// Workers AI · dad joke modeWhat did 2-Hydroxy-3-methyl-2-cyclopenten-1-one say? "I'm a compound fellow.
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| Names | |
|---|---|
| Preferred IUPAC name
3-Methylcyclopentane-1,2-dione | |
| Other names
Maple lactone, Methylcyclopentenolone, Corylon | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.001.186 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H8O2 | |
| Molar mass | 112.128 g·mol−1 |
| Density | 1.312 g/cm3 |
| Melting point | 104–108 °C (219–226 °F; 377–381 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]The compound is prepared by base-catalyzed condensation of 1-hydroxyhexane-2,5-dione, a derivative of hydroxymethylfurfural.[2]
The structure has been confirmed by X-ray crystallography.[2] Quantum calculations also indicate that the enol is strongly favored relative to the diketo tautomer. Furthermore, the enolization occurs at the methyl-substituted carbon.[3]
Use and occurrence
[edit]It is one of many products from the pyrolysis of lignocellulose.[4]
It is used in flavors and perfumery for its maple- or caramel-like odor.[5] It contributes to the flavor or odor of many foods including wines, coffee, paprika, salmon and tobacco.[6] It is sometimes called maple lactone because it occurs in maple syrup (it is not, however, a lactone).[7]
See also
[edit]References
[edit]- ↑ 3-Methyl-1,2-cyclopentanedione at Sigma Aldrich
- 1 2 Wozniak, Bartosz; Spannenberg, Anke; Li, Yuehui; Hinze, Sandra; De Vries, Johannes G. (2018). "Cyclopentanone Derivatives from 5-Hydroxymethylfurfural via 1-Hydroxyhexane-2,5-dione as Intermediate". ChemSusChem. 11 (2): 356–359. Bibcode:2018ChSCh..11..356W. doi:10.1002/cssc.201702100. PMID 29235723.
- ↑ Zborowski, Krzysztof K.; Grybos, Ryszard; Wesełucha-Birczyńska, Aleksandra; Kim, Younkyoo; Proniewicz, Leonard M. (2012). "Quantum Mechanical Study of the Tautomerism and Molecular Spectra of 2-Hydroxy-3-methyl-2-cyclopenten-1-one". Molecular Physics. 110 (6): 343–351. Bibcode:2012MolPh.110..343Z. doi:10.1080/00268976.2011.646336. S2CID 95003384.
- ↑ Zhang, Huiyan; Cheng, Yu-Ting; Vispute, Tushar P.; Xiao, Rui; Huber, George W. (2011). "Catalytic Conversion of Biomass-Derived Feedstocks into Olefins and Aromatics with ZSM-5: The Hydrogen to Carbon Effective Ratio". Energy & Environmental Science. 4 (6): 2297. doi:10.1039/C1EE01230D.
- ↑ "Cyclotene". Good Scents Company.
- ↑ "Buy Bulk - Methyl Cyclopentenolone | Manufacturer-Supplier". 2026-01-28. Retrieved 2026-07-12.
- ↑ Ball, David W. (2007). "The Chemical Composition of Maple Syrup". Journal of Chemical Education. 84 (10): 1647. Bibcode:2007JChEd..84.1647B. doi:10.1021/ed084p1647. S2CID 98149895.