Aroma profile and phenolic content of Merlot red wines produced in high-altitude regions in Brazil

Arcari, Stefany Grutzmann; Caliari, Vinícius; Souza, Edson Luiz de; Godoy, Helena Teixeira

doi:10.21577/0100-4042.20170687

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Nota Técnica • Quím. Nova 44 (5) • May 2021 • https://doi.org/10.21577/0100-4042.20170687 linkcopy

Aroma profile and phenolic content of Merlot red wines produced in high-altitude regions in Brazil

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

In Brazil, wine-growing regions of high altitude have been evaluated for the cultivation of grapes destined for the production of quality wines. In this study the phenolic content, the volatile compounds profile and the in vitro antioxidant activity of samples produced in Água Doce, Campos Novos and Tangará were determined using spectrophotometric and chromatographic techniques. A total of 95 volatile compounds were identified in the samples analyzed, of which borneol is reported in Brazilian Merlot wines for the first time. The quantitative results showed that the most important volatile compounds for wine aroma were esters, fatty acids, 1-hexanol and 2-phenylethanol alcohols, and C₁₃-norisoprenoids β-damascenone and α-ionone. The phenolic content observed was comparable to the results obtained for Merlot red wines from other regions in Brazil and in other countries. Also, the wine samples were effective in capturing the free radicals DPPH and ABTS.

Keywords:
Merlot wines; volatile compounds; phenolic compounds; antioxidant activity

Retention time	Compound	LTPRI calculated	LTPRI literature	Identification method	Odor descriptors	Threshold (μg L^-1)
6.312	Methyl acetate	601	NF	MS	NF	NF
7.592	Ethyl acetate	621	620^a	STD, MS	Solvent^b, fruity^c,d, balsamic^d	12000^e
13.689	Ethyl butanoate	787	799^a	STD, MS	Fruity^b,f,g, strawberry^g,h	400^e
14.558	Isoamyl acetate	825	855^a	STD, MS	Banana^c,d,f,g,h	30^l
15.408	Ethyl 2-methylbutanoate	841	850^l	STD, MS	Strawberry^f, sweet fruits^d,g	18^l
17.636	Ethyl isovalerate	850	853^a	STD, MS	Fruity, apple^g	1^e
17.759	Ethyl hexanoate	931	917^j	STD, MS	Fruity^b,f,h, green apple^c,f,h, strawberry^f, spices and anise^h	14^l
18.316	1-hexanol	1002	990^j	STD, MS	Herbaceous, fattyⁱ, resinous^k; floral, green, cut grass^{c, d, h}	110^e
24.715	Hexyl acetate	1003	1014^a	STD, MS	Fruity, herbsⁱ, apple^f,h, pear^{d, g,h}, cherry^d	670^e
25.428	2-propyl-1-heptanol	1019	1016^j	MS	Mushrooms^j	NF
25.772	Furfuryl heptanoate	1020	NF	MS	NF	NF
26.292	1-propanol	1029	1038^J	STD, MS	Ripe fruit, alcohol^c,f,g	306000^e
27.790	2-ethyl-1-hexanol	1050	1032^j	MS	Sweet fruits^e, roses, green^j	8000^e
28.926	Ethyl lactate	1071	1101^j	STD, MS	Acid, medicine^c, strawberry, raspberry^g	150000^e
31.440	Ethyl heptanoate	1079	1083^j	STD, MS	Fruity, pineapple^d	2.2^e
32.612	2,2-dimethyl-1-propanol	1081	1091^e	MS	Alcohol, sweet^j	75000^e
34.193	1-butanol	1105	1113^k	MS	Medicine^e	150000^e
34.233	2-ethyl-1-pentanol	1107	1107^j	MS	Synthetic, balsamic^e	64000^e
34.692	Methyl octanoate	1108	1110^a	MS	Fruity, citric^e	200^e
34.978	3-hexen-1-ol	1134	1129^j	MS	Green, fat^e	1000^e
35.057	Ethyl 2-hydroxy-3-methyl-butanoate	1141	1130^k	MS	Pineapple, strawberry, tea, honey^e	1000^e
35.262	Thioacetic acid	1167	1163^j	MS	Toasty^j	NF
35.275	3-sec-butyl-2-methoxypyrazine	1181	1172^l	STD, MS	Green pepper, earthy^l	0.002^l
35.571	Nonan-2-one	1184	1184^j	MS	Fruity^e	41^e
38.647	Linalool oxide	1185	1161^j	MS	Floral^g	25^l
38.653	Ethyl octanoate	1191	1192^a	STD, MS	Fruity, sweet^{c, f},pineapple, pear, floral^{d, h}	580^e
38.670	2-hexen-1-ol	1198	1228^k	MS	Grass, herbaceous^e	400^e
39.741	3-methyl-1-butanol	1202	1205^J	STD, MS	Burnt, alcohol^c,h, nail polish, whiskey^d	30000^l
40.086	1-heptanol	1205	1225^k	MS	Herbaceous^k	200^e
40.279	2’(trifluoromethyl)-acetophenone	1207	1208^j	MS	Floral, almonds^j	NF
40,627	Citronelal	1231	1229^k	STD, MS	Sweet, citric^e	100^e
41.415	Furfuryl acetate	1240	1238^j	STD, MS	Toasty^j	540^m
42.633	Borneol	1244	1253^j	MS	Camphor^j	NF
43.044	2-hydroxy-2-methylbutanoic acid	1259	NF	MS	NF	NF
43.206	1-decanol	1273	1263^j	MS	Sweet, fatty^e	400^e
44.138	Ethyl nonanoate	1281	1280^a	STD, MS	Fruity, floral^e	1300^e
44.400	2-ethyl-1-decanol	1283	1265ⁱ	MS	Fatty^e	400^e
44.516	Isobutyric acid	1283	1306^j	STD, MS	Cheese^e	200000^e
44.751	2-hepten-3-ol	1341	1350^e	MS	NF	NF
44.844	3-octenol	1364	1394^j	MS	Chesnut flower, mushrooms^e	1^e
45.724	1-undecanol	1379	1371^j	MS	Tangerine^j	NF
45.921	Ethyl decanoate	1388	1384^j	STD, MS	Fruity, grape^e	200^l
45.980	Ethyl 2-hydroxy-3-methylbutanoate	1390	1399^e	MS	Pineapple, strawberry, tea, honey^e	1000^e
46.369	Furfural	1453	1455^j	MS	Bread, almonds, sweet^j	14100^l
46.711	Isoamyl caproate	1455	1445^e	MS	Sweet fruity^e	1000^e
47.139	Benzaldehyde	1493	1495^j	MS	Almonds^e	2000^e
47.315	Ethyl 3-hydroxy-butanoate	1536	1524^j	STD, MS	Green grape^h, marshmallow^j	20000^l
49.169	Ethyl 2-hydroxy-hexanoate	1556	1542^e	MS	Cherry^e	NF
50.011	4-terpineol	1604	1602^e	MS	Sweet, herbaceous^e	250^e
50.167	Methyl benzoate	1609	1600^j	MS	Prune, herbaceous, sweet^j	NF
50.571	Isoamyl lactate	1610	1615^e	MS	NF	NF
50.948	Ethyl furoate	1612	1617^e	MS	Balsamic^e	16000^e
51.060	Butanoic acid	1619	1619^j	STD, MS	Cheese, rancidity^e	173^l
52.212	Ethyl-methyl succinate	1623	1624^e	MS	NF	NF
52.330	Cinnamaldehyde	1632	1631^j	MS	Cinnamon, paint^j	NF
52.587	Isovaleric acid	1666	1660^e	STD, MS	Sweet, cheese^k, rancidity^e	3000^e
52.810	Isoamyl octanoate	1669	1668^e	MS	Oily, cheese, cream, sweet^e	152^e
53.213	Furfuryl alcohol	1670	1673^k	STD, MS	Burnt^j	2000^l
53.497	Ethyl benzoate	1675	1664^e	MS	Camomile, floral, fruity, celery^j	56^e
54.040	Diethyl succinate	1691	1690^e	STD, MS	Wine^c,d,h, caramel^f, fruity^d	200000^l
54.711	Ethyl 9-decenoate	1700	1708^e	MS	Roses^e	100^e
55.946	α-terpineol	1711	1713^e	STD, MS	Floral, sweet^e, anise, mint^j	250^l
58.252	3-methylthio-1-propanol	1726	1729^e	MS	Cooked vegetables^e	500^e
58.608	Methyl salicylate	1744	1745^j	MS	Pepper mint^j	0.1^m
58.707	Furfuryl thioacetate	1781	1785^j	STD, MS	Toasty^j	1.5^m
59.136	Ethyl salicylate	1782	1784^j	MS	Mint^j	NF
59.337	Phenylethyl acetate	1790	1796^e	STD, MS	Roses^l, floral^e, honey^g	250^l
59.363	2-phenylethyl formate	1793	NF	MS	NF	NF
60.401	Diethyl glutarate	1806	1806^j	MS	Cotton candy^j	NF
61.241	α-ionone	1808	1809^j	STD, MS	Fruity, floral, raspberry, violet^h	2.6^l
61.925	β-damascenone	1815	1813^j	STD, MS	Baked apple^l, floral, honey^d,l	0.05^l
62.388	Ethyl laurate	1838	1835^e	STD, MS	Sweet, floral^e, waxy, soap^h	1500^e
62.686	Geraniol	1849	1847^j	STD, MS	Roses, geranium^c,g	20^l
62.733	2-phenylethanol	1851	1859^k	STD, MS	Roses, honey^e,k	14000^l
63.044	Hexanoic acid	1869	1863^e	STD, MS	Cheese, fatty^e	420^l
64.386	Benzyl alcohol	1871	1865^j	MS	Sweet, fruity^e	200000^l
66.238	1-hexadecanol	1883	1870^j	MS	Floral, waxy^j	NF
67.360	1-dodecanol	1890	1895^k	MS	Waxy^k	1000^e
69.071	Thujopsene (sesquichamene)	1909	NF	MS	NF	NF
71.382	β-ionone	1915	1912^j	STD, MS	Violet^d,h,i, balsamic, roses^d	0.09^l
71.915	Ethyl palmitate	1994	1993^j	MS	Waxy, fatty^e	1500^e
71.957	Ethyl myristate	1998	1999^j	MS	Lily^j	NF
72.488	Nerolidol	2006	2009^j	MS	Roses, apple, citric, herbaceous^e	1000^e
72.530	Trans-nerolidol	2016	2010^j	MS	Waxy^j	NF
72.881	γ-nonalactone	2032	2042^j	STD, MS	Coconut, peach^b,g,j	30^l
73.523	4-ethylguaiacol	2033	2031^j	MS	Wood, clove of garlic, smoke^e,j	33^l
76.672	Octanoic acid	2082	2083^j	STD, MS	Rancidity^d,k, sweet, cheese^c, animal, spices^f, unpleasant^d	500^l
78.453	Nonanoic acid	2091	2090^e	STD, MS	Cheese^d,k, waxy^d	3000^e
78.806	Tetradecanol	2092	2099^j	MS	Coconut^j	NF
80.756	Ethyl cinnamate	2140	2139^j	STD, MS	Honey, cinnamon^c,f, floral, strawberry, plum^f	1.1^l
81.983	4-ethylphenol	2153	2154^e	MS	Bitumen, leather^l	440^l
82.331	α-bisabolol	2235	2235^j	MS	Spices, floral^j	90^m
83.270	Ethyl vanillate	2247	2247^j	MS	Vanilla, honey^l	3000^l
87.799	Decanoic acid	2279	2287^e	STD, MS	Unpleasant^d,k, fat, rancidity^c, animal^f	1000^e
98.137	1-heptadecanol	2466	2461^e	MS	NF	NF

Compounds	Region
	Água Doce			Campos Novos			Tangará
	2012	2013	2014	2012	2013	2014	2012	2013	2014
Ethyl butanoate	< 5.82^c	69.78^b (1.68)	138.87^a (3.23)	55.86^b (8.86)	17.65^bc (2.37)	137.58^a (0.12)	< 5.82^c	< 5.82^c	63.73^b (4.99)
Ethyl hexanoate	95.19^c (2.82)	102.04^c (7.46)	121.33^c (2.31)	120.98^c (1.62)	974.43^a (3.53)	490.01^b (2.62)	54.85^c (5.10)	104.90^c (8.37)	114.19^c (1.28)
Ethyl heptanoate	nd	nd	nd	27.39^a (7.51)	nd	nd	nd	nd	nd
Ethyl octanoate	165.45^b (7.00)	219.55^b (2.31)	284.96^ab (2.18)	411.10^a (1.97)	254.16^ab (7.94)	244.72^ab (3.78)	226.56^b (7.99)	321.06^ab (1.87)	204.82^b (1.48)
Ethyl nonanoate	< 0.31^c	< 0.31^c	< 0.31^c	< 0.31^c	< 0.31^c	9.86^a (1.61)	5.14^b (7.20)	< 0.31^c	5.73^b (1.64)
Ethyl decanoate	50.39^c (2.33)	88.25^bc (0.92)	196.80^bc (7.68)	203.36^bc (8.32)	206.79^bc (1.47)	123.10^bc (9.50)	58.48^c (3.87)	273.76^b (0.23)	470.43^a (2.16)
Ethyl dodecanoate	< 6.28^c	< 6.28^c	9.05^a (1.13)	20.29^b (4.14)	< 6.28^c	< 6.28^c	< 6.28^c	< 6.28^c	21.67^b (8.73)
Ethyl acetate	3694.83^cd (7.15)	5883.48^a (6.26)	1730.46^de (2.21)	1552.82^e (2.62)	2966.74^bcde (2.19)	2657.86^cde (2.90)	5550.04^a (6.05)	4312.99^ab (1.20)	3282.75^bcd (1.86)
Furfuryl acetate	nd	nd	nd	< 67.00^a	nd	< 67.00^a	nd	nd	nd
Hexyl acetate	25.69^a (0.25)	nd	nd	nd	nd	nd	nd	nd	nd
Isoamyl acetate	73.62^b (5.56)	74.75^b (2.95)	81.07^b (1.62)	83.04^b (1.51)	75.59^b (1.20)	89.36^b (8.04)	66.82^b (8.94)	82.44^b (5.08)	250.31^a (9.00)
Phenylethyl acetate	28.91^d (2.70)	114.69^bc (1.31)	35.71^d (1.69)	70.86^cd (1.31)	80.09^cd (2.07)	< 28.06^d	161.22^b (2.62)	296.81^a (8,39)	308.41^a (8.41)
Ethyl 2-methylbutanoate	127.22^b (2.21)	< 28.00^d	< 28.00^d (3.14)	175.38^a (2.09)	87.82^c (9.29)	< 28.00^d	< 28.00^d	< 28.00^d	< 28.00^d
Ethyl isovalerate	354.38^b (2.04)	366.96^b (1.90)	275.32^b (1.98)	375.30^b (8.30)	351.64^b (4.66)	659.71^a (3.03)	< 15.04^c	< 15.04^c	< 15.04^c
Diethyl succinate	13199.38^bc (1.88)	15950.47^b (3.69)	3674.91^d (6.71)	24516.77^a (1.23)	7858.45^cd (2.15)	12239.90^bc (2.43)	25271.90^a (8.40)	18259.38^b (1.41)	12759.54^bc (6.90)
Ethyl lactate	<10.02^d	25633.24^a (2.35)	< 10.02^d	< 10.02^d	< 10.02^d	< 10.02^d	334.88^d (7.69)	6267.35^c (1.07)	10058.30^b (4.06)
Ethyl cinnamate	< 4.36^d	54.99^b (1.71)	< 4.36^d	< 4.36^d	63.52^a (2.09)	< 4.36^d	< 4.36^d	26.02^c (9.79)	< 4.36^d
3-methyl 1-butanol	< 5.06^d	5130.33^c (1.38)	< 5.06^d	< 5.06^d	6343.24^b (2.64)	< 5.06^d	5785.29^bc (4.15)	8298.84^a (5.40)	< 5.06^d
1-propanol	< 5.03^b	< 5.03^b	< 5.03^b	< 5.03^b	< 5.03^b	7383.87^a (3.34)	< 5.03^b	< 5.03^b	374.72^a (1.25)
Furfuryl alcohol	335.11^bc (1.57)	973.54^b (1.45)	< 5.09^d	529.83^bc (1.33)	< 5.09^d	< 5.09^d	< 5.09^d	1578.29^a (2.22)	< 5.09^d
1-hexanol	199.74^b (1.96)	209.33^b (2.54)	152.74^bc (2.02)	183.00^bc (0.23)	160.55^bc (1.33)	165.76^bc (2.63)	113.31^c (1.29)	140.34^bc (0.63)	424.41^a (4.43)
2-phenylethanol	40806.29^b (2.08)	41762.51^b (4.78)	37141.63^b (1.42)	82741.04^a (2.95)	63690.00^ab (1.44)	61635.22^ab (2.73)	78706.68^a (1.03)	89854.11^a (1.50)	75619.16^a (8.02)
Propanoic acid	nd	nd	nd	nd	nd	nd	nd	nd	254.35^a (2.47)
Butanoic acid	nd	nd	nd	nd	nd	527.18^a (2.43)	nd	nd	nd
Hexanoic acid	266.41^b (2.02)	< 31.13^c	217.25^b (5.38)	< 31.13^c	< 31.13^c	< 31.13^c	< 31.13^c	< 31.13^c (1.67)	852.37^a (8.61)
Octanoic acid	< 5.00^d	5988.99^c (3.57)	11403.43^ab (2.11)	193.83^d (1.67)	8254.89^bc (6.10)	1365.27^d (2.74)	6185.59^c (8.21)	5716.23^c (1.46)	14536.01^a (8.05)
Nonanoic acid	nd	nd	< 31.72^a	nd	nd	nd	nd	nd	nd
Decanoic acid	< 32.03^d	< 32.03^d	< 32.03^d	< 32.03^d	190.84^b (5.23)	39.08^c (1.46)	< 32.03^d	< 32.03^d	289.76^a (3.33)
Isobutyric acid	6718.61^bc (3.03)	8330.71^b (8.23)	8592.77^b (2.49)	nd	3135.42^cd (2.87)	5740.87^bc (1.97)	8102.94^b (1.17)	5758.10^bc (1.28)	15323.06^a (4.50)
Isovaleric acid	nd	92.55^a (1.31)	801.01^a (2.87)	nd	385.59^a (1.22)	5347.30^b (2.26)	2251.68^c (6.72)	287.16^a (2.07)	6265.72^b (1.25)
Geraniol	nd	nd	nd	nd	nd	nd	nd	nd	23.88^a (2.91)
α-terpineol	89.50^a (2.73)	< 10.76^c	< 10.76^c	26.74^bc (2.36)	17.39^bc (3.46)	< 10.76^c	21.45^bc (1.45)	35.91^b (1.60)	< 10.76^c
Citronelal	nd	nd	nd	nd	nd	nd	nd	nd	43.70^a (2.69)
γ-nonalactone	nd	nd	nd	nd	nd	nd	nd	nd	703.56^a (8.64)
β-damascenone	13.66^a (3.79)	< 3.05^b	15.69^a (6.73)	< 3.05^b	< 3.05^b	10.91^a (2.52)	< 3.05^b	< 3.05^b	14.93^a (1.18)
β-ionone	< 1.71^a	< 1.71^a	< 1.71^a	< 1.71^a	< 1.71^a	< 1.71^a	< 1.71^a	< 1.71^a	< 1.71^a
α-ionone	< 2.61^b	< 2.61^b	< 2.61^b	< 2.61^b	< 2.61^b	24.35^a (2.55)	< 2.61^b	< 2.61^b	< 2.61^b

Compounds	Region
	Água Doce			Campos Novos			Tangará
	2012	2013	2014	2012	2013	2014	2012	2013	2014
Caffeic acid	4.15^c (3.97)	< 0.06^f	12.21^a (3.19)	7.55^e (4.57)	10.19^b (0.54)	16.27^d (2.98)	< 0.64^f	6.69^e (3.59)	17.32^d (2.51)
p-coumaric acid	0.83^e (7.78)	< 0.10^e	3.13^ab (4.15)	1.65^cd (4.53)	3.00^abc (2.83)	2.47^bcd (4.05)	< 0.10^e	2.12^cd (1.98)	3.58^a (2.79)
Ferulic acid	< 0.05^d	< 0.05^d	1.47^bc (4.41)	11.29^a (2.39)	< 0.05^d	0.97^c (6.18)	< 0.05^d	0.13^d (3.70)	1.98^b (3.03)
Vanillic acid	0.14^d (1.03)	8.99^b (1.61)	2.82^cd (4.61)	5.43^c (5.98)	4.03^c (1.74)	3.63^c (6.34)	21.68^a (6.78)	2.76^cd (3.26)	11.07^b (1.53)
Syringic acid	< 0.11^f	1.50^e (7.33)	< 0.11^f	3.35^c (6.27)	4.74^a (0.10)	1.00^e (3.48)	3.99^b (4.55)	2.42^d (4.55)	0.31^f (1.64)
Protocatechuic acid	1.86^c (3.48)	2.63^c (2.09)	2.56^c (0.39)	3.21^c (1.01)	8.75^b (2.11)	3.00^c (6.15)	2.53^c (1.58)	21.05^a (3.37)	0.77^c (5.80)
Gallic acid	9.34^cd (2.89)	7.95^d (2.51)	12.74^abc (3.30)	13.72^ab (6.56)	13.42^ab (1.56)	10.35^abc (1.14)	15.81^a (6.45)	8.20^d (3.11)	10.23^abc (1.76)
Quercetin	6.69^e (9.78)	11.13^de (5.16)	24.45^b (0.74)	21.49^b (0.86)	7.46^e (2.74)	14.99^cd (4.73)	30.91^a (8.02)	7.37^e (2.17)	16.10^c (4.41)
Kaempferol	0.90^d (6.67)	0.98^cd (1.73)	3.87^ab (2.71)	3.35^b (0.89)	1.40^cd (3.36)	0.71^d (2.25)	4.34^a (2.55)	1.27^cd (2.30)	1.82^c (8.79)
(+)-Catechin	38.80^bc (0.37)	65.41^a (1.88)	33.88^bc (3.02)	31.80^bcd (3.60)	20.96^e (2.90)	48.04^b (7.75)	66.75^a (1.87)	38.00^bc (1.33)	25.02^cd (1.25)
(-)-Epicatechin	11.91^def (1.26)	89.29^a (2.02)	32.60^bc (8.48)	19.83^cde (6.35)	7.53^ef (7.83)	5.78^f (1.43)	8.25^ef (5.60)	22.24^cd (1.40)	37.81^b (1.73)
Tyrosol	6.15^e (0.65)	13.80^bcd (0.43)	19.36^b (2.97)	47.32^a (6.48)	46.67^a (5.00)	11.28^cde (3.32)	7.34^de (7.02)	7.63de (1.18)	18.04^bc (2.47)
Trans-resveratrol	0.60^c (1.00)	0.58^c (2.99)	0.27^d (3.70)	2.17^a (1.84)	0.61^c (1.38)	0.75^c (9.33)	< 0.05^d	0.45^cd (3.30)	0.85^c (7.60)

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Sociedade Brasileira de Química Instituto de Química, Universidade Estadual de Campinas (Unicamp), CP6154, 13083-0970 - Campinas - SP - Brazil
E-mail: quimicanova@sbq.org.br

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[TFN1] ^a ref. 17; ^b ref. 18; ^c ref. 19; ^d ref. 20; ^e ref. 21; ^f ref. 22; ^g ref. 23; ^h ref. 8; ⁱ ref. 24; ^j ref. 25; ^k ref. 26; ^l ref. 27; ^m ref. 28. NF = not found. STD = mass spectra and retention index are agreement with the volatile compound standard. MS = mass spectra in agreement with the NIST spectral database (considering minimum similarity 70%). LTPRI = linear temperature programmed retention index.