BENZYL 2,3-DIMETHYLCROTONATE

CAS: 7492-69-5 FLAVORING AGENT OR ADJUVANT

BENZYL 2,3-DIMETHYLCROTONATE (CAS 7492-69-5) is a synthetic flavoring agent used in food products under FDA regulation 21 CFR 172.515 and evaluated internationally by JECFA with no safety concern at current intake levels. It is typically used in minimal quantities for sensory impact.

What It Is

BENZYL 2,3-DIMETHYLCROTONATE is a synthetic flavoring agent used in foods to impart specific sensory characteristics consistent with its chemical structure and functional class. Technically defined by its CAS number 7492-69-5, this compound belongs to a class of aromatic esters used to contribute warm, herbaceous, fruity-spicy aromatic notes in food formulations. It may also be referred to by other names such as benzyl methyltiglate, benzyl 2,3-dimethyl-2-butenoate, and related synonymous descriptors that reflect its ester linkage of a substituted crotonic acid moiety to a benzyl alcohol derivative. As a flavoring agent or adjuvant, its role is to support or enhance the organoleptic profile of a beverage, confectionery, or other consumer food product where minimal concentrations are used to achieve the desired flavor impact. In regulatory contexts, this compound has been recognized in authoritative lists such as the United States Food and Drug Administration’s Substances Added to Food inventory under the Synthetic Flavoring Substances and Adjuvants provisions (21 CFR 172.515), which sets conditions under which such substances may be safely used. Internationally, it has been evaluated by expert bodies such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which concluded that there is no safety concern at current levels of intake when used as a flavoring agent. Structurally, BENZYL 2,3-DIMETHYLCROTONATE features a benzyl ester of a dimethyl-substituted crotonic acid, with physicochemical properties typical of ester-based flavoring agents, including limited water solubility and compatibility with organic solvents and lipid matrices. Its sensory contribution and formulation roles are consistent with its chemical profile.

How It Is Made

The production of BENZYL 2,3-DIMETHYLCROTONATE typically involves an esterification reaction between 2,3-dimethylcrotonic acid and benzyl alcohol under controlled conditions. In broad terms, esterification refers to the chemical reaction where an acid and an alcohol combine to form an ester and water; this transformation may be catalyzed by acids such as sulfuric acid or p-toluenesulfonic acid in industrial synthesis settings. The reaction conditions—such as temperature, pressure, and catalyst concentration—are optimized to favor the formation of the desired ester while minimizing by-product formation. Industrial production often takes place in reactors that allow efficient mixing and temperature control to ensure high conversion and purity of the ester product. After reaction completion, purification steps such as distillation and solvent removal are applied to isolate the ester at a high degree of purity suitable for use in food applications. In manufacturing for food use, the resulting product is subjected to quality control measures, including identification and quantification of key characteristics such as purity, acid value, refractive index, and residual catalysts, according to applicable specifications. While the exact manufacturing and purification protocols may vary among producers, the general principle is to yield an ester consistent with the established industrial chemistry of flavor esters. The physicochemical profile—such as its solubility in organic solvents, relative immiscibility with water, and stability under typical storage conditions—reflects its ester functional group and aromatic substituents. Appropriate handling and quality assurance ensure that the final product meets criteria relevant to its use as a flavoring ingredient. These criteria are defined by regulatory guidelines and industry standards, which focus on purity and identity to ensure consistent performance and compliance with safety expectations.

Why It Is Used In Food

BENZYL 2,3-DIMETHYLCROTONATE is used in food products principally to contribute specific flavor attributes that cannot be achieved by base ingredients alone. Flavoring agents play a critical role in modern food formulation by enhancing sensory profiles, masking off-notes, and creating distinctive flavor signatures that align with consumer preferences. In the case of BENZYL 2,3-DIMETHYLCROTONATE, its organoleptic character has been described as having warm, herbaceous, fruity-spicy qualities that complement fruit, spice, and herbal flavor profiles. As a flavoring agent or adjuvant, it is applied in very small amounts to augment the overall taste experience of beverages, confectioneries, baked goods, and other prepared foods. From a formulation perspective, the use of synthetic flavoring agents such as this compound allows food scientists to tailor flavor profiles with precision and consistency, independent of natural ingredient variability. Regulatory frameworks permit such use under defined conditions of good manufacturing practice, with the expectation that the compounds are used at the minimum effective level required to achieve the intended sensory effect. This functional role is particularly important in complex formulations where multiple sensory attributes—sweetness, acidity, fruitiness, spice, and warmth—must be balanced to achieve a harmonious product profile. Furthermore, such flavoring esters can be more stable, cost-effective, and scalable compared to analogous natural extracts, enabling broader application across product lines. Safety evaluations by expert bodies such as JECFA have concluded that, when used at current intake levels typical in food applications, there is no safety concern. This assessment underlies regulatory acceptance in jurisdictions like the United States and supports continued use by formulators seeking consistent sensory impact. In practice, the compound’s contribution is part of an integrated flavor strategy that includes other esters, aldehydes, essential oils, and taste modulators to achieve the desired consumer experience.

Adi Example Calculation

To illustrate how an acceptable daily intake (ADI) concept might be applied in a regulatory context, consider a hypothetical scenario involving BENZYL 2,3-DIMETHYLCROTONATE. While JECFA’s evaluation did not define a numeric ADI due to its conclusion of no safety concern at typical intake levels, a hypothetical calculation can help clarify how intake estimates relate to risk assessment. Suppose a food product contains a flavoring blend with BENZYL 2,3-DIMETHYLCROTONATE at 1 part per million (ppm) and a consumer ingests 1 kilogram of that product in a day. Under these assumptions, the consumer’s intake of the compound would be 1 milligram per day. If this consumption were to be scaled to body weight for a 70-kilogram adult, the intake would be approximately 0.014 milligrams per kilogram body weight per day. In regulatory evaluation, such estimates are compared with toxicological benchmarks such as doses associated with no observed adverse effect levels in animal studies, with safety or uncertainty factors applied to derive a conservative ADI. For example, if animal studies identify a no observed adverse effect level of 100 milligrams per kilogram body weight per day, regulators might apply a safety factor of 100 to account for interspecies differences and human variability, yielding a numeric ADI of 1 milligram per kilogram body weight per day. In this hypothetical scenario, the estimated daily intake of 0.014 milligrams per kilogram body weight per day would be well below the hypothetical ADI, indicating a wide margin of safety under these assumptions. It is important to emphasize that this example is illustrative and not based on specific numeric ADI values established for BENZYL 2,3-DIMETHYLCROTONATE. Regulatory evaluations take into account detailed toxicological data and use conservative assumptions to protect public health. The actual regulatory conclusion for this compound, based on expert evaluation, was that typical exposure levels do not raise safety concerns when the compound is used according to good manufacturing practice.

Safety And Health Research

Safety assessment of flavoring agents such as BENZYL 2,3-DIMETHYLCROTONATE involves consideration of toxicological data, exposure estimates, and expert evaluations to determine whether typical use conditions pose risks to consumers. International expert panels, including the Joint FAO/WHO Expert Committee on Food Additives (JECFA), have evaluated this compound and concluded that there is no safety concern at current levels of intake when used as a flavoring agent. This conclusion is based on available data from toxicological studies, exposure assessments, and an understanding of the compound’s metabolism, distribution, and elimination in biological systems. While JECFA’s evaluation does not provide a specific numerical acceptable daily intake, its qualitative assessment supports the conclusion that the compound does not pose significant health risks at levels consistent with its intended use in food. Regulatory bodies like the FDA also consider safety in their permissive framework; listing under 21 CFR 172.515 reflects a determination that, when used in accordance with good manufacturing practice, the compound’s use does not raise safety issues requiring numerical intake limits. Good manufacturing practice implies that the compound is used in minimal amounts necessary to achieve its technical effect, and not in excess. Safety research for flavoring agents typically examines endpoints such as acute toxicity, chronic exposure, genotoxicity, reproductive toxicity, and potential for metabolic disruption. While specific studies on BENZYL 2,3-DIMETHYLCROTONATE may not be widely published in accessible peer-reviewed literature, the expert evaluations incorporate relevant data to support safety conclusions. It is important to note that regulatory assessments focus on usage patterns in food and that general toxicological investigations are considered as part of a weight-of-evidence approach. Absence of a specific numeric ADI does not imply absence of safety evaluation; rather, it reflects expert judgment that typical exposure levels, based on known use patterns, do not necessitate a defined numerical limit. Such assessments are periodically revisited as new data become available, ensuring that safety standards evolve with scientific understanding.

Regulatory Status Worldwide

Regulatory frameworks in different jurisdictions govern the use of flavoring agents in food products to ensure safety and appropriate application. In the United States, BENZYL 2,3-DIMETHYLCROTONATE is listed in the Food and Drug Administration’s inventory of Substances Added to Food, specifically under the Synthetic Flavoring Substances and Adjuvants section of 21 CFR 172.515, which allows its use in food in accordance with conditions of good manufacturing practice and at the minimum effective level to achieve its intended sensory effect. This regulatory provision reflects a determination that, under specified usage conditions, the compound does not present safety concerns for the general population when incorporated into food products. The CFR citation provides legal context for manufacturers regarding permissible conditions and expectations around quantity and application. Internationally, this compound has been evaluated by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which assigned it a JECFA number of 847 and noted that there is no safety concern at current levels of intake when used as a flavoring agent, based on available toxicological and exposure data. The JECFA evaluation does not establish a numeric acceptable daily intake but provides a qualitative assessment supportive of continued use within conventional practice. In jurisdictions that reference JECFA evaluations, such as Codex Alimentarius and various national food safety authorities, this assessment can inform local regulatory decisions and help align international perspectives on safety. European regulation of flavoring agents may reference both JECFA and region-specific assessments, though an E-number designation for this particular compound has not been identified in the authoritative lists of permitted flavoring substances. Where regional regulatory bodies require specific evaluations or approvals, manufacturers and importers may need to consult local guidelines and ensure compliance with labeling and usage criteria. Across jurisdictions, the common theme is that flavoring agents are subject to oversight to ensure that their use does not compromise consumer safety and that their application is consistent with established good manufacturing practices.

Taste And Functional Properties

The sensory characteristics of BENZYL 2,3-DIMETHYLCROTONATE are rooted in its chemical structure, which includes a benzyl ester moiety and a substituted crotonic acid backbone. Esters are a well-known class of compounds in flavor chemistry, often associated with fruity, floral, or herbaceous sensory notes depending on their specific substituents. In this case, the compound’s aroma and taste profile have been described in flavor chemistry resources as presenting warm, herbal, fruity-spicy nuances that contribute complexity to a formulation. Such sensory properties are expressed at trace concentrations and are perceived holistically within a food matrix, interacting with other flavor notes to enhance or modify the overall profile. Functionally, this compound is compatible with lipid and alcohol-based systems due to its solubility characteristics, as it is generally insoluble in water but soluble in alcohols and oils. This solubility profile facilitates its use in beverages, confections, and flavoring blends where organic components predominate. The heat and pH stability of ester-based flavoring agents can vary; formulators consider these properties when incorporating the ingredient into products exposed to processing conditions such as baking or pasteurization. While specific stability data for BENZYL 2,3-DIMETHYLCROTONATE may not be publicly available in the regulatory literature, the broader class of aromatic esters typically exhibits sufficient stability under standard processing conditions when used at appropriate concentrations. Flavor interaction is another important functional consideration. In complex formulations, flavoring agents may interact synergistically with other compounds to amplify desirable taste attributes or suppress off-notes. BENZYL 2,3-DIMETHYLCROTONATE may be blended with other esters, aldehydes, and essential oil components to achieve a balanced profile that aligns with product goals. Understanding the functional and sensory properties of this compound helps food scientists predict how it will behave in different matrices and under various processing conditions, enabling effective formulation decisions.

Acceptable Daily Intake Explained

The concept of an acceptable daily intake (ADI) is a key element in regulatory toxicology and risk assessment, representing an estimate of the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. For many food additives and flavoring agents, expert bodies such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA) derive an ADI based on toxicological data, applying conservative safety factors to account for uncertainties. In the case of BENZYL 2,3-DIMETHYLCROTONATE, JECFA’s evaluation concluded that there is no safety concern at current levels of intake when used as a flavoring agent, which suggests that the typical exposures associated with its use do not approach levels of toxicological concern. This qualitative conclusion means that, within the range of expected consumption from food products containing the compound at approved use levels, the likelihood of adverse health effects is considered low. Regulatory assessments such as this consider multiple lines of evidence, including animal studies examining acute and chronic toxicity, metabolism data indicating how the compound is processed by biological systems, and exposure estimates based on usage levels in various food categories. When expert panels determine that typical exposures are well below levels associated with adverse effects in toxicological studies, they may conclude that a formal numeric ADI is not necessary or that the compound can be used according to good manufacturing practice. It is important to understand that an ADI is not a recommended intake level for consumers; rather, it is a risk management tool that helps regulators set safe use conditions and guide manufacturers. A conclusion of no safety concern at current intake levels implies that routine consumption through food products is unlikely to pose health risks, provided that the compound is used within established regulatory frameworks and in minimal quantities necessary for its intended sensory effect. This approach emphasizes a balance between consumer safety and functional application in food formulation, and it aligns with broader principles of risk assessment and management.

Comparison With Similar Additives

Flavoring agents are a diverse group of compounds used to modify or enhance the sensory attributes of food products. BENZYL 2,3-DIMETHYLCROTONATE can be compared with other ester-based flavoring agents, such as isoamyl acetate, ethyl butyrate, and benzyl acetate. Each of these compounds contributes distinctive sensory notes due to differences in chemical structure. For example, isoamyl acetate is often associated with banana-like fruity notes, while ethyl butyrate is linked to pineapple-like fruitiness, and benzyl acetate offers sweet, floral characteristics. In contrast, BENZYL 2,3-DIMETHYLCROTONATE’s warm, herbaceous, and fruity-spicy profile occupies a different niche in flavor formulation. Understanding these differences allows food scientists to select appropriate combinations of flavoring agents to achieve multi-dimensional sensory profiles. Functional properties also vary among these compounds. Solubility in different food matrices can influence how readily a flavoring agent integrates into water-based beverages versus lipid-rich confections. Ester-based agents like ethyl butyrate and isoamyl acetate are typically volatile and can contribute noticeable aroma at low concentrations, similar to BENZYL 2,3-DIMETHYLCROTONATE. However, the presence of additional substituents on the ester backbone can alter volatility and sensory perception thresholds. For instance, branched-chain esters often have lower volatility and may provide more sustained aroma profiles compared with linear esters. By comparison, BENZYL 2,3-DIMETHYLCROTONATE’s aromatic benzyl moiety may confer a balance of volatility and persistence suited to specific flavor applications. In terms of regulatory status, many ester-based flavoring agents are permitted for use under frameworks that allow synthetic flavoring substances when used according to good manufacturing practice. This includes compounds regulated under sections of 21 CFR Part 172 or evaluated by international bodies like JECFA. The specific regulatory provisions for each compound depend on available safety data and historical usage patterns. Comparing BENZYL 2,3-DIMETHYLCROTONATE with these similar additives highlights how formulation choices are informed by both sensory characteristics and regulatory context, enabling tailored application in various food categories.

Common Food Applications Narrative

In contemporary food and beverage products, flavor complexity is a key driver of consumer preference and product differentiation. BENZYL 2,3-DIMETHYLCROTONATE is part of a category of flavoring agents used to enhance specific sensory profiles in items where fruity, herbal, or spicy notes are desired. For example, in nonalcoholic beverages, where fruit flavors are blended to create an appealing aroma and taste, trace amounts of this compound can contribute depth and nuance without overwhelming the primary fruit character. Similarly, in confectioneries such as hard candies, chewable sweets, or flavored coatings, it may be used to support complementary flavor notes that make the product more distinctive. In baked goods, flavoring agents are often employed to augment the natural sensory contributions of ingredients like fruits, spices, and extracts. This compound’s warm and herbal profile can support spice blends in cookies, pastries, and snacks, contributing subtle complexity that enhances the overall flavor experience. Beyond sweet products, savory applications such as sauces, seasonings, and dressings can also benefit from carefully calibrated flavor contributions that help balance acidity, sweetness, and spice. Flavor ingredients like BENZYL 2,3-DIMETHYLCROTONATE are used by product developers alongside a suite of other esters, aldehydes, and natural extracts to build rich sensory profiles in a broad range of categories. Its role is not to provide bulk taste but to influence specific notes that elevate the consumer experience when combined with other ingredients and flavor systems. This nuanced use underscores the sophistication of modern flavor formulation, where individual compounds are selected for their ability to contribute targeted sensory attributes in complex food matrices.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: EFSA-specific evaluation and E-number were not identified in available authoritative sources

JECFA

  • Year: 2001
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent

Sources

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