• Title/Summary/Keyword: Hydroxy Esters

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Flavor Components in Mash of Takju Prepared by Different Raw Materials (원료를 달리하여 담금한 탁주 술덧의 향기성분)

  • Lee, Joo-Sun;Lee, Taik-Soo;Park, Sung-Oh;Noh, Bong-Soo
    • Korean Journal of Food Science and Technology
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    • v.28 no.2
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    • pp.316-323
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    • 1996
  • Flavor components in mash of Takju prepared by different raw materials such as nonglutinous rice, glutinous rice, barley and wheat flour were detected by GC and GC-MS method using non-polar column. Seven alcohols, 15 esters, 10 organic acids, 1 aldehyde, 4 benzenes, 3 phenols, 8 alkans, 2 ketones and 5 others were found in takju after 16 day of fermentation. takju by wheat flour had the most various components of volatile flavor. Treatment with addition starter had less flavor component than that without addition starter in takju by nonglutinous rice. Nine kinds of flavor components including acetic acid ethyl ester, 3- methyl-1-butanol, acetic acid, ethyl benzene, acetic acid 3-methyl butyl ester, 2-phenylethanol, 2,6-di-tert-butyl-4-methyl phenol. plumbagic acid and 1,2-benzenedicarboxylic acid dibutyl ester were commonly detected in all the treatments. Especially, 2,4,0-trimethyl-1,3-benzenediamine was isolated in takju that was made of nonglutinous rice without addition starter. Diethyl sulfide, 4-methoxy benzaldehyde, docosane and 2-methyl propyl octadecanoic acid were isolated from takju by nonglutinous rice with addition starter. Propionic acid ethyl ester, acetic acid butyl ester, 2-methyl butane and 3-methyl pentane were isolated from takju glutinous rice. 2-Hydroxy-4-methyl pentanoic acid and 2-methyl tridecane were isolated from akju by barley 3-(Methylthio)-1-propanol. hexanoic acid ethyl ester, butanoic acid monomethyl ester, tridecanoic acid, ethyl tetramethyl cyclopentadiene and 1,5-diaza-2,9-diketocyclotetradecane were isolated from takju by wheat flour. Major volatile flavor components were acetic acid ethyl ester, 3-methyl-1-butanol, acetic acid and 2-phenylethanol.

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Stereoselective Synthesis of Novel Bestatin Analogs (새로운 베스타틴 유사체의 입체선택적 합성)

  • Seo, Youngran;Lee, SooBeom;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.26 no.1
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    • pp.111-115
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    • 2015
  • Two new analogs of bestatin were prepared from $\small{D}$-leucine and $\small{D}$-valine in a stereoselective and efficient way. An aminopeptidase inhibitor bestatin shows significant biological effects on immunomodulation and is marketed for the treatment of acute myelocytic leukemia. The key intermediates, trans-oxazolidine methyl esters 2a and 2b, were obtained with more than 20 to 1 stereoselectivity in a one-pot procedure by the three cascade reactions between N-hydroxymethyl protected ${\alpha}$-amino aldehydes (4a and 4b) and phenylsulfonylnitromethane ($PhSO_2CH_2NO_2$) and the following in-situ ozonolysis. Basic hydrolysis of 2a and 2b, and then the peptide coupling with $\small{L}$-Leu-OMe produced the protected derivatives of two new bestatin analogs, 3a and 3b, respectively. The new isobutyl and isopropyl analogs of bestatin (1a and 1b) were produced in overall 51% and 38% yields, respectively, with high stereoselectivity from the corresponding protected ${\alpha}$-amino aldehydes 4 in a six-step process.

Volatile Flavor Constituents of the Low-Salt Fermented Ascidian (저염 우렁쉥이 젓갈의 휘발성성분)

  • Hwang, Seok-Min;Kim, Yeong-A;Ju, Jong-Chan;Lee, So-Jeong;Choi, Jong-Duck;Oh, Kwang-Soo
    • Journal of agriculture & life science
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    • v.45 no.6
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    • pp.141-150
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    • 2011
  • In order to elucidate a flavor characteristics of the low-salt fermented ascidian (LFA), a volatile flavor constituents were extracted and analyzed by SDE apparatus and GC/MS. Salinity, pH and volatile basic nitrogen of the LFA were 8.0%, 5.17 and 23.0 mg/100 g, respectively. Total content of volatile flavor compounds identified from the LFA was $1,221.42{\mu}g/100g$ as cyclohexanol (internal standard), it were composed of 23 alcohols ($644.85{\mu}g/100g$) such as 1-octanol and 2-pentanol, 16 acids ($293.91{\mu}g/100g$) such as 2-hydroxy-propanoic acid and butanoic acid, 15 aldehydes ($153.61{\mu}g/100g$) such as trans-2-hexanal and benzaldehyde, 29 hydrocarbons ($97.65{\mu}g/100g$) such as 1,4-dimehyl-cyclooctane and 1-nonene, six aromatic compounds ($6.20{\mu}g/100g$), two esters ($2.07{\mu}g/100g$), two nitrogen-containing compounds ($19.09{\mu}g/100g$) and three micellaneous compounds ($4.04{\mu}g/100g$).

Anti-aging Effects of L-Carnitine on Human Skin (L-카르니틴의 사람피부에 대한 항노화 효과)

  • Lee Bum-Chun;Choe Tae-Boo;Sim Gwan-Sub;Lee Geun-Soo;Park Sung-Min;Lee Chun-Il;Pyo Hyeong-Bae
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.3 s.47
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    • pp.393-397
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    • 2004
  • L-Carnitine $({\beta}-hydroxy-{\gamma}-trimethyl-ammoniumbutyric{\;}acid)$ is a small water-soluble molecule important in mammalian fat metabolism. It is essential for the normal oxidation of fatty acids by the mitochondria, and is involved in the trans-esterification and excretion of acyl-CoA esters. In this paper, to investigate the relationship between aging and L-carnitine, we investigated the effects of in vitro matrix-metalloproteinase (MMP) inhibition and activity and expression of UYA-induced MMPs in human skin fibroblasts. Also, we studied to develop as anti-aging cosmetics with L-carnitine. Fluorometric assays of the proteolytic activities of MMP-1 (collagenase) were performed using fluorescent collagen substrates. ELISA (enzyme linked immune sorbent assay), gelatin-substrate zymography, RT-PCR ELISA techniques were used for the effects of L-carnitine on MMP expression, activity, and MMP mRNA expression in UVA irradiated fibroblast $(5\;J/cm^2)$, respectively. In addition, we performed clinical study with L-carnitine cream. L-carnitine inhibited the activities of MMP-1 in a dose-dependent manner and the $IC_{50}$ values calculated from semi-log plots were 2.45 mM, and L-carnitine showed strong inhibition on MMP-2 (gelatinase) activity in UVA irradiated fibroblast by zymography. Also, UVA induced MMP-1, 2 expression was reduced $43\%,\;53\%$ by treated with L-carnitine at 1.25 mM, and MMP-1 mRNA expression was reduced dose-dependent manner. Therefore L-carnitine was able to significantly inhibit the MMP activity, and regulate MMP expression in protein and mRNA level. The results of clinical study showed that $1.0\%$ L-carnitine treated group reduced wrinkle significantly compared with placebo treated group (P<0.05). All these results suggest that L-carnitine may be useful as new anti-aging cosmetics for protection against UVA induced Mm expression and activity.

Solution Phase Photolyses of Substituted Diphenyl Ether Herbicides under Simulated Environmental Conditions (모조(模造) 환경조건하(環境條件下)에서의 치환(置換) Diphenyl Ether 제초제(除草劑)의 광분해(光分解)에 관(關)한 연구(硏究))

  • Lee, Jae-Koo
    • Applied Biological Chemistry
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    • v.17 no.3
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    • pp.149-176
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    • 1974
  • Eight substituted diphenyl ether herbicides and some of their photoproducts were studied in terms of solution phase photolysis under simulated environmental conditions by using a Rayonet photochemical reactor. The test compounds absorbed sufficient light energy at the wavelength of 300 nm to undergo various photoreactions. All the photoproducts were confirmed by means of tlc, glc, ir, ms, and/or nmr spectrometry. The results obtained are summarized as follows: Solution phase photolysis of C-6989: An exceedingly large amount of p-nitrophenol formed strongly indicates the readiness of the ether linkage cleavage of this compound as the main reaction in all solvents used. Photoreduction of nitro to amino group(s) and photooxidation of trifluoromethyl to carboxyl group were recognized as minor reactions. Aqueous photolysis of p-nitrophenol: Quinone(0.28%), hydroquinone (0.66%), and p-aminophenol (0.42%) were confirmed as photoproducts, in addition to a relatively small amount of an unknown compound. The mechanisms of formation of these products were proposed to be the nitro-nitrite rearrangement via $n{\rightarrow}{\pi}^*$ excitation and the photoreduction through hydrogen abstractions by radicals, respectively. Solution phase photolysis of Nitrofen: Photochemical reduction leading to the p-amino derivative was the main reaction in n-hexane. In aqueous solution, the photoreduction of nitro to amino group and hydroxylation predominated over the ether linkage cleavage. Nucleophilic displacement of the nitro group by hydroxide ion and replacement of chlorine substituents by hydroxyl group or, to a lesser extent, hydrogen were also observed as minor reactoins. Solution phase photolysis of MO-338: Photoreduction of the nitro to amino group was marked in the n-hexane solution photolysis. In the aqueous solution, photoreduction of the nitro substituent and hydroxylation were the main reactions with replacement of chlorine substituents by the hydroxyl group and hydrogen, and cleavage of the ether linkage as minor reactions. Photolyses of MC-4379, MC-3761, MC-5127, MC-6063, and MC-7181 in n-hexane and cyclohexane: Photoreduction of the nitro group leading to the corresponding amino derivative and replacement of one of the halogen substituents by hydrogen from the solvent used were the key reactions in each compound. Aqueous photolysis of MC-4379: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, hydroxylation, and replacement of the nitro by hydroxy group were prominent with photoreduction and dechlorination as minor reactions. Aqueous photolysis of MC-3761: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, and photoreduction followed by hydroxylation were the main reactions. Aqueous photolysis of MC-5127: Replacement of carboxyethyl by hydrogen was predominant with ether linkage cleavage, photoreduction, and dechlorination as minor reactions. It was obvious that the decarboxyethylation proceeded more readily than decarboxymethylation occurring in the other compounds. Aqueous photolysis of MC-6063: Cleavage of the ether linkage and photodechlorination were the main reactions. Aqueous photolysis of MC-7181: Replacement of the carboxymethyl group by hydrogen and monodechlorination were the remarkable reactions. Cleavage of the ether linkage and hydroxylation were thought to be the minor reactions. Aqueous photolysis of 3-carboxymethyl-4-nitrophenol: The photo-induced Fries rearrangement common to aromatic esters did not appear to occur in the carboxymethyl group of this type of compound. Conversion of nitro to nitroso group was the main reaction.

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