• Title/Summary/Keyword: cinnamate

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Cationic Iridium(I) Complex of Ethyl Cinnamate and Hydrogenation of Unsaturated Esters with Iridium(I)-Perchlorato Complex

  • Yang, Kyung-Joon;Chin, Chong-Shik
    • Bulletin of the Korean Chemical Society
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    • v.7 no.6
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    • pp.466-468
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    • 1986
  • Reaction of $Ir(ClO_4)(CO)(PPh_3)_2$ with trans-$C_6H_5CH$ = $CHCO_2C_2H_5$ produces a new cationic iridium(I) complex, [Ir (trans-$C_6H_5CH$ = $CHCO_2C_2H_5)(CO)(PPh_3)_2]ClO_4$ where trans-$C_6H_5CH$ = $CHCO_2C_2H_5$ seems to be coordinated through the carbonyl oxygen rather than through the $\pi$-system of the olefinic group according to the spectral data. It has been found that Ir$(ClO_4)(CO)(PPh_3)_2$ catalyzes the hydrogenation of $CH_2$ = $CHCO_2C_2H_5$, trans-$CH_3CH$ = $CHCO_2C_2H_5$ and trans-$C_6H_5CH$ = $CHCO_2C_2H_5$ to $CH_3CH_2CO_2C_2H_5$, $CH_3CH_2CH_2CO_2C_2H_5$ and $C_6H_5CH_2CH_2CO_2C_2H_5$, respectively at room temperature under the atmospheric pressure of hydrogen. The relative rates of the hydrogenation of the unsaturated esters are mostly understood in terms of steric reasons.

Reaction of Organic Halogen Compounds with Metals (Part II) A Formation of Organic Chlorine Zinc Complex in Various Solvents (有機할로겐 化合物과 金屬과의 反應 (第 2 報) 有機亞鉛 클로린콤푸렉쓰 生成에 關한 各種 용매효과)

  • Kim, You-Sun
    • Journal of the Korean Chemical Society
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    • v.9 no.1
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    • pp.1-7
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    • 1965
  • Reaction of monochloroacetic acid with zinc in presence of toluene, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, acetonitrile, and dioxane solvents showed the solvent effect in order of dimethylformamide, dioxane, dimethyl sulfoxide, toluene, acetonitrile, and tetrahydrofuran. The increasing reactivity of the reagents was observed in order of the polarity and hydrophilicity of the solvent. The same reaction of ethyl monochloroacetate in the same series of solvents showed also the solvent effect, but the difference was not large as compared to that of the acid. The reaction of the acid, ester, zinc, and carbonyl precursors such as benzaldehyde and 4-heptanone gave the Reformatsky reaction product in the case of the aldehyde, but the reactivity with 4-heptanone was slight. The yield of the product was varied by the method of addition of reagents. The best yield observed in case of the acid reaction was 38.5% of the hydroxy acid and 0.8g of the salt in presence of acetonitrile and in case of the ester reaction 19.3% of ethyl cinnamate and 21.6% of polymer. The variation of the reactivity of reagents due to the reaction temperature was observed in case of carbonyl reaction. The result was discussed in terms of the solvent effect and the procedures were described.

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Effect of Burkholderia contaminans on Postharvest Diseases and Induced Resistance of Strawberry Fruits

  • Wang, Xiaoran;Shi, Junfeng;Wang, Rufu
    • The Plant Pathology Journal
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    • v.34 no.5
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    • pp.403-411
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    • 2018
  • This study takes strawberry-fruits as the test material and discusses the effect of Burkholderia contaminans B-1 on preventing postharvest diseases and inducing resistance-related substances in strawberry-fruits. Soaking and wound inoculating is performed to analyze the inhibitory effects of different treatment solutions on the gray mold of postharvest strawberry-fruits. The count of antagonistic bacteria colonies in the wound is found, and the dynamic growth of antagonistic bacteria and the pathogenic fungus is observed by electron microscopy. The results indicated that, either by soaking/wound-inoculating, the fermentation and suspension of antagonistic bacteria significantly reduced the incidence of postharvest diseases of strawberry-fruits. With wound inoculation, the inhibition rate of antagonist fermentation and suspension ($1{\times}10^{10}cfu/ml$) respectively reached 77.4% and 66.7%. It also led to a significant increase in the activity of resistance-related enzymes, i.e., phenylalanine ammonia lyase (PAL), 4-coumarate coenzyme A ligase (4CL), cinnamate-4-hydroxylase (C4H) and chalcone isomerase (CHI). On 1 d and 2 d post-treatment, the activity of 4CL was respectively 3.78 and 6.1 times of the control, and on 5 d, the activity of PAL was increased by 4.47 times the control. The treatment of antagonistic bacteria delayed the peaking of cinnamyl-alcohol dehydrogenase (CAD) activity and promoted the accumulation of lignin and total phenols. The antagonistic bacteria could be well colonized in the wounds. On 4-5 d post-inoculation, the count of colonies was $10^8$ times of that upon inoculation. Electronmicroscopy indicated that the antagonistic bacteria delayed the germination of pathogenic spores in the wounds, and inhibited further elongations of the mycelia.

Invirto alternatives to photosensitization Test (광감작성 시험에서의 동물대체 시험법)

  • Lee, Ho;Nam, Ki-Taek;Koh, Jae-Sook;Park, Won-Jae
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.22 no.1
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    • pp.84-101
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    • 1996
  • To minimize the use of animals in toxicity testing, and to reduce the cost in vivo test, more rational test method was described which determines, in the same animal, photoxic and photoallergic potential of a substance, and is daptable to routine testing. The other purpose of this study was to investigate the usefulness of in vivo alternatives ; photostability and spectrophotometric carbonyl assay. In this modified photosensitization model, animal numbers and resting periods, the number and method of topical application were simplified. Two positive photoreactive agents, Benzocaine and 6-methyl coumarine, showed a similar photoallergic potential to that of Ichikawa's method. Two sunscreens, Octyl methoxy cinnamate, Butyl methoxyl dibenzoyl methane, hardly showed photoallergic potentials. The photostability test could be used in the step of prescreening of photosensitization potential because most of the photoreactive agents represented the reduction of more than 20% in the absorbance. And photoreactive agents have a high potential of photosensitization in the sddessment of spectrophotometric carbonyl level although two sunscreens have a low possibility of photosensitization. Therefore this method was assumed as a valuable in vivo alternatives in the respect even in the very low concentrations which phototoxicity test using almonella showed no phototoxic potential.

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"KALEIDOSCOPIC" TOPOCHEMICAL PHOTOPOLYMERIZATION BEHAVIOR OF DIOLEFIN COMPOUNDS

  • Hasegawa, Masaki;Chung, Chan-Moon;Kinbara, Kazushi
    • Journal of Photoscience
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    • v.4 no.3
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    • pp.147-160
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    • 1997
  • INTRODUCTION : Various types of organic reactions in the crystalline state, so-called "topochemical reaction", have been reported in this century." Among the reactions, [2+2] photocycloaddition of diolefin crystals are one of the most intensively investigated examples. In the topochemical reaction in a pure sense, the space group symmetry is perfectly preserved throughout the reaction as were demonstrated by the crystalline-state photopolymerization of 2,5-distyrylpyrazine (2,5-DSP) and photodimerization of propyl $\alpha$-cyano-4-[2-(4-pyridyl) ethenyl]cinnamate. 2,5-DSP was initially prepared by Franke and in 1958 Koelsch and Gumprecht described briefly in their article of diazine-derivatives that it was found that the compound (2,5-DsP) was converted into a colorless insoluble polymer (\ulcorner) dec. 331~331$\circ$ when the solid was exposed for a few hours to ultraviolet light. Wright described in his book as if Koelsch and Gumprecht had investigated both the structure of the photoproduct and the crystal structure 2,5-DSP in detail. However, in the paper, they have not described any study on chemically correct analysis and crystallography of the resulting photoproduct at all. In 1967, one of present authors (M. H.) independently made the same observation as Franke that brilliant yellow crystal of 2,5-DSP was converted into powdery white substance under the sunlight in the course of a preparative study of pyrazine-2,5-dicarboxylic acid from 2,5-DSP. He investigated this phenomenon and concluded for the first time that a linear highmolecular-weight polymer crystal ([$\eta$] > 3.0 in $CF_3COOH$ solution) with recurring cyclobutane units in the main chain, had been produced from 2,5-DSP crystal by the action of sunlight.on of sunlight.

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Flavor Components of the Fruit Peel and Leaf Oil from Zanthoxylum piperitum DC (초피(Zanthoxylum piperitum DC)의 과피와 잎의 방향성분)

  • Kim, Jung-Han;Lee, Kyung-Seok;Oh, Won-Taek;Kim, Kyoung-Rae
    • Korean Journal of Food Science and Technology
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    • v.21 no.4
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    • pp.562-568
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    • 1989
  • The essential oils from ripe fruit peel and leaf of Zanthoxylum piperitum DC were extracted by gas co-distillation method and analyzed by gas chromatography/mass spectrometry (GC/ MS) and retention index matching. The experimental results revealed the presence of over 100 volatile components. Major components were 1,8-cineol (25.47%), limonene (11.91%), geranyl acetate (9.01%), myrcene (6.15%) in fruit peel and citronellal (23.11%), 1,8-cineol (18.38%), citronellol (6.04%) in leaf. Among the components identified were the following; in fruit peel, ${\alpha}-pinene$ and 13 hydrocarbons, linalool and 8 alcohols, citronellal and 3 aldehydes, carvone and 2 kotones, methyl salicylate and 7 esters, and 1,8-cineol and oxides, and in leaf, ${\alpha}-pinene$ and 7 hydrocarbons, linalool and 7 alcohols, citronellyl acetate and 5 esters, citronellal and 1 aldehyde, carvone, and 1,8-cineol and 1 oxide.

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Studies on the Extraction Method and Polysaccharide of Tricholoma matsutake using the Supersonic wave and Microwave (초음파와 극초단파를 이용한 송이버섯의 추출법과 다당체에 관한 연구)

  • Yu, Seung-Hyun;Chong, Myong-Soo;Kim, Hae-Ja;Lee, Ki-Nam
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.21 no.6
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    • pp.1431-1436
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    • 2007
  • In order to optimize the extract condition and improve physiological activity of the extract form Tricholoma matsutake, experiments related to extraction methods, totale yield, content of total soluble polysaccharide, SOD-like activity, total polyphenol amount, and volatile flavor compound and the others were carried out, results were obtained as following: Compare with traditional hydrothermal extraction method (Hot water extraction : HWEW), it illustrates that the low temperature extraction method which combines a supersonic waves and microwave (Supersonic microwave extraction : SMEW) causes of increasing the total yield, total soluble polysaccharide. As to the anti-oxident effect, SMEW method leds to increasing of the SOD-like activity, total polyphenol amount as well. Also, cytotoxic effect and growth inhibitory effect against cancer cell line are much higher in SMEW method than HWEW method, especially SMEW5 extracts treated by supersonic 15 min. and microwave 120W, 3 min. and 2 times. The main volatile flavor compound and infinitesimal volatile flavor compound both increase significantly by SMEW method. It is concluded the main components of the volatile flavor compounds extracted from Tricholoma matsutake are 1-octen-3-0l, Methyl cinnamate, 2-octeno1 et al. alcohol typies. Consequently, SMEW5 method is considered as the most effective one for anti-oxidant and is prior to any other methods. And the optimun conditions of this method are : supersonic waves (supersonic, 25KHz, 50W) 15 minutes, microwave spectroscopy (microwave, 2,450MHz, 120W) 3 minutes, and every treatment is performed once followed twice repeats.

The inhibitory effects of 3,4,5-Trimethoxy cinnamate thymol ester(TCTE, Melasolv$\circledR$) on Melanogenesis

  • Hwang, Jae-Sung;Hyunjung Shin;Noh, Ho-Sick;Park, Hyunjung;Ahn, Soo-mi;Park, Dong-Soon;Kim, Duck-Hee;Lee, Byeong-Gon;Ihseop Chang
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.28 no.1
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    • pp.135-149
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    • 2002
  • To date, research on the regulation of melanogenesis has focused on factors which affect tyrosinase, the rate-limiting enzyme in the melanogenic pathway, by searching for chemicals which competitively inhibit tyrosinase function. Many types of tyrosinase inhibitors have been developed, but no satisfactory results have been made clinically until now, To find a new whitening agent, which effectively inhibits melanogenesis, we synthesized several compounds and selected compounds by cell-based assay system. Finally, 3, 4, 5-trimethoxy cinnamaie thymol ester(TCTE, Melasolv) was selected and the effects of TCTE on melanogenesis were investigated. Treatment of mouse-derived melanocyte melan-a cells with TCTE results in a marked down-regulation of tyrosinase activity. 80% decrease of tyrosinase activity occurs with 30uM TCTE treatment for 72 hours without affecting cell growth. The inhibition of tyrosinase activity is dose-dependent and melanin content was also decreased to 40%. From the in vitro tyrosinase assay using cell extract, TCTE does not act as a direct inhibitor of the enzyme. Treatment of melan-a cultures with TCTE blocks the increase in tyrosinase activity by either forskolin, 3-isobutyl-1-methtyl-xanthine. TCTE decreased the expression of tyrosinase, TRP-1 without effects on TRP-2 protein expression through the down regulation of tyrosinase and TRP-1 mRNA. From the results of cAMP immunoassays, intracellular levels of the cyclin nucleotide are unaffected in cells treated with TCTE. The inhibitory effects of melanin synthesis were also shown in reconstitute human epidermis model by topical application. These findings suggest that TCTE can be used for studying the regulation of melanogenesis and depigmenting agent.

Inorganic-organic nano-hybrid; Preparation of Nano-sized TiO$_2$ Paste Trapped OMC Nano-emulsion and it's Application for Cosmetics (OMC Nano-emulsion을 포집하고 있는 Nano-TiO$_2$-Paste의 합성과 화장품의 응용)

  • Byung Gyu, Park;Jong Heon, Kim;Jin Hee, Im;Kyoung Chul, Lee
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.2
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    • pp.181-187
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    • 2004
  • Preparations of mesoporous materials using various templates and their applicability have been intensively investigated for many years. We studied on synthesizing mesoporous Ti02 with pores in which sensitive compounds having weak physico-chemical properties such as thermal or UV irradiation and low solubility in solvent are trapped. Prior to trapping OMC in the pores of mesoporous titania, OMC was nano-emulsified in O/W system using Lecithin. Thereafter the OMC was trapped in the pores of mesoporous titania using sol-gel method. Main focus of this work is to prepare OMC-trapped mesoporous titania and to trace the stability and solubility of nano-emulsified OMC in the pores of mesoporous titania, and compared with that of mesoporous silica. OMC-trapped mesoporous Inorganic-Organic hybrid titania showed higher factors in sun protecting and a skin penetration phenomenon was reduced.

Formation of Secondary Products by Plant Cell Culture - II. Effects of Growth Regulators on the Formation of Capsaicinoide, Phenylpropanoids and PAL Activity in Cultured Cell of Capsicum annuum L. - (식물세포(植物細胞) 배양(培養)에 의(依)한 이차대사산물(二次代謝産物)의 생성(生成)에 관(關)한 연구(硏究) - II. Capsicum annuum L.의 배양세포(培養細胞)에 있어서 Growth Regulator가 Capsaicinoids, Phenylpropanoids 생성(生成) 및 Phenylalanine Amnonia-lyase (PAL) 활성(活性)에 미치는 영향 -)

  • Choi, Bong-Soon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.16 no.1
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    • pp.10-17
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    • 1987
  • In order to investigate the effects of growth regulators on the formation of capsaicinoids in callus of Capsicum annuum L. tissues were cultured in the Linsmaier and Skoog RM 1964 medium containing various growth regulators. Production of capsaicinoids during culture was monitored by gas chromatography. In the presence of $10^{-6}M$ of 2,4-D and kinetin in the medium, $1182{\mu}g$ of capsaicinoids were formed per 100g dry wt. of tissue, of which was greater than with any of three other growth regulators. IAA, NAA, and kinetin of same concentrations had 65%, 38%, 68% effect of 2.4-D in capsaicinoids formation, respectively. Production of capsaicinoids increased gradually in the presence of 2,4-B as culture period was proceeded. Of phenylpropanoids formed, cinnamic acid and coumaric acid were not significantly different in their levels, although growth regulators were varied. On the other hand, caffeic acid and ferulic acid formation were highest in the presence of 2,4-D. Effects of kinetin and IAA were about 70 percent of that of 2,4-D, whereas NAA had only about 30 percent effect. Phenylalanine ammonia-lyase activity in cultured tissue was increased during the periods; 52, 81, and 209 n moles of cinnamic acid per g fresh wt. were formed after 5, 15, and 25 days of culture, respectively.

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