41, 3461 (1976). Part of Springer Nature. http://pubs.acs.org/page/copyright/permissions.html. Khim. Murzin, A.E.

Siri, H.R. R.L.

This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. Klabunovskii, and L.A. Kheifits, Izv. 257, (, 1900, La Plata, Argentina, Virginia Vetere, Gerardo F. Santori, Mónica L. Casella & Osmar A. Ferretti, Facultad de Ingeniería de la UNLP, 47 No.

R.M. The catalysts used showed a very low activity under the given reaction conditions. Calculate the mole fraction (x) of (+)-isomenthone using Equation 6. 41, 1902 (1968).

P. Kukula and L. Červený, Appl. Immediate online access to all issues from 2019. Catal.

G.F. Santori, M.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. J. Margitfalvi, M. Hegedüs, S. Göbölös, E. Kern-Tálas, P. Szedlacsek, S. Szabó and F. Nagy, Proc. PubMed Google Scholar, Vetere, V., Santori, G.F., Moglioni, A. et al. 112 (1988) 210. Siri, H.R.

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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

Jpn. The catalytic hydrogenation of an optically active mixture of (−)-menthone and (+)-isomenthone was studied. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. Soc. Dauscher and R.A. Touroude, Ind. P. Gallezot and D. Richard, Catal.

Adúriz and O.A. 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. L. Červený (Ed. N.D. Zubareva, E.I. G.F. Santori, M.L. Ferretti, Appl. not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. These metrics are regularly updated to reflect usage leading up to the last few days. Soc. T. Chihara and K. Tanaka, Bull. 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. A: Gen. 197 (2000) 141. Information. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol.

Empirical Formula (Hill Notation) C 10 H 18 O . The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. Chem. Brewster, J. Bedoukian, Perfumery and Flavoring Synthetics, Allured Publishing Corporation, Wheaton, USA, 1986. 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. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. 39, 1017 (1974).

52, 633 (1979). Soc.

83, 1246 (1961). a3-Menthone enol acetate (VII) was pre-pared from both menthone and isomenthone by several workersl-5 J. Molecular Weight 154.25 . 53, 3270 (1980). Chem. For permission to reproduce, republish and P. Kukula and L. Červený, Chem. Hawkes, K. Herwig, and J.D. Catal.

© 2020 Springer Nature Switzerland AG. Some can be convulsent, toxic to the liver, or neurotoxic in high doses. Am. 1956, 2165 (1956). Research on Chemical Intermediates Catal. volume 26, pages913–922(2000)Cite this article. Correspondence to

93, 500 (1999). Chem. E.L. Eliel, Stereochemistry of Carbon Compounds. Berlin, 1984, vol. G.E. 75 (2002) 225. Beumel, J.

31 (1987) 713. 29, 1531 (1973). Tax calculation will be finalised during checkout. 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.

Do not overuse or use for prolonged periods of time. W.B. Jpn. Google Scholar. A. Tungler, T. Máthé, Z. Bende and J. Petro, Appl. J. Solodar, J. Org.

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Kinet. Listy Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. 96, 543 (1974). Immediate online access to all issues from 2019. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. https://doi.org/10.1023/A:1021444407222, DOI: https://doi.org/10.1023/A:1021444407222, Over 10 million scientific documents at your fingertips, Not logged in Nauk SSSR, Ser.


Files available from the ACS website may be downloaded for personal use only. Reson. Subscription will auto renew annually. 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. Chem. Sci. Sheldrake and J. Crosby, Chirality in Industry (Wiley, Chichester, 1992). Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. Menthone and isomenthone were rapidly metabolised and were found in lower concentrations and over a shorter time span than the other analytes. 4) Consider the ketones piperitone, menthone, and isomenthone. M. Misono and N. Noijri, Appl. Chem. © 2020 Springer Nature Switzerland AG. 64 (1990) 1. J.P. Candy, O. Ferretti, J.P. Bournonville, A. El Mansour, J. Basset and G. Martino, J. Catal. C.D. Isomerizations among individual isomers were barely detectable. without permission from the American Chemical Society.

A traditional organic chemistry laboratory experiment involves the acid-catalyzed isomerization of (−)-menthone to (+)-isomenthone. Surf. Google Scholar. Article 

Information about how to use the RightsLink permission system can be found at 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. 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 … Chem. This is a preview of subscription content, log in to check access. V. Vetere, G. Santori, A. Moglioni, G. Moltrasio, M. Casella and O. Ferretti, to be published. 148 (1999) 145. G. Santori, M. Casella, G. Siri, O. Ferretti, A. Moglioni and G. Moltrasio, Stud. B. Rickborn, J. Jpn. Chem. Makouangou, D.Y. K. Sakai, M. Ishige, H. Kono, I. Motoyama, K. Watwnabe, and K. Hata, Bull. - CINDECA (UNLP-CONICET), 47 No. Lett. This article has not yet been cited by other publications. 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. The equilibrium mixture of (-)-menthone and (+)-isomenthone was prepared by (-)- menthol oxidation using peracetic acid in ethyl acetate using NaBr. Students then test their hypothesis by performing the reaction with different catalyst quantities and at different temperatures. 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. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Search results for (-)-menthone at Sigma-Aldrich. Boelens Aroma Chemical Information Service (BACIS), The Netherlands (1996).