Composition of Typical Grape Brandy Fusel Oil

Webb, A. Dinsmoor; Kepner, Richard E.; Ikeda, Robert M.

doi:10.1021/ac60072a020

Cited by 44 publications

(17 citation statements)

References 12 publications

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“…Apparently, consistent with their high affinity (V max /K m ) for 2-oxo-butanoate found in cell extracts, pyruvate decarboxylase can compete efficiently for this substrate in vivo with isoleucine biosynthesis. This high affinity, combined with the high-level expression of pyruvate decarboxylase in anaerobic, fermentative yeast cultures (54), provides an adequate explanation for the occurrence of low concentrations of n-propanol in a wide range of yeast-based alcoholic beverages (i.e., wine, cider, and brandy [43,50,63]). Pyruvate decarboxylase is also likely to be responsible for the production of propanoate by aerobic S. cerevisiae cultures (35).…”

Section: Discussionmentioning

confidence: 99%

“…By analogy with previous studies of norvaline production in E. coli (6), such a pathway could encompass the carbon chain elongation of 2-oxobutanoate by the leucine biosynthesis enzymes Leu4/9, Leu2, and Leu1. Alternatively, the frequent occurrence of low con-centrations of n-butanol in fermented beverages (50,63) may reflect the pyruvate decarboxylase-mediated decarboxylation of plant-derived 2-oxo-pentanoate by S. cerevisiae. Extensive metabolic engineering of S. cerevisiae for the expression of a Clostridium n-butanol pathway (49) resulted in n-butanol titers that were 2 orders of magnitude lower than those observed for norvaline-grown batch cultures of a wild-type S. cerevisiae strain (Fig.…”

Section: Discussionmentioning

confidence: 99%

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Substrate Specificity of Thiamine Pyrophosphate-Dependent 2-Oxo-Acid Decarboxylases in Saccharomyces cerevisiae

Romagnoli

Luttik

Kötter

et al. 2012

Appl Environ Microbiol

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dFusel alcohols are precursors and contributors to flavor and aroma compounds in fermented beverages, and some are under investigation as biofuels. The decarboxylation of 2-oxo acids is a key step in the Ehrlich pathway for fusel alcohol production. In Saccharomyces cerevisiae, five genes share sequence similarity with genes encoding thiamine pyrophosphate-dependent 2-oxoacid decarboxylases (2ODCs). PDC1, PDC5, and PDC6 encode differentially regulated pyruvate decarboxylase isoenzymes; ARO10 encodes a 2-oxo-acid decarboxylase with broad substrate specificity, and THI3 has not yet been shown to encode an active decarboxylase. Despite the importance of fusel alcohol production in S. cerevisiae, the substrate specificities of these five 2ODCs have not been systematically compared. When the five 2ODCs were individually overexpressed in a pdc1⌬ pdc5⌬ pdc6⌬ aro10⌬ thi3⌬ strain, only Pdc1, Pdc5, and Pdc6 catalyzed the decarboxylation of the linear-chain 2-oxo acids pyruvate, 2-oxobutanoate, and 2-oxo-pentanoate in cell extracts. The presence of a Pdc isoenzyme was also required for the production of n-propanol and n-butanol in cultures grown on threonine and norvaline, respectively, as nitrogen sources. These results demonstrate the importance of pyruvate decarboxylases in the natural production of n-propanol and n-butanol by S. cerevisiae. No decarboxylation activity was found for Thi3 with any of the substrates tested. Only Aro10 and Pdc5 catalyzed the decarboxylation of the aromatic substrate phenylpyruvate, with Aro10 showing superior kinetic properties. Aro10, Pdc1, Pdc5, and Pdc6 exhibited activity with all branched-chain and sulfur-containing 2-oxo acids tested but with markedly different decarboxylation kinetics. The high affinity of Aro10 identified it as a key contributor to the production of branched-chain and sulfur-containing fusel alcohols. P yruvate decarboxylase (PDC) catalyzes the thiamine pyrophosphate (TPP)-dependent decarboxylation of pyruvate to acetaldehyde. In Saccharomyces cerevisiae, PDC is not only a key enzyme of alcoholic fermentation but is also required for the synthesis of cytosolic acetyl coenzyme A (acetyl-CoA) (15, 16), a key precursor for the synthesis of lipids and lysine. Three PDC isoenzymes are encoded by the S. cerevisiae PDC1, PDC5, and PDC6 genes (25). Pdc1, the main isoenzyme, is highly expressed under most conditions, while PDC5 exhibits tight transcriptional control, with high expression levels in the absence of a functional PDC1 gene (48), under nitrogen-limited conditions (3-5, 53), and under conditions of thiamine limitation (40). PDC1 and PDC5 expressions are subject to autoregulation (24) and require the transcription factor Pdc2 (23). The third PDC isoenzyme, Pdc6, has a very low content of sulfur-containing amino acids and is highly expressed in sulfur-limited cultures (4, 53). This transcriptional regulation of PDC6 has been interpreted as a "sulfur economy" response (4, 14, 53).The ARO10 and THI3 genes show sequence homology to the PDC genes but do not encode pyruva...

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Substrate Specificity of Thiamine Pyrophosphate-Dependent 2-Oxo-Acid Decarboxylases in Saccharomyces cerevisiae

Romagnoli

Luttik

Kötter

et al. 2012

Appl Environ Microbiol

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“…A carefully weighed amount (87.5 9.) of absolute ethanol (>99.95%) was added to the essence at this point to remove any remaining traces of water as the ethanol-water azeotrope (22) in the subsequent distillation. Distillation was then continued through the micro Podbielniak column over a period of several days until the remaining material in the boiler started to darken from decomposition, during which time 480 g. of essence, in addition to the added ethanol above, had been collected as distillate.…”

Section: Methodsmentioning

confidence: 99%

“…The alcohols present in approximately 15 mg. of each distillation fraction were converted to the 3,s-dinitrobenzoate derivatives by reaction with 3,s-dinitrobenzoyl chloride in anhydrous pyridine (22). The crude derivative preparation was then chromatographed (25), the bands eluted and identified by means of melting points and mixed melting points with known derivatives.…”

Section: Absorbtion Of 1% Bromine In CCL Solutionmentioning

confidence: 99%

Some Volatile Aroma Constituents of Vitis Vinifera Var. Muscat of Alexandria

Webb

Kepner

1957

Journal of Food Science

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“…Penniman et al (1937), through colorimetric methods, Schicktanz et al (1939) using azeotropic distillation, and Ikeda et al (1956) from chromatographic analysis, were able to identify the main alcohols (C2 to C5) present in fusel oil from different sources. Marvel and Hager (1924) and Webb et al (1952) found esters derived from short-chain alcohols, mainly i-amyl alcohol, and some carboxylic acids (C10 to C20). Results from comprehensive studies developed with improved analytic techniques, such as mass spectrometry (MS), high resolution gaseous chromatography (HRGC), headspace solid phase microextraction (SPME), among others, have shown a higher amount of components in different fractions of fusel oil.…”

Section: Introductionmentioning

confidence: 99%

Colombian fusel oil

Montoya¹,

Duran²,

Córdoba³

et al. 2016

ing.inv.

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By-products valorization in bio-fuels industry is an important issue for making the global process more efficient, more profitable and closer to the concept of biorefinery. Fusel oil is a by-product of bioethanol production that can be considered as an inexpensive and renewable raw material for manufacturing value-added products. In this work, results in terms of composition and physicochemical properties of six samples of fusel oil from industrial alcohol facilities are presented. Composition of the main components was established by gas chromatography. Complementary techniques, such as headspace solid-phase microextraction and gas chromatography-mass spectrometry (GC-MS), were used for detection of minor components. Fifty-five compounds were identified. Physicochemical properties such as density, acid value, moisture content and true boiling point curves were determined. Results are useful in the conceptual design of separation strategies for recovering higher alcohols, as well as to consider new options of valorization alternatives for fusel oil.Keywords: Fuel ethanol, higher alcohols, GC-MS analysis, solid-phase microextraction, TBP. RESUMENLos subproductos para valorización en la industria de los biocombustibles es un tema importante para alcanzar un proceso global más eficiente, más rentable y más cerca del concepto de biorrefinería. El aceite de fusel es un subproducto de la producción de bioetanol que se puede considerar como una materia prima barata y renovable para la fabricación de productos de valor agregado. En este trabajo se presentan los resultados en términos de composición y de las propiedades físico-químicas de seis muestras de aceite de fusel de las instalaciones industriales de alcohol. La composición de los componentes principales se estableció mediante cromatografía de gases. Técnicas complementarias, como espacio de cabeza, microextracción en fase sólida, y cromatografía de gasesespectrometría de masas (GC-MS), fueron utilizadas para la detección de componentes menores. Se identificaron cincuenta y cinco compuestos. Se determinaron las propiedades físico-químicas, como la densidad, el índice de acidez, el contenido de humedad y las curvas de puntos verdaderos de ebullición. Los resultados son útiles en el diseño conceptual de las estrategias de separación para la recuperación de alcoholes superiores, así como para comprobar las opciones de alternativas de valorización del aceite de fusel Palabras Clave: Etanol-combustible, alcoholes pesados, análisis GC-MS, micro-extracción en fase sólida, TBP.

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Composition of Typical Grape Brandy Fusel Oil

Abstract: °Paste titration method for acidity. de-ashed oxidized starches based on the corrected acidity is believed to be a better approximation to the "real carboxyl content" than calculations based on the uncorrected acidity.

Cited by 44 publications

References 12 publications

Substrate Specificity of Thiamine Pyrophosphate-Dependent 2-Oxo-Acid Decarboxylases in Saccharomyces cerevisiae

Substrate Specificity of Thiamine Pyrophosphate-Dependent 2-Oxo-Acid Decarboxylases in Saccharomyces cerevisiae

Some Volatile Aroma Constituents of Vitis Vinifera Var. Muscat of Alexandria

Colombian fusel oil

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