• Title/Summary/Keyword: furan-2-ol

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Isolation and Identification of Low Molecular Volatile Compounds from Ethyl Acetate Layer of Korean Black Raspberry (Rubus coreanus Miq.) Wine (복분자(Rubus coreanus Miquel) 와인의 ethyl acetate 획분으로부터 저분자 휘발성 화합물들의 분리 및 구조해석)

  • Cho, Jeong-Yong;Kim, Seong-Ja;Lee, Hyoung-Jae;Kim, Jin-Young;Lym, Ik-Jae;Kang, Seong-Koo;Park, Keun-Hyung;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.43 no.5
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    • pp.558-563
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    • 2011
  • In the course of our investigation for chemical constituents in the ethyl acetate layer of Korean black raspberry wine, five compounds were isolated and purified by silica gel column chromatography and high-performance liquid chromatography. The isolated compounds were identified as ethyl succinate (1), vanillic acid (2), ethyl 3,4-dihydroxybenzoate (3), furan-2-ol (4), and 4-(4-hydroxyphenyl)butan-2(S)-ol (5) based on the spectroscopic data of electrospray ionization tandem mass spectrometry and nuclear magnetic resonance. The presence of 2 in Korean black raspberry has previously reported. However, 1 and 3-5 in Korean black raspberry and its wine were isolated for the first time.

Identification of 1-Furan-2-yl-3-pyridin-2-yl-propenone, an Anti-inflammatory Agent, and Its Metabolites in Rat Liver Subcellular Fractions

  • Lee, Sang-Kyu;Jeon, Tae-Won;Basnet, Arjun;Jeong, Hye-Gwang;Lee, Eung-Seok;Jeong, Tae-Cheon
    • Archives of Pharmacal Research
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    • v.29 no.11
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    • pp.984-989
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    • 2006
  • 1-Furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) has been characterized to have an anti-inflammatory activity through the inhibition of the production of nitric oxide and tumor necrosis $factor-{\alpha}$. In the present studies, the phase 1 metabolism of FPP-3 was investigated in rat liver microsomes and cytosols. When FPP-3 was incubated with rat liver microsomes and cytosols in the presence of NADPH. 2 major peaks were detected on a liquid chromatography/electrospray ionization-mass spectrometry. Two metabolites (i.e., M1 and M2) were characterized as reduced forms on propenone: M1 (1-furan-2-yl-3-pyridin-2-yl-propan-1-one) was the initial metabolite and M2 (1-furan-2-yl-3-pyridin-2-yl-propan-1-ol) was a secondary alcohol believed to be formed from M1.

Changes in Aroma Compounds of Several Byeolmijang during Aging (여러 가지 별미장의 숙성과정 중 향기성분의 변화)

  • Woo, Koan-Sik;Yu, Sun-Mi;Im, Sung-Kyung;Chun, Hye-Kyung;Kwon, Oh-Chan;Lee, Junsoo
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.33 no.10
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    • pp.1689-1697
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    • 2004
  • Aroma compounds in 6 different Byeolmijang were extracted by SDE (simultaneous steam distillation extraction) and analyzed with GC (gas chromatography) and GC/MS (mass-spectrometry). The major aroma compounds in the 6 different Byeolmijang during aging were 1-octene-3-ol, hexanal, benzeneacetaldehyde, benzaldehyde, furfural, pyrazine compounds, benzyl-alcohol, furan compounds and phenol type compounds. Generally, benzeneacetaldehyde, benzaldehyde, furfural, pyrazine compounds and phenol type compounds were increased during aging. On the other hand, 1-octene-3-ol, hexanal, benzyl-alcohol and furan compounds were decreased during aging. 2-Heptenal and 2,4-decadienal in Daemaekjang, pyrazine and phenol type compounds in Sanghwangjang and phenol type compounds including phenol, 4-methoxy-phenol and 4-ethyl-phenol in Mujang were identified as major aroma compounds, respectively. The major aroma compound in Bizijang was 2,4-decadienal and in Sodujang, the major aroma compounds were 2,3-dihydro-benzofuran and 2-methoxy-4-vinylphenol. Linaool, geraniol, 6-elemene, 6-lonone and ledene were detected in Jigeumjang possibly due to the addition of powdered red pepper.

A Model Study toward the Synthesis of Xestoquinone and Halenaquinone

  • Ahn, Chan-Mug;Woo, Ho-Bum
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.240.2-240.2
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    • 2003
  • A strategy for synthesis of the furan-fused tetracyclic core of xestoquinone and halenaquinone was explored through a model study. Methyl 8-oxo-4-methyl-4-phenyl-2,7-nonadiynoate was prepared from hydratroponitrile and 3-butyn-1-ol as starting materials. The intramolecular cycloaddition of this intermediate as a key step will be involved.

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A Model Study toward the Synthesis of Xestoquinone (Xestoquinone의 합성에 대한 모델연구)

  • Ahn Chan Mug;Ho Bum Woo
    • Journal of the Korean Chemical Society
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    • v.47 no.4
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    • pp.354-362
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    • 2003
  • A strategy for synthesis of the furan-fused tetracyclic system of xestoquinone was explored through a model study. Using 3-butyn-1-ol as a starting material, 5-iodo-1-methoxymethoxy pentyne (5) was prepared in 5 steps. Reaction of ethyl 2-phenylpropanoate with 5 gave ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate (6) in 88% yield, and then methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate (13), the key intermediate, was synthesized in 6 steps from the ester 6. Intramolecular cycloaddition reaction of 13 afforded isobenzofuran 14 in 5% yield, which was converted to the tetracyclic structure 15 in the presence of Lewis acid.

검은비늘버섯(Pholiota adiposa)의 향기특성

  • 오은희;정은경;윤향식;주선종;김기식;장후봉;김숙종
    • Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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    • 2003.10a
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    • pp.139.1-139
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    • 2003
  • 검은비늘버섯(Pholiota adipose)의 향기성분을 조사하기 위해 생버섯을 SDE로 추출하여 농축한 후 GC/MS로 정성하였으며 향기특성은 GC/olfactometry를 이용하여 확인하였다. GC/MS로 정성된 화합물은총 52종이었으며 함량이 높은 화합물로는 hexanal (8.55%), n-heptadehyde(13.02%), 2-pentyl furan(4.82%), benzeneacetaldehyde (3.34%), (E,Z) -2,4-Decadienal(3.06%), 6,10-dimethyl 5,9-undecadien-2-one(11.75%) 이었으며 1-octen-3-ol, 3-octanone, 3-octanol, 2-octanol, 1-octanol 등의 C8화합물이 검출되었다. Sniffing test 결과 주요한 향기특성으로는 burnt odor(843, +++), fresh fruity odor(1-hexanol ++), fresh mushroom(n-heptaldehyde, +++), mushroom like(1023, +++), refreshing sweet(benzeneacetaldehyde, +) 등으로 나타났다.

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Aroma Characteristics of Byeolmijang with Optional Ingredients (부재료 첨가에 따른 별미장의 향기특성)

  • Woo, Koan-Sik;Han, Seo-Young;Yoon, Hyang-Sik;Lee, Jun-Soo;Jeong, Heon-Sang;Kim, Haeng-Ran
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.35 no.6
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    • pp.738-746
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    • 2006
  • Aroma compounds in four different Byeolmijang made from optional ingredient addition were extracted by SDE (simultaneous steam distillation extraction) and analyzed with GC (gas chromatography) and GC/MS (mass-spectrometry). The major aroma compounds in the four different Byeolmijang during aging were 1-octene-3-ol, hexanal, benzeneacetaldehyde, benzaldehyde, fufural, pyrazine, furan and phenol type compounds. Generally, benzeneacetaldehyde, benzaldehyde, fufural and phenol type compounds were increased during aging. On the other hand, 1-octen-3-ol, hexanal and furan were decreased during aging. Furfural, 2-furanmathanol and benzeneacetaldehyde in Sanghwangjang, 3-methyl-1-butanol, phenol and 1H-indole in Mujang, hexanal, 1-octen-3-ol and 2,4-decadienal in Bizijang and hexanal, tetramethylpyrazine and 2-methoxy-4-vinylphenol in Jigeumjang were identified as major aroma compounds, respectively. Generally, the major aroma compound in four different Byeolmijang with optional ingredient was similar with control and pyrazine, furan and phenol type compounds were decreased to addition with optional ingredient. The major aroma compound in Sanghwangjang with optional ingredient (onion) were 1-hexanol and 2,5-dimethylthiophene and the major aroma compounds were 1,2,4-trithiolane and 2-buthyl-2-octenal in Mujang with optional ingredient (Letinus edodes). Furfural, benzaldehyde, benzeneacetaldehyde, 1,2,4-trithiolane and lenthionine were detected in Bizijang due to the addition of powdered Letinus edodes. Linaool and ${\beta}-lonone$ were detected in Jigeumjang due to the addition of powdered red pepper.

Volatile Flavor Components in Soybean Sprouts (콩나물의 향기 성분 분석)

  • Kim, Yong-Ho;Lee, Kyong-Ae;Kim, Hee-Seon
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.54 no.3
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    • pp.314-319
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    • 2009
  • The identification of volatile constituents in foods is important in creating flavor compounds to improve the flavor of foods. This study was conducted to identify the flavor compounds in soybean sprouts cultivated with 4 different types of soybean seeds. A total of 52 flavor compounds were identified and composed mainly of alcohols (16), aldehydes (17), ketones (10), acids (2), furans (2), and miscellaneous compounds (5). Sprouts cultivated with Dawonkong and Orialtae showed 46 flavor compounds whereas Pungsannamulkong and Nokchaekong was 49 and 50. In total flavor compounds contents, Orialtae was the highest (19.3 mg/kg RC) and followed by Pungsannamulkong (15.83 mg/kg RC), Dawonkong (13.2 mg/kg RC), and Nokchaekong (11.3 mg/kg RC) in that order. Two groups including alcohols and aldehydes were detected high amounts in which their ratio were analyzed 32% and 51% in total flavor contents, respectively. It may be responsible for flavor in soybean sprouts. In case each flavor compound content, 2-hydroxybenzaldehyde was detected the major compound and hexanol, 1-octen-3-ol, and hexanal that the main compounds in lipid oxidation of soybean products were identified the main volatile flavor compounds in soybean sprouts.

Effect of Refrigerated and Thermal Storage on the Volatile Profile of Commercial Aseptic Korean Soymilk

  • Kim, Hun;Cadwallader, Keith R.;Jeong, Eun-Jeong;Cha, Yong-Jun
    • Preventive Nutrition and Food Science
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    • v.14 no.1
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    • pp.76-85
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    • 2009
  • This study determined the effect of refrigerated and thermal storage on the volatile profile of commercial aseptic soymilk. Volatile components in commercial aseptic soymilk stored either under refrigerated ($4^{\circ}C$) or thermal ($55^{\circ}C$) conditions for 30 days were periodically analyzed by combined solvent-assisted flavor evaporation-gas chromatography-mass spectrometry (SAFE-GC-MS). The concentrations of most of the volatile components, including aldehydes, ketones, alcohols, acids, nitrogen- and sulfur-containing compounds, alkylfurans, furan derivatives and phenolic compounds, were affected to a greater extent by thermal storage compared with refrigerated storage. Profound increases in some volatile compounds with low odor detection thresholds, such as hexanal, octanal, (E)-2-octenal, (E,E)-2,4-decadienal, 1-octen-3-ol, 3-ethyl-2,5-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 2-pentylfuran, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, dimethyl trisulfide, guaiacol, 4-vinylguaiacol and 4-vinylphenol, were observed in thermal stored soymilk. The volatile profile changes caused by thermal storage may influence the aroma quality of thermal-stored aseptic soymilk.

Volatile Flavor Compounds Identified from the Sauces Made with Waste of Shrimp, Crab and Lobster (새우, 게 및 바다가재의 부산물로 만든 소스의 휘발성 향기 성분)

  • Lee, Kyeoung-Im;Cho, Ji-Eun;Ahn, Hung-Ki
    • Culinary science and hospitality research
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    • v.13 no.1 s.32
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    • pp.119-128
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    • 2007
  • Volatile flavor compounds of sauces made from shrimps, crabs or lobsters were analyzed by the combination of canister system, gas chromatography(GC) and mass selective detector(MSD). Of 72 total volatile compounds from 4 kinds of sauces, 45 compounds were identified from shrimp sauce(SS). Ten alkanes, 5 ketones, 3 aldehydes were obtained from SS. Especially, 3-methyl-2-butanone, 2-pentanamine, isobutane, 3-methyl-2-butanol, carbon disulfide and dimethyl sulfide were predominant compounds in SS. In crab sauce(CS), there were 18 compounds identified, including 4 alcohols, 4 alkanes, 3 aldehydes, 2 ketones, acid and amine. 2-Methoxy ethanol, trimethyloxirane and 3-buten-1-ol were special volatile compounds in CC. Volatile compounds from lobster head sauce(LHS) or lobster shell sauce(LSS) were 16 or 18 kinds respectively. The major volatile compounds of LHS were formic acid, 1-propanethiol, $\beta$-pinene and allyl sulfide, and those of LSS were acids, pentane, 3-methyl-1-butanol and 2,4-dimethyl-3-pentanone. It was thought that the volatile compounds identified from sauces as well as shrimps, crabs or lobsters might come from wine, onions, bay leaves or celery used as minor ingredients.

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