• Microbiology and Biotechnology Letters
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• v.26 no.1
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• pp.50-54
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• 1998

Ethyl caproate is one of the important flavor compounds produced during the brewing of rice wine. The rice wine yeast and koji were reported to produce the esterases which synthesize and also hydrolyze ethyl caproate. From the results of monitoring the esterase activities of rice wine yeast and koji, their roles for producing ethyl caproate during brewing were postulated. In case of rice wine yeast, the production of esterase synthesizing ethyl caproate was influenced by the substrate, caproate but that of esterase hydrolyzing ethyl caproate was promoted by ethyl caproate but inhibited by caproate. The production of esterases of koji were not influenced by the substrates for ethyl caproate production but influenced by the growth of koji. The maximum concentration of ethyl caproate produced by rice wine yeast was 0.4 ppm in this research but the production of ethyl caproate by koji was not detected under our experimental conditions. Considering the results of this research, ethyl caproate is not produced by the esterases of koji during brewing but produced by the esterases of rice wine yeast. The growth of rice wine yeast represses that of koji because of the high concentration of ethanol produced by rice wine yeast. The esterases of rice wine yeast may decide the production of ethyl caproate during brewing.

• Journal of Microbiology and Biotechnology
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• v.5 no.5
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• pp.274-279
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• 1995

Ethyl caproate, one of the major flavor compounds deciding the quality of sake (Japanese wine), is produced during the brewing by the action of alcohol acyltransferase and esterases of sake yeast and koji mold. Extracellular esterases of Aspergillus oryzae required for ethyl caproate synthesis were purified partially. The enzymes had different optimum pH and affinity toward substrates. Substrate preferences and inhibition features showed the three enzymes to be B-type esterases or carboxylesterases (EC 3.1.1.1).

• Korean Journal of Food Science and Technology
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• v.32 no.5
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• pp.1035-1042
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• 2000

Volatile compounds of kochujang prepared with meju and koji were analyzed by using a purge and trap method during fermentation and identified with GC-MSD. Thirteen alcohols, seventeen esters, seven acids, six aldehydes and nine others were identified. Twenty four volatile flavor detected immediately after making kochujang including 7 alcohols and 9 esters. Six volatile flavor compounds including 1 alcohol and 3 esters were more found after 30 day of fermentation and increased to forty nine of volatile compounds after 150 days. Six alcohols such as ethanol, 3-methyl-butanol, 2-methyl-1-propanol, 1-butanol and nine esters such as ethyl acetate, ethyl butyrate, ethyl caproate, ethyl carpylate and seven others were commonly found through the fermentation period. Peak area (%) of 1-butanol was the highest one among the volatile flavor compounds after 30 day of fermentation and ethanol showed the highest peak area after 60-90 day and 150 day of fermentation, and 3-methyl-1-butanol showed the highest peak area after 120 day of fermentation, 2-Methyl-1-propanol, ethyl butyrate, ethyl acetate, acetaldehyde, ethoxyethene, ethenone, methylbenzene were detected in the kochujang during the fermentation.

• Applied Biological Chemistry
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• v.49 no.2
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• pp.97-102
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• 2006

This study was carried out to investigate the components of organic acids and flavour in flour ferment composed of water, flour, seed mash, yeast and lactic acid bacteria. The pH and TTA in the control (flour ferment without seed mash and lactic bacteria) were 5.6 and 2.5, respectively at 6 hrs after culturing; however, those in flour ferment with seed mash and different lactic acid bacteria were 4.63-4.69 and 9.0-9.9, respectively. Organic acid contents were propionic acid 0.09 mg/g, lactic acid 0.06 mg/g and acetic acid 0.04 mg/g in flour ferment without seed mash, whereas lactic acid 0.23-0.27 mg/g, propionic acid 0.21 mg/g, and acetic acid 0.06-0.08 mg/g in flour ferment with seed mash and lactic acid bacteria. Flavour compounds including ethyl capylate, ethyl caproate, ethyl acetate, ethyl caprate and phenylethyl acetate were detected to be high in flour ferment with seed mash and different lactic acid bacteria than in the control. This results show that the use of flour ferment with seed mash and lactic acid bacteria in making bread will enhance bread flavour.

• Mycobiology
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• v.45 no.2
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• pp.119-122
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• 2017

Herein, nuruks derived from non-glutinous and glutinous rice inoculated with Aspergillus oryzae N159-1 (having high alpha-amylase and beta-glucosidase activities) were used to produce Korean alcoholic beverages. The resultant beverages had enhanced fruity (ethyl caproate and isoamyl alcohol) and rose (2-phenethyl acetate and phenethyl alcohol) flavors and high taste scores.

• Microbiology and Biotechnology Letters
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• v.27 no.6
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• pp.491-499
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• 1999

A great variety of the volatile metabolic by-products was formed in yeast cell during alcohol fermentation. The seibel grape (Vitis labrasca) which was grown in the Southern Korea used for wines. The objective of this research was to identify the volatile flavor compounds during alcohol fermentation and aging at 12$^{\circ}C$. saccharomyces cerevisiae and Schizosaccharomyces pombe were inoculated and fermented in seibel grape must. The volatile flavor compounds of logarithmic, stationary and death phases were extracted, concentrated and identified by gas chromatography/mass spectrometer (GC/MS). The volatile flavor compounds were determined by a Hewlett-Packard 5890 II Plus GC which was equipped with Supelcowax 10 fused silica capillary column (60m$\times$0.32mm$\times$0.25${\mu}{\textrm}{m}$ film thickness) wall coated with polyethyleneglycerol. The scan detection method allowed the comparison of the spectrum from the chromatogram of volatile flavor compounds to those in data Wileynbs base library. Among the volatile compounds collected by ether-hexane extraction method, the evolution of 20 main compounds, such as 9 esters (ethyl butyrate, isoamyl acetate, ethyl caproate, n-hexyl acetate, ethl caprylate, ethyl caprate, diethy succinate, ethyl hexadecanoate, 2-pheneethyl acetate), 4 alcohols (3-methyl-1-butanol, 1-hexanol, 1-heptanol, benzoethanol), 4 ketones and acids (2-octanone, caproic acid, caprylic acid, capric acid), 2 furan and phenol (2,6-bis(1,1-dimethyl ethyl)phenol, 2,3-dihydrobenzofuran) were observed during alcohol fermentation and aging. The production of the esters during alcohol fermentation with S. cerevisiae was higher than those of Sch. pombe. The sensory scores of the aged wine samples in aroma, taste and overall acceptability were not significantly different(p<0.05).

• Journal of Microbiology and Biotechnology
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• v.33 no.10
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• pp.1337-1350
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• 2023

Caproic acid is a precursor substance for the synthesis of ethyl caproate, the main flavor substance of nongxiangxing baijiu liquor. In this study, Clostridium butyricum GD1-1, a strain with high caproic acid concentration (3.86 g/l), was isolated from the storage pit mud of nongxiangxing baijiu for sequencing and analysis. The strain's genome was 3,840,048 bp in length with 4,050 open reading frames. In addition, virulence factor annotation analysis showed C. butyricum GD1-1 to be safe at the genetic level. However, the annotation results using the Kyoto Encyclopedia of Genes and Genomes Automatic Annotation Server predicted a deficiency in the strain's synthesis of alanine, methionine, and biotin. These results were confirmed by essential nutrient factor validation experiments. Furthermore, the optimized medium conditions for caproic acid concentration by strain GD1-1 were (g/l): glucose 30, NaCl 5, yeast extract 10, peptone 10, beef paste 10, sodium acetate 11, L-cysteine 0.6, biotin 0.004, starch 2, and 2.0% ethanol. The optimized fermentation conditions for caproic acid production by C. butyricum GD1-1 on a single-factor basis were: 5% inoculum volume, 35℃, pH 7, and 90% loading volume. Under optimal conditions, the caproic acid concentration of strain GD1-1 reached 5.42 g/l, which was 1.40 times higher than the initial concentration. C. butyricum GD1-1 could be further used in caproic acid production, NXXB pit mud strengthening and maintenance, and artificial pit mud preparation.

• Journal of Nutrition and Health
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• v.4 no.4
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• pp.39-46
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• 1971

Since ${\beta}-aminoethylphosphonic$ acid was discovered in the living organism, the biosynthesis and biological function of aminophosphonic acids have been extensively studied. The purpose of this project consists in the two parts: 1)the preparation of DL-1-amino-2-phenylethylphosphonic acid (Phenylalanine aminophosphonic acid) and DL-1-amino-3-methylbutyl-phosphonic acid (Isoleucine aminophosphonic acid) by the method of Chamber and Isbell. 2) the study of metabolism and biological functions of those synthetic materials by the animal experiment (white rats) The importance of this project proved to be the first experience fed by animals for the elucidation of biochemical and metabolic functions in the animal body. The following organic synthesis of DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenylethylphosphonic acid are studied. 1)Synthesis of DL-1-amino-3-methylbutylphosphonic acid a) Synthesis of Iso-butylbromide b) Synthesis of Ethyl iso-butylmalonate c) Synthesis of Iso-caproic acid d) Synthesis of $Ethyl-{\alpha}-bromo$ iso-caproate e) Synthesis of $Triethyl-{\alpha}-phosphono$ iso-caproate f) Synthesis of DL-1-amino-3-methylbutylphosphonic acid 2)Synthesis of DL-1-amino-2-phenylethylphosphonic acid a) Synthesis of Diethyl phosphite b) Synthesis of Ethylchloro acetate c) Synthesis of Triethyl phospho acetate d) Synthesis of Triethyl benzyl phospho acetate e) Synthesis of DL-1-amino-2-phenylethylphosphonic acid The synthetic compounds; DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenyl ethylphosphonic acid which are essential amino acid (isoleucine, phenylalanine)analogue are supplemented to the animal diet at the level of 0.2% and 0.4% for isoleucine analogue and 0.35% and 0.7% for phenylalanine analogue. The plain isoleucine and phenylalanine at the same level in the diet are fercilitated as comparable groups in this study. Two sets of experience including 100 male rats were carried out for seven weeks each total 14 weeks. During this period, urine samples, and each big organs were collected for the analysis of total nitrogen, phosphorus, and glycogen contents in the individual samples by Micro Kjeldahl Fisk & Subbarow and Nelson Somogye, method. 1) The result of the project a) The yield of DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenylethylphosphonic acid showed low tendency at the level of 12.5% and 20% Melting point of those two compounds were very high and the ${\alpha}-amino$ group in the synthetic compounds showed positive reaction with ninhydrin in the violet color. b) Ail the experimental groups included in this study revealed statistically no significant difference in the organ weight, total body nitrogen retention and urinary phosphorus excretion This means isoleucine aminophosphonic acid and Phenylalanine aminophosphonic acid were utilized in the body as much as the plain amino acids, isoleucine and phenylalanine did. c) The glycogen contents in the liver of the phenylalaine aminophosphonic acid gruop showed higher statistically significant(p<0.05) in the comparision with the group of the Phenylalanine and the Standard-2. It was noteworthy that the higher glycogen content in the liver might indicate the significance in the incorporation of phenylalanine aminophosphonic acid into the intermediate of tricarboxylic acid cycle as activated state.