• Title/Summary/Keyword: Benzoquinone

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Structural and Solubility Characteristics of Coenzyme Q10 Complexes Including Cyclodextrin and Starch (사이클로덱스트린과 전분을 이용한 coenzyme Q10 복합체의 특성 연구)

  • Lee, Joon-Kyoung;Lee, Hyun-Joo;Lim, Jae-Kag
    • Korean Journal of Food Science and Technology
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    • v.46 no.2
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    • pp.180-188
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    • 2014
  • This study focused on assessing the solubility and structural characteristics of two types of coenzyme $Q_{10}$ ($CoQ_{10}$) complexes: the $CoQ_{10}$-starch and the $CoQ_{10}$-cyclodextrin complexes. The solubility of $CoQ_{10}$-starch complex increased significantly as the temperature was increased. However, the solubility of $CoQ_{10}$-cyclodextrin complex reached a peak at $37^{\circ}C$, and strong aggregation occurred at $50^{\circ}C$. When the temperature was raised to $80^{\circ}C$, the $CoQ_{10}$-cyclodextrin complex dissociated owing to the weakening of bonds, resulting in $CoQ_{10}$ emerging at the surface of water. Therefore, $CoQ_{10}$-cyclodextrin complexes have lower solubility, due to their reduced heat-stability, than do the $CoQ_{10}$-starch complexes. Structural differences between the two $CoQ_{10}$ complexes were confirmed by Fourier transform infrared (FT-IR) spectroscopy, X-ray diffractometer (XRD), and differential scanning calorimeter (DSC). The $CoQ_{10}$-cyclodextrin complex included an isoprenoid chain of $CoQ_{10}$, while the $CoQ_{10}$-starch complex included both the benzoquinone ring and the isoprenoid chain of $CoQ_{10}$. These results suggest that $CoQ_{10}$-starch complexes possess higher heat-stability and solubility than do the $CoQ_{10}$-cyclodextrin complexes.

Saturated- and Unsaturated-Azamacrocyclic Complexes $(M = Co^{3+}, Fe^{3+}$ or $Mn^{3+})$ Catalyzed Oxidation of Hindered Phenols by Molecular Oxygen under Sodium Borohydride (Sodium Borohydride 하에서 산소에 의한 포화- 및 불포화-질소주게 거대고리 착물 $(M=Co^{3+},\;Fe^{3+}$$Mn^{3+})$을 촉매로 한 Hindered Phenols의 산화반응)

  • Yu-Chul Park;Seong-Su Kim;Hun-Gil Na
    • Journal of the Korean Chemical Society
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    • v.37 no.7
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    • pp.648-654
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    • 1993
  • $[M(cyclam)X_2]Y(M=Co^{3+},\;Fe^{3+},\;Mn^{3+}\;:\;X=Cl-^,\;Br^-,\;NCS^-\;:\;Y=Cl^-,\;Br^-,\;NCS^-),\;[Co(trans-14-diene)X_2]Y(X=Cl^-,\;Br^-\;:\;Y=ClO_4^-)\;and\;[Co(trans-14-diene)](ClO_4)_2$ were able to activate an molecular oxygen under sodium borohydride. 2,4-di-tert-butylphenol and 2,6-di-tert-butylphenol reacted with activated molecular oxygen to give 2,4-tert-butyl-1,6-benzoquinone(BQ) and 3,5,3',5'-tetra-tert-butyldiphenoquinone(DPQ). The saturated tetraazamacrocyclic complexes, $[Co(cyclam)X_2]Y$, were more an effective catalyst than $[Co(trans-14-diene)X_2]Y$ the unsaturated complexes in the formation of BQ and DPQ. The mole ratio of $O_2$ vs. catalyst $(O_2/M)$ for $[Co(cyclam)X_2]Y$ and [Co(trans-14-diene)X_2]Y$ was 1/1, while it was 1/2 for $[M(cyclam)Cl_2]Cl(M=Fe(III),\;Mn(III))$. The results suggested that Co(III)-macrocyclic complexes activated molecular oxygen as superoxolike ${O_2}^-$ and $[M(cyclam)Cl_2]Cl(M=Fe(III),\;Mn(III))$ activated that as peroxolike $O_2^{2-}$.

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Changes in chemical characteristics of cellulase-treated wheat germ extract (효소 처리 밀 배아 추출물의 화학적 특성 변화)

  • Lee, Jae-Kang;Jang, Davin;Kang, Dongwoo;Lee, Jeonghoon;Kum, Hyeim;Choi, Yonghyoun;Kang, Hee;Choi, Yong-Seok;Kim, Dae-Ok
    • Korean Journal of Food Science and Technology
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    • v.51 no.2
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    • pp.97-102
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    • 2019
  • Wheat germ, which is rich in nutrients and phytochemicals, is a by-product during the milling process of wheat kernel. In this study, we aimed to increase the amount of bioactive 2,6-dimethoxy-1,4-benzoquinone (2,6-DMBQ) in wheat germ using the cell-wall-degrading enzyme cellulase (Celluclast 1.5L). The amounts of organic acids, free sugars, and 2,6-DMBQ in wheat germ treated with Celluclast 1.5L were evaluated at various reaction times and temperatures. The results of reversed-phase high-performance liquid chromatography of Celluclast 1.5L-treated wheat germ revealed 2,6-DMBQ, four organic acids (tartaric, acetic, lactic, and succinic acids), and three free sugars (sucrose, fructose, and glucose). As reaction time and temperature of the mixture of wheat germ and Celluclast 1.5L increased, the contents of four organic acids, glucose, fructose, and 2,6-DMBQ increased, but that of sucrose decreased. Taken together, these results suggest that Celluclast 1.5L-treated wheat germ containing increased amounts of 2,6-DMBQ serves as a source of functional ingredients in food industry.

The Effects of Tungsten Electrode on Electrochemical Synthesis of Polyaniline (텅스텐 전극이 폴리아닐린의 전기화학적 중합에 미치는 영향)

  • Jung-Kyoon Chon;Byoung Hoon Min
    • Journal of the Korean Chemical Society
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    • v.38 no.12
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    • pp.885-890
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    • 1994
  • Kinetics of electrochemical polymerization of aniline on a tungsten electrode in acidic aqueous solution was studied by means of cyclic voltammetry and kinetic measurements of anodic oxidation. Aniline molecule appeared to be intially oxidized via two-electron transfer to produce oxidized deprotonated aniline ion, which subsequently undergoes nucleophilic attack to the parent aniline and results in head to tail coupling to yield a dimerized species. But, being contrary to the case of Pt electrode, the propagation of polymerization occured through attack of the monomer by the oxidized aniline monomer to polymer. The growth rate of polyaniline was slow in comparison with the growth on Pt electrode. The degradation products were confirmed to be not p-benzoquinone(BQ) but p-phenylenediamine(p-PDA) by spectrophotometry, which agrees with the fact that oxidation of p-PDA was not observed below 1.0 V.

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Analgesic Effect of DA-5018, a New Capsaicin Derivative, against Experimental Acute Pain (새로운 캅사이신 유도체 DA-5018의 급성통증 모델에서의 진통작용)

  • 손문호;배은주;김희기;신명수;김순희;김원배;양중의;박노상
    • Biomolecules & Therapeutics
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    • v.5 no.1
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    • pp.67-73
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    • 1997
  • Analgesic effect of DA-5018, a new capsaicin derivative, was evaluated in various rat models of experimentally induced acute pain. DA-5018(0.2∼10.0 mg/kg, p.o.) prevented the writhing syndromes induced by acetic acid or phenol-p-benzoquinone(PBQ). It increased the pain threshold of inflamed paw when tested by the Randall-Selitto method at the dose of 2.0∼20.0 mg/kg by oral administration. And also it showed antinociceptive activities in tail-pinch(1.0∼20.0 mg/kg, p.o.) and tail-flick test(5.0∼50.0 mg/kg, p.o.). the potency and efficacy of DA-5018 were comparable to morphine · HCI in all the models mentioned above. Acetaminophen exhibited the inhibition of acetic acid-induced writhing syndromes and also analgesic activity in Randall-Selitto test, but it showed the limited efficacy in tail-pinch and tail-flick test. These results mean that DA-5018 has a broader analgesic activity profile than acetaminophen. And we found out that the analgesic activity of DA-5018 was 100 times more potent when administered centrally than administered orally in tail-flick test. These results suggest that DA-5018 has an orally active analgesic activity, and central nervous system may be involved in the action of DA-5018.

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Bioactive Phenolic Constituents from the Culms of Phyllostachys bambusoides

  • Kim, Hyun-Jung;Kang, Min-Ah;Kim, So-Hyun;Yim, Soon-Ho;Lee, Ik-Soo
    • Natural Product Sciences
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    • v.17 no.4
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    • pp.267-272
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    • 2011
  • In our search for bioactive phenolics from plants, the culms of Phyllostachys bambusoides has been selected for investigation of anti-cariogenic and 1,1-diphenylpicrylhydrazyl (DPPH) radical scavenging agents based on the initial screening results. Fractionation process of n-hexane and $CHCl_3$ extracts afforded four phenolic constituents, ferulic acid (1), vanillin (2), coniferaldehyde (3), and coniferyl alcohol (4) as guided by their DPPH free radical scavenging activities. Additionally, activity-guided fractionation of EtOAc extract with anti-cariogenic activity has resulted in the isolation of coniferaldehyde (3), 2,6-dimethoxy-p-benzoquinone (5), p-methoxycinnamic acid (6), (${\pm}$)-balanophonin (7), and 6-methoxychromanone (8). The structures of 1 - 8 were determined by spectroscopic data interpretation, and also by comparison of their data with the published values. Phenolic compounds 1 - 4 exhibited similar DPPH radical scavenging activities compared with the synthetic antioxidant, butylated hydroxytoluene (BHT), and compounds 3 and 5 - 8 showed significant antibacterial activity against cariogenic oral streptococci, Streptococcus mutans and S. sobrinus.

Covalent Interactions of Reactive Pentachlorophenol Metabolites with Cellular Macromolecules (Pentachlorophenol 대사물과 세포내 거대분자물의 반응에 관한 연구)

  • 정요찬;윤병수;이영순;조명행
    • Toxicological Research
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    • v.13 no.3
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    • pp.257-263
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    • 1997
  • Pentachlorophenol(PCP) which ks widely used in wood preservation, pulp and paper mills, has led to a substantial envirortmental contamination. To get the reliable data for the effective health risk assessment with PCP, covalent binding potential of PCP to cellular macromolecules and glutathione(GSH) was investigated after intraperitoneal administration of $^{14}C-PCP$ to rats. PCP metabolites were able to bind covalently to serum albumin and hepatic protein in a dose- and time-dependent manner. Hepatic protein adducts of PCP metabolites were increased as a function of cytochrome P-450 activities, whereas, albumin adducts significantly decreased. Covalent binding of PCP metabolites with DNA or hemoglobin was not observed. GSH levels in liver tissue decreased over 12hrs, however, the level was recovered after 48hrs. Tetrachloro-1,4-benzoquinone (1,4-TCBQ), one of the most reactive PCP metabolites, conjugated with GSH very rapidly. Base on our results, we could conclude that PCP metabolized to reactive electrophilic metabolites by cytochrome P-450 isoenzymes and conjugated rapidly with neighboring protein or nonprotein sulfhydryl before reacting with DNA or hemoglobin. We propose that albumin adducts and mercapturic acids of PCP metabolites can be used good biomarker of recent PCP exposure.

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Characteristics of the sonolytic reaction of refractory aromatic compounds in aqueous solution by ultrasound (초음파에 의한 수중의 난분해성 방향족화합물의 반응특성)

  • Sohn, Jong-Ryueul;Mo, Se-Young
    • Journal of Korean Society on Water Environment
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    • v.18 no.4
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    • pp.411-419
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    • 2002
  • In this study, the series of ultrasonic irradiation for removal of refractory aromatic compounds has been selected as a model reaction in the batch reactor system in order to obtain the reaction kinetics. The products obtained from the ultrasonic irradiation were analysed by GC and GC/MSD. The decomposition of benzene produced toluene, phenol, and C1-C4 compounds, while the intermediates during the ultrasonic irradiation of 2,4-Dichlorophenol(DCP) were phenol, HCl, catechol, hydroquinone, and benzoquinone. It was found that more than 80% of benzene, and 2,4-DCP solutions were removed within 2 hours in all reaction conditions. The reaction order in the degradation of these three compounds was verified as pseudo-zero or first order. From the fore-mentioned results, it can be concluded that the refractory organic compounds could be removed by the ultrasonic irradiation with radicals, such as $H{\cdot}$ and $OH{\cdot}$ radical causing the high increase of pressure and temperature. Finally, it appeared that the technology using ultrasonic irradiation can be applied to the treatment of refractory compounds which are difficult to be decomposed by the conventional methods.

Electrochemical Oxidation of Phenol using Persulfate and Nanosized Zero-valent Iron (과황산염과 나노영가철을 이용한 페놀의 전기화학적 산화)

  • Kim, Cheolyong;Ahn, Jun-Young;Kim, Tae Yoo;Hwang, Inseong
    • Journal of Soil and Groundwater Environment
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    • v.22 no.2
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    • pp.17-25
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    • 2017
  • The efficiency and mechanism of electrochemical phenol oxidation using persulfate (PS) and nanosized zero-valent iron (NZVI) were investigated. The pseudo-first-order rate constant for phenol removal by the electrochemical/PS/NZVI ($1mA^*cm^{-2}/12$ mM/6 mM) process was $0.81h^{-1}$, which was higher than those of the electrochemical/PS and PS/NZVI processes. The electrochemical/PS/NZVI system removed 1.5 mM phenol while consuming 6.6 mM PS, giving the highest stoichiometric efficiency (0.23) among the tested systems. The enhanced phenol removal rates and efficiencies observed for the electrochemical/PS/NZVI process were attributed to the interactions involving the three components, in which the electric current stimulated PS activation, NZVI depassivation, phenol oxidation, and PS regeneration by anodic or cathodic reactions. The electrochemical/PS/NZVI process effectively removed phenol oxidation products such as hydroquinone and 1,4-benzoquinone. Since the electric current enhances the reactivities of PS and NZVI, process performance can be optimized by effectively manipulating the current.

Transition Metal Catalyzed the Double Hydrohydroxymethylation of Carbonyl Compounds by a Carbon Monoxide-Water System (전이금속촉매-일산화탄소-물계에 의한 카르보닐화합물의 이중 히드로히드록시메틸화 반응)

  • Sang Chul Shim;Kyung Eun Min;Keun Tae Huh
    • Journal of the Korean Chemical Society
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    • v.30 no.1
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    • pp.101-104
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    • 1986
  • Dialdehydes such as adipaldehyde, glutaraldehyde, and succinaldehyde were readily reduced to give their corresponding 1,6-hexanediol, 1,5-pentanediol, and 1,4-butanediol in good yields in the presence of catalytic amount of hexarhodium hexadecacarbonyl or iron pentacarbonyl in water and methoxyethanol or ethanol at 180$^{\circ}C$ for 4 hr under carbon monoxide atmosphere. Under the same reaction conditions, diketones such as 2,5-hexanedione, 2,4-pentanedione, and 2,3-butanedione afforded their corresponding 2,5-hexanediol, 2,4-pentanediol and 2,3-butanediol in moderate yields. For double hydrohydroxymethylation of dialdehydes or diketones, rhodium or iron carbonyl complexes are more effective than others. Particularly, benzoquinone gave hydroquinone quantitatively.

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