Contract/grant number: 0058018

and organic acids (citric and malic acids are the major organic acids) content.8 A high percentage of tomatoes produced in Croatia are processed, mainly as double-concentrated tomato paste. Thermal treatments during processing cause changes in the sensory and nutritional characteristics of tomatoes and tomato derivatives, due to co-oxidation reactions of carotenoids and Maillard reactions.9 Buttery7 reported that fresh tomato aroma could be closely duplicated with 10 compounds (cis-3-hexanal, cis3-hexanol, hexanal, 1penten-3-one, 3-methylbutanal, cis-2-hexenal, 6-methyl5-hepten-2-one, methyl salicylate, 2-isobuthylthiazole and -ionone) and with processed tomato the number of compounds necessary to duplicate the aroma is as low as seven {dimethyl sulphide, 3-methylbutyric acid, eugenol, 1-nitro-2-phenylethane, methional [3-(methylthio) propanal], 3-methylbutanal and -damascenone}. The compounds contributing to fresh tomato aroma have been the subject of several studies.6,8,1014 However, there are investigations in which aroma volatiles of tomato products were taken into consideration. Buttery et al.15 studied volatile compounds of tomato paste, Servilli et al.9 investigated volatile compounds in tomato juice, while the volatiles of other tomato products have not been studied. Therefore, the aim of this study was the evaluation of aroma proles of fresh tomatoes and tomato products (tomato juice, tomato puree, tomato paste and

Copyright 2007 John Wiley & Sons, Ltd.

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canned diced tomatoes) by solid-phase microextraction (SPME) coupled with gas chromatography (GC). The HSSPME method was applied to the analysis of the aroma prole of 12 fresh tomato cultivars and approximately 50 commercial tomato products.

Experimental
Materials
Samples representing 12 tomato cultivars (ve fruits from each cultivar: Alange, Heinz, Perfect Peel, Karibe, Urbana, Hektor, Monte Carlo, Serdica, Hekto, Toco 70, Bagera and Belle) grown during the 2004 growing season for industrial processing, were harvested at the ripe stage and used for aroma analyses. Samples representing different brands of tomato products, viz. 10 tomato juices, 15 tomato purees, 15 tomato pastes and 11 canned diced tomatoes, were purchased from markets in Zagreb, Croatia.

maintained at 200 C. The detector was kept at 250 C. The GC oven was programmed from 40 C (3 min hold) to 190 C at a rate of 5 C/min, where it was held for 7 min. The same conditions were used for the GCMS analysis. A Hewlett-Packard 5890 (Hewlett-Packard, Palo Alto, CA, USA) gas chromatograph with a Hewlett-Packard 5970 series mass selective detector. The ionization of the samples was achieved at 70 eV using the scan mode. The mass range studied was m/z 30250. Helium was used as the carrier gas at a ow rate of 5 ml/min. All of the volatiles were identied by MS and cochromatography with standard substances (NBS75K library spectra). The results were expressed as area ratio: A/IS = (peak area component)/(peak area internal standard); the internal standard was n-amyl alcohol (0.5 p.p.m. v/v). All the analyses were performed in triplicate for each sample.

Statistics
On the basis of the aromatic proles obtained by GC analysis, multivariate principal component analysis (PCA) was used in order to obtain a relationship between the samples of fresh and processed tomatoes. Multivariate analysis was performed, using the Statistica 7.0 package.16

Chemicals
Authentic reference chemical compounds (all of the volatiles identied in this study) were obtained from Sigma-Aldrich Chemie GmbH (Steinheim, Germany) and Merck (Darmstadt, Germany). A Boiling Point Calibration Sample (Item 50808716, Lot CB-2840) was obtained from Agilent Technologies (Santa Clara, CA, USA).

Results and Discussion

Tables 15 present the amounts (relative to the ISTD) of volatiles found in fresh tomato, tomato juice, tomato

Sample Preparation: HeadspaceSolid Phase Microextraction (HSSPME)

Before analysis, samples of fresh tomatoes (5 fruits from each of 12 cultivars) and canned diced tomatoes were homogenized in a blender for 30 s. Thirty ml of each sample, internal standard (IS) n-amyl alcohol (0.5 p.p.m. v/v) and 3 g NaCl were put in 50 ml glass vials (Schot Duran, Germany) and warmed to 40 C in a water bath. The samples were gently mixed and equilibrated for 5 min at 40 C. All the SPME operations were manual, using a manual SPME bre holder containing a 65 m Carbowax/divinylbenzene-coated bre (Supelco Inc., Bellefonte, PA, USA). The SPME bre was exposed to the sample headspace for 55 min at 40 C. The volatile compounds were desorbed by inserting the bre into the GC injection port for 5 min at 200 C.

Table 1. Volatile compounds of fresh tomatoes Meanc

Acetaldehydea,b 3-Methyl-2-butanola,b cis-3-Hexenala,b 2-Ethyl-thiophenea,b cis-3-Hexen-1-ola,b trans-2-Hexenala,b 1-Hexanola,b 2-Heptanonea,b 2-Methylbutyric acida,b 6-Methyl-5-hepten-2-onea,b Hexyl acetatea,b 2-Isobutyl-thiazolea,b Hexanoic acida,b Benzyl alcohola,b Linaloola,b Divinylbenzenea,b Nerola,b Geraniola,b Nerala,b Geraniala,b Eugenola,b
a

Standard deviationc
0.543 0.082 0.164 0.007 0.002 0.054 0.010 0.063 0.009 0.498 0.130 0.264 0.050 0.250 0.068 0.101 0.044 0.033 0.087 0.197 0.113

No. samplesd
12 9 12 5 1 2 3 11 3 12 9 11 7 12 7 7 10 10 12 12 8

GCFID and GCMS Analysis

A Varian 3300 gas chromatograph (Varian Inc., Palo Alto, CA, USA) equipped with a ame ionization detector (FID) was used in this study. A DB 624 column (6% cyanopropylphenyl:94% dimethyl polysiloxane stationary phase; 30 m 0.32 mm i.d., 1.8 m lm thickness; J&W Scientic, Folsom, CA, USA) was employed. Nitrogen was used as the carrier gas at a ow rate of 5 ml/min. A split/splitless injector was used (ratio 1:5) and

1.463 0.188 0.461 0.021 0.027 0.055 0.022 0.114 0.034 1.708 0.148 0.424 0.078 0.982 0.111 0.252 0.088 0.097 0.282 0.488 0.241

GCMS spectra comparison with NBS75K library. Co-elution with pure reference compound and GCMS spectra. Area ratio: A/IS = (peak area component)/(peak area IS); n = 3; IS, internal standard n-amyl alcohol (0.5 ppm) and standard deviation. d Number of cultivars of fresh tomatoes where the compound was found.
b c

Copyright 2007 John Wiley & Sons, Ltd.

Flavour Fragr. J. 2007; 22: 395400 DOI: 10.1002/ffj

AROMA VOLATILES OF TOMATOES AND TOMATO PRODUCTS 397

Table 2. Volatile compounds of tomato juice Meanc

Acetaldehydea,b 2-Methylfurana,b 3-Methyl-2-butanola,b cis-3-Hexenala,b Ethylbenzenea,b 2-Ethyl-thiophenea,b Furfurala,b cis-3-Hexen-1-ola,b 1-Hexanola,b 2-Heptanonea,b 2-Methylbutyric acida,b 6-Methyl-5-hepten-2-onea,b Hexyl acetatea,b 2-Isobutyl-thiazolea,b Hexanoic acida,b Benzyl alcohola,b Linaloola,b Divinylbenzenea,b Nerola,b Nerala,b Geraniala,b Eugenola,b
a

Table 4. Volatile compounds of tomato paste No. samplesd

10 1 5 9 4 8 9 3 3 10 2 10 4 9 3 10 10 9 8 10 10 9 Acetaldehydea,b 3-Methyl-2-butanola,b cis-3-Hexenala,b 2-Ethyl thiophenea,b Furfurala,b 2-Heptanonea,b 2-Methylbutyric acida,b 6-methyl-5-hepten-2-onea,b Hexyl acetatea,b 2-Isobutyl-thiazolea,b Hexanoic acida,b Benzyl alcohola,b Linaloola,b Divinylbenzenea,b Nerola,b Nerala,b Geraniala,b Eugenola,b
a

Standard deviationc
0.421 0.001 0.184 0.027 0.027 0.029 0.078 0.090 0.060 0.088 0.002 0.884 0.110 0.084 0.010 0.068 0.142 0.027 0.122 0.055 0.023 1.284

Meanc

Standard deviationc
0.026 0.350 0.008 0.082 0.029 0.086 0.083 0.203 0.008 0.014 0.005 0.027 0.087 0.015 0.010 0.025 0.018 0.003

No. samplesd
15 6 15 10 14 13 4 15 1 8 4 14 15 15 12 15 13 1

0.277 0.121 0.319 0.037 0.046 0.057 0.091 0.109 0.098 0.159 0.030 0.989 0.121 0.115 0.047 0.128 0.219 0.052 0.096 0.088 0.039 0.666

0.029 0.293 0.012 0.062 0.054 0.139 0.081 0.431 0.017 0.045 0.026 0.074 0.164 0.033 0.030 0.048 0.039 0.041

GCMS spectra comparison with NBS75K library. Co-elution with pure reference compound and GCMS spectra. Area ratio: A/IS = (peak area component)/(peak area IS); n = 3; IS, internal standard n-amyl alcohol (0.5 ppm) and standard deviation. d Number of different brands of tomato juice where the compound was found.
b c

GCMS spectra comparison with NBS75K library. Co-elution with pure reference compound and GCMS spectra. Area ratio: A/IS = (peak area component)/(peak area IS); n = 3; IS, internal standard n-amyl alcohol (0.5 ppm) and standard deviation. d Number of different brands of tomato paste where the compound was found.
b c

Table 5. Volatile tomatoes

compounds Meanc

of

canned

diced

Table 3. Volatile compounds of tomato puree Meanc

Acetaldehydea,b 3-Methyl-2-butanola,b cis-3-Hexenala,b 2-Ethyl thiophenea,b Furfurala,b 2-Heptanonea,b 6-Methyl-5-hepten-2-onea,b Hexyl acetatea,b 2-Isobutyl-thiazolea,b Hexanoic acida,b Benzyl alcohola,b Linaloola,b Divinylbenzenea,b Nerola,b Nerala,b Geraniala,b Eugenola,b
a

Standard deviationc
0.415 0.156 0.174 0.076 0.025 0.080 0.067 0.028 0.002 0.318 0.097 0.012 0.062 0.047 0.029 0.019 0.020 0.017 0.030

No. samplesd
11 6 11 11 10 10 10 11 1 11 11 2 11 11 8 11 11 10 8

Standard deviationc
0.063 0.283 0.010 0.047 0.036 0.045 0.524 0.012 0.040 0.027 0.040 0.215 0.023 0.014 0.053 0.180 0.022

No. samplesd
15 3 15 14 13 15 15 1 13 4 14 13 14 14 15 14 13

0.075 0.193 0.022 0.041 0.045 0.119 0.913 0.062 0.052 0.033 0.086 0.260 0.052 0.030 0.086 0.155 0.046

Acetaldehydea,b 3-Methyl-2-butanola,b cis-3-Hexenala,b 2-Ethyl-thiophenea,b Furfurala,b cis-3-Hexen-1-ola,b trans-2-Hexenala,b 2-Heptanonea,b 2-Methylbutyric acida,b 6-Methyl-5-hepten-2-onea,b 2-Isobutyl-thiazolea,b Hexanoic acida,b Benzyl alcohola,b Linaloola,b Divinylbenzenea,b Nerola,b Nerala,b Geraniala,b Eugenola,b
a

0.857 0.722 0.089 0.095 0.042 0.088 0.082 0.097 0.032 1.171 0.159 0.079 0.069 0.195 0.034 0.082 0.047 0.024 0.057

GCMS spectra comparison with NBS75K library. Co-elution with pure reference compound and GCMS spectra. c Area ratio: A/IS = (peak area component)/(peak area IS); n = 3; IS, internal standard n-amyl alcohol (0.5 ppm) and standard deviation. d Number of different brands of tomato puree where the compound was found.
b

GCMS spectra comparison with NBS75K library. Coelution with pure reference compound and GCMS spectra. c Area ratio: A/IS = (peak area component)/(peak area IS); n = 3; IS, internal standard n-amyl alcohol (0.5 ppm) and standard deviation. d Number of different brands of canned diced tomatoes where the compound was found.
b

puree, tomato paste and canned diced tomatoes. Fresh tomato aroma was composed of terpenes and lactones (linalool,7,9 nerol,9 geraniol,9 eugenol,7,9 geranial,7,9,10,13 neral,7,9), ester (hexyl acetate,9), carbonyls and alcohols (cis-3-hexen-1-ol,9 1-hexanol,8,9,17 acetaldehyde,18,19 3methyl-2-butanol,7,11 cis-3-hexenal,79,11,13,17 2-heptanone,20

trans-2-hexenal,79,11,17 6-methyl-5-hepten-2-one,79,11,13,17 benzyl alcohol,9 divinylbenzene9), sulphur compounds (2ethyl-thiophene,9 2-isobutyl-thiazole79,11,17) and free acids (2-methylbutyric acid,9 hexanoic acid7,9). Five volatiles were found in all the fresh tomato samples: cis-3-hexenal, 6-methyl-5-hepten-2-one, benzyl alcohol, geranial (citrus

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and fruity aroma character18) and neral (citrus, fruity volatile18). These carbonyls, alcohols and lactones, including the sulphur compound 2-isobutyl-thiazole, comprised the largest proportion of the total aroma in fresh tomatoes. 2-Heptanone and 2-isobutyl-thiazole (one of the key aroma compounds in fresh tomatoes,21 with an aroma character described as musty, sharp, mouldy, pungent and medicinal10,14,18) were determined in 11/12 fresh tomato samples (Table 1). Data in Tables 25 show that commercial tomato products contained almost all compounds found in fresh tomatoes. In most processed tomato products, except for juice samples, most volatiles were present in lower relative concentrations than in fresh tomatoes. Exceptions were increases in specic amino acid-derived6 volatiles (3-methyl-2-butanol and 2-ethyl-thiophene) and linalool (derived from the isopreneterpenoid pathway, having a characteristic citrus, fruity aroma and sweet taste19) common to nearly all processed tomato products. An increase in the concentration of linalool in heated tomato has been reported previously in a study by Buttery et al.15 Tomato juices contained higher concentrations of 2-ethylthiophene, some lipid-derived6 volatiles (cis-3-hexen-1-ol and 1-hexanol), 2-heptanone (also in the samples of canned diced tomatoes) and eugenol. The possibility exists that these aroma compounds could be formed in the tomato products (especially tomato juice) during the manufacturing process. Compounds found in all the fresh tomatoes, such as cis-3-hexenal, 6-methyl-5-hepten-2-one, benzyl alcohol, geranial and neral, were also found in almost all the samples of tomato products, but in much lower relative concentrations. cis-3-Hexenal is a volatile compound with a fresh green, fruity and sweet aroma character, characteristic of fresh tomatoes.10,14,19,22 Tandon et al.8 studied aroma perception of individual volatile compounds in fresh tomatoes as affected by the evaluation medium (deionized water, ethanol:methanol:water mixture and a deodorized tomato homogenate) and in their study cis-3-hexenal was described as tomato-like in all three media. Our results showed that the relative concentration of this aldehyde determined in fresh tomatoes (0.461; Table 1) was much higher than in tomato products. In tomato products, the lowest relative concentration of cis-3-hexenal was determined in the samples of tomato paste (0.012; Table 4) and the highest (0.089) in the samples of canned diced tomatoes (Table 5). In a quantitative and sensory study on tomato paste volatiles, Buttery et al.15 also observed that one of the most marked differences between fresh tomato and tomato paste was the almost complete loss of cis-3-hexenal. Our study supports earlier results and observations12,14,23 that cis-3-hexenal is probably the most important contributor to fresh tomato aroma. The volatile compound present in the highest relative concentrations in all the samples (fresh tomatoes, tomato juice, tomato puree,

tomato paste and canned diced tomatoes) was 6-methyl5-hepten-2-one. This ketone was in the highest relative concentration (ratio of 1.708) of all volatiles in fresh tomatoes (Table 1). Regarding tomato products, 6-methyl5-hepten-2-one was in the highest relative concentration (1.171) in canned diced tomatoes (Table 5) and in the lowest (0.43) in the tomato paste (Table 4). 6-Methyl5-hepten-2-one, a carotenoid-related6,24 volatile, has a tomato-like avour, musty aroma and fruity taste.10,17,20,22 trans-2-Hexenal, 2-methylbutyric acid, 1-hexanol, cis-3hexen-1-ol, hexyl acetate and geraniol, compounds found in fresh tomatoes, were not found in some of the tomato products. These compounds were lost during processing of the tomatoes. trans-2-Hexenal (an important component of fresh tomato aroma21 with a green aroma character closely associated with attributes fresh-cut grass, intensive, fruity and sweet10,14,22) was not detected in tomato juice, tomato puree or tomato paste, while it was found in 10/11 samples of canned diced tomatoes. 2Methylbutyric acid was not found in tomato puree, while this free acid was found in two tomato juices, four tomato pastes and just one sample of sliced tomatoes. 1Hexanol was found in 3/10 samples of tomato juice, while in other tomato products this alcohol was not found at all. cis-3-Hexen-1-ol was not detected in the samples of tomato puree and tomato paste, while it was found in 3/10 analysed tomato juices and also in 10/11 samples of sliced tomatoes. Hexyl acetate was found in four tomato juices, one tomato puree, one tomato paste, but not in sliced tomatoes. Geraniol was not found in any of the tomato products. Furfural7,9 was found in most of the tomato products but was not detected in fresh tomatoes. Ethylbenzene9 was found in four samples of tomato juices and the oxygen-containing heterocyclic compound, 2-methyl furan9 (Table 2), was found in one. Furfural25 was present in the highest relative concentration (0.091) in tomato juices (Table 2) and in the lowest relative concentration (0.042) in the canned diced tomatoes (Table 5). Servilli et al.,9 in a study of the optimization of the hot break treatment of tomato juice, selected furfural as the major cooked avour compound. The presence of this heat-induced volatile26 in tomato products is closely related to the thermal processing treatment given to tomatoes. On the basis of the results presented on aromatic compounds (Tables 15), relationships between fresh and processed tomato samples were obtained using multivariate PCA analysis. The results of PCA statistical analysis were projected on two-dimensional plots (Figures 1 and 2) dened by the rst two factors (Tables 6 and 7). PCA analysis showed that samples of fresh and processed tomatoes were divided into three groups: tomato puree, tomato paste and canned diced tomatoes were in the same group, while fresh tomatoes, and samples of tomato juice were in separate groups.

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Flavour Fragr. J. 2007; 22: 395400 DOI: 10.1002/ffj

AROMA VOLATILES OF TOMATOES AND TOMATO PRODUCTS 399

Table 6. Factor scores, based on correlations Case

Fresh tomatoes Tomato juice Tomato puree Tomato paste Canned diced tomatoes

Factor 1
1.751862 0.519519 0.416192 0.686295 0.129856

Factor 2
0.086208 1.705360 0.499170 0.645833 0.646565

Factor 3
0.29894 0.14401 0.80824 0.69586 1.65904

Factor 4
0.18488 0.03332 1.45752 1.35191 0.11260

Table 7. Factor variable correlations (factor loadings) Variable

1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. Acetaldehyde 2-methylfuran 3-methyl-2-butanol Cis-3-hexenal Ethylbenzene 2-ethyl-thiophene Furfural Cis-3-hexen-1-ol Trans-2-hexenal 1-hexanol 2-heptanone 2-methylbutiric acid 6-methyl-5-hepten-2-one Hexyl acetate 2-isobutyl-thiazole Hexanoic acid Benzyl alcohol Linalool Divinylbenzene Nerol Geraniol Neral Geranial Eugenol

Factor 1
0.921607 0.290420 0.240611 0.996123 0.290420 0.590830 0.835135 0.102158 0.553440 0.072862 0.422103 0.135701 0.893572 0.619488 0.981086 0.708863 0.974117 0.734351 0.972364 0.465692 0.979321 0.952223 0.940787 0.020053

Factor 2
0.004805 0.953325 0.218579 0.034843 0.953325 0.209021 0.544048 0.646349 0.311751 0.995418 0.721707 0.162752 0.185489 0.690567 0.120402 0.025511 0.104776 0.094399 0.109401 0.645344 0.048192 0.178643 0.012071 0.997558

Factor 3
0.385336 0.080503 0.941422 0.014376 0.080503 0.759430 0.068005 0.756146 0.772321 0.044382 0.450849 0.078485 0.290574 0.345943 0.129105 0.702413 0.176068 0.010642 0.203191 0.603083 0.167112 0.246206 0.321366 0.049139

Factor 4
0.046193 0.018626 0.089741 0.079488 0.018626 0.174631 0.044003 0.006326 0.006040 0.043184 0.312576 0.974134 0.287560 0.140269 0.079411 0.058980 0.095485 0.672089 0.035405 0.054338 0.103354 0.027223 0.107225 0.045403

Figure 1. Plot of PC-1 vs. PC-2 for fresh and processed tomato samples

Figure 2. Plot of PC-1 vs. PC-2 for volatile compounds of fresh and processed tomatoes

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AcknowledgementsThis study was supported by the Ministry of Science, Education and Sports, Republic of Croatia, Project No. 0058018.

12.

13.

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Flavour Fragr. J. 2007; 22: 395400 DOI: 10.1002/ffj