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Journal articles on the topic 'Brominated acids'

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Published: 4 June 2021

Last updated: 20 February 2023

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1

Blume, Rüdiger, Dagmar Wiechoczek, Heinrich Meier, and Frank Wedekind. "Degradation of Lactic Acid and Pyruvic Acid in Belousov-Zhabotinskii Reactions." Zeitschrift für Naturforschung B 44, no. 5 (May 1, 1989): 598–608. http://dx.doi.org/10.1515/znb-1989-0516.

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The temporal degradation of the Belousov-Zhabotinskii substrates lactic acid, pyruvic acid, bromo- and dibromo pyruvic acid is investigated. The only final product of non-brominated substrates is acetic acid. From brominated educts only brominated acetic acids result. The concentrations of the stable products are determined as a function of time. The gross reactions are mainly based on simple consecutive first order reactions. For the pyruvic acid rate constants are determined.

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2

Hirsh, Shulamit, Shmuel Carmely, and Yoel Kashman. "Brominated unsaturated acids from the marine sponge ." Tetrahedron 43, no. 14 (January 1987): 3257–61. http://dx.doi.org/10.1016/s0040-4020(01)90293-5.

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3

Řezanka, Tomáš, and Valery Dembitsky. "Brominated fatty acids from lichen Acorospora gobiensis." Phytochemistry 50, no. 1 (January 1999): 97–99. http://dx.doi.org/10.1016/s0031-9422(98)00499-3.

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4

Tandon, Manju, Piyush Kumar, Haiyan Xia, Lili Wang, and Leonard I. Wiebe. "Synthesis of Bromophenyl β-D-Glucuronides: Hydrophilic Precursors of Lipophilic Standards in the Analysis of Environmental Polychlorinated Biphenyls." Collection of Czechoslovak Chemical Communications 71, no. 7 (2006): 1042–50. http://dx.doi.org/10.1135/cccc20061042.

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A rapid PCB-screening protocol, based on a combination of extraction techniques and instrumental nuclear activation analysis (INAA), required water soluble brominated internal standard that undergoes facile hydrolysis to a lipophilic brominated counterpart. Bromophenyl glucuronic acids 2, 3, 7 were synthesized for this application. Glucuronic acids 2 and 3 were prepared by bromination of phenyl β-D-glucopyranosiduronic acid in 81 and 54%, respectively, whereas compound 7 was prepared by coupling methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyluronate bromide (5) with 2,4,6-tribromophenol. Incubation with β-glucuronidase indicated that tribromophenyl derivative 7 is an excellent substrate, with near quantitative conversion to tribromophenol within seconds of incubation with the enzyme.

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5

Cetó, Xavier, Christopher Saint, Christopher W. K. Chow, Nicolas H. Voelcker, and Beatriz Prieto-Simón. "Electrochemical fingerprints of brominated trihaloacetic acids (HAA3) mixtures in water." Sensors and Actuators B: Chemical 247 (August 2017): 70–77. http://dx.doi.org/10.1016/j.snb.2017.02.179.

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6

Carballeira, Néstor M., and Anastacio Emiliano. "Novel brominated phospholipid fatty acids from the Caribbean spongeAgelas sp." Lipids 28, no. 8 (August 1993): 763–66. http://dx.doi.org/10.1007/bf02536001.

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7

Barrow, Russell A., and Robert J. Capon. "Brominated Pyrrole Carboxylic Acids from an Australian Marine Sponge, Axinella SP." Natural Product Letters 1, no. 4 (February 1993): 243–50. http://dx.doi.org/10.1080/10575639308050055.

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8

Yin, Sheng, Glen M. Boyle, Anthony R. Carroll, Michael Kotiw, John Dearnaley, Ronald J. Quinn, and Rohan A. Davis. "Caelestines A−D, Brominated Quinolinecarboxylic Acids from the Australian AscidianAplidium caelestis." Journal of Natural Products 73, no. 9 (September 24, 2010): 1586–89. http://dx.doi.org/10.1021/np100329w.

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9

Carballeira, Néstor M., and Fathi Shalabi. "Novel Brominated Phospholipid Fatty Acids from the Caribbean Sponge Petrosia Sp." Journal of Natural Products 56, no. 5 (May 1993): 739–46. http://dx.doi.org/10.1021/np50095a011.

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10

Brantley, Sarah E., Tadeusz F. Molinski, Chris M. Preston, and Edward F. DeLong. "Brominated acetylenic fatty acids from Xestospongia sp., a marine spongebacteria association." Tetrahedron 51, no. 28 (July 1995): 7667–72. http://dx.doi.org/10.1016/0040-4020(95)00405-w.

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11

Pourmoghaddas, H., and A. A. Stevens. "Relationship between trihalomethanes and haloacetic acids with total organic halogen during chlorination." Water Supply 2, no. 5-6 (December 1, 2002): 509–14. http://dx.doi.org/10.2166/ws.2002.0211.

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The effects of bromide ion, pH and reaction time on the formation of four trihalomethanes, nine haloacetic acids and total organic halogens in chlorinated drinking water have been investigated. In this extensive study, the relationship of total trihalomethanes and total haloacetic acids with total organic halogen have been evaluated. The study determined the concentration range of nine haloacetic acids and four trihalomethanes as a percentage of total organic halogen. The results showed that the percentage of total organic halogen made up of total trihalomethanes plus total haloacetic acids significantly increases with increasing bromide ion concentrations and pH. These observations suggest that both a higher bromide concentration and pH cause the formation of mainly brominated trihalomethanes with the reduction of haloacetic acids which could be identified and quantified by current USEPA methods.

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12

Abdel-Moety, Ezzat M., Abdel-Kader S. Ahmad, and Mohie Sharaf El-Din. "Determination of Iodine Values of Lipids by Bromide Ion Selective Electrode." Journal of AOAC INTERNATIONAL 69, no. 1 (January 1, 1986): 67–69. http://dx.doi.org/10.1093/jaoac/69.1.67.

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Abstract A semimicro method for determination of iodine values of lipids is described. An accurately weighed smear of sample (10-20 mg) on a strip of ashless filter paper, 14 × 40 mm, is brominated with bromine vapors for about 5 min. Excess bromine adsorbed on the filter paper is allowed to sublime. Bromine absorbed by the sample is directly related to the degree of unsaturation. Paper with brominated sample is subjected to oxygen flask combustion in the presence of 2 mL 1M sodium hydroxide solution and 10 mL water as absorbing liquid. Bromide formed, which is equivalent to unsaturation, is determined by bromide ion selective electrode. Bromide ions can be also determined by gravimetry or by indirect argentometric titration. The results were statistically analyzed. The iodine values of some fatty acids and oils, determined by this technique, are in accord with those of some officially approved methods.

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13

Fusetani, Nobuhiro, Hong-yu Li, Kazuhiro Tamura, and Shigeki Matsunaga. "Antifungal Brominated C18 Acetylenic Acids from the Marine Sponge, Petrosia volcano Hoshino." Tetrahedron 49, no. 6 (February 1993): 1203–10. http://dx.doi.org/10.1016/s0040-4020(01)85811-7.

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14

Taniguchi, Masashi, Yasuto Uchio, Ko Yasumoto, Takenori Kusumi, and Takashi Ooi. "Brominated Unsaturated Fatty Acids from Marine Sponge Collected in Papua New Guinea." CHEMICAL & PHARMACEUTICAL BULLETIN 56, no. 3 (2008): 378–82. http://dx.doi.org/10.1248/cpb.56.378.

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15

Knight, Nicole, Kalinda Watson, Stewart Carswell, Eva Comino, and Glen Shaw. "Temporal and Spatial Variation of Trihalomethanes and Haloacetic Acids Concentration in Drinking Water: A Case Study of Queensland, Australia." Air, Soil and Water Research 4 (January 2011): ASWR.S5618. http://dx.doi.org/10.4137/aswr.s5618.

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A broad survey of regulated trihalomethanes (THM) and haloacetic acids (HAA) concentrations in Queensland drinking water was undertaken and the data were evaluated to assess the overall compliance of the region to Australian Drinking Water Guidelines (ADWG). The results presented here indicate that drinking water total trihalomethane (tTHM) concentrations were predominantly compliant with ADWG, with regions using chlorination being the only regions that exceeded the ADWG for THM. tTHM levels were highest in chlorinated water, whereas levels in combined chlorinated/chloraminated water were much lower. Chloraminated water produced the lowest tTHM levels in the regions examined. tTHM levels generally increased during summer and decreased in winter regardless of disinfection method. Surface waters formed a higher proportion of more highly chlorinated THM species relative to more highly brominated THM species, whereas bore water had a higher proportion of more highly brominated THM species due to the frequently higher bromide concentration and lower natural organic matter (NOM) concentration of these waters. The majority of regions were continuously compliant with ADWG for HAA concentrations, with primarily the trichloroacetic acid guideline value being exceeded, in chlorinated waters only.

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16

Patil, Ashok D., Wilhelmus C. Kokke, Sally Cochran, Terry A. Francis, Thaddeus Tomszek, and John W. Westley. "Brominated Polyacetylenic Acids from the Marine Sponge Xestospongia muta: Inhibitors of HIV Protease." Journal of Natural Products 55, no. 9 (September 1992): 1170–77. http://dx.doi.org/10.1021/np50087a002.

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17

Liu, Dong, Jing Xu, Wei Jiang, Zhiwei Deng, Nicole J. de Voogd, Peter Proksch, and Wenhan Lin. "Xestospongienols A-L, Brominated Acetylenic Acids from the Chinese Marine Sponge Xestospongia testudinaria." Helvetica Chimica Acta 94, no. 9 (September 2011): 1600–1607. http://dx.doi.org/10.1002/hlca.201100015.

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18

Xie, Donghang, and Hsien C. Wang. "FTIR Spectroscopic Studies on Curing of Brominated Poly(Isobutylene-co-4-Methylstyrene)." Rubber Chemistry and Technology 77, no. 1 (March 1, 2004): 161–75. http://dx.doi.org/10.5254/1.3547809.

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Abstract The curing of brominated poly(isobutylene-co-4-methylstyrene) or BIMS with ZnO/HSt, ZnO/Zn(St)2 or Zn(St)2 was investigated using FTIR spectroscopy. Changes of carbonyl absorption were monitored by FTIR during the course of curing, which revealed a four-step curing process: 1) formation of zinc salts, 2) esterification to generate Zn-containing Lewis-acid catalysts, 3) Friedel-Crafts alkylation, and 4) post cure. It was found that for the ZnO/HSt system, the ZnO concentration had to be high enough to meet the ZnO/Br molar ratio of 0.9 for complete conversion of curing functionalities. HSt was an effective accelerator, which reduces the induction time and increases the curing rate. HSt of 2 to 3 phr was recommended to achieve optimum acceleration results. Over use of HSt would lead to dramatic reduction of crosslinking density, due to the fact that significant amounts of curing functionalities were consumed to form stearate esters instead of crosslinks. The curing with ZnO/Zn(St)2 was similar to the ZnO/HSt system but faster due to the fact that zinc salt was directly added. Zn(St)2 alone was effective to initiate a cure, but the reversion of curing was observed at high concentrations, probably due to the presence of large amount of acids, such as HSt and HBr both of which were generated during curing, and the stearate esters. Addition of ZnO eliminates the reversion through neutralization of the acids.

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19

Kogan, E. M., N. G. Dyatlova, N. S. Sidorova, L. M. Vilner, O. Vrána, and V. Brabec. "Biophysical studies of the complexes of polyriboguanylic acid with brominated and chlorinated polyribocytidylic acids." Biophysical Chemistry 40, no. 3 (July 1991): 231–39. http://dx.doi.org/10.1016/0301-4622(91)80023-k.

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20

Blumenberg, Martin, and Walter Michaelis. "High occurrences of brominated lipid fatty acids in boreal sponges of the order Halichondrida." Marine Biology 150, no. 6 (August 31, 2006): 1153–60. http://dx.doi.org/10.1007/s00227-006-0445-7.

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21

Pham, Ngoc B., Mark S. Butler, John N. A. Hooper, Roger W. Moni, and Ronald J. Quinn. "Isolation of Xestosterol Esters of Brominated Acetylenic Fatty Acids from the Marine SpongeXestospongia testudinaria." Journal of Natural Products 62, no. 10 (October 1999): 1439–42. http://dx.doi.org/10.1021/np9901635.

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22

Kristiana, I., B. P. Allpike, C. A. Joll, A. Heitz, and R. Trolio. "Understanding the behaviour of molecular weight fractions of natural organic matter to improve water treatment processes." Water Supply 10, no. 1 (March 1, 2010): 59–68. http://dx.doi.org/10.2166/ws.2010.788.

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Water utilities have experienced increasing pressure to minimise the formation of disinfection by-products (DBPs), as reflected in the increasingly stringent regulations and guidelines for the concentrations of DBPs in drinking water. Understanding the disinfection characteristics and molecular weight (MW) distribution of natural organic matter (NOM) will assist in the optimisation of drinking water treatment processes to minimise the formation of DBPs. This study investigated the disinfection behaviour of MW fractions of NOM isolated from a Western Australian source water. The NOM was fractionated and separated using preparative size exclusion chromatography (SEC) and the fractions were chlorinated in the presence of bromide ion. The larger MW fractions of NOM were found to produce the highest concentrations of DBPs (trihalomethanes, haloacetic acids, haloacetonitriles, haloketones, and haloaldehydes), with the low MW fractions still producing significant amounts of these DBPs. The results also showed a trend of an increasing proportion of brominated DBPs with decreasing MW and aromatic character. Considering that the smaller MW fractions of NOM produce significant amounts of DBPs, with a higher relative contribution from brominated DBPs, water treatment processes need to be optimised for either bromide removal or the removal of aliphatic, small MW fractions of NOM, in order to meet DBP guidelines and regulations.

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23

Ahmad, Shama, Juan Xavier Masjoan Juncos, Aftab Ahmad, Ahmed Zaky, Chih-Chang Wei, Wayne E. Bradley, Iram Zafar, et al. "Bromine inhalation mimics ischemia-reperfusion cardiomyocyte injury and calpain activation in rats." American Journal of Physiology-Heart and Circulatory Physiology 316, no. 1 (January 1, 2019): H212—H223. http://dx.doi.org/10.1152/ajpheart.00652.2017.

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Halogens are widely used, highly toxic chemicals that pose a potential threat to humans because of their abundance. Halogens such as bromine (Br2) cause severe pulmonary and systemic injuries; however, the mechanisms of their toxicity are largely unknown. Here, we demonstrated that Br2 and reactive brominated species produced in the lung and released in blood reach the heart and cause acute cardiac ultrastructural damage and dysfunction in rats. Br2-induced cardiac damage was demonstrated by acute (3–24 h) increases in circulating troponin I, heart-type fatty acid-binding protein, and NH2-terminal pro-brain natriuretic peptide. Transmission electron microscopy demonstrated acute (3–24 h) cardiac contraction band necrosis, disruption of z-disks, and mitochondrial swelling and disorganization. Echocardiography and hemodynamic analysis revealed left ventricular (LV) systolic and diastolic dysfunction at 7 days. Plasma and LV tissue had increased levels of brominated fatty acids. 2-Bromohexadecanal (Br-HDA) injected into the LV cavity of a normal rat caused acute LV enlargement with extensive disruption of the sarcomeric architecture and mitochondrial damage. There was extensive infiltration of neutrophils and increased myeloperoxidase levels in the hearts of Br2- or Br2 reactant-exposed rats. Increased bromination of sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA) and increased phosphalamban after Br2 inhalation decreased cardiac SERCA activity by 70%. SERCA inactivation was accompanied by increased Ca2+-sensitive LV calpain activity. The calpain-specific inhibitor MDL28170 administered within 1 h after exposure significantly decreased calpain activity and acute mortality. Bromine inhalation and formation of reactive brominated species caused acute cardiac injury and myocardial damage that can lead to heart failure. NEW & NOTEWORTHY The present study defines left ventricular systolic and diastolic dysfunction due to cardiac injury after bromine (Br2) inhalation. A calpain-dependent mechanism was identified as a potential mediator of cardiac ultrastructure damage. This study not only highlights the importance of monitoring acute cardiac symptoms in victims of Br2 exposure but also defines calpains as a potential target to treat Br2-induced toxicity.

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24

Dey, Mishtu, Ryan C. Kunz, Derek M. Lyons, and Stephen W. Ragsdale. "Characterization of Alkyl-Nickel Adducts Generated by Reaction of Methyl-Coenzyme M Reductase with Brominated Acids†." Biochemistry 46, no. 42 (October 2007): 11969–78. http://dx.doi.org/10.1021/bi700925n.

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25

Richardson, Susan D., Alfred D. Thruston, Chaim Rav-Acha, Ludmila Groisman, Inna Popilevsky, Olga Juraev, Victor Glezer, A. Bruce McKague, Michael J. Plewa, and Elizabeth D. Wagner. "Tribromopyrrole, Brominated Acids, and Other Disinfection Byproducts Produced by Disinfection of Drinking Water Rich in Bromide." Environmental Science & Technology 37, no. 17 (September 2003): 3782–93. http://dx.doi.org/10.1021/es030339w.

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26

Gewurtz, Sarah B., Paula Guerra, Min Gu Kim, Frankie Jones, Jane Challen Urbanic, Steven Teslic, and Shirley Anne Smyth. "Wastewater Treatment Lagoons: Local Pathways of Perfluoroalkyl Acids and Brominated Flame Retardants to the Arctic Environment." Environmental Science & Technology 54, no. 10 (April 28, 2020): 6053–62. http://dx.doi.org/10.1021/acs.est.9b06902.

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27

Zheng, Lili, Hongjie Sun, Chouye Wu, Yibo Wang, Yuanyuan Zhang, Guangcai Ma, Hongjun Lin, Jianrong Chen, and Huachang Hong. "Precursors for brominated haloacetic acids during chlorination and a new useful indicator for bromine substitution factor." Science of The Total Environment 698 (January 2020): 134250. http://dx.doi.org/10.1016/j.scitotenv.2019.134250.

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28

Monserrate, E., and M. M. Häggblom. "Dehalogenation and biodegradation of brominated phenols and benzoic acids under iron-reducing, sulfidogenic, and methanogenic conditions." Applied and environmental microbiology 63, no. 10 (1997): 3911–15. http://dx.doi.org/10.1128/aem.63.10.3911-3915.1997.

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29

Garson, Mary J., Mary P. Zimmermann, Max Hoberg, Rundi M. Larsen, Christopher N. Battershill, and Peter T. Murphy. "Isolation of brominated long-chain fatty acids from the phospholipids of the tropical marine spongeAmphimedon terpenensis." Lipids 28, no. 11 (November 1993): 1011–14. http://dx.doi.org/10.1007/bf02537123.

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30

Garcia-Villanova, Rafael J., César Raposo Funcia, M. Vilani Oliveira Dantas Leite, Ivania M. Toruño Fonseca, Miguel Espinosa Nieto, and Javier Espuelas India. "Direct injection ion chromatography for the control of chlorinated drinking water: simultaneous estimation of nine haloacetic acids and quantitation of bromate, chlorite and chlorate along with the major inorganic anions." Journal of Water and Health 12, no. 3 (February 19, 2014): 443–51. http://dx.doi.org/10.2166/wh.2014.180.

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Most methods for the analysis of haloacetic acids published in recent years are based on ion chromatography with direct injection, employing a gradient elution with potassium hydroxide (KOH). This work reports the exploration of an alternative eluent, a buffer of sodium carbonate/sodium hydrogen carbonate, aimed at the simultaneous analysis of nine haloacetic acids along with bromate, chlorite and chlorate. The alternative of both a less alkaline eluent and a lower temperature of operation may prevent the partial decomposition of some of the haloacetic acids during the analytical process, especially the more vulnerable brominated ones. Gradient elution at temperature of 7 °C yielded the best results, with an acceptable separation of 17 analytes (which includes the major natural inorganic anions) and a good linearity. Precision ranges from 0.3 to 23.4 (% V.C.), and detection limits are within units of μg L−1, except for tribromoacetic acid – somewhat high in comparison with those of the official methods. Nonetheless, with the basic instrumentation setup herein described, this method may be suitable for monitoring when the drinking water treatments are to be optimized. This is especially interesting for small communities or for developing/developed countries in which regulations on disinfection by-products others than trihalomethanes are being addressed.

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31

Shin, Bohyun, Se Hee Hong, Sumin Seo, Cho Hee Jeong, Jiyu Kim, Eunbin Bae, Donghee Lee, et al. "Hepatocellular Metabolic Abnormalities Induced by Long-Term Exposure to Novel Brominated Flame Retardant, Hexabromobenzene." Toxics 11, no. 2 (January 21, 2023): 101. http://dx.doi.org/10.3390/toxics11020101.

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Novel brominated flame retardants (NBFRs) are widely used to avoid environmental accumulation concerns and because of the regulations imposed on classical BFRs. However, recent studies have not revealed the negative effects of NBFR accumulation and exposure on humans. We conducted a metabolomics study on hexabromobenzene (HBB), one of the NBFRs, to investigate its effect on hepatocytes. Gas chromatography–mass spectrometry-based metabolite profiling was performed to observe metabolic perturbations by treating human livertissue-derived HepG2 cell lines with HBB for maximum 21 days. Metabolic pathway enrichment using 17 metabolite biomarkers determined via univariate and multivariate statistical analysis verified that long-term accumulation of HBB resulted in distinct diminution of eight amino acids and five other metabolites. Molecular docking of the biomarker-related enzymes revealed the potential molecular mechanism of hepatocellular response to HBB exposure, which disrupts the energy metabolism of hepatic cells. Collectively, this study may provide insights into the hidden toxicity of bioaccumulating HBB and unveil the risks associated with non-regulated NBFRs.

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32

Ells, Barbara, David A. Barnett, Randy W. Purves, and Roger Guevremont. "Detection of Nine Chlorinated and Brominated Haloacetic Acids at Part-per-Trillion Levels Using ESI-FAIMS-MS." Analytical Chemistry 72, no. 19 (October 2000): 4555–59. http://dx.doi.org/10.1021/ac000341v.

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33

Wang, Lei, Ruilan Niu, Baiyang Chen, Liwei Wang, and Guan Zhang. "A comparison of photodegradation kinetics, mechanisms, and products between chlorinated and brominated/iodinated haloacetic acids in water." Chemical Engineering Journal 330 (December 2017): 1326–33. http://dx.doi.org/10.1016/j.cej.2017.08.086.

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34

Labine, Lisa M., and Myrna J. Simpson. "Targeted Metabolomic Assessment of the Sub-Lethal Toxicity of Halogenated Acetic Acids (HAAs) to Daphnia magna." Metabolites 11, no. 2 (February 10, 2021): 100. http://dx.doi.org/10.3390/metabo11020100.

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Halogenated acetic acids (HAAs) are amongst the most frequently detected disinfection by-products in aquatic environments. Despite this, little is known about their toxicity, especially at the molecular level. The model organism Daphnia magna, which is an indicator species for freshwater ecosystems, was exposed to sub-lethal concentrations of dichloroacetic acid (DCAA), trichloroacetic acid (TCAA) and dibromoacetic acid (DBAA) for 48 h. Polar metabolites extracted from Daphnia were analyzed using liquid chromatography hyphened to a triple quadrupole mass spectrometer (LC-MS/MS). Multivariate analyses identified shifts in the metabolic profile with exposure and pathway analysis was used to identify which metabolites and associated pathways were disrupted. Exposure to all three HAAs led to significant downregulation in the nucleosides: adenosine, guanosine and inosine. Pathway analyses identified perturbations in the citric acid cycle and the purine metabolism pathways. Interestingly, chlorinated and brominated acetic acids demonstrated similar modes of action after sub-lethal acute exposure, suggesting that HAAs cause a contaminant class-based response which is independent of the type or number of halogens. As such, the identified metabolites that responded to acute HAA exposure may serve as suitable bioindicators for freshwater monitoring programs.

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35

Heller-Grossman, L., J. Manka, B. Limoni-Relis, and M. Rebhun. "THM, haloacetic acids and other organic DBPs formation in disinfection of bromide rich Sea of Galilee (Lake Kinneret) water." Water Supply 1, no. 2 (March 1, 2001): 259–66. http://dx.doi.org/10.2166/ws.2001.0046.

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Lake Kinneret (Sea of Galilee) is the main freshwater body in Israel and is the water source for the National Water Carrier (NWC). The lake water has a uniquely high bromide content 1.9 mg/L which affects DBPs (disinfection by-products) formation. Controlled experiments using different disinfectants were carried out with the lake water in order to study DBPs formation. Formation and distribution of TOX (total organic halogen) trihalomethanes (THM), haloacetic acids (HAA) and cyanogen halides were studied during the application of the following disinfectants: Chlorine, chloramine, chlorine dioxide and a combination of chlorine dioxide with chloramine. Brominated species dominated the distribution of THM, HAA and cyanogen halide. When a high dose of chlorine was applied an unusually high percent (75%) of the TOX formation potential was identified; THM constituted about 50% of the TOX formation potential and haloacetic acids 22-28%. Tribromoacetic acid was found to undergo decomposition to form bromoform. Chlorine dioxide produced insignificant concentrations of organic DBPs and chloramine produced low concentrations. Chlorine dioxide in combination with chloramine enhanced production of CNBr and THM, but their concentrations were much lower than during chlorination.

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36

Evans, Sydney, Chris Campbell, and Olga V. Naidenko. "Analysis of Cumulative Cancer Risk Associated with Disinfection Byproducts in United States Drinking Water." International Journal of Environmental Research and Public Health 17, no. 6 (March 24, 2020): 2149. http://dx.doi.org/10.3390/ijerph17062149.

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Hundreds of different disinfection byproducts form in drinking water following necessary treatment with chlorine and other disinfectants, and many of those byproducts can damage DNA and increase the risk of cancer. This study offers the first side-by-side comparison of cancer risk assessments based on toxicological and epidemiological studies of disinfection byproducts using a comprehensive contaminant occurrence dataset for haloacetic acids and trihalomethanes, two groups of disinfection byproducts that are regulated in drinking water. We also provide the first analysis of a new occurrence dataset for unregulated haloacetic acids that became available from the latest, fourth round of the U.S. EPA-mandated unregulated contaminant monitoring program (UCMR4). A toxicological assessment indicated that haloacetic acids, and in particular brominated haloacetic acids, are more carcinogenic and are associated with a greater number of attributable cancer cases than trihalomethanes. Based on the toxicological analysis, cumulative lifetime cancer risk due to exposure to trihalomethanes and haloacetic acids for community water systems monitored under UCMR4, estimated with standard default parameters for body weight and water intake, corresponds to 7.0 × 10−5 (3.5 × 10−5–1.3 × 10−4). The same analysis conducted with age sensitivity factors to account for elevated risk in infants and children yielded a cumulative risk estimate of 2.9 × 10−4 (1.7 × 10−4–6.2 × 10−4). Epidemiological data suggest that lifetime cancer risk from disinfection byproducts for the U.S. population served by community water systems is approximately 3.0 × 10−3 (2.1 × 10−4–5.7 × 10−3), or a lifetime cancer risk of three cases per thousand people. Overall, this analysis highlights the value of using human data in health risk assessments to the greatest extent possible.

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37

Bendig, Paul, Lisa Maier, Katja Lehnert, Holger Knapp, and Walter Vetter. "Mass spectra of methyl esters of brominated fatty acids and their presence in soft drinks and cocktail syrups." Rapid Communications in Mass Spectrometry 27, no. 9 (April 10, 2013): 1083–89. http://dx.doi.org/10.1002/rcm.6543.

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38

Gudelis, Emilis, Sonata Krikštolaitytė, Monika Stančiauskaitė, Urtė Šachlevičiūtė, Aurimas Bieliauskas, Vaida Milišiūnaitė, Rokas Jankauskas, Neringa Kleizienė, Frank A. Sløk, and Algirdas Šačkus. "Synthesis of New Azetidine and Oxetane Amino Acid Derivatives through Aza-Michael Addition of NH-Heterocycles with Methyl 2-(Azetidin- or Oxetan-3-Ylidene)Acetates." Molecules 28, no. 3 (January 21, 2023): 1091. http://dx.doi.org/10.3390/molecules28031091.

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In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (N-Boc-azetidin-3-ylidene)acetate was obtained from (N-Boc)azetidin-3-one by the DBU-catalysed Horner–Wadsworth–Emmons reaction, followed by aza-Michael addition with NH-heterocycles to yield the target functionalised 3-substituted 3-(acetoxymethyl)azetidines. Methyl 2-(oxetan-3-ylidene)acetate was obtained in a similar manner, which was further treated with various (N-Boc-cycloaminyl)amines to yield the target 3-substituted 3-(acetoxymethyl)oxetane compounds. The synthesis and diversification of novel heterocyclic amino acid derivatives were achieved through the Suzuki–Miyaura cross-coupling from the corresponding brominated pyrazole–azetidine hybrid with boronic acids. The structures of the novel heterocyclic compounds were confirmed via 1H-, 13C-, 15N-, and 19F-NMR spectroscopy, as well as HRMS investigations.

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39

Seidel, Rüdiger W., Nils Nöthling, Richard Goddard, and Christian W. Lehmann. "Structural Elucidation of Enantiopure and Racemic 2-Bromo-3-Methylbutyric Acid." Chemistry 2, no. 3 (July 30, 2020): 691–99. http://dx.doi.org/10.3390/chemistry2030044.

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Halogenated carboxylic acids have been important compounds in chemical synthesis and indispensable research tools in biochemical studies for decades. Nevertheless, the number of structurally characterized simple α-brominated monocarboxylic acids is still limited. We herein report the crystallization and structural elucidation of (R)- and rac-2-bromo-3-methylbutyric acid (2-bromo-3-methylbutanoic acid, 1) to shed light on intermolecular interactions, in particular hydrogen bonding motifs, packing modes and preferred conformations in the solid-state. The crystal structures of (R)- and rac-1 are revealed by X-ray crystallography. Both compounds crystallize in the triclinic crystal system with Z = 2; (R)-1 exhibits two crystallographically distinct molecules. In the crystal, (R)-1 forms homochiral O–H···O hydrogen-bonded carboxylic acid dimers with approximate non-crystallographic C2 symmetry. In contrast, rac-1 features centrosymmetric heterochiral dimers with the same carboxy syn···syn homosynthon. The crystal packing of centrosymmetric rac-1 is denser than that of its enantiopure counterpart (R)-1. The molecules in both crystal structures adopt a virtually identical staggered conformation, despite different crystal environments, which indicates a preferred molecular structure of 1. Intermolecular interactions apart from classical O–H···O hydrogen bonds do not appear to have a crucial bearing on the solid-state structures of (R)- and rac-1.

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40

Rivière, Gilles, Julien Jean, Sébastien Gorecki, Marion Hulin, Martine Kolf-Clauw, Cyril Feidt, Nicole Picard-Hagen, Paule Vasseur, Bruno Le Bizec, and Véronique Sirot. "Dietary exposure to perfluoroalkyl acids, brominated flame retardants and health risk assessment in the French infant total diet study." Food and Chemical Toxicology 131 (September 2019): 110561. http://dx.doi.org/10.1016/j.fct.2019.06.008.

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41

FUSETANI, N., H. LI, K. TAMURA, and S. MATSUNAGA. "ChemInform Abstract: Bioactive Marine Metabolites. Part 46. Antifungal Brominated C18 Acetylenic Acids from the Marine Sponge, Petrosia volcano Hoshino." ChemInform 24, no. 24 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199324310.

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42

Lekkas, Themistokles D., and Anastasia D. Nikolaou. "Development of Predictive Models for the Formation of Trihalomethanes and Haloacetic Acids during Chlorination of Bromide-Rich Water." Water Quality Research Journal 39, no. 2 (May 1, 2004): 149–59. http://dx.doi.org/10.2166/wqrj.2004.022.

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Abstract The formation of disinfection by-products (DBPs) during chlorination of drinking water is an issue which has drawn significant scientific attention over the last few years, due to the adverse effects of these compounds on human health. The complicated mechanisms of the formation of DBPs are still under investigation, and modelling attempts are being made. One of the major factors affecting the yields of DBPs is the concentration of bromide ion. In bromide-rich waters, the brominated species—bromoform, dibromoacetic acid—which are considered more toxic than their chlorinated analogues, may be the major species formed and therefore the consumption of these waters may be more harmful to human health than the consumption of water containing chlorinated species (chloroform, dichloroacetic acid). During this study, the effect of bromide ion on DBP formation was investigated by bench-scale chlorination experiments and statistically evaluated for individual species of DBPs. The importance of interactions between pairs of chlorination factors, pH, bromide concentration, chlorine dose and time for DBP formation was highlighted by statistical analysis results. Moreover, multiple regression models were developed for the concentrations of total trihalomethanes and total haloacetic acids, the two major DBP groups formed. The models developed provide satisfactory estimations of, but also indicate different formation mechanisms for, these two groups of DBPs.

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43

Latifah, L. A., N. H. Soekamto, and A. Tahir. "NEW ANTIBACTERIAL ACTIVITIES OF BROMINATED C18 AND C20 FATTY ACIDS ISOLATED FROM MARINE SPONGE Xestospongia testudinaria AGAINST SHRIMP PATHOGENIC BACTERIA." Rasayan Journal of Chemistry 14, no. 01 (2021): 460–65. http://dx.doi.org/10.31788/rjc.2021.1415999.

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44

Manny, Anthony J., Staffan Kjelleberg, Naresh Kumar, Rocky de Nys, Roger W. Read, and Peter Steinberg. "Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones." Tetrahedron 53, no. 46 (November 1997): 15813–26. http://dx.doi.org/10.1016/s0040-4020(97)10034-5.

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45

Creed, John T., Matthew L. Magnuson, and Carol A. Brockhoff. "Determination of Bromate in the Presence of Brominated Haloacetic Acids by Ion Chromatography with Inductively Coupled Plasma Mass Spectrometric Detection." Environmental Science & Technology 31, no. 7 (July 1997): 2059–63. http://dx.doi.org/10.1021/es960887s.

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46

Garson, Mary J., Mary P. Zimmermann, Christopher N. Battershill, Janet L. Holden, and Peter T. Murphy. "The distribution of brominated long-chain fatty acids in sponge and symbiont cell types from the tropical marine spongeAmphimedon terpenensis." Lipids 29, no. 7 (July 1994): 509–16. http://dx.doi.org/10.1007/bf02578249.

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47

Šindelář, Karel, Jiří Holoubek, Emil Svátek, Jan Metyš, Hana Blehová, and Zdeněk Polívka. "Potential antihistaminics: Tricyclic carboxylic acids derived from 6,11-dihydrodibenzo[b,e]thiepine and 4,9-dihydrothieno[2,3-c]-2-benzothiepine." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2482–93. http://dx.doi.org/10.1135/cccc19912482.

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Reaction of nitrile IVa with the Grignard’s reagent 1-methyl-4-piperidylmagnesium chloride gave carbinol XIb as product. Carbinols XIa and XIb were dehydrated and hydrolysed with dilute hydrochloric acid to give hydrochlorides of the tricyclic amino acids Vb and Vc. Isomeric compounds with a carboxyl group in position 9 of the tricyclic skeleton were obtained either by hydrolysis of the formely prepared nitrile VIIb (compound VIIIb) or on reaction of bromoketone VIa with 1-methyl-4-piperidylmagnesium chloride, nucleophilic substitution of the bromine atom by the cyano group at the stage of carbinol XIIIb, and subsequent dehydration and hydrolysis of the cyano group, to give amino acid VIIIc. In the first case the synthesis of thiophene analogues XVIIIb and XVIIIc started from ketone XVa, which was brominated with bromine in acetic acid into position 2 of the tricyclic skeleton, followed by Grignard’s reaction with 3-dimethylaminopropylmagnesium chloride in tetrahydrofuran and hydrolysis to bromo derivative XVIb. In the second case derivative XVIc was obtained directly by bromination of hydrochloride XVc. Basic bromo derivatives XVIb and XVIc were reacted with butyllithium in tetrahydrofuran at –60°C to afford corresponding organometallic reagents which, when reacted with solid carbon dioxide, afforded the required amino acids XVIIIb and XVIIIc. Further, some other tricyclic nitriles were synthesized as potential intermediates. The prepared tricyclic amino acids Vb, Vc, VIIIb, VIIIc, XVIIIb and XVIIIc were tested both on animals and in assays of biochemical pharmacology. Some of them displayed considerable antihistaminic activity. The most interesting compound of this series, hydrochloride Vc (VUFB-17689) is a strong antihistaminic with distinctly suppressed sedative effects and it was therefore selected for a more detailed pharmacological testing.

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48

Long, Stephen M., and Hao L. Tang. "A feasibility study of disinfection by-product precursor removal from surface water by a membrane bioreactor acclimatized with wastewater organic matter." Water Science and Technology 78, no. 4 (August 31, 2018): 991–98. http://dx.doi.org/10.2166/wst.2018.386.

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Abstract A membrane bioreactor (MBR) acclimatized with wastewater organic matter was employed for surface water treatment, and the feasibility of the MBR for the removal of disinfection by-product (DBP) precursors was studied. With a low pressure microfiltration hollow-fiber membrane module, a hydraulic retention time of 1.5 hours and a solids retention time of 180 days, the MBR was able to achieve 35% removal of trichloroacetic acid precursors and 21% removal of dichloroacetic acid precursors. The removal of trichloromethane (TCM) and brominated DBP precursors was unsatisfactory. The TCM yield and bromine substitution factors for trihalomethanes and dihaloacetic acids increased. The phenomena could be attributed to an extended treatment time for hydrophobic dissolved organic matter (DOM), production of soluble microbial products from biomass activities, and an increased Br/DOM ratio by the MBR. Since the MBR treatment would lead to the production of some new DBP precursors and a change of DOM composition, the toxic potency of the DBPs formed needs to be taken into consideration if this process is employed for surface water treatment.

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49

Hammerschmidt, Adrienne, Illenora Beckmann, Mechtild Läge, and Bernt Krebs. "A Novel Crown-Ether Stabilized Oxonium Halogenochalcogenate(IV): [H7O3(Bis-dibromo-dibenzo-30-crown-10)][Se2Br9]·1.5CH2Cl2." Zeitschrift für Naturforschung B 59, no. 11-12 (December 1, 2004): 1438–43. http://dx.doi.org/10.1515/znb-2004-11-1211.

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The title compound [H7O3(bis-dibromo-dibenzo-30-crown-10)][Se2Br9] ·1.5CH2Cl2 (1) was isolated from a solution of SeBr4 and dibenzo-30-crown-10 in CH3CN/CH2Cl2 containing a small amount of hydrobromic acid. During the reaction the crown ether is brominated by HBr. The compound crystallizes in the monoclinic space group P21/n with a = 17.688(11), b = 14.921(6), c = 20.521(12) Å , β = 97.71(5)°, and Z = 4. 1 is a novel example in the series of supramolecular halogenochalcogeno acids prepared in our group in which different oxonium cations are stabilized and encapsulated by crown ethers. Especially in this class of superacids complexation by cyclic polyethers offers covenient and variable possibilities for the controlled synthesis of oxonium cations. In the present case the large dibenzo-30-crown-10 ring systems are able to stabilize trinuclear [H7O3]+ cations within their cavities. Besides the macromolecular cations and some dichloromethane solvent molecules, the crystal structure of 1 contains molecular [Se2Br9]− ions with approximate D3h symmetry, each consisting of two face-sharing SeBr6 octahedra.

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50

Pinto, Diana C. G. A., Marie L. Lesenfants, Gonçalo P. Rosa, Maria Carmo Barreto, Artur M. S. Silva, and Ana M. L. Seca. "GC- and UHPLC-MS Profiles as a Tool to Valorize the Red Alga Asparagopsis armata." Applied Sciences 12, no. 2 (January 16, 2022): 892. http://dx.doi.org/10.3390/app12020892.

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Asparagopsis armata Harvey is a red alga native from the southern hemisphere and then introduced in the Mediterranean Sea and the Atlantic Ocean, including the Azores Archipelago, where it is considered an invasive alga. Some studies show that the extracts exhibit antimicrobial and antifouling activities, and it is incorporated in some commercialized cosmetic products. (e.g., Ysaline®). However, knowledge of this species chemical composition is scarce. The GC-MS and UHPLC-MS profiles of both the nonpolar and polar extracts were established to contribute to this problem solution. According to the results, A. armata is rich in a great structural variety of halogenated lipophilic and aromatic compounds, some of them identified here for the first time. In the lipophilic extract, 25 compounds are identified, being the halogenated compounds and fatty acids, the two major compound families, corresponding to 54.8% and 35.7% of identified compounds (224 and 147 mg/100 g of dry algae, respectively). The 1,4-dibromobuten-1-ol and the palmitic acid are the two most abundant identified compounds (155 and 83.4 mg/100 g of dry algae, respectively). The polar extract demonstrated the richness of this species in brominated phenolics, from which the cinnamic acid derivatives are predominant. The results obtained herein open new perspectives for valuing the A. armata as a source of halogenated compounds and fatty acids, consequently improving its biotechnological and economic potential. Promoting this seaweed and the consequent increase in its demand will contribute to biodiversity conservation and ecosystem sustainability.

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