2-Hydroxy-3-methyl-2-cyclopenten-1-one

MeC5-ol-one.png 120px 3-Methylcyclopentane-1,2-dione Maple lactone, Methylcyclopentenolone, Corylon correct chemspider 55153 correct FDA 627E92X64B changed EBI correct EBI correct chemspider 1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h4H,2-3H2,1H3 correct chemspider OACYKCIZDVVNJL-UHFFFAOYSA-N correct CAS 765-70-8 80-71-7 (enol form) CC1C(=O)C(=O)CC1 212-154-8 61209 6660 (enol form) 1.312 g/cm3 6 8 2 104-108 3-Methyl-1,2-cyclopentanedione at Sigma Aldrich 2-Hydroxy-3-methyl-2-cyclopenten-1-one is an organic compound related to 1,2-cyclopentanedione. It is the enol tautomer of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound is often called methylcyclopentenolone. It is a colorless solid. Synthesis and structure The compound is prepared by base-catalyzed condensation of 1-hydroxyhexane-2,5-dione, a derivative of hydroxymethylfurfural. The structure has been confirmed by X-ray crystallography.10.1002/cssc.201702100 Cyclopentanone Derivatives from 5-Hydroxymethylfurfural via 1-Hydroxyhexane-2,5-dione as Intermediate 2018 Wozniak Bartosz Spannenberg Anke Li Yuehui Hinze Sandra De Vries Johannes G. ChemSusChem 11 2 356–359 29235723 2018ChSCh..11..356W Quantum calculations also indicate that the enol is strongly favored relative to the diketo tautomer. Furthermore, the enolization occurs at the methyl-substituted carbon.10.1080/00268976.2011.646336 Quantum Mechanical Study of the Tautomerism and Molecular Spectra of 2-Hydroxy-3-methyl-2-cyclopenten-1-one 2012 Zborowski Krzysztof K. Grybos Ryszard Wesełucha-Birczyńska Aleksandra Kim Younkyoo Proniewicz Leonard M. Molecular Physics 110 6 343–351 2012MolPh.110..343Z 95003384 Use and occurrence It is one of many products from the pyrolysis of lignocellulose.10.1039/C1EE01230D Catalytic Conversion of Biomass-Derived Feedstocks into Olefins and Aromatics with ZSM-5: The Hydrogen to Carbon Effective Ratio 2011 Zhang Huiyan Cheng Yu-Ting Vispute Tushar P. Xiao Rui Huber George W. Energy & Environmental Science 4 6 2297 https://works.bepress.com/cgi/viewcontent.cgi?article=1022&context=george_huber It is used in flavors and perfumery for its maple- or caramel-like odor. http://www.thegoodscentscompany.com/data/rw1012711.html Good Scents Company Cyclotene It contributes to the flavor or odor of many foods including wines, coffee, paprika, salmon and tobacco.2026-01-28 Buy Bulk - Methyl Cyclopentenolone Manufacturer-Supplier https://sinofoodsupply.com/methyl-cyclopentenolone/ 2026-07-12 en-GB It is sometimes called maple lactone because it occurs in maple syrup (it is not, however, a lactone).10.1021/ed084p1647 The Chemical Composition of Maple Syrup 2007 Ball David W. Journal of Chemical Education 84 10 1647 2007JChEd..84.1647B 98149895 See also 1,2-Cyclopentanedione References Category:Diketones Category:Cyclopentanes