Cyanate as an Active Precursor of Ethyl Carbamate Formation in Sugar Cane Spirit

Galinaro, Carlos Alexandre; Ohe, Thiago Hideyuki Kobe; Silva, Augusto C. H. Da; Silva, Sebastião C. da; Franco, Douglas Wagner

doi:10.1021/acs.jafc.5b03146

Cited by 20 publications

(20 citation statements)

References 36 publications

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“…EC was not formed in the koji -making stage. Although EC precursors largely accumulated during the fermentation stage, the EC content only slightly increased because the reaction rate of EC formation was very low [11,21]. In Cantonese soy sauce, 83.5% of EC formed during the hot extraction of raw soy sauce and sterilization stage, indicating that these are the crucial stages of EC formation in soy sauce.…”

Section: Discussionmentioning

confidence: 99%

“…The major precursors and dominantly emerging stages of EC differ with disparate food types and processing crafts. For instance, urea, the most important EC precursor in Chinese yellow wine, mainly accumulates during yeast metabolism [10], and cyanide is the precursor to EC in any form of cyanogenic plant material used in food production, such as Prunus species and sugar cane species [11,12]. Little research has been conducted on the major precursors of EC in the production of soy sauce because of the complexity and diversity of the soy sauce production process.…”

Section: Introductionmentioning

confidence: 99%

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Formation of Ethyl Carbamate during the Production Process of Cantonese Soy Sauce

et al. 2019

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The aim of this work was to clarify the formation of ethyl carbamate (EC) and its influence factors throughout the production process of Cantonese soy sauce. The results showed that EC was not detected in the koji-making and early moromi fermentation stages, but started to be generated when pH of the moromi decreased to about 4.9—at the same time, the levels of ethanol, urea and citrulline increased significantly. Most EC was formed during raw soy sauce hot extraction (40.6%) and sterilization (42.9%) stages. The EC content exhibited the highest correlation with ethanol throughout the whole production process (R = 0.97). The simulation soy sauce produced in laboratory led the same conclusion—moreover, the contents of EC, ethanol and citrulline were higher in soy sauce fermented at 30 °C than in soy sauce fermented at 15 °C. Extraction of raw soy sauce by squeezing contributed little to EC formation. Further research showed that citrulline and ethanol led to significant increases in EC levels in raw soy sauce upon heating. These results indicate that ethanol and citrulline are two critical precursors of EC and that EC is mainly formed during the heat treatment stage of soy sauce.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Formation of Ethyl Carbamate during the Production Process of Cantonese Soy Sauce

et al. 2019

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“…In addition to the effect of heating, the presence of precursors was also important for the formation of ethyl carbamate. As shown in Figure 1 B, ethyl carbamate is known to be produced from the reaction of ethanol with cyanate oxidized from HCN [ 24 , 25 ]. Thus, the amount of ethyl carbamate in the fermented liquid was slightly higher than those in the steamed and saccharified samples, since ethanol was produced only after fermentation.…”

Section: Resultsmentioning

confidence: 99%

Effect of Fermentation on Cyanide and Ethyl Carbamate Contents in Cassava Flour and Evaluation of Their Mass Balance during Lab-Scale Continuous Distillation

Duan

Shin

et al. 2021

Foods

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When cassava is used for the production of distilled spirits through fermentation and distillation, toxic hydrogen cyanide (HCN) is released from linamarin and carcinogenic ethyl carbamate is produced. Herein, cyanide and ethyl carbamate contents were monitored during the fermentation and lab-scale continuous distillation processes. Thereafter, mass balance and the influence of copper chips were evaluated. Results showed that 81.5% of cyanide was removed after fermentation. Use of copper chips completely prevented the migration of cyanide into the distilled spirits, while 88.3% of cyanide migrated from the fermented liquid in the absence of copper chips. Formation of ethyl carbamate was significantly promoted during distillation. Most of the produced ethyl carbamate (73.2%) was transferred into the distilled spirits in the absence of copper chips, only 9.6% of the ethyl carbamate was transferred when copper chips were used. Thus, copper chips effectively prevented the migration of cyanide and ethyl carbamate into the distilled spirts during continuous distillation.

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“…In distillation or even after this process, cyanide (CN-) is also classified as a precursor to EC. Another pathway involving the cyanide (CN-) ion for the formation of ECCE, occurs as a result of the enzymatic action and oxidation of cyanogenic glycosides (Alexander et al, 2007;Galinaro et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Monitoring the content of ethyl carbamate and copper in organic and conventional cachaça

Silva

Verruma-Bernardi

Medeiros

et al. 2020

Sci. agric. (Piracicaba, Braz.)

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Ethyl carbamate (EC) (NH 2 COOCH 2 CH 3) is found in cachaça, and its presence in the beverage is conspicuous for its toxicity. Copper, the metal of choice used in the construction of stills, is also considered a beverage contaminant and is often related to the presence of EC in beverages. The study aimed to monitor the quality of cachaça by measuring the presence of copper and EC, and comparing the influences of sugarcane cultivation systems on the concentration of these contaminants. The varieties, RB 867515, RB 962869 and RB 85553, were cultivated under the following management systems: planting without fertilization; organic planting; and conventional planting. For cultivation, a completely randomized design in a factorial scheme of 3 varieties × 3 managements was used as experimental planning, in 4 replications. The concentrations of copper and EC in beverages were evaluated and submitted to univariate analysis of variance (p ≤ 0.05). The organic and conventional systems presented no significant variations in copper content, both of which are recommended for the planting of sugarcane as raw material for cachaça. From amongst the varieties evaluated, RB966928 presented the lowest concentrations of copper for the organic and conventional systems, and was the most recommended for the production of cachaça. To evaluate the EC concentration (μg L-1) in the cachaças produced, all beverages were considered in accordance with national legislation. Significant differences were observed between them, but the conventional and organic systems are favored for deployment in the cultivation of sugarcane as the raw material of cachaça. The same applies to the RB966928, RB867515 and RB855453 varieties.

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Cyanate as an Active Precursor of Ethyl Carbamate Formation in Sugar Cane Spirit

Cited by 20 publications

References 36 publications

Formation of Ethyl Carbamate during the Production Process of Cantonese Soy Sauce

Formation of Ethyl Carbamate during the Production Process of Cantonese Soy Sauce

Effect of Fermentation on Cyanide and Ethyl Carbamate Contents in Cassava Flour and Evaluation of Their Mass Balance during Lab-Scale Continuous Distillation

Monitoring the content of ethyl carbamate and copper in organic and conventional cachaça

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