Enzymatic Esterification of Carboxylic Acids and Higher Alcohols in Organic Medium
The studying of enzymatic esterification of carboxylic
acids and higher alcohols was performed by esterase Saccharomyces
cerevisiae in water-organic medium. Investigation of the enzyme
specificity to acetic substrates showed the best result with acetic acid
in esterification reactions with ethanol whereas within other
carboxylic acids the esterification decreased with acids: hexanoic >
pentanoic > butyric > decanoic. In relation to higher alcohols C3-C5,
esterification increased with alcohols propanol < butanol < amylol.
Also it was determined that esterase was more specific to alcohols
with branched chain such as isobutyl alcohol and isoamyl alcohol.
Data obtained may have important practical implications, for
example, for application of yeast esterase in producing various
volatile esters as well as in enzymatic transformation of volatile acids
and toxic fusel alcohols into volatile esters by providing the
production of the high quality alcoholic beverages with redused
content of higher alcohols as well as with improved degustational and
hygienic properties.
[1] H. Chuang, P. Chen, W. Wang, Y. Chen, J. Shaw, "Functional
proteomic analysis of rice bran esterases/lipases and characterization of
a novel recombinant esterase", J. Agric. Food. Chem., vol.59, pp. 2019-
2025, 2011.
[2] D.De Barros, P.Fernandez, J.Cabral, L.Fonseca, "Operational stability of
cutinase in organic solvent system: model esterification of alkyl esters",
Journal of Chemical Technology&Biotechnology, vol.85, pp.1553-
1560, 2010.
[3] N.Paroul, L.Grzegozeski, V.Chiaradia, H.Treichel, R.Cansian,
J.Oliveira, D. de Oliveira, "Production of geranyl propionate by
enzymatic esterification of geraniol and propionic acid in solvent-free
system", Journal of Chemical Technology&Biotechnology, vol.85,
pp.1636-1641, 2010.
[4] A.Faujan Bin, M.Mansour Ghaffari, B.Mahiran, A.Rahman,
M.Basyaruddin, "Ensymatic synthesis of betulinic acid ester as an
anticancer agent: optimization study", Biocatalysis and
Biotrandformation, vol.28, pp.192-200, 2010.
[5] Y.Inoue, S.Trevanichi, K.Fukuda, S.Izawa, Y.Wakai. A.Kimura, "Roles
of esterase and alcohol ecetyltransferase on production of isoamyl
acetate in Hansenula mrakii", J. Agric. Food. Chem., vol.45, pp.644-
649, 1997.
[6] S.Saerens, F.Delvaux, K.Verstrepen, P.Van Dijck, J.Thevelein,
F.Delvaux, "Parameters affecting ethyl ester production by
Saccharomyces cerevisiae during fermentation", Appl. Environ.
Microbiol., vol.74, pp.454-461, 2008.
[7] E.Rayder, D.Mirzarakhmetova, "Yeast esterase in water-organic
medium", Uzbek biological journal, Ôäû2, pp. 9-11, 2010.
[8] Vodka and ethyl alcohol. State Standard 30536-97, Minsk: IPK
Izdatelstvo standartov, 1998.
[9] O. Lowry, N.Rosenbryl, A.Farr, "Protein measurement with the folin
phenol reagent", J. Biol. Chem., vol.193, pp.265-275, 1954.
[10] D.Mirzarakhmetova, M.Rakhimov, S.Abdurazakova, Z.Akhmedova,
"Enzymatic conversion of invertase substrates in a water-organic
medium", Applied Biochemistry and Microbiology, vol.42, pp.150-155,
2006.
[11] N.Hu, D.Wu, K.Cross, S.Burikov, T.Dolenko, S.Patsaeva, D.Scheafer,
"Structurability: A collective measure of the structural differences in
VODKAs", J.Agric.Food.Chem., vol.58, pp.7394-7401, 2010.
[12] J.Ledauphin, H.Guichard, J.Saint-Clair, B.Picoche, D.Barillier,
"Chemical and sensorial aroma characterization of freshly distilled
Calvados. 2. Identification of volatile compounds and key odorants",
J.Agric.Food.Chem., vol.51, pp.433-442, 2003.
[13] J.Ledauphin, C. Le Milbeau, D.Barillier, D.Hennequin, "Differences in
the volatile compositions of French labeled brandies (Armagnac,
Calvados, Cognac, Mirabelle) using GC-MS and PLS-DA",
J.Agric.Food.Chem., vol.58, pp.7782-7793, 2010.
[1] H. Chuang, P. Chen, W. Wang, Y. Chen, J. Shaw, "Functional
proteomic analysis of rice bran esterases/lipases and characterization of
a novel recombinant esterase", J. Agric. Food. Chem., vol.59, pp. 2019-
2025, 2011.
[2] D.De Barros, P.Fernandez, J.Cabral, L.Fonseca, "Operational stability of
cutinase in organic solvent system: model esterification of alkyl esters",
Journal of Chemical Technology&Biotechnology, vol.85, pp.1553-
1560, 2010.
[3] N.Paroul, L.Grzegozeski, V.Chiaradia, H.Treichel, R.Cansian,
J.Oliveira, D. de Oliveira, "Production of geranyl propionate by
enzymatic esterification of geraniol and propionic acid in solvent-free
system", Journal of Chemical Technology&Biotechnology, vol.85,
pp.1636-1641, 2010.
[4] A.Faujan Bin, M.Mansour Ghaffari, B.Mahiran, A.Rahman,
M.Basyaruddin, "Ensymatic synthesis of betulinic acid ester as an
anticancer agent: optimization study", Biocatalysis and
Biotrandformation, vol.28, pp.192-200, 2010.
[5] Y.Inoue, S.Trevanichi, K.Fukuda, S.Izawa, Y.Wakai. A.Kimura, "Roles
of esterase and alcohol ecetyltransferase on production of isoamyl
acetate in Hansenula mrakii", J. Agric. Food. Chem., vol.45, pp.644-
649, 1997.
[6] S.Saerens, F.Delvaux, K.Verstrepen, P.Van Dijck, J.Thevelein,
F.Delvaux, "Parameters affecting ethyl ester production by
Saccharomyces cerevisiae during fermentation", Appl. Environ.
Microbiol., vol.74, pp.454-461, 2008.
[7] E.Rayder, D.Mirzarakhmetova, "Yeast esterase in water-organic
medium", Uzbek biological journal, Ôäû2, pp. 9-11, 2010.
[8] Vodka and ethyl alcohol. State Standard 30536-97, Minsk: IPK
Izdatelstvo standartov, 1998.
[9] O. Lowry, N.Rosenbryl, A.Farr, "Protein measurement with the folin
phenol reagent", J. Biol. Chem., vol.193, pp.265-275, 1954.
[10] D.Mirzarakhmetova, M.Rakhimov, S.Abdurazakova, Z.Akhmedova,
"Enzymatic conversion of invertase substrates in a water-organic
medium", Applied Biochemistry and Microbiology, vol.42, pp.150-155,
2006.
[11] N.Hu, D.Wu, K.Cross, S.Burikov, T.Dolenko, S.Patsaeva, D.Scheafer,
"Structurability: A collective measure of the structural differences in
VODKAs", J.Agric.Food.Chem., vol.58, pp.7394-7401, 2010.
[12] J.Ledauphin, H.Guichard, J.Saint-Clair, B.Picoche, D.Barillier,
"Chemical and sensorial aroma characterization of freshly distilled
Calvados. 2. Identification of volatile compounds and key odorants",
J.Agric.Food.Chem., vol.51, pp.433-442, 2003.
[13] J.Ledauphin, C. Le Milbeau, D.Barillier, D.Hennequin, "Differences in
the volatile compositions of French labeled brandies (Armagnac,
Calvados, Cognac, Mirabelle) using GC-MS and PLS-DA",
J.Agric.Food.Chem., vol.58, pp.7782-7793, 2010.
@article{"International Journal of Chemical, Materials and Biomolecular Sciences:63570", author = "D.T. Mirzarakhmetova", title = "Enzymatic Esterification of Carboxylic Acids and Higher Alcohols in Organic Medium", abstract = "The studying of enzymatic esterification of carboxylic
acids and higher alcohols was performed by esterase Saccharomyces
cerevisiae in water-organic medium. Investigation of the enzyme
specificity to acetic substrates showed the best result with acetic acid
in esterification reactions with ethanol whereas within other
carboxylic acids the esterification decreased with acids: hexanoic >
pentanoic > butyric > decanoic. In relation to higher alcohols C3-C5,
esterification increased with alcohols propanol < butanol < amylol.
Also it was determined that esterase was more specific to alcohols
with branched chain such as isobutyl alcohol and isoamyl alcohol.
Data obtained may have important practical implications, for
example, for application of yeast esterase in producing various
volatile esters as well as in enzymatic transformation of volatile acids
and toxic fusel alcohols into volatile esters by providing the
production of the high quality alcoholic beverages with redused
content of higher alcohols as well as with improved degustational and
hygienic properties.", keywords = "enzymes in non-conventional media, esterification,
higher alcohols, volatile esters, yeast esterase", volume = "6", number = "4", pages = "395-3", }