Evaluation of the Formation and Stability of Hydroxyalkylsulfonic Acids in Wines

Abstract

The presence of carbonyl compounds (CCs) in wines has sparked the interest of researchers in several countries. The quantification of some of these compounds has been used as a parameter of quality for many fermented beverages. Although present in minute quantities (except for acetaldehyde), they have a strong olfactory impact. In addition, the CCs found in wines have a strong affinity for bisulfite and can form stable adducts, which will also interfere in the characteristics of aroma. The greatest challenge, however, is to predict which CCs have the strongest affinity for S(IV) and what conditions favor this interaction. To better understand the reaction of CC-bisulfite adduct formation (HASA), this study has evaluated the profile of 22 CCs in a "synthetic wine" containing bisulfite and in 10 real samples of different wines from the São Francisco Valley, northeastern Brazil. On the basis of principal component analysis (PCA) and dissociation constants, the results revealed that aliphatic aldehydes form adducts with S(IV), whereas ketones, cyclic aldehydes, and trans-alkenes interact weakly and are found predominantly in their free form. These results revealed also that pH 10 and 11 were defined as the most appropriate for CC-SO 2 adduct dissociation, and the total CCs were quantified reliably.

Solubilidade e reatividade de gases

“…Em um processo típico de elaboração de vinhos a faixa de pH é de 3-4, sendo o bissulfito a espécie predominate. 36 (19) Os compostos carbonílicos presentes no vinho reagem com o bissulfito, levando à formação de ácidos alquilsulfônicos, 36 num mecanismo semelhante ao que ocorre em reações na atmosfera envolvendo SO 2 e formaldeído, que resulta na formação de um aduto formaldeído-bissulfito (ácido hidroximetanosulfônico). 37 O acetaldeído também reage rapidamente com o bissulfito, formando o ácido α-hidroxietanossulfônico, não volátil, que diminui a percepção olfativa indesejável do acetaldeído presente no vinho.…”

“…37 O acetaldeído também reage rapidamente com o bissulfito, formando o ácido α-hidroxietanossulfônico, não volátil, que diminui a percepção olfativa indesejável do acetaldeído presente no vinho. 36 …”

Sulfites in beer: reviewing regulation, analysis and role

“…For example, glyceraldehyde forms stable hydroxysulfonate adduct, which could contribute to the mechanism of the inhibition of Maillard browning by sulfite species (Keller et al, 1999). Dissociation constants of carbonyl bisulfite compounds at pH 3.5 have been reported by Azevedo et al, (2007). They revealed that aliphatic aldehydes form adducts with S (IV), whereas ketones, cyclic aldehydes, and trans-alkenes interact weakly and are found predominantly in the free form.…”

Efeito da presença e concentração de compostos carbonílicos na qualidade de vinhos

“…O conhecimento sobre as concentrações dos ácidos hidroximetanossulfônico (AHMS) e α-hidroxietanossulfônico (AHES) e dos demais ácidos hidroxialquilssulfônicos (AHAS) formados com compostos carbonílicos de cadeias mais longas é fundamental para entender o equilíbrio entre os CC na forma livre e na forma de aduto (AHAS), e como essas espécies influenciam na qualidade sensorial de vinhos ou de outras bebidas fermentadas 69 .…”