2-ACETYL-5-METHYLTHIOPHENE

CAS: 13679-74-8 FLAVORING AGENT OR ADJUVANT

2-ACETYL-5-METHYLTHIOPHENE (CAS 13679-74-8) is a chemical flavoring agent evaluated by international expert panels for use as a flavouring in foods. It is used for its characteristic sensory properties in formulations.

What It Is

2-ACETYL-5-METHYLTHIOPHENE is a defined organic compound belonging to the class of substituted thiophenes characterized by an acetyl group at the 2 position and a methyl group at the 5 position of the thiophene ring. The primary identifier for this substance in chemical registries is CAS number 13679-74-8, and it is recognized in flavor industry inventory listings, including the Flavor and Extract Manufacturers Association (FEMA) flavor library with FEMA number 4643, indicating its use and evaluation as a flavoring substance. This compound is one of many flavouring agents used in formulations to contribute specific sensory profiles, and its identification often includes other systematic and trade synonyms reflecting its structure and flavor application context.(femaflavor.org) Thiophene derivatives, such as 2-ACETYL-5-METHYLTHIOPHENE, are heterocyclic compounds containing sulfur in a five-membered ring. This structural class is common among flavoring agents that provide distinctive notes in complex food matrices, especially where volatiles contribute to overall aroma and taste sensation. The inclusion of both acetyl and methyl substituents influences both volatility and sensory perception, making these derivatives suitable for low-level additions in food flavoring. Because flavoring agents are typically used in minute amounts, regulatory evaluations focus on safety at expected exposure levels rather than bulk use.(webbook.nist.gov) For clarity, although it is primarily referenced in flavor industry databases and safety evaluations, 2-ACETYL-5-METHYLTHIOPHENE is not assigned a numerical E number for additives in the European Union and does not have a specific CFR designation for food additive use in the United States; rather, its assessment for safety has been undertaken by expert committees who evaluate flavouring substances in general.

How It Is Made

The synthesis of 2-ACETYL-5-METHYLTHIOPHENE typically involves organic chemical methods that introduce an acetyl functional group onto a methyl-substituted thiophene ring. A common approach in heterocyclic chemistry involves Friedel-Crafts type acylation, in which an acyl chloride or anhydride reacts with an activated aromatic or heteroaromatic substrate under the influence of a Lewis acid catalyst. In this class of reactions, 2-methylthiophene serves as the starting substrate, and reagents such as acetyl chloride or acetic anhydride effect the placement of the acetyl group at a defined position on the ring. This process yields the characteristic ketone functionality that defines 2-ACETYL-5-METHYLTHIOPHENE.(ChemicalBook) After synthesis, the reaction mixture is commonly purified through standard organic purification techniques such as solvent extraction, washing to remove inorganic byproducts, and chromatographic methods to separate the desired product from unreacted precursors or side products. The final purified product is typically characterized by analytical approaches such as mass spectrometry and nuclear magnetic resonance to confirm structural identity and purity. Industrial or preparative scale chemistry for flavoring agents is designed to meet quality specifications suitable for food use, although specific regulatory monographs describe identity and purity criteria where applicable.(ChemicalBook) Because flavoring agents are used at very low levels in finished food products, the commercial preparation of these substances, whether by traditional organic synthesis routes or biosynthetic approaches, emphasizes reproducibility of structure and sensory profile rather than large-volume manufacture. Analytical standards may also be produced to support quality control in flavor laboratories.

Why It Is Used In Food

Flavoring agents like 2-ACETYL-5-METHYLTHIOPHENE are incorporated into food and beverage formulations to enhance aroma and taste characteristics that are desirable to consumers. In sensory science, small changes in volatile composition can significantly alter perceived flavor, and thiophene derivatives contribute complex notes that interact with other aroma compounds to create balanced sensory profiles. This specific compound is valued for its contribution to floral or sweet-spicy nuances, and it can be blended in minute amounts with other flavor compounds to achieve a particular profile in finished goods.(The Good Scents Company) In foods, flavoring agents are generally added to amplify or recreate natural aromas that may be diminished through processing, storage, or formulation. For example, in baked products, confectionery, or beverage applications, volatile compounds derived from flavor molecules complement inherent food aromas to maintain consumer appeal. The choice of a specific agent like 2-ACETYL-5-METHYLTHIOPHENE will depend on the desired sensory effect, synergy with other ingredients, and regulatory acceptability in the target market.(The Good Scents Company) Because its function is to affect sensory perception rather than nutritional value or preservation, the use of this compound is guided by flavor formulation expertise and regulatory evaluation to ensure that the levels present in foods pose no safety concern at expected intakes. Expert panels assess such compounds in the context of overall dietary exposure, comparing typical use concentrations against available toxicological data to conclude whether use at these levels is acceptable.

Adi Example Calculation

Illustrative calculations of intake involve estimates of typical usage levels in food categories combined with consumption data. For example, if a flavoring agent is added at parts-per-million levels in beverages and baked goods, average daily intake for a person consuming these products would be in the microgram-to-low milligram range. Such intake estimates are often orders of magnitude below levels of toxicological concern identified in studies, informing expert panel conclusions that there is no safety concern at expected intakes. These illustrations are conceptual and are not recommendations for individual intake.

Safety And Health Research

Safety evaluations of flavoring agents center on the principle that exposure levels expected from typical use are far below thresholds associated with adverse effects in toxicological studies. For 2-ACETYL-5-METHYLTHIOPHENE, international expert committees such as JECFA and FEMA assess available data on structure, metabolism, and any relevant toxicology to determine whether expected intake poses a safety concern. The conclusion of no safety concern reflects that the compound’s use at the low concentrations typical of food flavorings does not exceed levels that raise toxicological red flags.(世界卫生组织) These evaluations consider endpoints such as genotoxicity, subchronic toxicity, and potential for bioaccumulation, as appropriate to the compound’s chemistry and available data. For many flavoring substances, complete toxicological datasets may be limited, but expert panels use structural analogies and established safety assessment frameworks to conclude that typical dietary exposure is safe. As such, no specific limitations on use levels are prescribed beyond those inherent in good manufacturing practice for flavouring ingredients.(femaflavor.org) It is important to differentiate between safety evaluation and nutritional effect: flavoring agents are not intended to provide nutrients or functional health benefits, and safety assessments focus solely on absence of harm at expected use levels.

Regulatory Status Worldwide

International expert bodies have evaluated 2-ACETYL-5-METHYLTHIOPHENE in the context of its use as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated this compound, identified in its database with number 2107, and concluded that there is no safety concern at current levels of intake when used as a flavouring agent. This type of conclusion reflects a safety assessment of expected exposures based on typical use levels rather than assignment of a numerical acceptable daily intake.(世界卫生组织) In the United States, the Flavor and Extract Manufacturers Association (FEMA) has assigned FEMA number 4643 to 2-ACETYL-5-METHYLTHIOPHENE, indicating that it has been reviewed by the FEMA Expert Panel for its safety in flavor use. FEMA’s evaluations are used by industry and submitted to regulatory inventories, such as the FDA’s Substances Added to Food Inventory, to document substances used as flavorings.(femaflavor.org) Because flavoring agents are typically used at very low levels, they are not given distinct additive numeric codes such as E numbers in the European Union; rather, their regulatory status is reflected through inclusion in flavor inventories and expert panel conclusions that the substance poses no safety concern under conditions of intended use.

Taste And Functional Properties

As a flavoring compound, 2-ACETYL-5-METHYLTHIOPHENE exhibits sensory properties that are described by industry flavor evaluations as having floral and sweet-spicy characteristics. These descriptors reflect how this compound contributes to composite flavor profiles when combined with other aroma compounds in complex food systems. The sensory perception of flavor is a combination of volatile aromatic signals and taste reception, and heterocyclic ketones such as this often contribute appreciable aromatic complexity even at low concentrations.(The Good Scents Company) Functionally, flavoring agents are expected to be stable under typical processing conditions and to interact with solvents and carriers in a predictable manner. Factors such as volatility, solubility in water and fats, and stability to heat and pH influence how the compound behaves during manufacturing and storage. Thiophene derivatives are generally volatile and may partition into headspace during heating, contributing to aroma, while their moderate solubility in food matrices allows them to persist without rapid loss. While precise functional behavior depends on the matrix, these general properties are considered when formulating flavor blends.(米立克瑞) Because flavor perception is subjective and multi-faceted, sensory panels and analytical tools such as gas chromatography-olfactometry are used to characterize how such compounds contribute to the overall flavor of a product. These evaluations guide formulators in selecting and balancing flavoring agents to achieve consistent sensory outcomes.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a concept used by regulators to describe an estimate of the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. For many flavoring agents, including 2-ACETYL-5-METHYLTHIOPHENE, expert committees conclude that typical exposures from food use are so low that a formal numeric ADI is not necessary; instead, they conclude that there is no safety concern at current levels of intake. This means that, based on available data and estimated exposures, intake from flavor use is unlikely to pose risk.(世界卫生组织) Because ADIs are derived with considerable uncertainty factors to ensure safety, the absence of an ADI for this compound in regulatory texts reflects confidence that the exposure does not approach levels requiring numerical specification. Consumers should understand that such safety conclusions apply only to typical use concentrations in flavourings and not to large, unregulated exposures.

Comparison With Similar Additives

2-ACETYL-5-METHYLTHIOPHENE can be compared with other heterocyclic flavoring agents, including substituted furans or thiophenes, which similarly contribute complex aroma notes in flavor formulations. For example, 2-acetylfuran is another aroma compound used for sweet and roasted notes; both compounds are evaluated by expert panels in terms of their expected exposure and toxicological profiles. Whereas the structural differences between these molecules affect sensory properties, the safety evaluation framework applied by committees such as JECFA and FEMA is similar, focusing on exposure levels and structural alerts. This comparison emphasizes how flavor chemists select agents based on sensory needs while regulators assess them for safety in the context of typical use.

Common Food Applications Narrative

Flavoring agents like 2-ACETYL-5-METHYLTHIOPHENE are employed across a broad range of food and beverage products where subtle aroma enhancement is desirable. In baked goods, small quantities of volatile compounds can contribute to the perception of freshly baked or caramelized notes when combined with other flavor constituents. In confectionery, floral and sweet-spicy nuances can round out sweet profiles, providing depth that consumers associate with high-quality tastes. Beverage formulations, both alcoholic and non-alcoholic, may incorporate such agents to augment natural aromatic components that can be muted by processing or base ingredients.(The Good Scents Company) Beyond traditional categories, flavoring compounds are used in snack foods, dairy desserts, and even savory applications where a hint of complexity enhances the overall sensory experience. Because these usages occur at very low levels, they do not contribute significant nutritional value but rather fulfill a functional role in shaping how products are experienced. Flavorists and product developers select such agents based on the desired profile, interactions with other ingredients, and regulatory acceptance in the markets where the products will be sold.(The Good Scents Company) In many cases, the inclusion of specific flavoring agents is proprietary to formulation, and manufacturers balance sensory goals with cost, stability, and consumer expectations. As a result, compounds like 2-ACETYL-5-METHYLTHIOPHENE are one of many tools in the flavor chemist’s repertoire, contributing targeted aromatic notes to achieve overall product objectives.

Safety & Regulations

FDA

  • Notes: No specific CFR listing identified; use as flavoring documented through FEMA and FDA Substances Added to Food Inventory without a numeric regulation.

EFSA

  • Notes: No specific EFSA additive evaluation with numeric ADI could be confirmed.

JECFA

  • Notes: JECFA concluded no safety concern at current intake but did not specify a numeric ADI on the d entry.

Sources

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