• Title/Summary/Keyword: 4-hydroxy-5-methyl-3[2H]-furanone

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Isolation of 4-hydroxy-5-methyl-3[2H]-furanone from Pine Needles as an Antioxidative Principle (솔잎으로부터 항산화 성분인 4-hydroxy-5-methyl-3[2H]-furanone의 분리)

  • Boo, Yong-Chool;Jeon, Che-Ok;Oh, Ji-Yeon
    • Applied Biological Chemistry
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    • v.37 no.4
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    • pp.310-314
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    • 1994
  • An antioxidant was isolated from pine needles. This compound was identified as 4-hydroxy-5-methyl-3[2H]-furanone on the basis of spectroscopic evidences and by the comparison with the synthetic one from the Maillard reaction of xylose and glycine. It scavenged 1,1-diphenyl-2-picrylhydrazyl free radicals more efficiently than 4-hydroxy-2,5-dimethyl-3[2H]-furanone and $3-hydroxy-2-methyl-{\gamma}-pyrone$ did. It exhibited inhibitory effects on the autoxidation of 3,4-dihydroxyphenylalanine and linolenic acid.

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Anti-melanogenesis effect of 4-hydroxy-5-methyl-3[2H]-furanone, an antioxidant isolated from pine needles (솔잎에서 분리된 항산화 물질인 4-hydroxy-5methyl-3[2H]-furanone의 멜라닌 생성 억제작용)

  • 부용출;전체옥
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.20 no.1
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    • pp.1-13
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    • 1994
  • An antioxidative compound was isolated from pine needles. This compound was identified as 4-hydroxy-5-methyl-3[2H]-furanone on the basis of spectroscopic evidences. It scavenged 1,1-diphenyl-2-picrylhydrazyl free radicals more efficiently than maltol and tocopherol did. It exhibited an inhibitory effect on the lipid peroxidation of rat liver microsome induced by Fe(ll)/ascorbate, and the protective effect against UV cytotoxicity in cultured human fibroblasts. In addition, HMF appeared to prevent the cellular melanogenesis in the cultured murine melanoma cells, more effectively than kojic acid, a well known inhibitor of melanogenesis, while the former was not so effective as the latter for the inhibilion of the tyrosinase. Considering that cellular melanogenesis is a metabolic process triggered by oxidative stress, it was tentatively deduced that the antioxidative property of HMF may afford the effect against cellular pigmentation by alleviating the causative stress. This study provided a novel inhibitor of melanogenesis, that might be useful for the cosmetic applications.

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Quantitative determination of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in chlorinated drinking water using sample enrichment followed by liquid-liquid extraction and GC-MS (시료 농축 후 액-액-추출과 GC-MS를 이용한 염소 소독 음용수중 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone(MX)의정량 분석)

  • Kim, Hekap;Song, Byeong yeol
    • Analytical Science and Technology
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    • v.29 no.1
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    • pp.29-34
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    • 2016
  • This study explores the means by which MX can be effectively extracted from chlorinated water 3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), a potent mutagen commonly found in chlorinated drinking water at concentrations of up to a few hundred ng/L, was quantitatively determined using sample enrichment followed by liquid-liquid extraction (LLE), derivatization to methylated form, and analysis with GC-MS. A 4-L water sample was enriched to a concentration of 0.4 L using a vacuum rotary evaporator at 30 ℃. MX in the water was extracted using ethyl acetate (100 mL × 2) as a solvent and MX in the extract was methylated with 10 % H2SO4 in methanol. MX was recovered at a rate of 73.8 %, which was higher than that (38.1 %) for the resin adsorption method. The limit of quantification and repeatability (as relative standard deviation) were estimated to be 10 ng/L and 2.2 %, respectively. This result suggested that LLE can be used for the determination of MX in chlorinated water as an alternative to more time-consuming resin adsorption method.

Formation of Volatile Compounds from Maillard Reaction of D-Glucose with DL-Alanine in Propylene Glycol Solution (Propylene Glycol 용매계에서 DL-Alanine과 D-Glucose의 마이야르 반응에 의한 휘발성 화합물의 생성)

  • Kim, Young-Hoi;Kim, Ok-Chan;Lee, Jung-Il;Yang, Kwang-Ku
    • Korean Journal of Food Science and Technology
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    • v.20 no.2
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    • pp.157-163
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    • 1988
  • The volatile compounds produced from the browning reaction of 0.5M DL-alanine and 0.5M D-glucose mixture using propylene glycol as a reaction medium were analysed by gas chromatography and gas chromatography-mass spectrometry and effects of temperature($100^{\circ}C,\;120^{\circ}C,\;140^{\circ}C$) and time(20min, 2hours) on the formation of volatile compounds were investigated. Browning reaction were rapidly increased as the reaction temperature and time increased. From methylene chloride extracts, twenty six compounds, including 7 alkyl pyrazines. 4 pyrroles, 3 furans, 1 furanone and 11 miscellaneous compounds were identified. The relative amounts of pyrazines, pyrroles and furans were markedly increased as reaction temperature and time increased. The results showed that caramel-like and burnt sugar-like aroma produced by alanine -glucose reaction must be mainly comprised of nitrogeneous heterocyclic such as pyrazines, pyrroles and oxygen heterocyclic compounds such as 2-hydroxy-3-methyl-2-cyclopenten-1-one and 2,5-dimethyl-4-hydroxy-3(2H)-furanone.

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Changes in Fructosazines and Major Volatile Components of Burley Leaf Tobacco Extracts by Heat Treatment (버어리잎담배 추출물의 열처리에 의한 화학성분 변화)

  • 이재곤;곽재진;장희진;김옥찬
    • Journal of the Korean Society of Tobacco Science
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    • v.19 no.2
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    • pp.151-158
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    • 1997
  • Burley leaf tobacco extracts has been heated at loot for 2 hours and changes in non-volatile fructosazines and volatile components were investigated. Major changes for the heat treatment with corn syrup of burley leaf tobacco extracts were as follows, increases in the contents of 2,5-deoxyfructosazine and 2,5-fructosazine that is produce for the heating reaction of sugar and ammonia, production of pyraEine compounds, such as 2,6-dimethyl pyrazine,2,4-dimethyl pyrazine, ethrnyl pyrazine, methylethyl pyraxine, trimethyl pyrazine, 2-ethenyl-5-methyl pyrazine, 2-acetyl parazine and 2-acetyl-3-methyl pyrazine, increases in the content of furfuryl alcohol derived from sugar degrad ation, production of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one derived from thermal degradation of Amadori compounds.

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Studies on Volatile Flavor Compounds of Soy Sauce Residue (간장박의 휘발성 향기성분에 관한 연구)

  • Cha, Yong-Jun;Wang, Wenfeng;Cha, Ha-Ram
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.12
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    • pp.1755-1761
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    • 2016
  • Volatile flavor compounds in soy sauce residue (SSR) and acid hydrolysate of SSR (AHSSR) were analyzed by solid phase micro extraction (SPME)/gas chromatography (GC)/mass spectrometry (MSD) methods. A total of 79 compounds were detected in samples (66 SSR and 60 AHSSR). Quantitatively, alcohols (433.37 ng/g), aldehydes (273.01 ng/g), esters (236.80 ng/g), and aromatic hydrocarbons (180.66 ng/g) were dominant in the volatiles of SSR, whereas furans (249.27 ng/g) were only dominant in AHSSR (P<0.05). Among these, four esters, 3-methylbutyl acetate (banana/pear-like), ethyl 3-methyl butanoate (fruity), ethylbenzene acetate (wine-like), and ethyl 3-methyl butanoate (apple-like), three alcohols, 3-methyl-1-butanol (fruity/whisky-like), 2-phenylethanol (floral/sweet), and 1-octen-3-ol (mushroom-like), four aldehydes, (E)-2-phenyl-2-butenal (chocolate-like), benzaldehyde (almond-like), 3-methylbutanal (malty), and 2-phenylacetaldehyde (floral), four aromatic hydrocarbons, 4-ethyl-2-methoxyphenol (smoky/soy sauce-like), 4-ethylphenol (medicine-like), 4-vinyl-2-methoxyphenol (woody), and phenol (woody), and two furans, furfural (almond-like) and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), were major compounds in SSR, whereas seven compounds, including furfural, 5-methylfurfural (almond-like), 3-methyl-1-butanol, 2-phenylethanol, 4-ethyl-2-methoxyphenol, 3-methylbutanal, and benzaldehyde were major compounds in AHSSR.

Development of a Novel Yeast Strain Which Ferments Soy Sauce by Protoplast Fusion

  • Lee, Eun-Ju;Kim, Jong-Kyu
    • Journal of Microbiology and Biotechnology
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    • v.3 no.1
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    • pp.24-30
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    • 1993
  • In order to develop a novel yeast which produces the charateristic aroma of soy sauce, a protoplast fusion between Zygosaccharomyces rouxii WFS4 and Torulopsis versatilis IAM 4993 was carried out. Auxotrophic mutants as selective markers were obtained from Zygosaccharomyces rouxii and Torulopsis versatilis by treatment of N-methyl-N -nitro-N-nitrosoguanidine. The conditions of the protoplast formation and the regeneration for fusion were examined. The protoplast fusion using polyethylene glycol 4000 led to the fusion frequency of $4~5{\times}10^{-7}\;cells/ml$. Among fusants, a fusant ST723-F31 presented the best results in terms of the aromaticity of fragrance, the growth pattern, the resistance against salt and the degree of growth according to pH. It makes easy to control the production and the balance of aroma components so that it gives a good flavor, shortens the fermentation period and, simplifies the preparation process when using a bioreactor into which fusant is immobilized.

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Comparison of Flavor Compounds in Steamed- and Nonsteamed-Roasted Polygonatum odoratum Roots by Solid-Phase Microextraction (Solid-Phase Microextraction(SPME)을 이용한 둥굴레차의 증자 여부에 따른 향기성분 특성 비교)

  • Park, Nan-Young;Seo, Ji-Hyung;Kim, Young-Hoi;Kwon, Joong-Ho
    • Korean Journal of Food Science and Technology
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    • v.32 no.3
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    • pp.507-512
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    • 2000
  • The headspace flavors of roasted tea, prepared with steamed and nonsteamed polygonatum roots, were absorbed in solid-phase microextraction(SPME) fiber coated with $65\;{\mu}m$ of carbowax/divinylbenzene(CW/DVB) and analysed by GC-MS. The absorption conditions of SPME fiber for equilibrated headspace were selected as $60^{\circ}C$ and 30 min. In a comparison for both samples roasted at $130^{\circ}C$ for 15 min, gas chromatograms showed a similar pattern in overall profiles between steamed and nonsteamed samples before roasting, but some differences were observed in peak characteristics. From 40 separated peaks, 25 compounds were identified with both GC-MS and retention time comparison. The pyrazines including 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, 2-acetyl-1-pyrroline, etc. were higher in their contents in nonsteamed-roasted sample than steamed-roasted one. In particular, steamed-roasted polygonatum showed higher contents of acetic acid(8.17%) and hexanoic acid(5.43%) than the corresponding compounds of nonsteamed-roasted one, 2.40% and 2.00%.

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The Effect of pH on the Formation of Furfural Compounds in the Glucose and Fructose with Amino Acid Enantiomers in Maillard Reaction

  • Kim, Ji-Sang;Lee, Young-Soon
    • Preventive Nutrition and Food Science
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    • v.13 no.1
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    • pp.54-59
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    • 2008
  • This study was conducted to investigate the effect of pH on the formation of furfural compounds from glucose and fructose reacting with amino acid enantiomers in the Maillard reaction. Hydroxymethylfurfural (HMF) content was highest at pH 4.0, and decreased with increasing pH. HMF was significantly higher in glucose-based systems than fructose-based systems. Furfuryl alcohol (FFA) and 5-methyl-2-furaldehyde (MF) were not increased with increasing pH, and only small amounts were formed. In addition, 2-furaldehyde (F) was found to increase in the systems, as pH increased. However, the content was small and variable. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF) was only found in Glc/D-Asn, Glc/L-Lys and Fru/D-Lys system, but the content was not increased with increasing pH. 2-acetylfuran (AF) was higher in Glc (or Fru)/L-Lys and Glc (or Fru)/D-Lys systems at pH 7.0. However, at pH 4.0, the content of AF was higher in the Glc (or Fru)/Gly and Glc (or Fru)/L-Asn systems. Therefore, this study aimed to observe the effect of pH, sugars and amino acid enantiomers on the production of furfural and related compounds by the Maillard reaction. A clear tendency was observed for some classes of compounds to be more easily formed at higher or lower pH. HMF was more readily formed at lower pH, while FFA, F, DMHF and MF were inhibited by acidic conditions. Particularly, compounds like FFA, F and MF were not affected by pH changes. In addition, DMHF and MF were only formed in L-Lys and D-Lys system.

Evaluation of Lethality by Chemical Marker (Chemical Marker를 이용한 살균도 예측)

  • Choi, Yang-Mun;Kim, Hie-Joon
    • Korean Journal of Food Science and Technology
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    • v.29 no.1
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    • pp.32-37
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    • 1997
  • The rate constants and activation energies for formation of two chemical markers, M-1 and M-2 at sterilization temperatures were determined in a meatball system. Destruction rates for bacterial spores were also determined. The rate constants for M-1 and M-2 formation at $121^{\circ}C$ were 0.03 and 0.28 Abs/min, respectively. The activation energies for M-1 and M-2 were 27.9 and 24.6 Cal/mol. M-2 was formed faster than M-1 and reached a maximum and decreased. M-1 formation continued up to 30 min at $121^{\circ}C$ and 10 min at $131^{\circ}C$, which makes M-1 a more useful chemical marker for high $F_0$ values. The D-values for spores (B. stearothermophilus ATCC 12980) at 111, 114.4, 117.7 and $121^{\circ}C$ were 7.5, 4.5, 1.9 and 0.58 respectively. At temperatures between 111 and $121^{\circ}C$, there was a liner correlation between destruction of the spores and the M-1 formation. It was difficult to get accurate D-value at $126^{\circ}C\;and\;131^{\circ}C$, because almost all spores were dead before temperature at the center of the meatball reached $126^{\circ}C$. These data suggest that the chemical marker should be used to evaluate overprocessing as well as microbial lethality in aseptic processing.

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