• Title/Summary/Keyword: Cinnamyl alcohol

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Effect of Extraction Methods on Flavoring Compounds and Antioxidant Activity of Extracts from Cinnamon (Cinnamomum cassia Blume) (추출방법이 육계피 추출물의 향기 성분과 항산화 활성에 미치는 영향)

  • Cha, Jaeyoon;Kim, Chong-Tai;Cho, Yong-Jin
    • Food Engineering Progress
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    • v.22 no.4
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    • pp.304-308
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    • 2018
  • The interest in and development of healthy foods and nutraceuticals have increased because of the trend for a health-oriented society. Cinnamon is used as a food ingredient as well as a herbal medicine because of its functional properties. In this study, flavoring compounds and antioxidative activities of cinnamon extracts were investigated with different extraction solvents and extraction methods. The contents of flavoring compounds such as coumarin, cinnamic acid, cinnamaldehyde, and cinnamyl alcohol were investigated. The contents of courmarin, cinnamic acid, and cinnamylaldehyde in 70% ethanol extract were higher than those in hot water and subcritical water extracts. The contents of courmarin, cinnamic acid, and cinnamaldehyde in subcritical water extract were higher than those in hot water extract, whereas the content of cinnamyl alcohol was lower. DPPH scavenging activity increased with increasing concentration of the extracts, and the 70% ethanol extract showed the highest antioxidant activity. The ascorbic acid content of the 70% ethanol extract was largest in the antioxidative activity measurement by FRAP analysis. The ascorbic acid contents of the hot water and subcritical water extracts were similar.

Attractiveness of Host Plant Volatiles and Sex Pheromone to the Blueberry Gall Midge (Dasineura oxycoccana) (블루베리혹파리에 대한 기주식물 휘발성 물질과 성페로몬의 유인 효과)

  • Yang, Chang Yeol;Seo, Mi Hye;Yoon, Jung Beom;Shin, Yong Seub;Choi, Byeong Ryeol
    • Korean journal of applied entomology
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    • v.59 no.4
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    • pp.393-398
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    • 2020
  • The blueberry gall midge, Dasineura oxycoccana (Johnson) (Diptera: Cecidomyiidae), is an emerging pest on cultivated blueberries in Korea. To develop a sensitive tool for monitoring this pest in blueberry orchards, we compared the attractiveness of host plant volatiles and sex pheromone to D. oxycoccana adults. We performed gas chromatography-mass spectrometry (GC-MS) analysis of solid-phase microextraction (SPME)-collected volatiles that were released from blueberry ('Darrow' cultivar). The analysis revealed two major volatiles, cinnamaldehyde and cinnamyl alcohol from flowers; and three major volatiles, β-caryophyllene, germacrene D, and α-farnesene from shoots and young fruits. In field tests conducted in Gunsan, Korea in 2019, commercialized cinnamaldehyde, cinnamyl alcohol, β-caryophyllene, and α-farnesene, used singly or in quaternary combination, were unattractive to the blueberry gall midge. However, traps baited with the known sex pheromone (2R,14R)-2,14-diacetoxyheptadecane attracted significantly more males than the treatments with plant volatiles or the control. No synergistic effect was observed between sex pheromone and plant volatiles. Male D. oxycoccana were captured in the pheromone traps from May to August, with three peaks in mid-May, late June, and late July in Gunsan blueberry fields in 2020.

Correlation of the Rates of Solvolyses of Cinnamyl Bromide

  • Koo, In-Sun;Cho, Jun-Mi;An, Sun-Kyoung;Yang, Ki-Yull;Lee, Jong-Pal;Lee, I.
    • Bulletin of the Korean Chemical Society
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    • v.24 no.4
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    • pp.431-436
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    • 2003
  • Solvolytic rate constants at 25℃ are reported for solvolyses of cinnamyl bromide (1) in binary mixtures of water with acetone, ethanol, methanol, methanol-d, and 2,2,2-trifluoroethanol. Product selectivities are reported for solvolyses of 1 in aqueous ethanol and methanol. Rate ratios in solvents of the same $Y_{Br}$ value and different nucleophilicity provide measures of the minimum extent of nucleophilic solvent assistance (e.g. $[k_{40EW}/k_{97TFE}]$Y = 2.88, EW = ethanol-water). With use of the extended Grunwald-Winstein equation, the l and m values are similar to the values of 0.43 and 0.88 obtained for the solvolyses of 1 using the equation (see below) which includes a parameter (I) for solvation of aromatic rings. The magnitude of l and m values associated with a change of solvent composition predicts the $S_{N1}$ reaction mechanism rather than an $S_{N2}$ channel. Product selectivities (S), defined by S = [ether product]/[alcohol product]×[water]/[alcohol solvent] are related to four rate constants for reactions involving one molecule of solvent as nucleophile and another molecule of solvent as general base catalyst. A linear relationship between 1/S and molar ratio of solvent is derived theoretically and validated experimentally for solvolyses of the above substrates from water up 75% 1/S = $(k_{wa}/k_{aw})$([alcohol solvent]/[water]) + $k_{ww}/k_{aw}$ alcohol-water. The results are best explained by product formation from a “free” carbocation intermediate rather than from a solvent-separated ion pair.

Allylic fluorination

  • Park, Oee-Sook;Son, Hoe-Joo;Lee, Woo-Young
    • Archives of Pharmacal Research
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    • v.10 no.4
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    • pp.239-244
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    • 1987
  • An efficient and inexpensive method for the substitution of allylic hydroxyl group with fluoride, without allylic rearrangement, and elimination was developed. This method consists of treating an allylic alcohol with methylithium, followed by p-toluene sulfonyl fluoride, lithium fluoride and 12-Crown-4. This methodology was proved to be efficient by preparting geranyl fluoride, neryl fluoride, cinnamyl fluoride, E, E-farnesyl fluoride, retinyl fluoride and 4-fluoro-2-methyl-6-(ptolyl)-2-heptene.

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Synthesis and Ring-Opening Polymerization of 1,2-Disubstituted Cyclobutanes

  • Lee, Ju-Yeon;Cho, I-Whan
    • Bulletin of the Korean Chemical Society
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    • v.7 no.3
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    • pp.210-213
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    • 1986
  • 1,1-Dicyano-2-ethoxycyclobutane (1a) was prepared by [2 + 2] cycloaddition reaction of vinylidene cyanide with ethyl vinyl ether. 1,1-Dicyano-2-phenylcyclobutane (1b) was prepared by the reactions involving the reduction of cinnamyl alcohol, chlorination, cyanomethylation, bromination, and ring-closure reaction. Compound 1a was ring-opening polymerized with NaCN or n-butyllithium to give a low molecular weight polymer. The compound 1b however, failed to polymerize by either anionic or radical catalysts.

Physicochemical Properties and Volatile Compounds in Jeonju Moju (전주 모주의 이화학적 특성 및 휘발성 화합물 성분)

  • Kwon, Young-Hee;Jo, Sung-Jin;Kim, Hye-Ryun;Lee, Hyang-Jeong;Kim, Jae-Ho;Ahn, Byung-Hak
    • Korean Journal of Food Science and Technology
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    • v.41 no.5
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    • pp.503-508
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    • 2009
  • The principal objective of this study was to evaluate the physicochemical properties and volatile compound contents of Moju acquired from 12 restaurants in Jeonju. The alcohol contents were lower than 2.1%, and the pH values ranged from 3.85 to 4.38. Total acidity, $^{\circ}Bx$, and UV absorbance values differed among the samples according to the type of side materials added. Reducing sugar contents were found to be substantially superior to other commercial takju variants. Malic and lactic acid contents were higher than the contents of other organic acids, and the free sugar contents were as follows: maltose>glucose>fructose. Overall, the high b (yellowness) and cP values were attributable to the turbid yellow and heavy condition of the samples. The volatile compound contents of Moju were analyzed via GC and GC/MSD. 30 components were identified, including 3 alcohols, 12 esters, 7 hydrocarbons, and 4 aldehydes. Among the alcohol compounds, benzeneethanol levels were higher than the levels of isoamyl alcohol. Ethyl caprate, ethyl palmitate, and ethyl linoleate, which were fundamentally attributable to origin liquor, were highest among the 12 esters. (E)-cinnamaldehyde, which was the most abundant among 7 hydrocarbons, and (E)-cinnamyl acetate contents were attributed to the presence of cinnamon, a common supplement in the processing of Moju.

Volatile Flavor Characteristics of Propolis (Propolis의 휘발성 향기 성분 특성)

  • Song, Hyo-Nam;Kim, Young-Eon;Hwang, In-Kyeong;Ahn, Seung-Yo
    • Korean Journal of Food Science and Technology
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    • v.31 no.5
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    • pp.1153-1158
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    • 1999
  • Propolis is a resinous bee-hive product that honeybees collect from plant exudates, flower and leaves. Flavor characteristics of two varieties of propolis collected from different plant origins, falseacacia(Robinia psedoacacia L.) and chestnut tree(Castanea crenata), were analyzed using Aroma Scan and GC/MS. Two varieties of propolis were grouped with quite different aroma profiles by Aroma Scan. Fifty five flavor compounds were identified by GC/MS, of which 44 compounds were found from the propolis of falseacacia and 47 compounds from chestnut tree. Five aldehydes, eight alcohols. five ketones, three esters, one fatty acid, twenty seven hydrocarbons. two terpenes and four phenolic derivatives were identified. Thirty six compounds including benzaldehyde, cinnamyl alcohol, eudesmol and benzyl benzoate were detected in both propolis, eight compounds including geraniol and n-undecane only in propolis of falseacacia and eleven compounds including piperitenone and valencene only in chestnut tree.

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Preparation of (S)-(+)-Pranidipine by Optical Resolution (광학 분할에 의한 (S)-(+)-Pranidipine의 제조방법)

  • Baek, Du-Jong;Yoon, Ji Hye;Kim, Moon-Sik
    • Journal of the Korean Chemical Society
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    • v.59 no.6
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    • pp.488-492
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    • 2015
  • In this study, the effective preparation method of (S)-(+)-pranidipine, the active component of antihypertensive drug as a calcium channel blocker, was developed using optical resolution. The racemic monocarboxylic acid 5 obtained by the hydrolysis of (±)-pranidipine was mixed with optically active quinidine to form salts, and the insoluble diastereomeric salt was collected and successive treatment with base and acid furnished (R)-(-)-carboxylic acid 7. (S)-(+)-Pranidipine was prepared by esterification of this acid with cinnamyl alcohol, and the analysis by chiral HPLC showed 100% enantiomeric excess (ee). This process would be industrially very useful to prepare chiral (S)-(+)-pranidipine, since the use of strong base and anhydrous solvents, and ultra-low temperature condition were excluded in this process.

Isolation of Chemical Compounds from xBrassicoraphanus (배무채(xBrassicoraphanus)의 화학성분 분리)

  • Rhee, Yun-Hee;Ahn, Kyoo-Seok;Lee, Soo-Seong;Park, Young-Doo;Ryu, Shi-Yong;Kim, Sung-Hoon
    • Korean Journal of Pharmacognosy
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    • v.38 no.4
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    • pp.403-408
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    • 2007
  • xBrassicoraphanus is an intergenic breed crossed between Brassica campetris L. ssp. pekinensis and Raphanus sativus L. that have been daily consumed. xBrassicoraphanus was known to have good tastes and biological activities. Nevertheless, its constituetnts were not elucidated yet. Thus, in the present study, to indirectly evaluate the biological activity of xBrassicoraphanus, 12 compounds were isolated from leaves and roots of xBrassicoraphanus. On the basis of spectroscopic evidences, the structures of these compounds isolated from leaves of xBrassicoraphanus. were identified as ${\beta}-sitosterol$, indole-3-acetonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, linolenic acid and coniferyl alcohol, while the chemical structures of compounds isolated from the roots of were xBrassicoraphanus were characterized as ${\beta}-sitosterol$, indole-3-acetonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, 1-methoxyindole-3-acetonitrile, goitrin, 4-hydroxycinnamyl alcohol, coniferyl alcohol, palmitic acid and daucosterol. These can be classified as three steroids, two indole cyanides, two cinnamic acid derivatives, one cinnamyl alcohol derivative, three fatty acid derivatives one isothiocyanate. These results suggest that the compounds isolated from xBrassicoraphanus were almost identical with known components of Brassica campetris L. ssp pekinensis or Raphanus sativus L. However, it is necessary to investigate more about the difference of amounts of constituents according to harvest time and variant species amounts.