한국식품저장유통학회
[ Article ]
Korean Journal of Food Preservation - Vol. 25, No. 5, pp.491-500
ISSN: 1738-7248 (Print) 2287-7428 (Online)
Print publication date 31 Aug 2018
Received 18 Jul 2018 Revised 14 Aug 2018 Accepted 16 Aug 2018
DOI: https://doi.org/10.11002/kjfp.2018.25.5.491

Characteristics of aroma compounds of 11 red wines from international grape cultivars grown in Korea

Hyun Il Kim ; Youn Young Hur ; Sung Min Jung ; Dong Jun Im ; Kyeong Ho Chung ; Su Jin Kim*
Fruit Research Division, National Institute of Horticultural and Herbal Science, Wanju 55365
국내에서 재배된 세계 주요 와인 포도 품종으로 제조된 적포도주 11종의 향기 성분 특성
김현일 ; 허윤영 ; 정성민 ; 임동준 ; 정경호 ; 김수진*
국립원예특작과학원 과수과

Correspondence to: *E-mail: himssem@korea.kr Phone:82-63-238-6750, Fax:82-63-238-6705


Copyright ⓒ The Korean Society of Food Preservation. All rights reserved.

Abstract

The aroma compounds of 11 red wines grown and produced in Wanju region were characterized by headspace-solid phase microextraction combined with gas chromatography-mass spectrometry. Seventy-five aroma compounds were identified in the 11 red wines. The aroma compounds were grouped into five aroma series and their odor activity values were calculated to determine the aroma impact compounds in 11 wines. Alcohols, esters and C6compounds were the main contributors to the aroma in the 11 wines. Isoamyl alcohol and phenylethyl alcohol obtained from the 11 red wines contributed to the floral, sweet, and fatty odorants in the wine. Octanoic acid ethyl ester, and hexanoic acid ethyl ester contributed to the fruity, floral, and sweet odorants of all the red wines. 1-Hexanol was detected all the wines, which contributed to the green odorant. The major aroma contribution of Chanceller, Malbec, Marchel, Narsha, Pinot Meunier, and Sangiovetto wines were the fruity series. The green series was the major contribution of the Cabernet Franc, Cabernet Sauvignon, and Sauvignon Vert wines. The floral series was the major contribution of the MBA and Narsha wines. Based on the results of these studies, aroma component analysis could be used as a selection criterion for developing wine cultivars.

Keywords:

aroma, headspace-solid phase microextraction, gas chromatography-mass spectrometry, red wine

Introduction

Wine aroma is one of the most important factors in determining wine character and quality. Wine aroma was determined by more than 1,300 volatile compounds, including alcohols, esters, acetates, acids, aldehydes, isoprenoids, lactones and ketones, with a wide concentration range (1). The aroma profiles are the results of complex interactions among several factors: grape variety (2), vineyard geographical origin (3), soil and climate characteristics (4) and winemaking techniques (5). Wine aroma contents may be used as a tool for characterization and differentiation of wines from varieties and for establishing criteria to improve the quality of the wines. In particularly, attention has been devoted recently to the analytical characterization and the quality improvement of the varietal aroma of wines. Previous studies have focused on the identification of volatile components and on the establishment of character impact odorants of different varieties (6-8).

Korean winemakers made wine using table grape cultivars, such as ‘Campbell Early’, ‘Muscat Bailey A’ and ‘Kyoho’ (9,10). Korea wines are produced using the most cultivated Campbell Early, however, these wines have the limitations of containing low levels of sugar, high malic acid concentration and negatively foxy aroma content (11). Therefore, development of wine cultivar with good wine aptitude and aroma is desperately required.

The present study was aimed to characterize aroma compounds of cultivated 11 wine grape cultivars to accumulate basic data for making red wine cultivars by aroma using headspace-solid phase microextraction (HS-SPME) combined with gas chromatography-mass spectrometry (GC-MS).


Materials and methods

Reagents

Benzyl alcohol, 1-heptanol, Isoamyl alcohol, phenylethyl alcohol, Isobutyl alcohol, benzaldehyde, acetic acid hexyl ester, hexadecanoic acid ethyl ester, 1-hexanol, α-terpineol, 4-nonanol and sodium chloride (NaCl) were purchased form Sigma-Aldrich Korea Ltd. (Seoul, Korea). Fatty acid ethyl esters were purchased form Sigma-Aldrich Korea Ltd. (Supelco, Seoul, Korea). Calcium chloride (CaCl2) was purchased from Kanto Chemical Co., INC. (Tokyo, Japan). All used reagents were analytical grade.

Plant material

Eleven grape cultivars, Cabernat Franc, Cabernet Sauvignon, Chanceller, Malbec, Marchel, MBA, Merlot, Narsha, Pinot Meunier, Sangiovetto and Sauvignon Vert were obtained from experimental vineyards of the National Institute of Horticultural and Herbal Science, Wanju, Korea. All grape varieties used for winemaking were harvested at August in 2016. Samples were frozen at -20℃ prior to analysis.

Winemaking procedure

The winemaking process followed a modified Chang’s method (12) and micro-vinification method. Grapes were removed from grape bunches and potassium metabisulfite (K2S2O5) was added at a concentration of 200 mg kg-1. Before fermentation, grape must (800 g) was adjusted to 22 °Brix using table sugar. Five hours after the addition of potassium metabisulfite, active yeasts were inoculated into grape at a ratio of 0.02% (w/w). The yeast strain Saccharomyces cerevisiae (Fermivin, France) was used for fermentation in all winemaking processes. The grapes were first fermented for two weeks at a constant temperature of 25℃ in a 1,000 mL DURAN® laboratory bottle equipped with an airlock. After the initial fermentation, the fermented residual sugar and sediment were isolated from wine. The isolated wine was subjected to a second round of fermentation at a constant temperature of 15℃ for 1 week, after which the prepared wine samples were analysed.

Total soluble solids and total acidity of grape

The total soluble solids (TSS) of wine was determined using a digital refractometer (PAL-1; Atago, Tokyo, Japan). For measurement of the total acidity (TA), 20 mL of wine sample was titrated using 0.1 N NaOH to an end point of pH 8.2. The TA value was then converted to tartaric acid equivalents.

HS-SPME conditions

An SPME fibre coated with divinylbenzene/carboxen/ polydimethylsiloxane (50/30 μm, DVB/CAR/PDMS) (Supelco, Bellefonte, PA, USA) was used for the analysis owing to its high sensitivity for odorants and good reproducibility in grapes (13). Fermentation-finished wine (15 mL) was transferred into a capped 50 mL solid-phase microextraction vial, and 1.8 g of NaCl and 2 μL of internal standard (4-nonanol in EtOH, 1 mg/mL) were added. Samples were heated at 70℃ in an automated heating block (Wise Therm®, HB-48P). After 20 min of equilibration, the SPME fibre was manually inserted into the sample vial headspace. After 20 min, the fibre was withdrawn and introduced into the GC injection port for desorption at 250℃ and maintained for 10 min in splitless mode. All samples were examined in triplicate.

GC-MS analysis

An Agilent gas chromatograph model 6890N coupled to an Agilent 5975 series mass selective detector was used to perform the analysis. Volatile compounds were separated on an HP-INNOWAX capillary column (30 m×0.32 mm×0.25 μm; Agilent technologies, Santa Clara, CA, USA), with purified helium as the carrier gas, at a constant flow rate of 2 mL/min. Desorption of the DVB/CAR/PDMS fibre was carried out for 10 min in the GC injection port at 250℃. The oven temperature was held at 40℃ for 5 min, increased to 220℃ at a rate of 3℃ min-1 and finally held at 220℃ for 5 min. The injector and source temperature were set at 250℃ and 230℃, respectively. The mass detector was operated in electron impact ionisation mode at a voltage of 70 eV, with the range set at 50-700 m/z. Selected GC-MS peaks were identified based on the comparison of mass spectra with the NIST11 (Agilent, Gaithersburg, MD, USA) mass spectral database. Content of all compounds was quantified relative to the known concentration of 4-nonanol internal standard.

Statistical analysis

A one-way analysis of variance (ANOVA) was performed to identify statistically significant differences between samples. The R Commander (version 2.13.0, A Basic-Statistics GUI for R statistical software package; McMaster University, Ontario, Canada) was employed for this analysis where statistical significance was defined as p<0.05.


Results and discussion

Characteristics of 11 red wine grapes

To compare the characteristic of eleven red wine grapes, the titratable acid (TA), the total soluble solids (TSS) and the total soluble solids/titratable acid (TSS/TA) were identified (Table 1). In all grapes, the TA range from 5.50 to 10.80 g/L, and TSS value were higher than 18.40 °Brix in all grapes. The TSS/TA ranged from roughly 1.98 to 4.15. An outstanding parameter to evaluate the maturity of grape is the total soluble solids, predominantly sugars, measured as °Brix (13). These results, all harvested grapes in Wanju region were reached their appropriate maturity times, with the exception of Cabernet Franc and Pinot Meunier grapes.

Total soluble solids and titratable acid content in fruits of 11 grape cultivars

Identification and characterization of the aroma compounds in wines

Seventy five compounds were identified as follows 16 alcohols, 11 volatile acids, 3 aldehydes, 28 esters and acetates, 4 ketones, 3 C13-norisoprenoids, 2 C6-compounds, 1 furan, 1 phenolic acid derivative, 1 terpene and 5 others in 11 wines by HS-SPME and GC/MS analysis (Table 2).

Concentration of aroma compounds determined in 11 red wines

Higher alcohols are secondary products of yeast metabolism and have been related with pungent, sweet and fruity odors (14). Alcohols was the most abundant component in the aroma compounds of all wines like previous studies (15-18). 1-heptanol, isoamyl alcohol, 2,3-butanediol, [R-(R*,R*)]-, 2,3-butanediol,[S-(R*,R*)]-, 3-ethyl-1-butanol, phenylethyl alcohol, 1-propanol and isobutyl alcohol were identified in the all red grape wines. Isoamyl alcohol was largest aroma compound in all wine samples without Cabernet Sauvignon, Chanceller and Sauvignon Vert wines. Largest aroma compound of those 3 wines is isobutyl alcohol. 1-butanol and 2-ethyl-1-butanol were detected only in Chanceller and Marchel wines. And, benzyl alcohol was found in several wines, such as Cabernet. The alcohol profile of Chanceller wine was the most diverse in the all wines, containing 14 types of alcohols. However, Cabernet Sauvignon wine was shown in highest concentration of alcohol component. Franc, Cabernet Sauvignon, Chanceller, Marchel and Merlot wines. Studies performed by Tao et al. (19), Cheng et al. (20) and Vilanova et al. (21) reported high values for higher alcohols and ethyl esters in Cabernet Sauvignon wines.

Volatile acid compounds are mainly produced during fermentation and their concentration has been reported to depend on the initial composition of the must and fermentation conditions. The low concentration of these compounds had a positive contribution to the quality of the wine by increasing aroma complexity. However, at levels beyond 20 mg/L, these acids have been associated with negative odors (22). In present study, the total volatile acid concentration was less than 1.1 mg/L in all red wines.

Ester and acetate were identified largest number of the aroma component in 11 red wines, and this result is consistent with previous data for different red wine varieties (17,18). Ethyl esters of the fatty acid were formed from ethanolysis of acyl-CoA during fatty acid synthesis or degradation and appeared mainly at the first phase of the alcoholic fermentation of fatty acid (23,24). In the present study, octanoic acid ethyl ester, hexanoic acid ethyl ester and ethyl acetate were major esters identified in the aroma compounds of the 11 red wines. Ethyl acetate and Lactic acid ethyl ester increases its concentration with the malolactic fermentation (25). This compound was the most abundant ester in 11 redwines, in agreement with published data for Cabernet Sauvignon and Merlot wines (19-21) and new wine grape cultivar Meili (26). While, lactic acid ethyl ester was detected in 10 red wines, with the exception of Cabernet Sauvignon wine. Other ethyl ester, such as butanoic acid ethyl ester, heptanoic acid ethyl ester decanoic acid ethyl ester, dodecanoic acid ethyl ester and hexadecanoic acid ethyl ester were presented in some wines. Dodecanoic acid ethyl ester was found in 10 red wines, with the exception of Cabernet Sauvignon wine. In previous study, dodecanoic acid was found in only Pinot noir among 4 red wines (21). Butanoic acid ethyl ester was shown with high concentration in the Marchel, Narsha and Sangiovetto wines. Only two C6-compounds were identified from 11 red wines. 1-hexanol was found in every red wines, while (Z)-3-hexenol was found Cabernet Franc, MBA and Narsha wines. These C6-compounds were derived from fatty acid by the action of grape-derived lipoxygenase (LOX) and hydroperoxide lyase (HPL), and associated with negative green and herbaceous odors when their concentration is above their odor threshold values (27-28).

Benzaldehyde and acetaldehyde were only detected in aldehyde group. Acetaldehyde was shown in 11 red wines, however, benzaldehyde was detected only in Chanceller and MBA wines. Acetone aroma compound of ketone group was identified in 9 red wines without MBA and Sauvignon Vert wines. Terpene compounds belong to the secondary plant constituents, of which biosynthesis begins with acetyl-coenzyme A (Co A) (29). In this study, α-terpineol and furfural were detected only MBA wine. C13-norisoprenods have low odor threshold values and these compounds play on important role in the varietal typicity of wines (8) in this study, α-ionene, ionene and TDN were detected only Sangiovetto wine. MBA wine was shown only ionene.

Odor activity values (OAVs) and aroma series

The aroma compounds of wine depend on both concentration and threshold. However, only a limited number of aroma compounds can be found at concentration high enough to be perceived (OAV≥1) and considered as flavor contributors as well as active odorants (30). The OAV values for the 14 aroma compounds with OAV≥1 are shown in Table 3. Alcohol, aldehyde, ester and C6-compounds were the main contributors to aroma in 11 red wines. Phenylethyl alcohol obtained from 11 red wines was contributed to the floral odorant. While, isoamyl alcohol and isobutyl alcohol were contributed to sweet and fatty odorant in wines, the aroma of wines contributed by these compounds was week, because they have a high odor threshold. Acetaldehyde was detected only Cabernet Sauvignon and Chaceller wines. Ester and acetate were contributed to fruity, floral and sweet odorant in wines. Octanoic acid ethyl ester and hexanoic acid ethyl ester were most active esters, and they contributed to the fruity, floral and sweet odorant of all red wines. 1-hexanol was detected all wines, it was contributed to green odorant. C13-norisoprenoids and terpene were detected only Sangiovetto and MBA wines, respectively. Although present at low concentrations C13-norisoprenoids and terpene made significant contributions to the aroma of wines due to their low thresholds.

Odor active values (OAVs) of active aroma compounds detected in 11 red wines

To evaluate the global fermentative aroma of the wines, all aroma compounds were grouped into five aroma series and each compound was assigned to one or more aromatic series based on their similar odor descriptors. Aroma series were represented the main constituents of the aroma profile of the wine: 1-fruity, 2-floral, 3-green, 4-sweet, 5-fatty odors bearing in mind their descriptions in previous papers (31-33). The total intensities for each aromatic series were calculated as the sum of the OAV of each of the compounds assigned to this series and the results are shown in Fig. 1. The highest aroma contribution in Chanceller, Malbec, Marchel, Narsha, Pinot Meunier and Sangiovetto wines were fruity series. While, the green series was present in the highest level in Cabernet Franc, Cabernet Sauvignon and Sauvignon Vert wines. The floral series were higher in MBA and Narsha wines, probably it is due to the high quantity of ester and acetate compounds in these wines. In present study, fruity series were major aroma categories in all red wines, and similar result was reported in previous studies (30,34).

Based on the results of these studies, aroma component analysis could be used as a selection criterion developing wine cultivars.

Fig. 1.

Aromatic series of aroma contributors of 11 red wines.


요 약

본 연구는 완주에서 재배된 세계 주요 11개 적포도 품종으로 제조된 적포도주의 향기 성분을 headspace-solid phase microextraction 분석법으로 확인하였다. 향기성분은 총 75종이 확인되었다. 아로마화합물은 그들의 OAV 값에 의해 5 그룹으로 나뉘었다. 알콜, 알데하이드, 에스테르, C6화합물이 11개 적포도주의 주요한 향기성분이었다. Isoamy alcohol 알콜과 phenylethyl 알콜은 11개 포도주에서 공통적으로 꽃향기, 달콤한 향을 나타내는데 중요한 물질이었다. Octanoic acid, ethyl ester, hexanoic acid ethylester은 모든 레드와인에서 과실향과 꽃향, 달콤한 향을 내는 중요한 성분이었다. 1-Hexanol은 모든 포도주에서 분석되었으나 풀향을 나타내는 향으로 나타났다. Chanceller, Malbec, marchel, Nsrsha, Pinot Meunier, Sangiovetto 포도주의 주요 향기 성분은 과실 향인 것으로 나타났으며 Cabernet Franc, Cabernet Sauvignon, Sauvignon Vert 포도주의 주요 향기 성분은 풀향인 것으로 조사되었다. 또한, MBA와 Narsha 포도주의 경우 꽃향이 주요 향인 것으로 조사되었다. 본 연구 결과를 바탕으로 적포도주용 품종을 육성할 때 선발 기준으로 향기성분 분석을 활용할 수 있을 것으로 판단되었다.

Acknowledgments

This work was carried out with the support of the Cooperative Research Programme for Agriculture Science & Technology Development (Project No. 01272902), Rural Development Administration, Republic of Korea.

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Fig. 1.

Fig. 1.
Aromatic series of aroma contributors of 11 red wines.

Table 1.

Total soluble solids and titratable acid content in fruits of 11 grape cultivars

Cultivars Cabernet Franc Cabernet Sauvignon Chanceller Malbec Marchel MBA Merlot Narsha Pinot Meunier Sangiovetto Sauvignon Vert
1) Titratable acid.
2) Total soluble solids.
TA1) (g/L) 5.6 8.1 10.8 6.0 8.5 5.9 10.3 9.0 9.3 5.5 9.2
TSS2) (°Brix) 19.9 22.9 23.8 20.5 22.6 20.6 21.8 22.0 18.4 22.8 21.0
TSS/TA 3.6 2.8 2.2 3.4 2.7 3.5 2.1 2.4 2.0 4.2 2.3

Table 2.

Concentration of aroma compounds determined in 11 red wines

No. RI1) Compounds Cabernet Franc Cabernet Sauvignon Chanceller Malbec Marchel MBA Merlot Narsha Pinot Meunier Sangiovetto Sauvignon Vert ID2) 
Conc. (μg/L)3)
1) Retention index on a HP-Innowax column.
2) S, identified with standard compounds; MS, mass spectra database performed using NIST 11 spectral database, considering fit and retrofit values >70%.
3) Different letters within each rows indicates statistical differences (n=3, p<0.05).
Alcohols
1 4544 Benzyl
Alcohol
1,494.48bc 3,167
.25a
607.79de 0.00d 1,859
.74bc
0.00d 1,274.
42bc
0.00d 0.00d 0.00d 0.00d S/MS
2 2603 1-Heptanol 46.03de 79.61de 95.43de 351.89b 266.19bc 202.72ce 196.49cd 157.40ce 204.69cd 163.85ce 562.39e S/MS
3 1653 Isoamyl
alcohol
264,472.
81ab
219,102.
42ab
209,535.
85ab
332,626.
75ab
197,936.
04ab
337,254.
82ab
285,922.
91ab
253,026.
53ab
274,735.
60ab
294,962.
74ab
237,243.
39b
S/MS
4 1603 2-Methyl-
1-butanol
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 51.99a 0.00a 0.00a 61.23a MS
5 3060 2,3-Butanediol,
[R-(R*,R*)]-
173.78b 777.40a 431.50ab 207.31b 325.32b 187.44b 184.52b 275.26b 196.86b 193.14b 214.57b MS
6 3242 2,3-Butanediol,
[S-(R*,R*)]-
36.82bc 212.53a 174.00a 46.18bc 99.53ab 40.45bc 36.74c 66.33bc 42.94bc 43.34bc 41.98c MS
7 4083 2-Octen-1-ol,
3,7-dimethyl-
0.00c 0.00bc 17.40a 0.00c 7.09ac 6.10ab 0.00c 0.00c 0.00c 0.00c 0.00c MS
8 4347 1,2,3-
Butanetriol
0.00a 6.19a 6.73a 1.96a 4.50a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a MS
9 6104 2,3-Dihyd
rofarnesol
0.00a 0.00a 3.26a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a MS
10 2024 3-Ethyl-
1-butanol
8.15ac 14.45ac 9.28ac 4.19ac 3.31bc 10.52ac 10.56ab 9.54ac 7.34ac 5.16ac 13.52c MS
11 4677 Phenylethyl
Alcohol
162,570.
99ce
260,521.
24ab
149,694.
79de
231,597.
03ac
128,119.
23e
180,350.
31bcd
297,388.
95a
149,424.
61de
153,301.
73de
173,095.
78ce
152,864.
89de
S/MS
12 1966 4-Methyl-
1-pentanol
0.00a 0.00a 0.00a 0.57a 0.00a 2.94a 0.00a 2.99a 0.00a 3.22a 1.48a MS
13 1085 1-Propanol 24.38b 34.92b 154.64a 16.71b 146.80a 15.36b 28.18b 17.38b 15.18b 6.04b 23.79b MS
14 1420 1-Butanol 0.00a 0.00a 99.10a 0.00a 13.59a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a MS
15 1220 Isobutyl
alcohol
199,954
.87ab
462,540
.19ab
257,257
.41ab
220,455
.27ab
169,629
.07b
220.77b 176,872
.41b
162,439
.08b
127,824
.95b
221,874
.59ab
308,023
.55b
S/MS
16 1950 2-Ethyl-1-
butanol
0.00b 0.00b 117.55a 0.00b 7.98b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b MS
Total 628,7
82.33
946,4
56.21
618,2
04.75
785,3
07.85
498,4
18.40
518,2
91.45
761,9
15.17
565,4
71.11
556,3
29.29
690,3
47.85
699,0
50.80
Volatile
acids
17 7904 Pentadecanoic
acid
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 19.26a 0.00a 0.00a 0.00a 0.00a MS
18 5731 Nonanoic
acid
0.00a 3.47a 0.00a 0.00a 0.00a 0.00a 5.89a 0.00a 0.00a 0.00a 0.00a MS
19 5398 Octanoic
Acid
0.00a 3.72a 0.00a 0.00a 0.00a 11.92a 4.99a 0.00a 0.00a 0.00a 0.00a MS
20 4454 Hexanoic
acid
0.00a 5.74a 0.00a 3.17a 0.00a 0.00a 0.00a 5.34a 0.00a 0.00a 2.19a MS
21 6197 n-Decanoic
acid
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 5.20a 0.00a 0.00a 0.00a 0.00a MS
22 3673 2-Methyl
hexanoic
acid
0.00a 43.66a 0.00a 12.27a 6.32a 0.00a 0.00a 0.00a 0.00a 0.00a 20.81a MS
23 7584 Tetrade
canoic
acid
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 18.04a 0.00a 0.00a 0.00a 0.00a MS
24 8212 n-Hexa
decanoic
acid
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 160.35a 5.87a 0.00a 0.00a 0.00a MS
25 3378 4-Hydroxy
butanoic
acid
0.00a 15.94a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a MS
26 2710 Acetic acid 35.47fg 999.77a 222.75ce 167.03bc 54.97fg 134.78cd 82.38deg 48.26eg 0.00g 269.29b 33.10cef MS
27 3205 Isobutyric
acid
0.00d 103.88a 7.14cd 23.20b 8.45cd 10.89cd 0.00d 0.00d 0.00d 18.44bc 27.36d MS
Total 35.47 1176.18 229.89 205.67 69.75 157.59 296.10 59.47 0.00 287.73 83.46
Aldehydes
28 2844 Benzal
dehyde
0.00c 0.00bc 1,272.94a 0.00c 0.00c 252.93bc 0.00c 0.00c 0.00c 0.00c 450.74b S/MS
29 788 Acetal
dehyde
61.21de 974.69a 811.41a 173.02c 396.69b 21.86e 170.27cd 75.10de 69.49ce 131.45de 67.47de MS
30 809 Isobutanal 0.00b 3.14a 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b MS
Total 61.21 977.82 2,084.35 173.02 396.69 274.79 170.27 75.10 69.49 131.45 518.21
Esters
and
acetates
31 2823 Propanoic
acid,
3-methoxy-,
methyl ester
0.00a 16.28a 10.14a 5.67a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a MS
32 4118 Benzeneacetic
acid,
ethyl ester
0.00b 0.00b 4.24a 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.48ab 0.00b MS
33 4238 Acetic acid,
2-phenylethyl
ester
0.00e 4.59de 14.52ce 21.56cd 19.64ce 49.62a 35.08bc 59.97ab 2.89de 14.76ce 8.69de MS
34 1013 Butanoic
acid,
ethyl ester
0.00b 0.00b 0.00b 138.78ab 208.85ab 15.86ab 0.00b 219.70ab 0.00b 207.69ab 0.00b S/MS
35 1888 Heptanoic
acid,
ethyl ester
0.00b 0.00b 0.00b 4.29a 0.00b 0.00b 0.00b 0.00b 0.00b 0.52b 0.63b MS
36 2377 Octanoic
acid,
ethyl ester
116.20de 25.06e 159.42de 236.84ce 176.16ce 1,024.38a 283.93cd 672.98b 372.22c 257.23cd 295.66ce S/MS
37 4374 Dodecanoic
acid,
ethyl ester
0.00b 0.00b 0.00b 0.58b 2.31b 1.69a 0.00b 0.72a 0.00b 0.00b 0.00b S/MS
38 6523 Ethyl
hydrogen
succinate
0.00b 7.88a 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b MS
39 4270 Isovaleric
acid,
ethyl ester
3.72ce 38.44a 25.65ab 12.86ac 38.44ce 8.46ace 13.41acd 0.00e 0.00e 2.89de 11.94e MS
40 3428 Decanoic
acid,
ethyl ester
15.75de 0.00e 21.96bcd 20.32ce 13.34be 159.62a 29.62bcd 130.70a 46.03b 14.87de 13.01bc S/MS
41 1533 Hexanoic
acid,
ethyl ester
61.54c 7.98c 189.30bc 800.68a 370.21ac 60.66ab 181.80bc 424.02ac 392.37ac 554.27ac 395.41c S/MS
42 1221 Isoamyl
acetate
0.00a 0.00a 0.00a 0.00a 0.00a 30.98a 0.00a 0.00a 157.02a 0.00a 0.00a MS
43 844 Ethyl
Acetate
312.71ab 1,717.55ab 492.17ab 368.56ab 769.93ab 296.50ab 424.25ab 433.09ab 401.22ab 432.89ab 168.36b MS
44 1683 Acetic acid,
hexyl ester
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 1.42a 0.00a S/MS
45 4649 Butanedioic
acid,
ethyl 3-
methylbutyl
ester
1.59a 0.00a 2.11a 12.43a 0.00a 7.74a 8.37a 9.94a 1.66a 5.31a 6.33a MS
46 2921 Butanoic
acid,
3-hydroxy-,
ethyl ester
0.00a 0.00a 0.00a 0.00a 0.00a 0.97a 0.00a 0.00a 0.00a 0.00a 0.00a MS
47 6969 Linoleic
acid,
ethyl ester
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 2.60a 0.00a 0.00a 0.00a MS
48 6128 9-Hexadecenoic
acid,
ethyl ester
0.00a 0.00a 3.12a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a MS
49 7423 Hexadecyl
2-ethylhex
anoate
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 17.94a 0.00a 0.00a 0.00a 0.00a MS
50 6818 (E)-9-Octa
decenoic
acid,
ethyl ester
0.00b 0.00b 5.54a 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b MS
51 1345 trans-2-
Butenoic
acid,
ethyl ester
0.00b 0.00b 25.21a 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b MS
52 6042 Hexadecanoic
acid,
ethyl ester
0.00b 0.00b 5.54b 1.27b 0.98b 31.41a 0.00b 46.74a 0.00b 15.36ab 5.35b S/MS
53 6814 9-Octadecenoic
acid,
ethyl ester
0.00a 0.00a 0.00a 0.00a 1.16a 3.49a 0.00a 0.00a 0.00a 0.00a 0.00a MS
54 3685 4-Decenoic
acid,
ethyl ester, (E)-
0.00a 0.00a 0.00a 0.00a 0.00a 12.14a 4.41a 0.00a 11.51a 0.00a 14.31a MS
55 816 Acetic acid,
methyl ester
1.94a 0.00a 7.19a 0.00a 2.07a 2.09a 0.61a 2.12a 0.00a 0.00a 0.00a MS
56 6396 Diethyl
Phthalate
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 8.84a 0.00a 0.00a 0.00a 0.00a MS
57 2107 Lactic acid,
ethyl ester
16.67ab 0.00b 5.73b 15.22b 7.93b 12.93b 44.70ab 21.47ab 16.44b 20.91ab 7.04ab MS
58 4213 Methyl
N-hydroxy
benzenecar
boximidoate
86.55a 0.00a 5.09a 24.46a 11.90a 4.29a 0.00a 43.40a 106.16a 69.50a 6.12a MS
Total 616.68 1,817.78 976.94 1,663.53 1,622.92 1,722.85 1,052.94 2,067.44 1,507.52 1,598.09 932.83
Ketones
59 1981 Acetol 0.00c 0.00c 15.16a 0.00c 2.34b 0.00c 0.00c 0.00c 0.00c 0.00c 0.00c MS
60 1928 Acetoin 10.27def 32.66ce 465.40a 15.24ce 177.90b 0.00f 32.35c 7.54ef 5.30ce 16.94ce 0.00cd MS
61 811 Acetone 0.00b 0.00b 0.00b 0.00b 0.00b 2.16ab 0.00b 1.95ab 0.00ab 3.98ab 0.00b MS
62 2754 3-Isopropyl-
7a-methyl
-1,4,5,6,7,7a-
hexahydro-
2H-inden-
2-one
0.00a 0.00a 0.00a 0.00a 0.00a 7.81a 0.00a 0.00a 0.00a 6.22a 0.00a MS
Total 10.27 32.66 480.56 15.24 180.24 9.97 32.35 9.48 5.30 27.14 0.00
C13-
norisoprenoids
63 2308 α-
Ionene
0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 4.67a 0.00a MS
64 2774 Ionone 0.00b 0.00ab 0.00b 0.00b 0.00b 11.67a 0.00b 0.00b 0.00b 3.63ab 0.00b MS
65 3826 TDN 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 0.00a 8.55a 0.00a MS
Total 0.00 0.00 0.00 0.00 0.00 11.67 0.00 0.00 0.00 16.85 0.00
C6-compounds
66 2135 1-Hexanol 6,246
.35ce
6,933
.31ce
4,492
.25ce
1,6418
.01a
8,381
.96cd
3,577
.18de
6,162
.38ce
4,951
.91ce
9,386
.92bc
5,728
.51ce
14,397
.96e
S/MS
67 2261 (Z)-3-Hexenol 0.97bc 0.00bc 0.00b 0.00b 0.00b 23.99a 0.00b 15.16b 0.00b 0.00b 0.00b MS
Total 6,247.32 6,933.31 4,492.25 1,6418.01 8,381.96 3,601.17 6,162.38 4,967.07 9,386.92 5,728.51 14,397.96
Furans
68 2629 Furfural 0.00b 0.00b 0.00b 0.00b 0.00b 3.07a 0.00b 0.00b 0.00b 0.00b 0.00b MS
Total 0.00 0.00 0.00 0.00 0.00 3.07 0.00 0.00 0.00 0.00 0.00
Phenolic
acid
derivatives
69 4001 Methyl
Salicylate
0.00a 0.00a 0.00a 0.00a 2.27a 0.00a 0.00a 0.00a 0.00a 2.99a 0.00a MS
Total 0.00 0.00 0.00 0.00 2.27 0.00 0.00 0.00 0.00 2.99 0.00
Terpenes
70 3725 α-
Terpineol
0.00a 0.00a 0.00a 0.00a 0.00a 40.67a 0.00a 0.00a 0.00a 0.00a 0.00a S/MS
Total 0.00 0.00 0.00 0.00 0.00 40.67 0.00 0.00 0.00 0.00 0.00
Others
71 8631 Squalene 0.00a 31.26a 0.00a 0.00a 0.00a 0.00a 42.20a 0.00a 0.00a 0.00a 0.00a MS
72 1169 1-(1-Ethoxy
ethoxy)
pentane
0.00b 0.00ab 13.03ab 2.73ab 1.72ab 0.00b 0.00b 0.00b 0.00b 0.00b 0.00b MS
73 4339 1,3,6-
Trioxocane
0.00a 0.00a 0.00a 0.00a 0.61a 0.00a 0.00a 0.00a 0.00a 0.49a 0.00a MS
74 6246 Glycerin 0.00a 0.00a 0.00a 0.00a 0.00a 11.74a 0.00a 0.00a 0.00a 0.00a 0.00a MS
75 1761 Butylcy
clopropane
0.59a 0.00a 1.24a 0.00a 1.18a 0.84a 0.00a 0.00a 0.00a 0.00a 1.18a MS
  Total 0.59 31.26 14.27 2.73 3.50 12.58 42.20 0.00 0.00 0.49 1.18  

Table 3.

Odor active values (OAVs) of active aroma compounds detected in 11 red wines

No.  Compounds Odor descriptor Odor Series1) OTV
2)(μg/L)
Odor activity value (OAV)3)
Caber
net
Franc
Caber
net
Sauvignon
Chan
celler
Malbec Marchel MBA Merlot Narsha Pinot
Meunier
Sangi
ovetto
Sauvi
gnon
Vert
1) 1, fruity; 2, floral; 3, green; 4, sweet; 5, fatty.
2) Odor threshold value: a. Ferreira et al., 2000; b, Li et al., 2008; c, Sacks et al., 2012; d, Welke et al., 2014.
3) OAV, concentration/odor threshold.
Alcohol
1 Isoamyl
alcohol
alcohol, harsh, bitter 4, 5 30,000b 8.82 7.30 6.98 11.09 6.60 11.24 9.53 8.43 9.16 9.83 7.91
2 Phenylethyl
Alcohol
rose, honey 2 200,000d 5.42 8.68 4.99 7.72 4.27 6.01 9.91 4.98 5.11 5.77 5.10
3 Isobutyl
alcohol
alcohol 5 75,000d 1.00 2.31 1.29 1.10 0.85 0.00 0.88 0.81 0.64 1.11 1.54
total 15.23 18.30 13.26 19.91 11.72 17.25 20.33 14.23 14.91 16.71 14.54
  Aldehyde      
4 Acetal
dehyde
pungent 5 500d 0.12 1.95 1.62 0.35 0.79 0.04 0.34 0.15 0.14 0.26 0.13
total 0.12 1.95 1.62 0.35 0.79 0.04 0.34 0.15 0.14 0.26 0.13
  Ester
and
acetate
     
5 Acetic
acid,
2-phenylethyl
ester
flowery 2 1.9d 0.00 2.41 7.64 11.35 10.34 26.12 18.46 31.56 1.52 7.77 4.57
6 Butanoic
acid,
ethyl ester
strawberry,
apple
1 20a 0.00 0.00 0.00 6.94 10.44 0.79 0.00 10.98 0.00 10.38 0.00
7 Heptanoic
acid,
ethyl ester
fruity,
green apple
1 2.2d 0.00 0.00 0.00 1.95 0.00 0.00 0.00 0.00 0.00 0.24 0.29
8 Octanoic
acid,
ethyl ester
sweet,
fruity, pear
1, 2, 4 5a 23.24 5.01 31.88 47.37 35.23 204.88 56.79 134.60 74.44 51.45 59.13
9 Hexanoic
acid,
ethyl ester
fruity,
green apple
1 8d 7.69 1.00 23.66 100.09 46.28 7.58 22.73 53.00 49.05 69.28 49.43
10 Isoamyl
acetate
banana,
fruity,
sweet
1, 4 30a 0.00 0.00 0.00 0.00 0.00 1.03 0.00 0.00 5.23 0.00 0.00
total 30.93 8.42 63.19 167.69 102.29 240.40 97.97 230.15 130.25 139.12 113.41
  C13-norisoprenoid      
11 α-Ionene fruity, sweet 1, 4 2.6d 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.80 0.00
12 TDN kerosene 1, 5 2c 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 4.27 0.00
total 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 6.07 0.00
  C6-compound      
13 1-Hexanol herbaceous, grass, woody 3 110d 56.79 63.03 40.84 149.25 76.20 32.52 56.02 45.02 85.34 52.08 130.89
total 56.79 63.03 40.84 149.25 76.20 32.52 56.02 45.02 85.34 52.08 130.89
  Terpene      
14 α-Terpineol floral, sweet 2, 4 1.1d 0.00 0.00 0.00 0.00 0.00 36.97 0.00 0.00 0.00 0.00 0.00
  total       0.00 0.00 0.00 0.00 0.00 36.97 0.00 0.00 0.00 0.00 0.00