103, pp. Appl. Najafi Sayar, P. and Bahrololoom, M.E., J. Appl. 21852197. Yadav et al. National Library of Medicine Coat. [18], Saccharin was produced first in 1879, by Constantin Fahlberg, a chemist working on coal tar derivatives in Ira Remsen's laboratory at Johns Hopkins University. There are many researches recently carried out for the synthesis of organonitrogen chemicals from sustainable sources instead of ammonia. 689694. Silkin, S.A., Belevskii, S.S., Tsyntsaru, N.I., Shulman, A.I., Shchuplyakov, A.N., and Dikusar, A.I., Surf. 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. Chem. Met. We will formally learn how to name functional groups later. 26, pp. Nanostructural materials exhibit different mechanical, physical, chemical, and electrochemical properties relative to conventional structures. Appl. Mockute, D., Bernotiene, G., and Vilkaite, R., Surf. 47, pp. Coat. 1.6: Functional Groups is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts. Which enzyme hydrolyzes each carbohydrate? Technol., 2004, vol. 7. That makes it a sulfonamide: #"RSO"_2"NH"_2"#. 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. (Scheme 108).134 Under mild conditions corresponding saccharin adducts has been achieved. When the carbon of an alkane is bonded to one or more halogens, the group is referred to as a alkyl halide or haloalkane. Raffinose, a trisaccharide found in beans and sugar beets, contains D-galactose, D-glucose, and D-fructose. Surf. Identify the two functional groups that interact to form a peptide bond. Technol., 2007, vol. Technol., 2002, vol. 8486. Soc., 1973, vol. [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). Furthermore, many alkenes can take two geometric forms: cis or trans. Technol., 2011, vol. Electrochem., 2007, vol. IFA-13-CH-123. 30, pp. Over time, the rat's bladder responds to this damage by overproducing cells to repair the damage, which leads to tumor formation. 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. Gomes, C.R. Soc., 1997, vol. 95, pp. An imide is the nitrogen analogue of an anhydride. Other derivatives are carboxylic esters (usually just called esters), thioesters, amides, acyl phosphates, acid chlorides, and acid anhydrides. This is a preview of subscription content, access via your institution. Macheras, J., Vouras, D., Kollia, C., and Spyrellis, N., Trans. 52, pp. Coat. . This is greater step towards the greener approach in the organic synthesis. Saccharin (C6H4SO2CON) Water (H2O) Water (H2O) -Organic compounds always contain carbon and hydrogen, and they are typically structurally complex. Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. This condensing reagent was easily prepared by reacting saccharin and trichloromethyl chloroformate in 2:1 molar ratio under refluxing toluene as shown in Scheme 109.135. A group with a carbon-nitrogen double bond is called an imine, or sometimes a Schiff base (in this book we will use the term imine). 40, pp. Fix, G.L. As far the catalytic activity of saccharin and its derivatives is concerned it is found to be more effective with good yield than the standard archetype catalyst. Mosavat, S.H., Bahrololoom, M.E., and Shariat, M.H., Appl. The structure of lactulose is shown here. Eng. May 29, 2015 There is only one functional group in saccharine a carboxylic sulfonimide (highlighted with color in the image below). also investigated the oxidation of secondary alcohols such as allylic, benzylic, and aliphatic secondary alcohols to corresponding ketones in the presence of cobalt(ii) and copper(ii) tetrazole-saccharinate as an effective catalyst (Scheme 103).128 Full conversion was carried out under mild conditions and overcome the major drawback as oxidative (dehydrogenation) activation of alcohol. 21, pp. The aromatic group is exemplified by benzene (which used to be a commonly used solvent in the organic lab, but which was shown to be carcinogenic), and naphthalene, a compound with a distinctive mothball smell. National Library of Medicine. [14] It is safe to consume for individuals with diabetes or prediabetes. Hassan Zadeh Shirazi, S.M., Bahrololoom, M.E. Saccharin derivatives are also useful in carrying out named reaction as Kumar et al. 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. Fri 8:00am - 5:00pm. Pavlatou, E.A., Raptakis, M., and Spyrellis, N., Surf. The structure of saccharin is The NH group looks like an amine, but it isn't, because it is attached to a carbonyl group. 150, pp. [30] (It is, however, prohibited to mail saccharin tablets or packets to France. In the mice study, neither of the saccharin doses affected the glucose or hormonal responses to an oral glucose tolerance test (OGTT . This ester also serves as an alarm signal for honeybees. [34][35] One or more of the proteins that are more prevalent in male rats combine with calcium phosphate and saccharin to produce microcrystals that damage the lining of the bladder. Surface Engineering and Applied Electrochemistry Find the frequency range in the first column on the . The table lists IR spectroscopy frequency ranges, appearance of the vibration and absorptions for functional groups. 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. 517523. 33, pp. The enzyme -galactase catalyzes the hydrolysis of raffinose to galactose and sucrose. In a clash that had career consequences, Wiley told President Theodore Roosevelt, "Everyone who ate that sweet corn was deceived. Octane, C8H18, is a component of gasoline. The role of functional groups of saccharin in electrodeposition of nanocrystalline nickel. Ethyne, commonly called acetylene, is used as a fuel in welding blow torches. Huang, C.H., J. Saccharin can be divided into two types: water insoluble and soluble saccharin. Anesthetics such as procaine and benzocaine also contain esters. 45714577. 205, pp. 51, 427556. Starting in 1907, the United States Food and Drug Administration began investigating saccharin as a result of the Pure Food and Drug Act. Moti, E., Shariat, M.H., and Bahrololoom, M.E., Mater. Thu 8:00am - 5:00pm. A, 1998, vol. [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. Accessibility With over twenty million known organic compounds in existence, it would be very challenging to memorize chemical reactions for each one. The attempted ban was unsuccessful due to public opposition that was encouraged by industry advertisements,[28] and instead the following label was mandated: "Use of this product may be hazardous to your health. Pavlatou, E.A., Raptakis, M., and Spyrellis, N., Surf. 15891592. From this review it is inferred that saccharin and its derivative can provide a vast range of catalytic system for synthesis of various heterocyclic framework, protection of functional groups as well as for functional group conversion. Ethers are good solvents for other organic compounds because of their low reactivity. Nakamura, Y., Kaneko, N., Watanabe, M., and Nezu, H., J. Appl. Some amines, such as novocaine, are used as anesthetics. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. in 2003 reported the synthesis of peptides, esters and amides in the presence of new condensing reagent N,N-carbonyldisaccharin (Scheme 110). Some esters have very pleasant odors, so they are used in the manufacture of many perfumes. We reported all the available data on saccharin It nauseates me to hear my name mentioned in the same breath with him."[24]. 111, pp. and Kieling, V.C., Met. What reagent(s) could be used to carry out each conversion? - 210.65.88.143. Saccharin is heat-stable. Saccharin is one of the additives that is usually added to the Watts bath in the electroplating process as a grain refiner. 30, pp. Coat. The form used as an artificial sweetener is usually its sodium salt. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in Note: Khan Academy video tutorial on functional groups: A YouTube element has been excluded from this version of the text. [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. Functional Expectations & Requirements The Associate Administrator has responsibility for evaluating the performance of the various departments, as well as the performance of key managers and . { "1.01:_Introduction_to_organic_chemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.02:_History" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.03:_Basics_of_bonding" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.04:_Representing_structures" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.05:_1.5-._Isomerism" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.06:_Functional_Groups" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.07:_3D_Structure" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1.08:_Intermolecular_forces" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "01:_Introduction" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "02:_Bonding_and_Molecular_Structure" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "03:_Nomenclature_Isomerism_and_Conformations" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "04:_Stereochemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "05:_Physical_Organic_Chemistry" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "06:_Acids_Bases_and_Electron_Flow" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "07:_Organic_Reactions" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "08:_NUCLEOPHILIC_SUBSTITUTIONS_AND_ELIMINATIONS" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "09:_NUCLEOPHILIC_SUBSTITIONS_and_ELIMINATIONS_IN_PRACTICE" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "10:_Electrophilic_Addition" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FSUNY_Potsdam%2FBook%253A_Organic_Chemistry_I_(Walker)%2F01%253A_Introduction%2F1.06%253A_Functional_Groups, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Even if other parts of the molecule are quite different, certain functional groups tend to react in certain ways. and Shaw, L., Acta Mater., 2004, vol. [citation needed]. Consistently, the functional enrichment analysis of the gut microbes also displayed a huge distinction in bacterial functional repertoire between the saccharin and control group. Correspondence to Amines are characterized by nitrogen atoms with single bonds to hydrogen and carbon. 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. ", "Do Sweet 'N Low Dangers Still Exist? Bromoethane is a simple alkyl halide often used in organic synthesis. 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. Received 2020 Jul 8; Accepted 2020 Sep 24. Glycogen is the polysaccharide animals use to store excess carbohydrates from their diets. The amide Kevlar is widely employed for the production of body armor, and nylon is another type of amide-based polymer. We will learn more about the structure and reactions of aromatic groups next semester. 655660. Finally, a nitrile group is characterized by a carbon triple-bonded to a nitrogen. 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. 95, pp. Most sugars are either monosaccharides or disaccharides. If there had been two carbonyl groups on either side, we would have an imide: #"RCONHCOR"#. 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. 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. Olah G. A. Gupta B. G. B. Narang S. C. Malhorta R. Kochhar K. S. Bal B. S. Deshpande R. P. Rajadhyaksha S. N. Pinnick H. W. Zare A. Kaveh H. Merajoddin M. Moosavi-Zare A. R. Hasaninejad A. Zolfigol M. A. Zare A. Mokhlesi M. Hasaninejad A. Hekmat-Zadeh T. de Souza S. P. L. da Silva J. F. M. de Mattos M. C. S. Baharfar R. Alinezhad H. Azimi S. Salehian F. Firouzabadi H. Iranpoor N. Ebrahimzadeh F. Dawn H.-S. Pitman I. H. Higuchi T. Young S. Nockemann P. Thijs B. Driesen K. Janssen C. R. Hecke K. V. Meervelt L. V. Kossmann S. Kirchner B. Binnemans K. Kumar A. Kumar P. Tripathi V. D. Srivastava S. Ming L. Wei-Si G. Li-Rong W. Ya-Feng L. Hua-Zheng Y. Kumar A. Srivastava S. Gupta G. Kumar P. Sarkar J. Moghaddam F. M. Koozehgiri G. R. Dekamin M. G. Cochet T. Bellosta V. Greiner A. Roche D. Cossy J. Fang H.-P. Fu C.-C. Tai C.-K. Chang K.-H. Yang R.-H. Wu M.-J. Fahlberg would soon grow wealthy, while Remsen merely grew irritated, believing he deserved credit for substances produced in his laboratory. 83118316. 469474. Phosphate and its derivative functional groups are ubiquitous in biomolecules. Saccharin, cyclamates, aspartame, acesulfame-K are some of the widely used non-nutritive sweeteners. The deprotonated forms of alcohols, phenols, and thiols are called alkoxides, phenolates, and thiolates, respectively. Polyacrylamide is a very widely used amide; it is involved in t he treatment of drinking water and sewage, and in plastics manufacture. Saccharin is one of the additives that is usually added to the Watts bath in the electroplating process as a grain refiner. As we progress in our study of organic chemistry, it will become extremely important to be able to quickly recognize the most common functional groups, because they are the key structural elements that define how organic molecules react. 227232. El-Sherik, A.M. and Erb, U., J. 246253. Electrochem., 2010, vol. Delhi 110040 strong hydrogen bonds. 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. Department of Applied Sciences, National Institute of Technology, Delhi, Many smaller amines have very strong and offensive odors. Identify all the functional groups in each structure. Yoshimura et al. Telehealth services available. Paunovic, M. and Schlesinger, M., Fundamentals of Electrochemical Deposition, Chichester Wiley, 1998. Appl. 201, pp. Rashidi, A.M. and Amadeh, A., Surf. The article is published in the original. Troyon, M. and Wang, L., Appl. What reagents are necessary to carry out each conversion? 40, pp. In this synthesis, the methyl anthranilate successively reacts with nitrous acid (from sodium nitrite and hydrochloric acid), sulfur dioxide, chlorine, and then ammonia to yield saccharin:[41], The free acid of saccharin has a low pKa of 1.6 (the acidic hydrogen being that attached to the nitrogen). The simplest ketone is acetone, in which the carbonyl carbon is bonded to two $$\ce{CH_3}$$ groups. The disaccharide maltose contains two glucose units joined in an -1,4-glycosidic linkage. Priority order for functional groups in IUPAC nomenclature. This protocol was really helpful as the condensing reagent is easy to handle and sides products as saccharin is easily removed from the product mixture with 1% cold sodium hydrogen carbonate. National Institutes of Health. Neltner T. G. Kulkami N. R. Alger H. M. Maffini M. V. Bongard E. D. Fortin N. D. Olson E. D. Chattopadhyay S. Raychaudhuri U. Chakraborty R. Banerjee B. Bhardwaj V. Kaur A. Kaur G. Singh A. Nageswar Y. V. D. Reddy K. H. V. Ramesh K. Murthy S. N. Bandyopadhyay D. Mukherjee S. Granados J. C. Short J. D. Banik B. K. Balakrishna A. Aguiar A. Sobral P. J. M. Wani M. Y. Silva J. I. Synthesis of Aliphatic Secondary Amines", https://en.wikipedia.org/w/index.php?title=Saccharin&oldid=1142489456, 228.8 to 229.7C (443.8 to 445.5F; 501.9 to 502.8K), This page was last edited on 2 March 2023, at 17:53. Technol., 2000, vol. Electrochem., 2007, vol. 52855293. For example, citric acid (three carboxyl groups) is especially abundant in citrus fruits and it used as a flavoring and preservative in many foods and beverages. c) A compound with molecular formula C6H9NO that has an amide functional group, and does not have an alkene group. PubMedGoogle Scholar. Zemanova, M., Gal, M., Usak, E., and Jurisova, J., J. Appl. volume52,pages 434442 (2016)Cite this article. 4H2O salt (Scheme 102a). 25, pp. The #"NH"# group looks like an amine, but it isn't, because it is attached to a carbonyl group. [28] (See also: labeling below.) 55, pp. The default in organic chemistry (essentially, the lack of any functional groups) is given the term alkane, characterized by single bonds between carbon and carbon, or between carbon and hydrogen. Why does a deficiency of lactase lead to cramps and diarrhea? Huang S.-Q. 39, pp. Hypervalent iodine reagents have found to be efficient and eco-friendly and efficient oxidizing reagents for various oxidative transformations.129 Saccharin-based -oxo-bridged imidoiodane (19) was synthesized by reaction of (diacetoxyiodo)benzene and saccharin (Scheme 104). The cis and trans forms of a given alkene are different molecules with different physical properties because, as we will learn in chapter 2, there is a very high energy barrier to rotation about a double bond. Med. Ebrahimi, F., Bourne, G.R., Kelly, M.S., and Matthews, T.E., Nanostruct. 353358. 343350. around the world. A single compound often contains several functional groups, particularly in biological organic chemistry. Draw one example each of compounds fitting the descriptions below, using line structures. 8600 Rockville Pike Inst. Sci., 1996, vol. 415428. Do not be confused by how the terms primary, secondary, and tertiary are applied to alcohols and amines the definitions are different. 26, pp. 415428. Saccharin derives its name from the word "saccharine", meaning "sugary". A procedure of regioselective amination of unsymmetrical 3,5-substituted pyridine N-oxides using saccharin as an ammonium surrogate reported by Farrell et al. The word saccharine is used figuratively, often in a derogative sense, to describe something "unpleasantly over-polite" or "overly sweet". Hassani, S., Raeissi, K., and Golozar, M.A., J. Appl. Lowenheim, F.A., Modern Electroplating, Chichester: Wiley, 1974, 3rd ed. Pellicer, E., Varea, A., Pane, S., Sivaraman, K.M., Nelson, B.J., and Surinach, S., Surf. Krill, C.E. J. Electrochem. Saccharin is one of the additives that is usually added to the Watts bath in the electroplating process as a grain refiner. capable of acting as hydrogen donors (N-H) and hydrogen acceptors (S=O, C=O), forming. Esters are very important in synthesis and in nature. Its popularity further increased during the 1960s and 1970s among dieters, since saccharin is a calorie-free sweetener. Mater., 1999, vol. Choo, R.T.C., Toguri, J.M., El-Sherik, A.M., and Erb, U., J. Appl. With the exception of acid chlorides and acid anhydrides, the carboxylic acid derivatives are very common in biological molecules and/or metabolic pathways. Coat. [26] However, in 1912, Food Inspection Decision 142 stated that saccharin was not harmful.[27]. Meyer, M.A., Mishra, A., and Benson, D.J., Prog. Intestinal bacteria can act on the lactose present in the intestine to produce organic acids and gases. The simplest aldehyde has a carbonyl group bonded to two hydrogen atoms. and Birringer, R., Philos. 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. Production continued on the site until 1926. and Pollack, J.D., Anal. Pellicer, E., Varea, A., Pane, S., Sivaraman, K.M., Nelson, B.J., and Surinach, S., Surf. Electrochem., 1995, vol. 11, pp. Mordecai, A., Nonlinear Programming: Analysis and Methods, Newburyport Dover, 2003. It is indigestible in the human body but digestible by many microorganisms, including microorganisms found in the digestive tracts of many herbivores. 3). Mater. Draw the Fischer projections for D-galactose and D-fructose. Carbohydrates, a large group of biological compounds containing carbon, hydrogen, and oxygen atoms, include sugars, starch, glycogen, and cellulose. 52, pp. Eng. catalytic condensation, functional group protection and oxidation etc. Chang J.-Y. 257, pp. Brown, H., Plating, 1968, vol. | Everyday Health", "Toothpaste Allergy: Yes, You Can be Allergic to Toothpaste", "On the oxidation of substitution products of aromatic hydrocarbons. Surf. Electrochem., 2009, vol.