4-(2-BUTENYLIDENE)-3,5,5-TRIMETHYLCYCLOHEX-2-EN-1-ONE

CAS: 13215-88-8 FLAVORING AGENT OR ADJUVANT

4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is a synthetic flavoring agent and adjuvant used in food and fragrance formulations, notable for its tobacco-like and fruity aroma profile and its role in enhancing sensory complexity in flavor applications.

What It Is

4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is a chemical compound classified as a flavoring agent or adjuvant, widely recognized in flavor science for contributing nuanced aroma profiles in food and fragrance matrices. It is identified by the CAS number 13215-88-8 and is often referred to by synonymous terms including megastigmatrienone and various isomeric descriptors reflecting its structural complexity. This compound exists as a mixture of geometric isomers, typically designated by stereochemical descriptors (such as E,E and E,Z forms) that influence its sensory perception and functional behavior in formulation contexts. While not a naturally occurring food ingredient in large quantities, it can be present as a minor constituent in aged wines and tobacco where it contributes to characteristic bouquet notes. At a molecular level, 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one comprises a cyclohexene core substituted with an unsaturated butenylidene chain and three methyl groups. This structural arrangement confers a conjugated system and a ketone functional group, both of which play roles in its odor and reactivity. The existence of multiple isomeric forms suggests that the relative ratios of these forms can affect its olfactory impact, with some isomers perceived as more tobacco-like or fruity than others. In regulatory documentation and flavor specification databases, this compound is listed under various synonyms that reflect its structural nuances and functional application in flavor chemistry. Its classification as a flavoring agent indicates that it is utilized at low concentrations in consumer products to achieve targeted sensory effects rather than as a primary ingredient in formulations. In industrial and formulation contexts, 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is handled as a liquid or low-melting substance, often requiring controlled storage conditions to maintain stability and prevent degradation. The compound’s identity and purity are established through analytical techniques such as gas chromatography and mass spectrometry, which separate and characterize individual isomers. Its inclusion in flavor blends is carefully calibrated, as even minor changes in concentration can influence the overall sensory profile of the finished product. While not ubiquitous across all food categories, this flavoring agent occupies a specific niche where nuanced aroma enhancement is desired.

How It Is Made

The manufacture of 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one typically involves organic synthesis techniques that construct the cyclic core and append the butenylidene side chain through controlled condensation reactions. Industrial production often begins with precursor molecules such as substituted cyclohexenones and unsaturated aldehydes or ketones, which are reacted under conditions that favor the formation of the target conjugated system. These processes may utilize catalysts, controlled temperature regimes, and purification steps to isolate the desired isomeric forms while minimizing byproducts. Because the compound exists in multiple geometric isomeric forms, synthesis routes are designed to optimize the yield of isomers that exhibit the preferred sensory properties. Organic chemists leverage stereoselective reactions, and in some cases, chiral catalysts or conditions that favor specific geometric configurations, to achieve this optimization. After the primary synthesis, crude reaction mixtures undergo purification by techniques such as distillation, crystallization, or chromatographic separation to remove unreacted precursors and undesired isomers. Quality control in manufacturing often involves analytical measurements to quantify individual isomers, confirm structural identity, and ensure that the product meets specified purity standards suitable for use in flavor applications. The synthesis of flavoring agents like 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is governed by industry guidelines that emphasize safety, reproducibility, and traceability. Manufacturers maintain detailed records of reaction conditions, analytical results, and batch-level data to support regulatory compliance and formulation consistency. Although the specific proprietary methods for synthesizing this compound may vary among producers, they share common foundations in classical organic chemistry techniques that build complex flavor molecules from simpler building blocks. Given the compound’s functional role at low concentration levels, production focuses on achieving high purity and consistent sensory quality rather than large-scale bulk output. End-use formulations often receive further blending by flavor houses, where 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is combined with other flavor chemicals to achieve a balanced sensory profile tailored to specific applications.

Why It Is Used In Food

4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is used in food primarily for its flavoring properties, where it contributes distinct aroma notes that can enhance complexity and depth in sensory profiles. As a flavoring agent or adjuvant, its inclusion is strategic: at low concentrations, small changes in volatile composition can have outsized effects on the way a food or beverage is perceived by consumers. In particular, this compound is valued for its nuanced tobacco-like, fruity, and floral notes that can add warmth, richness, or background complexity to a blend of flavors. In flavor chemistry, such compounds are not intended to dominate the aroma profile but to support and accentuate other key notes, resulting in a more rounded and appealing overall sensory experience. The logic of using specialized flavoring agents like 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one relates to the challenges of replicating complex natural flavors in processed foods. Many natural extracts contain hundreds of volatile compounds in specific ratios; when trying to mimic or enhance these sensory qualities synthetically, formulators rely on targeted chemicals that deliver specific odor characteristics. Because of its particular scent profile, this compound fits into flavor applications where subtle tobacco-like or fruity notes are desired without overwhelming other components. Typical uses may include complex beverage formulations, baked goods where depth of aroma is sought, or confectionery applications that benefit from layered sensory impressions. Its role as an adjuvant means that it can help bridge gaps between dominant flavor notes, smoothing transitions and creating greater harmony in the sensory profile. In addition to its direct sensory impact, 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one may interact with other volatile compounds in ways that enhance overall flavor perception. Such interactions can influence volatility, persistence of aroma, and the way human olfactory receptors respond to the mixture of compounds. Flavorists often exploit these interactions to fine-tune products for specific consumer preferences, taking into account cultural and market trends in flavor perception. Its use is guided by sensory evaluation panels and analytical chemistry tools to ensure that the desired balance is achieved consistently across production batches. Because flavoring agents are used at very low concentrations relative to the bulk of the food matrix, their impact on nutritional composition is negligible, but their contribution to sensory appeal can be significant.

Adi Example Calculation

To illustrate how acceptable daily intake is applied in a regulatory context, consider a hypothetical illustrative scenario using a generic ADI value (for example, an ADI of X mg per kilogram of body weight per day). Suppose a person weighing 70 kilograms consumes a food product containing a flavoring agent at a concentration that results in an estimated daily intake of 0.Y mg per day. To assess whether this intake falls within regulatory guidance, one would multiply the ADI by the person’s body weight: X mg/kg bw/day times 70 kg equals 70X mg per day. If the individual’s estimated intake of 0.Y mg per day is considerably below this benchmark of 70X mg per day, it suggests that exposure is within the conservative safety threshold defined by regulatory authorities. It is important to emphasize that such calculations are illustrative and not specific to 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one, because a defined numeric ADI for this compound may not be established in certain regulatory frameworks. Nevertheless, the general principle remains: ADI calculations provide a way to contextualize exposure relative to a lifetime safety benchmark. Regulatory risk assessors derive ADIs by identifying the highest dose at which no adverse effects are observed in comprehensive toxicological studies and then applying safety factors to account for uncertainty and variability. This approach ensures that daily exposure remains at levels unlikely to pose health concerns, even with long-term consumption. Such examples help stakeholders understand how exposure assessments are interpreted in the context of regulatory safety guidance.

Safety And Health Research

Safety and health research related to 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one encompasses evaluations by international committees such as JECFA, which consider available toxicological data and physical chemical properties to develop specifications and usage guidance. In preparing flavouring specifications, expert panels review data on chemical identity, metabolic pathways, and potential toxicological endpoints to determine whether an additive’s use at intended levels is consistent with consumer safety. These evaluations typically consider genotoxicity, acute toxicity, and other hazard data to inform specification limits and advise on safe usage practices in food and beverage applications. Scientific literature and regulatory documents emphasize that flavoring agents are included at very low concentrations in food products, and safety assessments account for exposure relative to body weight and intake patterns. The absence of extensive publicly available toxicological data specific to this compound—such as chronic exposure studies or established acceptable daily intake levels in major regulatory bodies—means that detailed human health effects beyond general flavoring safety paradigms are limited or not widely documented. In cases where comprehensive toxicological studies are not available, regulatory guidance may rely on structural analogs or read-across approaches to infer potential hazard profiles, while specifying purity criteria and analytical methods to control impurities that could pose greater risks. Because 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is used at low levels in consumer products, it is important to differentiate between hazard and exposure: the potential for an adverse effect depends on both the intrinsic properties of a compound and the degree to which consumers are exposed. Safety research, therefore, informs specifications that aim to limit exposure to levels far below those associated with toxicological concern. Continued research and monitoring of published toxicological data support ongoing evaluation of flavoring substances, with expert committees updating specifications as new information becomes available. As with many flavoring agents, ongoing assessment of safety profiles and usage patterns informs regulatory decisions and industry practices.

Regulatory Status Worldwide

The regulatory status of 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one varies across jurisdictions, and authoritative evaluations are documented in international flavoring specification databases. In the Joint FAO/WHO Expert Committee on Food Additives (JECFA) flavouring specifications, this compound is listed with a JECFA number indicating its recognition as a flavoring substance for which specifications have been prepared; details of its physical characteristics and acceptable usage parameters are available in the JECFA flavouring specifications database maintained by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO) database of flavouring substances. These specifications describe chemical identity, allowable purity criteria, and analytical methods for confirming composition, supporting regulatory review and quality control in formulation contexts. The presence of a JECFA number reflects evaluation by an international scientific expert committee that produces specifications for flavoring agents used in food and beverages globally. Source documentation for this specification can be accessed in the FAO flavouring database entry for this compound. In the United States, there is no clear specific designation in the Code of Federal Regulations that explicitly names this compound as a permitted direct food additive; therefore, its status under U.S. food additive regulations remains uncertain without a specific CFR section citation available in public records. Likewise, within the European Union, an E-number designation—a common indicator of approved food additives—does not appear to be assigned to this compound, and authoritative EFSA evaluations specifically listing this substance with an E-number or established acceptable daily intake are not readily found in publicly available regulatory documents. In the absence of explicit regulatory citations for some jurisdictions, manufacturers and formulators refer to international specifications and regulatory guidance to ensure appropriate use levels and compliance with local food laws. Because regulatory frameworks evolve and specific additives may be subject to review or inclusion in updated permissible lists over time, formulators consult current national and regional regulations to confirm applicable status. The JECFA specification entry for this compound serves as a reference point for acceptable identity and purity standards recognized by an authoritative international body, supporting its application in food flavoring where permitted. Continued monitoring of regulatory updates is advisable for compliance with evolving food additive regulations in each market.

Taste And Functional Properties

4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one is characterized by an aromatic profile that combines subtle tobacco-like, fruity, and floral scent notes, making it a versatile component in flavor formulation. Sensory scientists describe compounds such as this one in terms of their odor descriptors rather than taste alone, because volatile molecules primarily interact with olfactory receptors to create perceived flavor. The compound’s molecular structure—featuring a conjugated carbonyl system and an unsaturated side chain—contributes to its volatility and the way it partitions into the headspace above a food or beverage matrix, where it can be detected by smell. Functionally, the sensory impact of this compound depends on its concentration and the surrounding chemical environment. At low usage levels typical of flavoring agents, it enhances complexity without overwhelming other flavor notes. Olfactory perception is inherently nonlinear; compounds with distinctive scent profiles can modulate the overall character of a formulation even when present at parts-per-million or parts-per-billion levels. The functional properties of 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one also relate to its interaction with other volatiles: synergistic effects can occur where the presence of certain molecules enhances or alters the perception of others. Such interactions are empirically determined through sensory panel evaluations and analytical methodologies like gas chromatography-olfactometry. In addition to its aromatic contribution, this compound has physical properties relevant to formulation. It is typically insoluble or poorly soluble in water but shows greater solubility in ethanol and other organic solvents, which influences how it is incorporated into different product types. For example, beverage applications that contain ethanol may accommodate this compound more readily than aqueous formulations without organic solvents. Its chemical stability under typical processing conditions—such as moderate heat or pH variations—also determines its suitability for baked goods or other thermally processed foods. Formulators assess stability through accelerated aging studies and sensory evaluations to ensure that the desired aroma profile persists through production and shelf life. These functional considerations are integral to effective application in real-world food systems.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory concept used to indicate the amount of a substance that can be consumed every day over a lifetime without appreciable risk to health. ADIs are typically expressed in milligrams of substance per kilogram of body weight per day and are derived by expert panels using available toxicological data, safety factors, and exposure assessments. For flavoring agents such as 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one, specific numeric ADIs may not be established in all regulatory jurisdictions, especially if comprehensive toxicological data are limited or if the compound’s use levels and exposure estimates do not warrant a formal ADI determination by bodies like EFSA or JECFA. In cases where an ADI is not explicitly established, regulatory specifications focus on defining purity criteria and acceptable use levels within food categories to ensure that consumer exposure remains well below any thresholds of concern based on available data. The concept of an ADI helps consumers and regulators contextualize safety; it does not represent a target level of consumption, but rather a conservative benchmark below which daily intake is considered unlikely to pose health risks. Importantly, ADIs incorporate safety factors to account for uncertainties in data and variability among populations. When an expert committee evaluates a food additive, it considers metabolic pathways, toxicological studies, and potential effects, and then applies safety factors—often orders of magnitude below observed effect levels—to derive an ADI. For flavoring agents without an explicit ADI declaration, industry and regulatory authorities may use analogous compounds or read-across approaches to assess safety, while maintaining usage practices that minimize consumer exposure. This conservative approach ensures that even without a specific numeric ADI, the compound’s inclusion in food products aligns with broader safety principles. Consumers and formulators should understand that the lack of a published numeric ADI for a given flavoring agent does not necessarily imply risk; rather, it reflects the regulatory process and the state of available data. Continued research and monitoring may eventually support the derivation of an explicit ADI when sufficient evidence becomes available, reinforcing the safety framework for its use.

Comparison With Similar Additives

4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one can be compared with other flavoring agents that serve related functions in food and beverage applications. For instance, compounds like β-damascenone and ionones are also prominent in flavor chemistry, contributing fruity, floral, and complex background aromas in diverse formulations. β-Damascenone, often found in wine and fruit-derived flavors, provides robust fruity notes at very low concentrations and is widely used in beverage and confectionery applications to enhance fruit character. In contrast, 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one tends to deliver a more tobacco-like or nuanced floral note, making it a complementary component when a formulation demands broader sensory depth. Ionones, including alpha-ionone and beta-ionone, share structural similarities with megastigmatrienone compounds and are used to impart violet-like or woody-fruity characteristics in flavors and fragrances. Compared to ionones, 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one may offer distinct olfactory nuances that fit specific flavor objectives, such as adding warmth or subtle tobacco-like richness. The choice among these additives depends on the desired sensory outcome and product category; for example, ionones might be preferred in fruit-flavored beverages, whereas 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one may find use in products seeking layered complexity beyond primary fruit notes. Other similar flavoring agents, such as damascenone isomers, also contribute to balanced aromatic profiles in baked goods and confectionery. While structural similarities provide some predictability in sensory function, each compound’s usage is informed by detailed sensory evaluation and formulation experience. Flavorists often combine multiple agents to achieve a harmonious blend, leveraging the unique attributes of each to enhance overall product appeal. Understanding the specific contributions of 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one relative to analogous compounds helps guide formulation strategies that meet consumer preferences in targeted food and beverage categories.

Common Food Applications Narrative

In practical food and beverage applications, 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one appears in products where nuanced aroma enhancement is desired. For example, in beverage sectors such as ready-to-serve drinks and flavored waters, this compound can add complexity to fruit or botanical flavor profiles, supporting top notes and creating a richer sensory experience. In baked products like sweet rolls, pastries, and cookies, it may be included as part of a flavor blend that evokes warmth and depth, contributing to lingering aromatic impressions that complement sweetness. Confectionery products—including chocolate-based candies and sugar confections—can also benefit from its subtle underlying notes, which help differentiate products in a crowded marketplace. In dairy-based beverages and frozen desserts, the compound’s mellow aromatic qualities can round out dominant flavor themes and improve overall balance. The inclusion of this flavoring agent extends into savory categories where background aroma modulation is key. Snack seasonings and sauces often rely on complex blends of volatiles to achieve appealing character; a compound with the specific scent notes of 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one can help bridge components within a blend, smoothing transitions between strong flavor elements. For instance, in spice mixes formulated for chips or crackers, it may play a supporting role that enhances perception without being a defining note. Beverage emulsions, such as certain types of alcoholic drinks or low-alcohol flavored products, might also exploit its properties to achieve a rounded aroma profile that persists through tasting. In all these food applications, the ingredient’s use is highly controlled, with precise formulation and sensory evaluation guiding inclusion levels. Because aroma perception varies by product matrix and consumer expectations, flavor houses typically adjust ratios and combinations of flavoring agents, including this compound, to achieve targeted sensory outcomes. Sensory panels and analytical measurements help ensure consistency and consumer acceptability across batches. Its ability to contribute subtle yet distinctive notes makes it a tool for product developers seeking to differentiate offerings in competitive categories such as confectionery, baked goods, flavored beverages, and savory snacks. Ultimately, its presence in these diverse applications reflects the nuanced role that carefully selected flavoring agents play in contemporary food formulation.

Safety & Regulations

FDA

  • Notes: No specific CFR approval citation found; status unclear in U.S. regulations.

EFSA

  • Notes: E-number and EFSA ADI not explicitly found in authoritative sources.

JECFA

  • Notes: JECFA specification exists but numeric ADI was not explicitly available in source.

Sources

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