2-Furoic acid

445283361 2-Furoic Acid File:Furan-2-carboxylic acid 200.svg Furan-2-carboxylic acid Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 746 10.1039/9781849733069-FP001 978-0-85404-182-4 Front Matter 2-Furoic acid Pyromucic acid 2-Furancarboxylic acid α-Furancarboxylic acid α-Furoic acid 2-Carboxyfuran 110149 correct EBI 30845 OC(=O)C1=CC=CO1 correct chemspider 10251740 3056 C01546 1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3 MZRVEZGGRBJDDB-NESCHKHYAE correct chemspider 1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7) correct chemspider SMNDYUVBFMFKNZ-UHFFFAOYSA-N correct CAS 88-14-2 correct FDA P577F6494A 6919 5 4 3 White/ Off-White (Beige) Crystalline Powder 0.55 g/cm3 Easily soluble in cold and hot water, 27.1 g/L 128 to 132 230 to 232 3.12 at 25 °C Irritating to eyes, respiratory system and skin. 2 1 0 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 2-Thiophenecarboxylic acid, 3-Furoic acid, Furfuryl alcohol, 2,5-Furandicarboxylic acid, Furfurylamine 2-Furoic acid is an organic compound, consisting of a furan ring and a carboxylic acid side-group. Along with other furans, its name is derived from the Latin word furfur, meaning bran, from which these compounds were first produced.Alexander Senning Elsevier's Dictionary of Chemoetymology Elsevier 2006 0-444-52239-5 The salts and esters of furoic acids are known as furoates. 2-Furoic acid is most widely encountered in food products as a preservative and a flavouring agent, where it imparts a sweet, earthy flavour. History The compound was first described by Carl Wilhelm Scheele in 1780, who obtained it by the dry distillation of mucic acid. For this reason it was initially known as pyromucic acid. This was the first known synthesis of a furan compound, the second being furfural in 1821. Ueber die medicinische und chemische Anwendung und die vortheilhafte Darstellung der Ameisensäure On the medical and chemical application and the profitable preparation of formic acid 141–146 J. W. Döbereiner 3 2 1832 Annalen der Pharmacie 10.1002/jlac.18320030206 https://zenodo.org/record/1426896 de From p. 141: "Ich verbinde mit diese Bitte noch die Bemerkung, ... Bittermandelöl riechende Materie enthält, ... " (I join to this request also the observation that the formic acid which is formed by the simultaneous reaction of sulfuric acid and manganese peroxide with sugar and which contains a volatile material that appears oily in an isolated condition and that smells like a mixture of cassia and bitter almond oil ...) On the Oils Produced by the Action of Sulphuric Acid upon Various Classes of Vegetables. [Abstract] 939–941 John Stenhouse 5 1843 Abstracts of the Papers Communicated to the Royal Society of London 111080 10.1098/rspl.1843.0234 https://zenodo.org/record/1432029 free See also: Stenhouse John On the oils produced by the action of sulphuric acid upon various classes of vegetables Philosophical Transactions of the Royal Society of London 1850 140 467–480 10.1098/rstl.1850.0024 186214485 free Despite this, it was furfural which came to set naming conventions for later furans. Preparation and synthesis thumbnail|left|310px|Biotransformation of furfuryl alcohol (R = CH2OH) or furfural (R = CHO) to 2-furoic acid by Nocardia corallina 2-Furoic acid can be synthesized by the oxidation of either furfuryl alcohol or furfural. This can be achieved either chemically or biocatalytically. The current industrial route involves the Cannizzaro reaction of furfural in an aqueous NaOH solution. This is a disproportionation reaction and produces a 1:1 ratio of 2-furoic acid and furfuryl alcohol (a 50% yield of each).Mariscal R. Maireles-Torres P. Ojeda M. Sádaba I. López Granados M. Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels Energy Environ. Sci. 9 4 2016 1144–1189 1754-5692 10.1039/C5EE02666K https://digital.csic.es/bitstream/10261/184700/1/Mariscal_Furfural-A%20renewable_versatile_2016_postprint.pdf 10261/184700 101343477 free It remains economical because both products have commercial value. The bio-catalytic route involves the microorganism Nocardia corallina. This produces 2-furoic acid in higher yields: 98% from 2-furfuryl alcohol and 88% from 2-furfural, Microbial biocatalytic preparation of 2-furoic acid by oxidation of 2-furfuryl alcohol and 2-furanaldehyde with Nocardia corallina Herminia Pérez 8 10 2009 African Journal of Biotechnology but has yet to be commercialised. Applications and occurrences thumb|left|Diloxanide, an amebicide derived from 2-feroic acid,Farthing Michael JG Treatment options for the eradication of intestinal protozoa Nature Clinical Practice Gastroenterology & Hepatology August 2006 3 8 436–445 10.1038/ncpgasthep0557 16883348 19657328 is on the World Health Organization's List of Essential Medicines. ((World Health Organization)) World Health Organization model list of essential medicines: 21st list 2019 2019 10665/325771 World Health Organization World Health Organization Geneva WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO free In terms of commercial uses, 2-furoic acid is often used in the production of furoate esters, some of which are drugs and pesticides.Zitt Myron Kosoglou Teddy Hubbell James Mometasone Furoate Nasal Spray: A Review of Safety and Systemic Effects Drug Safety 2007 30 4 317–326 10.2165/00002018-200730040-00004 17408308 42398133 In foods It is a flavoring ingredient and achieved a generally recognized as safe (GRAS) status in 1995 by the Flavor and Extract Manufacturers Association (FEMA). 2-Furoic acid has a distinct odor described as sweet, oily, herbaceous, and earthy.Burdock Encyclopedia of Food and Color Additives 0-8493-9414-7 George Bob Stern P–Z indexes 3 2359 1996 2-Furoic acid helps sterilize and pasteurize many foods. It forms in situ from 2-furfural. Hucker B. Varelis P. 2011 Thermal decarboxylation of 2-furoic acid and its implication for the formation of furan in foods Food Chemistry 126 3 1512–1513 10.1016/j.foodchem.2010.12.017 2-Furoic acid is also formed during coffee roasting, with up to 205 mg/kg. A novel UHPLC method for determining the degree of coffee roasting by analysis of furans Food Chemistry 341 128165 10.1016/j.foodchem.2020.128165 2021 Macheiner Lukas Schmidt Anatol Karpf Franz Mayer Helmut K. Pt 1 33038777 222280614 Optic properties 2-Furoic acid crystals are highly transparent in the 200–2000 nm wavelength region, are stable up to 130 °C, and generally have low absorption in the UV, visible, and IR ranges. Uma B. Das S. Jerome Krishnan S. Boaz B. Milton 2011 Growth, optical and thermal studies on organic nonlinear optical crystal: 2-Furoic acid Physica B: Condensed Matter 406 14 2834–2839 10.1016/j.physb.2011.04.038 2011PhyB..406.2834U In optical and dielectric studies, 2-furoic acid crystals may act as paraelectrics in the temperature range < 318 K and ferroelectrics in temperature ranges > 318 K.B. Uma K. Sakthi Murugesan S. Krishnan S. Jerome Das B. Milton Boaz Optical and dielectric studies on organic nonlinear optical 2-furoic acid single crystals Optik 124 17 2754–2757 10.1016/j.ijleo.2012.08.075 2013 2013Optik.124.2754U Microbial metabolism 2-Furoic acid can be the sole source of carbon and energy for the organism Pseudomonas putida. The organism aerobically degrades the compound. Ueber das Tetraphenol C4H4O On tetraphenol C4H4O 90–91 H. Limpricht 3 1 1870 Berichte der Deutschen Chemischen Gesellschaft 10.1002/cber.18700030129 https://zenodo.org/record/1424994 Molybdenum Involvement in Aerobic Degradation of 2-Furoic Acid by Pseudomonas putida Ful. KERSTIN KOENIG 55 7 1988 Applied and Environmental Microbiology 202958 16347977 1829–34 10.1128/aem.55.7.1829-1834.1989 Hazards The LD50 is 100 mg/kg (oral, rats).H. E. Hoydonckx W. M. Van Rhijn W. Van Rhijn D. E. De Vos P. A. Jacobs Furfural and Derivatives 2007 10.1002/14356007.a12_119.pub2 References Further reading Sciencelab.com October 9, 2005 2-Furoic Acid [Material Safety Data Sheet] http://www.sciencelab.com/msds.php?msdsId=9924109 March 15, 2013 https://web.archive.org/web/20121017150124/http://www.sciencelab.com/msds.php?msdsId=9924109 October 17, 2012 Category:Reagents for organic chemistry Category:Aromatic acids Category:2-Furyl compounds