Information. In the present investigation, menthols were oxidized with sodium dichromate in sulfuric acid by usual way to give menthone and iso menthone and then the menthones, having two … This experiment generates large quantities of organic and aqueous waste, and only allows the final ratio of isomers to be determined. Moulder, Handbook of X-Ray Photoelectron Spectroscopy, ed. A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. C.D. - 193.70.89.154. L. Červený (Ed. Soc. Sci. http://pubs.acs.org/page/copyright/permissions.html. 257, (, 1900, La Plata, Argentina, Facultad de Farmacia y Bioquímica, UBA, Departamento de Química Orgánica, Junín 954, (, 1113, Buenos Aires, Argentina, Albertina Moglioni & Graciela Y. Moltrasio Iglesias, You can also search for this author in Eng. 43, 442 (1970). The rotational spectra of the monoterpenoids menthol, menthone, and isomenthone are reported in the frequency range of 2-8.5 GHz, obtained with broadband Fourier-transform microwave spectroscopy. D.C. Wigfield and D.J. 4, p. 903.
Jpn. Kukula, P., Červený, L. Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts. The equilibrium mixture of (-)-menthone and (+)-isomenthone was prepared by (-)- menthol oxidation using peracetic acid in ethyl acetate using NaBr. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. http://pubs.acs.org/page/copyright/permissions.html. K. Sakai, M. Ishige, H. Kono, I. Motoyama, K. Watwnabe, and K. Hata, Bull. Res. Catal.
Eng. Sci. Akad. Pavel Kukula. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work.
64 (1990) 1. Catalysis Letters Soc. Users are Chem. D.C. Wigfield and D.J.
Ferretti, React.
Kinet. Empirical Formula (Hill Notation) C 10 H 18 O . McGraw-Hill, New York, N.Y., 1962. redistribute this material, requesters must process their own requests via the RightsLink permission Catal. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. © 2020 Springer Nature Switzerland AG. Phelps, J. Org. Casella, G.J. Catal. Beumel, J.
Hawkes, K. Herwig, and J.D. M. Misono and N. Noijri, Appl. L-Menthone mixture of isomers, ≥96%, FCC, FG Synonym: (−)-Menthone, (1R,4S)-p-Menthan-3-one, (2S,5R)-2-Isopropyl-5-methylcyclohexanone, trans-menthone CAS Number 14073-97-3. 257, (, 1900, La Plata, Argentina, Virginia Vetere, Gerardo F. Santori, Mónica L. Casella & Osmar A. Ferretti, Facultad de Ingeniería de la UNLP, 47 No. You have to login with your ACS ID befor you can login with your Mendeley account. This “green” modification dramatically reduces the quantity of waste, eliminates the hazards of concentrated acid, and allows for the isomer ratio to be monitored as a function of time. 8, 1920 (1989). 53, 3270 (1980). J.P. Candy, O. Ferretti, J.P. Bournonville, A. El Mansour, J. Basset and G. Martino, J. Catal. Davies and J.F. Am. Soc. Sodano, and M.J. Sisbarro, J. Org. You’ve supercharged your research process with ACS and Mendeley! 148 (1999) 145.
CAS Augustine, D.C. Migliorini, R.E. 6/28/11 Chirality, Gas Chromatography and Menthone Abstract The purpose of this experiment is to isomerize (-)-menthone to its diasteriomer (-)-isomenthone under acidic conditions. A. Tungler, T. Máthé, Z. Bende and J. Petro, Appl. Klabunovskii, and L.A. Kheifits, Izv. 96, 543 (1974). Ferretti, Appl. Surf. The Isomerization of (−)-Menthone to (+)-Isomenthone Catalyzed by an Ion-Exchange Resin, Department of Chemistry, California State University Channel Islands, One University Drive, Camarillo, California 93012, United States, Your Mendeley pairing has expired. ), Catalytic Hydrogenation, Elsevier, Amsterdam, 1986. Information about how to use the RightsLink permission system can be found at
a3-Menthone enol acetate (VII) was pre-pared from both menthone and isomenthone by several workersl-5 J. 33 (1994) 1881. 112 (1988) 210. E.L. Eliel, Stereochemistry of Carbon Compounds. Learn more about Institutional subscriptions. Article
Listy M. Sugahara, S. Tsuchida, I. Anazawa, Y. Takagi, and S. Teratani, Chem. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. P. Ravi, R. Ravichandran and S. Divakar, J. Mol. 5) The observed optical rotation of a mixture of (-)-menthone and (+)-isomenthone with a concentration of 0.0662 g/ml was measured at +0.891° in a 1 decimeter (dm) cell. Roberts, J. Org. Chem. 52, 633 (1979). G. Santori, M. Casella, G. Siri, O. Ferretti, A. Moglioni and G. Moltrasio, Stud. Chem. 36, S3 (1998). This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. Get article recommendations from ACS based on references in your Mendeley library. T. Chihara and K. Tanaka, Bull. 4) Consider the ketones piperitone, menthone, and isomenthone.
Chem. Google Scholar. The hydrogenation of these terpenones was favored by the presence of tin in the bimetallic phase. Nauk SSSR, Ser. Department of Organic Technology, Institute of Chemical Technology — ICT Prague, Technická 5, 166 28, Prague 6, Czech Republic, You can also search for this author in G.E. Catal. Do not overuse or use for prolonged periods of time. Immediate online access to all issues from 2019. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. Khim. Congr. P.Z. Siri, H.R. Catal. 41, 3461 (1976). The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. Jpn. https://doi.org/10.1163/156856700X00390, DOI: https://doi.org/10.1163/156856700X00390, Over 10 million scientific documents at your fingertips, Not logged in Search results for (-)-menthone at Sigma-Aldrich. Catalysis Letters 84, 251–257 (2002). Catal. Tax calculation will be finalised during checkout. K. Hanaya, Bull. Find more information on the Altmetric Attention Score and how the score is calculated. W.B. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. - 37.97.185.129. N.D. Zubareva, E.I. Some can be convulsent, toxic to the liver, or neurotoxic in high doses. 83, 1246 (1961). CAS Soc. J. Margitfalvi, M. Hegedüs, S. Göbölös, E. Kern-Tálas, P. Szedlacsek, S. Szabó and F. Nagy, Proc.
G.F. Santori, M.L. Jpn.
This experiment generates large quantities of organic and aqueous waste, and only allows the final ratio of isomers to be determined. Boelens Aroma Chemical Information Service (BACIS), The Netherlands (1996). PubMed Google Scholar, Vetere, V., Santori, G.F., Moglioni, A. et al. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. Lett.
A: Gen. 193 (2000) 285. 41, 2396 (1976). Sheldrake and J. Crosby, Chirality in Industry (Wiley, Chichester, 1992). OUILUIVI. Menthone is a constituent of the essential oils of peppermint, Pelargonium geraniums, pennyroyal, Mentha arvensis, and others. A: Chemistry 186 (2002) 223.
Rev. Molecular Weight 154.25 . O.A.
P. Gallezot and D. Richard, Catal. Students then test their hypothesis by performing the reaction with different catalyst quantities and at different temperatures. Lett. Surf. G.F. Santori, M.L. 39, 1017 (1974). Chem. R.L. Student laboratory manual procedure including molecular modeling instructions for MarvinSketch, and instructor notes consisting of background information, gas chromatography conditions and data, answers to prelab questions, and CAS registry numbers. 31 (1987) 713. Find more information about Crossref citation counts. Chem. 34, 1075 (1969). 76, 6361 (1954). Phelps, J. H. Rothbacher and F. Suteu, Pharmazie 222 (1969). R.M. Please reconnect. Reson. Catal. 8th Int. volume 84, pages251–257(2002)Cite this article. Soc. Calculate the mole fraction (x) of (+)-isomenthone using Equation 6. R.J. Wicker, J. Chem. PubMed Google Scholar. Sci. Many ketones can be toxic internally and topically. J. Solodar, J. Org.
Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. It is a monoterpene and a ketone; it is structurally related to menthol and is seen to have carbonyl positioned in the place of secondary alcohol. A. Tungler, T. Máthé, Z. Bende, and J. Petro, Appl. Subscription will auto renew annually. system. 11, 1389 (1974). © 2020 Springer Nature Switzerland AG. Adúriz and O.A. Bedoukian, Perfumery and Flavoring Synthetics, Allured Publishing Corporation, Wheaton, USA, 1986. Chem. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. Subscription will auto renew annually.
Hydrogenation of (–)-Menthone, (+)-Isomenthone, and (+)-Pulegone with Platinum/Tin Catalysts. Soc. For permission to reproduce, republish and Soc. J.H. the Altmetric Attention Score and how the score is calculated. Its optical rotation was -16.02° within the wavelength À = 589 nm and at the temperature 20°C. H. Kuivila and O.F. Chem.
Correspondence to A: Gen. 197 (2000) 141. Makouangou, D.Y. Electronic Supporting Information files are available without a subscription to ACS Web Editions. These metrics are regularly updated to reflect usage leading up to the last few days. A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. 19 (1985) 365. B. Rickborn, J. Files available from the ACS website may be downloaded for personal use only. CINDECA (UNLP-CONICET), 47 No. from the ACS website, either in whole or in part, in either machine-readable form or any other form As part of the experimental procedure, students generate their own hypothesis regarding the position of the equilibrium using molecular modeling of (−)-menthone and (+)-isomenthone. Jpn. G. Santori, M. Casella and O. Ferretti, J. Mol. Part of Springer Nature. This material is available via the Internet at http://pubs.acs.org. Google Scholar. Smith and C. Amezcua, Magn. Chem. Adúriz and O.A.
E. Eliel, S. Wilen and L. Mander, Stereochemistry of Organic Compounds (Wiley, 1994). not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information A.N. Res Chem Intermed 26, 913–922 (2000). Immediate online access to all issues from 2019. Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. Berlin, 1984, vol.
Research on Chemical Intermediates Catal. 1956, 2165 (1956). Isomenthone is a ketone derived from menthone, as found in geranium, cistus, pennyroyal, cornmint, calamint, and peppermint. Part of Springer Nature.
Chem. Isomerizations among individual isomers were barely detectable. Soc. The catalytic hydrogenation of an optically active mixture of (−)-menthone and (+)-isomenthone was studied. S. Mutsui, H. Saito, Y. Yamashita, M. Kaminaga, and Y. Senda, Tetrahedron