What is 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one?

5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one is an organic chemical compound with the CAS number 53263-58-4. It is characterized by a five-membered carbon ring structure (cyclopentenone) with an ethyl group, a hydroxyl group, and a methyl group attached. This specific chemical structure gives it unique aromatic properties, making it valuable in the food industry as a flavoring agent. While it can occur naturally in some cooked foods as a result of chemical reactions (e.g., Maillard reactions), the form used in food additive applications is typically synthetically produced to ensure purity, consistency, and cost-effectiveness. It is classified as an alkyl and alkenyl hydroxy-substituted alicyclic ketone or diketone, a class of compounds known for their diverse flavor profiles. Its molecular formula is C8H14O2, and it typically presents as a colorless to pale yellow liquid with a distinct aroma.

Common Uses

As a flavoring agent, 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one is primarily employed to impart or enhance specific taste and aroma characteristics in a wide range of food products. Its flavor profile is generally described as sweet, nutty, caramel-like, and roasted, often with undertones of coffee, maple, or fenugreek. These attributes make it particularly useful in formulations designed to mimic or boost the flavors of baked goods, confectionery, dairy products (like yogurts or ice creams), beverages, and savory items that benefit from a rich, cooked, or caramelized note. It can be used alone or, more commonly, as a component within complex flavor blends to achieve a desired overall taste experience. Its high impact at low concentrations makes it an efficient and versatile tool for flavorists looking to create authentic and appealing food products.

Safety Assessment

The safety of food additives, particularly flavoring agents, is rigorously evaluated by expert scientific bodies worldwide. For 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one, its safety has been assessed by the Flavor and Extract Manufacturers Association (FEMA) in the United States, which has granted it Generally Recognized As Safe (GRAS) status (FEMA GRAS No. 3550). This determination by FEMA signifies that, based on scientific procedures and widespread knowledge among qualified experts, the substance is safe for its intended use as a flavoring agent. These assessments typically consider its chemical structure, metabolism, potential for toxicity, and exposure levels from dietary intake. Furthermore, the European Food Safety Authority (EFSA) has evaluated this compound as part of its assessment of Flavoring Group Evaluation 26 (FGE.26), which includes alkyl and alkenyl hydroxy-substituted alicyclic ketones and diketones and related secondary alcohols and esters. EFSA concluded that there were no safety concerns for the group of flavorings at the estimated levels of intake under the specified conditions of use. The FDA's Adverse Event Reporting System shows 0 adverse events associated with this additive, and there have been no recalls linked to its use, further supporting its safety record in commercial applications.

Regulatory Status

In the United States, while 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one is not listed directly on the FDA's codified GRAS regulations (e.g., 21 CFR Part 182, 184, or 186) and thus does not hold an explicit 'FDA GRAS' affirmation number, it *is* recognized as GRAS by the expert panel of the Flavor and Extract Manufacturers Association (FEMA GRAS No. 3550). This FEMA GRAS determination allows for its legal use as a flavoring ingredient in food products marketed in the U.S. without requiring pre-market approval through a Food Additive Petition, provided its use adheres to good manufacturing practices and recognized safe levels. In the European Union, 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one is authorized for use as a flavoring agent following its positive evaluation by EFSA as part of FGE.26, which covers a group of related flavorings. This international consensus among leading food safety bodies underscores its acceptance for use in food globally, subject to local regulations and use limits, ensuring consumer safety.

Key Studies

Key studies and evaluations pertaining to 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one include its review by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) and assessments by regulatory bodies such as FEMA and EFSA. FEMA's GRAS dossier for No. 3550, which includes this compound, compiles data on its identity, specifications, estimated dietary exposure, and a summary of relevant toxicological and metabolic information supporting its GRAS status. These assessments often rely on a comprehensive review of existing scientific literature, including studies on structurally related compounds, in vitro assays, and sometimes animal studies for broader chemical classes. EFSA's scientific opinion on Flavoring Group Evaluation 26 (FGE.26), published in the EFSA Journal, provided a detailed toxicological evaluation of 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one and other compounds within the group. This evaluation considered data on genotoxicity, short-term and long-term toxicity, and metabolism to confirm the safety of these flavorings at anticipated intake levels. While specific stand-alone toxicity studies exclusively focused on 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one may not always be publicly highlighted individually, its safety is substantiated through these robust group evaluations by internationally recognized scientific expert panels.

Compare Food Additives