• Title/Summary/Keyword: amines

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Synthesis of N-Substituted Isoindolin-1-ones via Palladium-Catalyzed Carbonylative Heterocyclization of o-Bromobenzylbromide with Carbon Monoxide and Primary Amines

  • 심상철;Li Hong Jiang;이동엽;조찬식
    • Bulletin of the Korean Chemical Society
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    • v.16 no.11
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    • pp.1064-1067
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    • 1995
  • A convenient method for the synthesis of N-substituted isoindolin-1-ones is disclosed in palladium(0)-catalyzed heterocyclization of o-bromobenzylbromide with carbon monoxide (CO) and primary amines in DMF at 100 ℃.

Biogenic Amine Contents in Fish Products (수산가공품의 biogenic amine 함량 변화)

  • Cho, Young-Je;Son, Myoung-Jin;Kim, Seung-Mi;Park, Hyun-Kyu;Yeo, Hae-Kyung;Shim, Kil-Bo
    • Journal of Fisheries and Marine Sciences Education
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    • v.20 no.1
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    • pp.127-134
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    • 2008
  • The purpose of this study was to determine content of biogenic amines (Histamine, Cadaverine, Putrescine) in the salted mackerel, canned mackerel, mackerel pike, and freeze dried mackerel pike (Guamegi) collectively, all were purchased in the market. Salted mackerel was purchased at five markets (A, B, C, D, and F market) and stored for 10 days at $4{^{\circ}C}$. At the time of purchase, salted mackerel purchased at markets A, B and C was tested for biogenic amine, yet nothing was detected. However, salt mackerel purchased at market D was tested and the histamine concentration was 0.5 mg/100g. Mackerel from market F, exhibited content levels of 0.5 mg/100g histamine and 1.6 mg/100g cadaverine. Those make certain safety during self-life but that purchased F market gradually increased biogenic amine during storage. Prepared salted mackerel of varying levels of freshness and processing methods were analyzed for biogenic amines. Salting process was performed using functional brine salt. VBN (volatile basic nitrogen) was used to establish freshness levels of salted mackerel. Analyses of mackerel muscle determined the values of freshness to be 9.2 mg/100g (good freshness), 18.2 mg/100g (bad freshness), respectively. After 40 days of storage, the content of histamine, cadaverine, putrescine in the freshness of salted mackerel was 2.0 mg/kg, 2.4 mg/kg and 0 mg/kg, respectively. The content of histamine, cadaverine, putrescine in salted mackerel of poor freshness was 71.3 mg/kg, 22.9 mg/kg and 17.8 mg/kg, respectively. It was concluded the presence of biogenic amines during the salting process of salted mackerel significantly effected freshness of materials. The presence of biogenic amines were detected in mackerel that underwent the salting process after 1 month of storage at $4{^{\circ}C}$. The levels of biogenic amines in the brine salted mackerel were higher than those found in dry, salted mackerel; however, the freshness of fish had an insignificant effect on biogenic amines. The presence of histamine was detected in small quantities in canned mackerel and mackerel pike from three companies. Alternatively, cadaverine and putrescine were not detected. Guamegi, vacuumed packed or sealed with a rope was purchased from three markets (A, B, C seafood company). Guamegi was stored and observed for 180 days at $-20{^{\circ}C}$. Histamine was detected in small quantities in all products stored at $-20{^{\circ}C}$. Levels of histamine was dependent on the types of packaging, rope packaging yielded the highest level. However, other amines were not detected.

Biogenic-Amine Contents of Korean Commercial Salted Fishes and Cabbage Kimchi (젓갈류 및 배추김치에서의 바이오제닉 아민류 함량 조사 연구)

  • Shin, Sang-Woon;Kim, Young-Sug;Kim, Yang-Hee;Kim, Han-Taek;Eum, Kyoung-Suk;Hong, Se-Ra;Kang, Hyo-Jeong;Park, Kwang-Hee;Yoon, Mi-Hye
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.52 no.1
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    • pp.13-18
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    • 2019
  • We determined the contents of 11 biogenic amines in 20 types of cabbage kimchi, 10 types of fish sauce, and 40 types of salted fish purchased from small- and medium-sized grocery stores in Gyeonggi-Do, Republic of Korea, from June to October 2017. The content of each of the biogenic amines in the various types of cabbage kimchi was slightly lower than that in detection amounts of each of the 10 types of biogenic amines and the values reported by Joe et al. The histamine content of all five types of anchovy sauce was lower than the limit set by the European Union (400 mg/kg), but that of three of the five types of sand lance sauce was higher. Analyzing the ratios of the contents of five highly toxic biogenic amines to those of the 11 biogenic amines yielded no quantitative correlation. The estimated daily intake of the five highly toxic biogenic amines in cabbage-kimchi and fermented fish was ${\leq}6mg$.

Reactions of Iron Alkynyl(Ethoxy)Carbene Complexes with Amines (철 알킨일(에톡시)카르벤 착물 유도체와 아민의 반응)

  • Park, Jaiwook;Kim, Jinkyung;Jung, Hyunmin
    • Journal of the Korean Chemical Society
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    • v.40 no.8
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    • pp.571-578
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    • 1996
  • Iron alkynyl(amino)carbene complexes, (${\beta}$-aminovinyl)carbene complexes, ${\eta}^3$-(2-(alkylcarbonyl)vinyl)carbene complexes, and a 3-aminoallenylidene complex were formed in the reactions of iron alkynyl(ethoxy)carbene complexes with amines. The ratio of the products, which were formed by substitution reaction, the Michael addition of amines, rearrangements after the addition reaction, and the addition followed by the elimination of the ethoxy group, respectively, was dependent on reaction temperature, the substituent of the alkynyl moiety, and employed amines.

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Influence of Curing and Heating on Formation of N-Nitrosamines from Biogenic Amines in Food Model System using Korean Traditional Fermented Fish Product

  • Mah, Jae-Hyung;Yoon, Mi-Young;Cha, Gyu-Suk;Byun, Myung-Woo;Hwang, Han-Joon
    • Food Science and Biotechnology
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    • v.14 no.1
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    • pp.168-170
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    • 2005
  • The myeolchi-jeot samples were divided into different groups with or without the supplementation with biogenic amines. Subsequently, the samples were placed in an oven at $80^{\circ}C$ for 1 hr to allow the chemical reaction to proceed, and then were analyzed for N-nitrosamine contents using GC-TEA. N-nitrosamine was not detected in any of the myeolchi-jeot samples which had been treated with/without sodium nitrite. On the other hand, the yield of N-nitrosopyrrolidine from 1,000 mg/kg of putrescine and spermidine in the myeolchi-jeot samples (treated with 5 mg/kg of sodium nitrite) was 0.002 and 0.014%, respectively. N-nitrosamine was not produced from any other biogenic amines like, histamine, tyramine, cadaverine and spermine. In addition, curing and heating were the factors which influenced the formation of N-nitrosamine during the nitrosation of biogenic polyamines. For the formation of N-nitrosamine in the food systems, treatment with sodium nitrite and heating at appropriate temperature along with the satisfied supplementation of biogenic polyamines are required.

Synthesis and Characterization of a Hydroxylated Dendrimeric Gene Delivery Carrier

  • Kim, Tae-Il;Bai, Cheng-Zhe;Park, Jong-Sang
    • Bulletin of the Korean Chemical Society
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    • v.28 no.8
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    • pp.1317-1321
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    • 2007
  • Arginine conjugated PAMAM dendrimer, PAMAM-R was modified with propylene oxide via hydroxylation of primary amines of arginine residues. About 49 amines were detected to be converted to amino alcohols by 1H NMR. The newly synthesized polymer, PAMAM-R-PO was able to completely retard pDNA from a charge ratio of 2. The average diameter of PAMAM-R-PO polyplex was found to be 242 nm at a charge ratio of 30. The Zeta-potential value of PAMAM-R-PO polyplex was able to reach 20-30 mV over a charge ratio of 10. PAMAM-R-PO indicated higher cell viability than unmodified PAMAM-R on HeLa and 293 cells because of its hydroxylated amines. Transfection experiments on 293 cells showed that the transfection efficiency of PAMAM-R-PO was found to be 1.5-1.9 times higher than that of PEI25kDa at a charge ratio of 30. The polymer eventually displayed about 2 times greater transfection efficiency than PAMAM-R at the same charge ratio in the absence of serum. Therefore, we concluded that the modification of primary amines of PAMAMR to amino alcohols gives positive effects such as reduced cytotoxicity and enhanced transfection efficiency on 293 cells for gene delivery potency of PAMAM-R.

A Kinetic Study on Michael-type Reactions of 1-(X-Substituted Phenyl)-2-propyn-1-ones with Amines: Effect of Amine Nature on Reactivity and Mechanism

  • Um, Ik-Hwan;Hwang, So-Jeong;Lee, Eun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.29 no.4
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    • pp.767-771
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    • 2008
  • Second-order rate constants have been measured spectrophotometrically for the Michael-type reaction of 1-(Xsubstituted phenyl)-2-propyn-1-ones (2a-f) with amines in $H_2O$ at 25.0 ${\pm}$ 0.1 ${^{\circ}C}$. A linear Brønsted-type plot is obtained with ${\beta}_{nuc}$ = 0.25 ${\pm}$ 0.02, a typical $\beta_{nuc}$ value for reactions which proceed through a stepwise mechanism with attack of amine on the electrophilic center being the rate-determining step. Secondary alicyclic amines are found to be more reactive than isobasic primary amines. The Hammett plot for the reactions of 2a-f with morpholine is not linear, i.e., the substrate with a strong electron-donating group (e.g., 4-MeO) exhibits a negative deviation from the Hammett plot. However, the Yukawa-Tsuno plot for the same reactions exhibits an excellent linear correlation with ρ = 0.62 and r = 0.82. Thus, it has been proposed that the nonlinear Hammett plot is not due to a change in the ra te-determining step but due to ground-state stabilization through resonance interactions.

A Kinetic Study for the Reaction of 2,4-Dinitrophenyl Benzoate with Secondary Cyclic Amines

  • 엄익환;김명진;민지숙;권동숙
    • Bulletin of the Korean Chemical Society
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    • v.18 no.5
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    • pp.523-527
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    • 1997
  • Apparent second-order rate constants (kapp) have been measured spectrophotometrically for the reaction of 2,4-dinitrophenyl benzoate (DNPB) with 6 secondary cyclic amines in H2O containing 20 mole% DMSO at 25.0±0.1 ℃. The Bronsted-type plot (log kapp vs. pKa) shows a break at pKa near 9.1, e.g. two straight lines with βapp values of 0.67 and 0.44 for the low basic (pKa < 9.1) and the highly basic (pKa > 9.1) amines, respectively. Using an estimated k2 value of 3×109 sec-1, all the other microconstants (k1, k-1 and K) involved in the present aminolysis have been calculated. The k value decreases with increasing the basicity of amines while k1 and K values increase with increasing the amine basicity, as expected. Good linear Bronsted-type plots have been obtained for these microconstants of the present aminolysis of DNPB. The magnitudes of the slope of the Bronsted-type plots, k1 and k-1 have been calculated to be 0.43 and - 0.24, respectively, indicating the k-1 step is about two folds less sensitive than the k1 step to the amine basicity. The K value has been calculated to be 0.66, which appears to be much smaller than the one for other aminolyses showing general base catalysis. The small K value has been attributed to the absence of general base catalysis in the present aminolysis of DNPB.