(−)-Menthol was produced during these reactions to a limited extent, the production of (−)-isomenthol was barcly existent. Pavel Kukula. Ferretti, Appl. For permission to reproduce, republish and A.N. 40 (1988) 81 and references therein. Chem. E. Eliel, S. Wilen and L. Mander, Stereochemistry of Organic Compounds (Wiley, 1994).

Bedoukian, Perfumery and Flavoring Synthetics, Allured Publishing Corporation, Wheaton, USA, 1986. © 2020 Springer Nature Switzerland AG. 11, 1389 (1974). Jpn. P.Z. Tax calculation will be finalised during checkout. 76, 6361 (1954). G.E. 1956, 2165 (1956). Molecular Weight 154.25 . Catal.

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The hydrogenation of these terpenones was favored by the presence of tin in the bimetallic phase. Phelps, J. Phelps, J. Org. Files available from the ACS website may be downloaded for personal use only. Congr. R.M. 130 (2000) 2063. Some can be convulsent, toxic to the liver, or neurotoxic in high doses. CAS  Dauscher and R.A. Touroude, Ind. C.D. 84, 2414 (1962). This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. This experiment generates large quantities of organic and aqueous waste, and only allows the final ratio of isomers to be determined. R.L.

H. Rothbacher and F. Suteu, Pharmazie 222 (1969). Chem. T. Chihara and K. Tanaka, Bull. Casella, G.J. Soc. 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. Eng.

System Maintenance Alert: Due to planned maintenance of our internal systems, web functionality including order placement, price and availability checks and SDS display will not be available for Asia and several European countries from Saturday, November 7th at 2:30 CET until Sunday, November 8th at 7:00 AM CET. Google Scholar. Chem. Sci. 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. Isomerizations among individual isomers were barely detectable. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. Reson. Boelens Aroma Chemical Information Service (BACIS), The Netherlands (1996). 19, 365 (1985). A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. Gas chromatography is used to determine the percent isomerization. The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. Chem. 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. without permission from the American Chemical Society. Catal. 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. Chem. A: Gen. 193 (2000) 285. Electronic Supporting Information files are available without a subscription to ACS Web Editions. 148 (1999) 145. Soc. The pedagogical impact of the experiment has been significantly improved through examination of the effect of catalysis on the position of the equilibrium and on the kinetics of the reaction. Catal.

G. Santori, M. Casella, G. Siri, O. Ferretti, A. Moglioni and G. Moltrasio, Stud. J. Solodar, J. Org. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. Hawkes, K. Herwig, and J.D. A: Gen. 197 (2000) 141. Learn more about Institutional subscriptions. The catalytic hydrogenation of an optically active mixture of (−)-menthone and (+)-isomenthone was studied. - 37.97.185.129. P. Kukula and L. Červený, Appl. 41, 1902 (1968). Rev. R.J. Wicker, J. Chem. Beumel, J.

A: Chemistry 186 (2002) 223. L. Červený (Ed. a3-Menthone enol acetate (VII) was pre-pared from both menthone and isomenthone by several workersl-5 J. The oxidation itself produced (-)-menthone with a purity of 98%.

G.E. Immediate online access to all issues from 2019. Am. Makouangou, D.Y. Chem. Ferretti, Bettega de Pauli, J.P. Candy, G. Mabilon and J.P. Bournonville, Stud. This article has not yet been cited by other publications. J.H.

W.B. Klabunovskii, and L.A. Kheifits, Izv. Chem.

S. Mutsui, H. Saito, Y. Yamashita, M. Kaminaga, and Y. Senda, Tetrahedron

Am. Soc. Find more information about Crossref citation counts. Find more information about Crossref citation counts. O.A. Lett. Surf. Jpn. Chem. Surf. Adúriz and O.A. Sci. Find more information on the Altmetric Attention Score and how the score is calculated. The equilibrium mixture of (-)-menthone and (+)-isomenthone was prepared by (-)- menthol oxidation using peracetic acid in ethyl acetate using NaBr. Res.

McGraw-Hill, New York, N.Y., 1962. Research on Chemical Intermediates Kukula, P., Červený, L. Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts. Soc. Jpn. 4) Consider the ketones piperitone, menthone, and isomenthone. Jpn. Article  83, 1246 (1961). J.P. Candy, O. Ferretti, J.P. Bournonville, A. El Mansour, J. Basset and G. Martino, J. Catal. Catal. M. Misono and N. Noijri, Appl. Berlin, 1984, vol. redistribute this material, requesters must process their own requests via the RightsLink permission - 193.70.89.154. 41, 3461 (1976). system.

G. Santori, M. Casella and O. Ferretti, J. Mol. https://doi.org/10.1163/156856700X00390, DOI: https://doi.org/10.1163/156856700X00390, Over 10 million scientific documents at your fingertips, Not logged in ), Catalytic Hydrogenation, Elsevier, Amsterdam, 1986. 31 (1987) 713. Chem. Information about how to use the RightsLink permission system can be found at Res Chem Intermed 26, 913–922 (2000). 19 (1985) 365. You have to login with your ACS ID befor you can login with your Mendeley account. Chem. Foscante, C.S. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Article  K. Sakai, M. Ishige, H. Kono, I. Motoyama, K. Watwnabe, and K. Hata, Bull. P. Gallezot and D. Richard, Catal. Muilemberg (Minnesota, USA, 1978). Part of Springer Nature. Chem. Am. Catal. Khim. J. Margitfalvi, M. Hegedüs, S. Göbölös, E. Kern-Tálas, P. Szedlacsek, S. Szabó and F. Nagy, Proc. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information B. Rickborn, J. P. Kukula and L. Červený, Chem. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals.

CAS  Murzin, A.E.

G.F. Santori, M.L. 41, 2396 (1976). The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Davies and J.F. 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. 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
Kinet. http://pubs.acs.org/page/copyright/permissions.html. Chem. This material is available via the Internet at http://pubs.acs.org. 96, 543 (1974). Soc. Isomenthone is a ketone derived from menthone, as found in geranium, cistus, pennyroyal, cornmint, calamint, and peppermint. Riggs, L.E. Soc. Casella, G.J. Akad. Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. Augustine, D.C. Migliorini, R.E. By pooling their data, students can examine the effect of both catalyst quantity and temperature on the position of the equilibrium, and the rate of the reaction. E.L. Eliel, Stereochemistry of Carbon Compounds. V. Vetere, G. Santori, A. Moglioni, G. Moltrasio, M. Casella and O. Ferretti, to be published. M. Bartók, Stereochemistry of Heterogeneous Metal Catalysis, John Wiley & Sons, New York, 1985. 64 (1990) 1. Calculate the mole fraction (x) of (+)-isomenthone using Equation 6. volume 26, pages913–922(2000)Cite this article. Immediate online access to all issues from 2019. 52, 633 (1979).