saccharin functional groups

What reagents are needed for the conversion of D-glucosamine to N-acetylglucosamine? Abstract. Coat. In the case where a nitrogen has four bonds to carbon (which is somewhat unusual in biomolecules), it is called a quaternary ammonium ion. All carbohydrates contain alcohol functional groups, and either an aldehyde or a ketone group (or a functional group that can be converted to an aldehyde or ketone). Chem Phys., 2008, vol. Fri 8:00am - 5:00pm. It is also used as a precursor to various materials, including plastics, resins, and other polymers. 3). Electrochem., 2009, vol. Hassan Zadeh Shirazi, S.M., Bahrololoom, M.E. Mosavat, S.H., Bahrololoom, M.E., and Shariat, M.H., Appl. and Shaw, L., Acta Mater., 2004, vol. Identify the two functional groups that interact to form a peptide bond. Electrochem., 2008, vol. Identify all the functional groups in each structure. Krill, C.E. Below is the structure of diethyl ether, a common laboratory solvent and also one of the first compounds to be used as an anesthetic during operations. 52, pp. Notably, we found that orthologs related to bacterial pro-inflammatory mediators were significantly increased after saccharin consumption (Fig. In its acid form, saccharin is not water-soluble. However, saccharin and its derivatives offer other opportunities and challenges to the synthetic chemists and biologist for the appropriate use of the same in different way, and we believe that these opportunities will never end because these catalysts will indeed form a huge source for catalytic strategies. That makes it an amide: RCONH2. 493503. Alkanes are said to be saturated hydrocarbons, because the carbons are bonded to the maximum possible number of hydrogens in other words, they are saturated with hydrogen atoms. If 3.0 mmol (3.0 10 3 mol) samples of saccharin, cyclamate, aspartame, and acesulfame K were each dissolved in separate beakers containing 500 . Electrochem., 2008, vol. Starting in 1907, the United States Food and Drug Administration began investigating saccharin as a result of the Pure Food and Drug Act. Enantiomers have the same physical properties, such as melting point, but differ in the direction they rotate polarized light. 144, pp. Electrochem., 2011, vol. 1.6: Functional Groups is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts. An imide is the nitrogen analogue of an anhydride. Ketones undergo most of the same reactions as aldehydes, but they tend to be slightly less reactive. These investigations, which had originally argued against saccharin use, were shown to prove little about saccharin being harmful to human health. catalytic condensation, functional group protection and oxidation etc. In an aldehyde, the carbonyl carbon is bonded on one side to a hydrogen, and on the other side to a carbon. 15601566. Eng. Chlorodifluoromethane was used as a refrigerant and in aerosol sprays until the late twentieth century, but its use was discontinued after it was found to have harmful effects on the ozone layer. Amines are found as components in some lubricating materials, in developers, and are a part of waterproofing textiles. The aim of this study is to clarify the functional mechanism of saccharin as a grain refiner in order to realize which functional group of this molecule works as a grain refiner and causes enhancement of properties. Saccharin is one of the additives that is usually added to the Watts bath in the electroplating process as a grain refiner. [37] In 2001, the U.S. Food and Drug Administration and the state of California reversed their positions on saccharin, declaring it safe for consumption. 52, pp. 150, pp. This is a preview of subscription content, access via your institution. It is prepared industrially by the reduction of D-glucose. Later, we will study the nature of the bonding on alkenes and alkynes, and learn that that the bonding in alkenes is trigonal planar in in alkynes is linear. around the world. 30, pp. [43][44], InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9), InChI=1/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9), Except where otherwise noted, data are given for materials in their, The examples and perspective in this section, (As discussed below, the relative contributions of Fahlberg and Remsen to the discovery were later contested, with no final resolution in sight; the 1879 paper announcing the discovery lists both names as authors, with Fahlberg's name first.). Huang S.-Q. It nauseates me to hear my name mentioned in the same breath with him."[24]. Correspondence to Surf. Pellicer, E., Varea, A., Pane, S., Sivaraman, K.M., Nelson, B.J., and Surinach, S., Surf. For instance, nanostructural nickel shows enhanced properties compared to those of polycrystalline nickel, such as higher microhardness, increased wear resistance, higher brightness and lower roughness. As the name implies, carboxylic acids are weak acids. [11] However, further study determined that this effect was due to a mechanism that is not relevant to humans (deposition of crystals; see History section). The Environmental Protection Agency has officially removed saccharin and its salts from their list of hazardous constituents and commercial chemical products. Another study carried by Yan in 2015 showed that waste shrimp, lobster and crab shells could be turn in to nitrogen rich chemicals which would beneficial for environment as well as economy.132 A new heterogeneous catalytic system (saccharin/Ti-super oxide/TBHP) has found to be efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides over Ti-superoxide using TBHP as oxidant by Kamble et al. Coat. 47, pp. 95, pp. Tue 8:00am - 5:00pm. 469474. 135, pp. 74, pp. Sci., 1996, vol. 51, 427556. As far as saccharin as amine source is concerned it can also be recycle easily and the reaction are carried under favorable and less hazardous condition moreover it is reported as green catalyst. The carbohydrate is being oxidized; Tollens or Benedicts reagent could be used. 621640. How do you find density in the ideal gas law. A carboxylate ion (see figure below), in which the negative charge is spread over two different oxygen atoms through resonance structures, is more stable than an isolated oxygen-centered anion. HHS Vulnerability Disclosure, Help Fahlberg would soon grow wealthy, while Remsen merely grew irritated, believing he deserved credit for substances produced in his laboratory. Finish., 2009, vol. For example the structure of capsaicin, found in chili peppers, incorporates several functional groups, labeled in the figure below and explained throughout this section. That makes it a sulfonamide: #"RSO"_2"NH"_2"#. Yadav et al. The results also showed that the presence of materials containing a benzene ring with a weak ionic group enhances adsorption on the electrode surface. and Kieling, V.C., Met. A, 1998, vol. Electrochem., 1995, vol. The aim of this study is to clarify the functional mechanism of saccharin as a grain refiner in order to realize which functional group of this molecule works as a grain refiner and causes enhancement of properties. 30, pp. In the process of nickel electroplating these materials were added to the Watts bath as additives. Ethene, the simplest alkene example, is a gas that serves as a cellular signal in fruits to stimulate ripening. An $$\ce{OH}$$ group that is directly connected to a carbonyl will ionize to a small extent when dissolved in water. Kamalpreet Kaur is a Project Assistant in National Institute of Technology, Delhi, India under Dr Suman Srivastava Assistant Professor, NIT, Delhi. 52, 434442 (2016). The six-carbon sugar molecules glucose and fructose, for example, contain aldehyde and ketone groups, respectively, and both contain five alcohol groups (a compound with several alcohol groups is often referred to as a ,,,, CC BY-NC-SA: Attribution-NonCommercial-ShareAlike,,, status page at 8486. Glycogen is the polysaccharide animals use to store excess carbohydrates from their diets. Fix, G.L. National Library of Medicine Gomes, C.R. Use this table when you already know the frequency of your material. The carbonyl group present in monosaccharides is easily oxidized by Tollens or Benedicts reagents (as well as others). Technol., 2007, vol. This molecule, called formaldehyde, can be used as a tissue preservative or as a very harsh disinfectant. Finally, a nitrile group is characterized by a carbon triple-bonded to a nitrogen. It summarizes characteristic group frequencies, mainly of functional groups capable of forming hydrogen bonds. [reveal-answer q=628316]Show Solution[/reveal-answer] [hidden-answer a=628316], a) carboxylate, sulfide, aromatic, two amide groups (one of which is cyclic). Mater. Sucrose is not a reducing sugar because it has no anomeric carbon that can reform a carbonyl group, and it cannot undergo mutarotation because of the restrictions imposed by this linkage. A, 1998, vol. Soc., 1997, vol. 25, pp. Mockute, D., Bernotiene, G., and Vilkaite, R., Surf. The eponymous member of this family is the carboxylic acid functional group, in which the carbonyl is bonded to a hydroxyl group. The functional group binding Gibbs free energy additivity maps are presented which may provide insights into the design of compounds with increased affinity towards selected CAs. A molecule containing a chiral carbon is nonsuperimposable on its mirror image, and two molecules that are nonsuperimposable mirror images of each other are a special type of stereoisomer called enantiomers. 52855293. [11][12] The International Agency for Research on Cancer (IARC) originally classified saccharin in Group 2B ("possibly carcinogenic to humans") based on the rat studies, but downgraded it to Group 3 ("not classifiable as to the carcinogenicity to humans") upon review of the subsequent research. In turn . Carbohydrates, a large group of biological compounds containing carbon, hydrogen, and oxygen atoms, include sugars, starch, glycogen, and cellulose. Appl. reported Saccharin-based -oxo-bridged imidoiodane used for the synthesis of -aminated carbonyl compounds using silyl enol ethers (Scheme 105).130 The reagent showed high reactivity and selectivity than other reagents. What are the units used for the ideal gas law? Methyl ethyl ketone is used as a paint stripper and a solvent. 135, pp. 4951. What reagents are necessary to carry out each conversion? How does galactosemia differ from lactose intolerance in terms of the cause of the disease and its symptoms and severity? 52855293. Raffinose, a trisaccharide found in beans and sugar beets, contains D-galactose, D-glucose, and D-fructose. [17] Saccharin in toothpaste can cause burning sensations, swelling, and rashes of the mouth and lips in sensitive individuals. [26] However, in 1912, Food Inspection Decision 142 stated that saccharin was not harmful.[27]. Cellulose, glycogen, and starch are polysaccharides. (The linkage from galactose to the glucose unit is -1,6). Priority order for functional groups in IUPAC nomenclature. Amines are characterized by nitrogen atoms with single bonds to hydrogen and carbon. Similar in structure to amylopectin, glycogen is hydrolyzed to glucose whenever an animal needs energy for a metabolic process. The disaccharide sucrose (table sugar) consists of a glucose unit and a fructose unit joined by a glycosidic linkage. Department of Materials Science and Engineering, School of Engineering, Shiraz University, Shiraz, Iran, S. M. Hassan Zadeh Shirazi,M. E. Bahrololoom&M. H. Shariat, You can also search for this author in [9][22] In 1884, then working on his own in New York City, Fahlberg applied for patents in several countries, describing methods of producing this substance that he named saccharin. Ebrahimi, F., Bourne, G.R., Kelly, M.S., and Matthews, T.E., Nanostruct. 246253. 127133. 112. Do not be confused by how the terms primary, secondary, and tertiary are applied to alcohols and amines the definitions are different. The deprotonated forms of alcohols, phenols, and thiols are called alkoxides, phenolates, and thiolates, respectively. In the case of chlordiazepoxide, absorption bands were distinguished at 3426.4, 1624.8, 1170.5, and 1029.4 cm 1 . Consequently, glucose in solution exists as an equilibrium mixture of three forms, two of them cyclic (- and -) and one open chain. 111, pp. Coat. Both groups were randomly assigned to drinking water with saccharin or water only for an additional 10 weeks. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at It has three functional groups, amino, imino and thiol, each with important biological . Moti, E., Shariat, M.H., and Bahrololoom, M.E., Mater. The six-carbon sugar molecules glucose and fructose, for example, contain aldehyde and ketone groups, respectively, and both contain five alcohol groups (a compound with several alcohol groups is often referred to as a polyol). 384403. The structure of lactulose is shown here. Electrochem., 2008, vol. 103, pp. IFA-13-CH-123. Nanostructural materials exhibit different mechanical, physical, chemical, and electrochemical properties relative to conventional structures. Water (H2O) is not carbon-based, therefore it is considered an inorganic compound. Rashidi, A.M. and Amadeh, A., Surf. Appl. She went to Indian Institute of Technology Mandi as a postdoc, and then she started her independent research as a DST Inspire faculty at National Institute of Technology Delhi. There are many possible correct answers for these, so be sure to check your structures with your instructor or tutor. Brown, H., Plating, 1968, vol. To be a reducing sugar, a disaccharide must contain an anomeric carbon atom that can open up to form an aldehyde functional group, as shown in this disaccharide (answers will vary). Part of Springer Nature. Any mono- or disaccharide containing a free anomeric carbon is a reducing sugar. Soc., 1973, vol. We are already familiar with several common alcohols. Najafi Sayar, P. and Bahrololoom, M.E., Trans. The article is published in the original. To investigate the impact of a functional group of saccharin in the production of nanocrystalline nickel deposits, three different materials with the same functional groups as saccharin were chosen: benzene sulfonic acid, methyl sulfonamide, and benzothiazole. 77, pp. 689694. Troyon, M. and Wang, L., Appl. A. Vlasov Y. G. Balova I. Chem. Sci., 2011, vol. When a carbonyl carbon is bonded on one side to a carbon (or hydrogen) and on the other side to an oxygen, nitrogen, or sulfur, the functional group is considered to be one of the carboxylic acid derivatives, a designation that describes a set of related functional groups. A procedure of regioselective amination of unsymmetrical 3,5-substituted pyridine N-oxides using saccharin as an ammonium surrogate reported by Farrell et al. 227232. Sodium saccharin is a sweetener intended for use in feed and water for drinking for piglets (suckling and weaned), pigs for fattening and calves for rearing and fattening as a sensory additive (functional group: flavouring compounds). Pavlatou, E.A., Raptakis, M., and Spyrellis, N., Surf. 55, pp. The amide group forms is extremely important in biological systems, where it is called a peptide, used for linking amino acids together to form polypeptides and (ultimately) proteins. In the European Union, saccharin is also known by the E number (additive code) E954. Balzar, D. and Ledbetter, H., J. Appl. Overall evaluation: in making the evaluation, the working group concluded that sodium saccharin produced urothelial bladder tumors in rats by a non-DNA reactive mechanism that involves the formation of a urinary calcium phosphate containing precipitate, cytotoxicity, and enhanced cell proliferation. Chem Phys., 2008, vol. 5558. On the matter, Remsen commented, "Fahlberg is a scoundrel. Technol., 2000, vol. 201, pp. The simplest ketone is acetone, in which the carbonyl carbon is bonded to two $$\ce{CH_3}$$ groups. 39, pp. B: Org. The episode proved the undoing of Wiley's career., DOI: Electrochem., 1995, vol. Lactose, D-ribose, and D-glyceraldehyde would give a positive Benedicts test. Coat. They are employed in the paper, plastic, and rubber industries. We envision that this review will help to stimulate research in the area of sugar and their derivatives that may release exhilarating perspectives in organic synthesis, material science and pharmaceutical industry. 2023 Springer Nature Switzerland AG. The hormone testosterone, the amino acid phenylalanine, and the glycolysis metabolite dihydroxyacetone phosphate all contain multiple functional groups, as labeled below. KK and SS acknowledges Department of Science and Technology (DST) for financial support through Inspire Faculty Award No. For example, the aptly-named compounds cadaverine and putrescine are foul-smelling amines, formed as a part of the decay process after death. The amide Kevlar is widely employed for the production of body armor, and nylon is another type of amide-based polymer. & Shariat, M.H. Google Scholar. Alkenes (sometimes called olefins) have carbon-carbon double bonds, and alkynes have carbon-carbon triple bonds. J. Electrochem. Saccharin 17. Mockute, D. and Bernotiene, G., Surf. Finish., 1997, vol. 13731377. [30] (It is, however, prohibited to mail saccharin tablets or packets to France. Ethyne, commonly called acetylene, is used as a fuel in welding blow torches. Sci., 1995, vol. Bethesda, MD 20894, Web Policies The chemical name of saccharin is benzoic sulfimide. Yin, K.M. PubChem . Paunovic, M. and Schlesinger, M., Fundamentals of Electrochemical Deposition, Chichester Wiley, 1998. [31]), Saccharin was formerly on California's list of chemicals known to the state to cause cancer for the purposes of Proposition 65, but it was delisted in 2001. 565574. 43, pp. The T1R2- KO deficient mice lacked functional sweet taste receptors and thus could not taste saccharin. The linkage is designated as an -1,-2-glycosidic linkage because it involves the OH group on the first carbon atom of glucose and the OH group on the second carbon atom of fructose. Most sugars are either monosaccharides or disaccharides. Esters are employed in the manufacture of fabrics (polyesters) and Plexiglass. Technol., 2002, vol. Ciszewski, A., Posluszny, S., Milczarek, G., and Baraniak, M., Surf. & Shariat, M.H. In order to produce nanostructural materials, some additives are used as grain refiners. 733739. Eng. In situ deprotection under acidic conditions allows for a one-pot process to substituted aminopyridines. 26, pp. Legal. 605612. NILERD Campus, Sec A-7, Narela, The table lists IR spectroscopy frequency ranges, appearance of the vibration and absorptions for functional groups. Part of Springer Nature. [23] Two years later, he began production of the substance in a factory in a suburb of Magdeburg in Germany. Both maltose and lactose contain a free anomeric carbon that can convert to an aldehyde functional group, so they are reducing sugars; they also undergo mutarotation. Which would give a positive Benedicts testlactose, amylopectin, D-ribose, sucrose, D-glyceraldehyde, or amylose? Coat. 4247. [33], However, in 2000, the warning labels were removed because scientists learned that rodents, unlike humans, have a unique combination of high pH, high calcium phosphate, and high protein levels in their urine. Wen Y.-S. Liu L.-K. Wei F. Zhu H. Li Z. Wang H. Zhu Y. Zhang L. Yao Z. Luo Z. Zhang C. Guo K. Frija L. M. T. Alegria E. C. B. 96, pp. Electrochem., 1991, vol. Silkin, S.A., Belevskii, S.S., Tsyntsaru, N.I., Shulman, A.I., Shchuplyakov, A.N., and Dikusar, A.I., Surf. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in Technol., 2002, vol. Morrison, R.T. and Boyd, R.N., Organic Chemistry, Englewood Cliffs, NJ Prentice Hall, 1992. Ciszewski, A., Posluszny, S., Milczarek, G., and Baraniak, M., Surf. 2023 Springer Nature Switzerland AG. Any solid sugar can be all alpha or all beta. Mater. Propose a structure for D-glucitol. Fahlberg's account of how he discovered the sweetness of saccharin appears in: International Agency for Research on Cancer, Learn how and when to remove this template message, United States Food and Drug Administration, "The Catalyzed Dehydration of Acetaldehyde Hydrate, and the Effect of Structure on the Velocity of Protolytic Reactions", "ber die Oxydation des Orthotoluolsulfamids", "Artificial sweeteners--do they bear a carcinogenic risk? t. Lactose would have the least sweet taste because it has the lowest relative sweetness. L-Fucose is an aldohexose that is often incorporated into oligosaccharides attached to cell membranes. It is indigestible in the human body but digestible by many microorganisms, including microorganisms found in the digestive tracts of many herbivores. With over twenty million known organic compounds in existence, it would be very challenging to memorize chemical reactions for each one. In Wikipedia, The Free Encyclopedia. Franklin, T.C., Surf. If there had been two sulfonyl groups on either side, we would have a sulfonimide: #"RSO"_2"NHSO"_2"R"#. Silkin, S.A., Belevskii, S.S., Tsyntsaru, N.I., Shulman, A.I., Shchuplyakov, A.N., and Dikusar, A.I., Surf. 40, pp. Many smaller amines have very strong and offensive odors. Phosphate and its derivative functional groups are ubiquitous in biomolecules. Moti, E., Shariat, M.H., and Bahrololoom, M.E., Mater. 38, pp. Surf. Appl. [28] The FDA's decision followed a 2000 determination by the U.S. Department of Health and Human Services' National Toxicology Program to remove saccharin from its list of carcinogens. 55, pp. Mockute, D., Bernotiene, G., and Vilkaite, R., Surf. Meyer, M.A., Mishra, A., and Benson, D.J., Prog. Yoshimura et al. Because of the difficulty of importing sugar from the West Indies, the British Saccharin Company was founded in 1917 to produce saccharin at its Paragon Works near Accrington, Lancashire. When ingested by humans and other animals, starch is hydrolyzed to glucose and becomes the bodys energy source. El-Sherik, A.M. and Erb, U., J. Troyon, M. and Wang, L., Appl. 40, pp. Gamburg, Y.D., Grosheva, M.Y., Biallozor, S., and Hass, M., Surf. Coat. Chen H.-C. Li C.-J. On the other side, the #"NH"# is attached to a sulfonyl group. There are a number of functional groups that contain a carbon-oxygen double bond, which is commonly referred to as a carbonyl. Technol., 2002, vol. Electrochem., 1994, vol. Find the frequency range in the first column on the . 51. 15891592. in 2003 reported the synthesis of peptides, esters and amides in the presence of new condensing reagent N,N-carbonyldisaccharin (Scheme 110). Department of Applied Sciences, National Institute of Technology, Delhi, Crucial issues include the poor regioselectivity and functional group tolerance of the protocol, as it is clearly unamenable to acid-sensitive functional groups, and side products resulting from . In a release in December 2010, the EPA stated that saccharin is no longer considered a potential hazard to human health. 11, pp. How does Charle's law relate to breathing? 45714577. [8] The calcium salt is also sometimes used, especially by people restricting their dietary sodium intake. Chem., 1980, vol. Engin. In an ether functional group, a central oxygen is bonded to two carbons. Technol., 1987, vol. A. Nicolaou K. C. Petasis N. A. Claremon D. A. Tingoli M. Tiecco M. Testaferri L. Temperini A. Tiecco M. Testaferri L. Tingoli M. Chianelli D. Bartoli D. Castanheiro T. Suffert J. Donnard M. Gulea M. Wu D. Qiu J. Karmaker P. G. Yin H. Chen F.-X. Studies in laboratory rats during the early 1970s linked saccharin with the development of bladder cancer in rodents. Ketones are also used in the production of various polymers, either as a building block or as a solvent. Pavlatou, E.A., Raptakis, M., and Spyrellis, N., Surf. She received her Master of Science degree in Chemistry under the supervision of Dr Sonia Kaushal Assistant Chemist, Punjab Agricultural University, Ludhiana, India in 2019. Mag. Coat. A. Sutradhar M. Cristiano M. L. S. Ismael A. Kopylovich M. N. Pombeiro A. J. L. Frija L. M. T. Kuznetsov M. L. Rocha B. G. M. Cabral L. Cristiano M. L. S. Kopylovich M. N. Pombeiro A. J. L. Ismael A. Paixo J. May 29, 2015 There is only one functional group in saccharine a carboxylic sulfonimide (highlighted with color in the image below). Paunovic, M. and Schlesinger, M., Fundamentals of Electrochemical Deposition, Chichester Wiley, 1998. These particular stereoisomers contain at least one chiral carbon, a carbon atom that has four different groups bonded to it. [38], Saccharin can be produced in various ways. 45714577. Mordecai, A., Nonlinear Programming: Analysis and Methods, Newburyport Dover, 2003. PubMedGoogle Scholar. To ensure that you understand the material in this chapter, you should review the meanings of the bold terms in the following summary and ask yourself how they relate to the topics in the chapter. 95100. Both salts are highly water-soluble: 0.67g/ml in water at room temperature. Najafi Sayar, P. and Bahrololoom, M.E., J. Appl. Describe the importance and purpose of functional groups in organic reactions. D-glucitol, also known as sorbitol, is added to shredded coconut to keep it soft and to pharmaceutical products to increase the absorption of nutrients. Bobanova, Z.I., Petrenko, V.I., Volodina, G.F., Grabko, D.Z., and Dikusar, A.I., Surf. Many adults, and some children, have a deficiency of the enzyme lactase (which is needed to break down lactose) and are said to be lactose intolerant. 15. [citation needed]. For instance, nanostructural nickel shows enhanced properties compared to those of polycrystalline nickel, such as higher microhardness, increased wear resistance, higher brightness and lower roughness. Najafi Sayar, P. and Bahrololoom, M.E., J. Appl. The disaccharide lactose contains a galactose unit and a glucose unit joined by a -1,4-glycosidic linkage. Inst. Google Scholar. Mater. Appl. Coat. and Pollack, J.D., Anal. What structural characteristics are necessary if a disaccharide is to be a reducing sugar? The role of functional groups of saccharin in electrodeposition of nanocrystalline nickel. Incl. In Haworth projections, the alpha form is drawn with the OH group on the former carbonyl carbon atom (anomeric carbon) pointing downward; the beta form, with the OH group pointing upward; these two compounds are stereoisomers and are given the more specific term of anomers. and Kieling, V.C., Met. Several artificial sweeteners are discussed in this chapter. Ebrahimi, F. and Ahmed, Z., J. Appl. A. Fausto R. Cristiano M. L. S. Tamura Y. Watanabe F. Nakatani T. Yasui K. Fuji M. Komurasaki T. Tsuzuki H. Maekawa R. Yoshioka T. Kawada K. Sugita K. Ohtani M. Bugalho S. C. S. Lapinski L. Cristiano M. L. S. Frija L. M. T. Fausto R. Frija L. M. T. Rocha B. G. M. Kuznetsov M. L. Cabral L. I. L. Cristiano M. L. S. Pombeiro A. J. L. Yoshimura A. Koski S. R. Fuchs J. M. Saito A. Nemykin V. N. Zhdankin V. V. Pelckmans M. Renders T. Van de Vyver S. Sels B. F. Kamble R. B. Mane K. D. Rupanawar B. R. Korekar P. Sudalai A. Suryavanshi G. Farrell R. P. Silva Elipe M. W. Bartberger M. D. Tedrow J. S. Vounatsos F. Indian J.

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