CITRONELLYL TRANS-2-METHYL-2-BUTENOATE

CAS: 24717-85-9 FLAVORING AGENT OR ADJUVANT

CITRONELLYL TRANS-2-METHYL-2-BUTENOATE is a synthetic ester used mainly for its aromatic and flavoring properties in food and beverages, particularly in floral, fruity, and herbaceous applications.

What It Is

CITRONELLYL TRANS-2-METHYL-2-BUTENOATE is a chemical compound classified as a flavoring agent or adjuvant, commonly used to impart or modify sensory characteristics in foods. It belongs to the class of organic esters and is recognized for its floral and fruity aromatic profile that can enhance or complement other ingredients in formulations. In flavor science, it is identified by its CAS number 24717-85-9 and has multiple synonyms including citronellyl tiglate and related ester descriptors. Its structural features, characteristic of esters, contribute to its volatility and interaction with olfactory receptors, making it useful in flavor applications where a nuanced aroma profile is desired. While not one of the most widely used flavoring agents compared to other esters, it plays a role in specialized flavor profiles in certain categories of foods and beverages. The compound's sensory characteristics are described in industry literature as floral and leafy with nuances of rose, geranium, and fruity undertones, which makes it particularly useful in products that benefit from a delicate, complex aroma profile. Its relatively low water solubility and moderate volatility influence how it is incorporated and perceived in products. Chemically, as a synthetic ester, it is similar to naturally occurring esters that contribute to flavor and fragrance in fruits and flowers. In commercial settings, it is typically supplied as a stabilized liquid, and quality parameters such as purity and odor consistency are controlled to meet flavor industry standards. Citronellyl trans-2-methyl-2-butenoate is a functional additive advised for use in accordance with good manufacturing practices, which generally requires that it be used at levels sufficient to achieve the intended sensory effect without exceeding typical use levels documented in flavor formulation guides. Its application and safety assessment draw on extensive flavor science knowledge, combining chemical understanding with sensory evaluation to achieve desired flavor outcomes.

How It Is Made

The manufacture of CITRONELLYL TRANS-2-METHYL-2-BUTENOATE typically involves an esterification reaction between citronellol, a naturally derived alcohol, and 2-methyl-2-butenoic acid under controlled conditions. Esterification, a well-established chemical reaction in organic chemistry, generally involves combining an alcohol and an acid in the presence of an acid catalyst to form an ester and water. The process may be conducted with techniques such as azeotropic distillation to facilitate water removal, thereby driving the reaction toward completion. The choice of catalyst, reaction temperature, and purification steps all influence the final product quality, particularly in achieving sufficient purity and desirable sensory properties suitable for flavoring applications. In industrial practice, manufacturers producing this compound for flavor use are expected to operate under quality control systems that ensure consistency, stability, and compliance with relevant specifications. These systems include analytical verification of identity and purity, often using techniques such as gas chromatography and mass spectrometry to confirm that the final product meets stringent criteria. Regulatory guidelines generally require that flavor compounds be produced to food-grade standards, which include limits on contaminants and impurities. This ensures that the additive performs as expected in food formulations while minimizing the presence of unwanted byproducts. Although production methods can vary among suppliers, the core principle remains consistent: efficient esterification with controlled reaction conditions and downstream purification that yields a compound suitable for food use. Given its primary role as a flavoring agent, the manufacturing process must also account for sensory quality, including odor profile and stability, which can be impacted by minor variations in production conditions. Producers often provide specifications that detail these quality attributes, aligning with industry norms for commercial flavor ingredients.

Why It Is Used In Food

CITRONELLYL TRANS-2-METHYL-2-BUTENOATE is used in food primarily for its ability to contribute nuanced aromatic and flavor characteristics that cannot easily be replicated by simpler compounds. Its ester structure confers a distinctive sensory profile that is floral, fruity, and leafy, which can complement or enhance the complexity of flavor formulations. Flavor chemists leverage such compounds to achieve specific taste and aroma balances, particularly in categories where a floral or herbaceous note is desirable. In formulations, flavoring agents like citronellyl trans-2-methyl-2-butenoate serve multiple roles. They can act as primary flavor components, adding characteristic notes, or as modifiers that smooth or refine the overall sensory experience when combined with other flavor molecules. Because tastes and aromas interact in complex ways, the presence of a compound with a distinct profile can help round out a flavor blend, masking undesirable elements or highlighting particular sensory dimensions. This is especially relevant in beverage and confectionery applications where layered profiles are common. The functional versatility of esters like this one also lies in their relatively well-understood behavior in food matrices. They are generally stable under normal processing conditions, making them suitable for a range of products that undergo heat processing or storage over time. Their contribution to perceived flavor and aroma is typically consistent when used within recommended levels, allowing formulators to predict their impact reliably. As consumer preference trends continue to favor more complex and refined flavor experiences, such compounds remain valuable tools in a flavorist's repertoire.

Adi Example Calculation

To illustrate the concept of acceptable daily intake (ADI) in a hypothetical scenario, consider a flavoring compound evaluated by an expert committee. Suppose an ADI were established at a certain conservative level based on toxicological studies. If an individual weighing 70 kilograms consumed foods containing this compound at a level that resulted in an intake of 0.1 milligrams per kilogram of body weight per day, the ADI framework would help determine whether that intake is within the safe range. In this hypothetical example, multiplying 0.1 mg/kg by 70 kg yields a total daily intake of 7 milligrams per day, which would be compared against the established ADI to assess safety. Using body weight in calculations provides a standardized way to relate exposure to safety thresholds across individuals of different sizes. It is important to emphasize that this example is illustrative and does not relate to a specific numeric ADI for CITRONELLYL TRANS-2-METHYL-2-BUTENOATE, as no explicit numeric value was defined in the referenced safety evaluations. The purpose of such examples is to clarify how ADIs are used in practice: they offer a benchmark against which estimated daily exposure from food can be compared. When a flavoring agent’s actual use levels result in exposure well below a conservative ADI, regulators consider it unlikely to pose a risk to health over a lifetime of consumption.

Safety And Health Research

Safety and health research for CITRONELLYL TRANS-2-METHYL-2-BUTENOATE focuses on its evaluation as a flavoring agent and its toxicological profile relative to expected human exposure in foods. Regulatory bodies and expert committees, including JECFA, base their assessments on available toxicological data such as acute toxicity, repeated-dose studies, and structure-activity considerations that relate chemical structure to potential biological effects. In the case of this compound, JECFA’s evaluation concluded that at typical use levels in food as a flavoring agent, there was no safety concern identified, reflecting a risk assessment that accounts for likely intake and toxicological thresholds. This evaluation incorporates conservative assumptions to protect public health while enabling the use of flavoring substances in foods. The toxicological data that inform such evaluations generally include studies measuring acute oral toxicity, which typically assess the dose required to produce harmful effects in animal models such as rodents. For many flavoring esters, acute toxicity is low relative to expected human exposures at flavor use levels. In addition to acute toxicity, subchronic and chronic toxicity studies, where available, help define dose levels that do not produce adverse effects when consumed over longer periods. These data collectively inform expert judgments about safety and support the conclusion that typical dietary exposure to this compound does not pose a significant health risk. Overall, the safety assessment framework emphasizes the difference between hazard (the inherent potential to cause harm) and risk (the likelihood of harm given actual exposure). Because flavoring agents are used at very low concentrations in foods, exposure levels are usually orders of magnitude below thresholds that elicit adverse effects in toxicological studies. This risk-based approach underpins regulatory evaluations and supports safe usage in food products when consistent with good manufacturing practices.

Regulatory Status Worldwide

The regulatory status of CITRONELLYL TRANS-2-METHYL-2-BUTENOATE varies by region and is influenced by international safety evaluations and local food additive regulations. At the international level, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated this compound as part of its ongoing review of flavoring agents and assigned it JECFA number 1823. According to the JECFA summary, when used as a flavoring agent at levels consistent with intended use, there was no safety concern identified at typical intake levels. This evaluation reflects expert assessment based on available data and informs regulatory frameworks and industry practices globally. However, the JECFA evaluation did not establish a specific numeric acceptable daily intake (ADI), which means individual jurisdictions interpret and implement regulatory positions based on their own food safety policies. In other jurisdictions such as the European Union, flavoring agents undergo assessment under EFSA’s flavoring evaluation programs. Regulatory status in these regions is derived from EFSA’s scientific advice and the EU’s flavoring regulation framework. Where specific references for this compound are not readily found in EU flavoring annexes, industry practice typically references JECFA evaluations and aligns with regional guidance for flavor safety and use levels. Overall, while exact regulatory codifications differ, the global trend is to recognize the compound as a flavoring ingredient that can be safely used within the bounds of established safety evaluations and good manufacturing practice.

Taste And Functional Properties

The sensory and functional properties of CITRONELLYL TRANS-2-METHYL-2-BUTENOATE are defined by its aromatic character and behavior in food systems. Esters in general are known for their ability to impart fruity, floral, and sweet notes, and this particular compound is no exception. Sensory evaluations describe it as having floral and leafy characteristics, with nuances reminiscent of rose, geranium, and gentle fruity undertones. These sensory traits make it suitable for enhancing or complementing complex flavor profiles where such notes are desired. The perceived intensity and quality of the aroma can vary depending on the food matrix and the concentration used. Functionally, flavoring agents like this one are chosen for their volatility and stability under typical food processing conditions. As an ester, it exhibits moderate volatility that allows it to contribute to the aroma of foods without dissipating too quickly during mixing or thermal processing. Its interaction with other ingredients and solvents in the food matrix affects how it is perceived, which is why flavorists often conduct careful blending trials to optimize its use. Additionally, its solubility profile, characterized by low water solubility and higher solubility in lipid or alcohol phases, influences how it distributes within products and contributes to overall sensory perception. While the compound adds desirable notes to flavor blends, it is typically used at concentrations sufficient to achieve the intended sensory effect without overwhelming other components. Sensory scientists assess such compounds through structured panels to determine optimal use levels, taking into account human perception thresholds as well as interactions with other flavor components. In doing so, they ensure that the compound enhances rather than detracts from the overall flavor experience.

Acceptable Daily Intake Explained

The concept of acceptable daily intake (ADI) is central to the safety assessment of food additives including flavoring agents like CITRONELLYL TRANS-2-METHYL-2-BUTENOATE. ADI represents an estimate of the amount of a substance in food or drinking water that can be consumed daily over a lifetime without an appreciable health risk. This estimate is typically derived from toxicological data, including studies in animal models, and incorporates safety factors to account for differences between animals and humans as well as variability within human populations. In the case of this compound, expert evaluations by bodies such as JECFA did not establish a specific numeric ADI, but instead concluded that there was no safety concern at current levels of intake when used as a flavoring agent. This type of conclusion reflects a risk assessment where actual exposure at intended use levels is sufficiently low relative to toxicological benchmarks that formal numeric ADI was not needed to affirm safety for its intended purpose. Regardless of whether a specific ADI value is assigned, the underlying principle remains that flavoring agents should be used at levels no higher than necessary to achieve the intended sensory effect, aligning with good manufacturing practice and minimizing unnecessary exposure. Consumers should understand that ADIs are established with conservative margins, meaning the amounts considered safe are well below levels at which any adverse effects have been observed in scientific studies. When expert committees state that there is ‘‘no safety concern at current levels of intake,’’ it reflects high confidence that typical dietary exposure is well within safe bounds, assuming that manufacturers adhere to recommended use practices. This risk-based approach ensures that food additives contribute to product quality without compromising public health.

Comparison With Similar Additives

Comparing CITRONELLYL TRANS-2-METHYL-2-BUTENOATE with other flavoring esters highlights both commonalities and differences that influence their application in food formulations. Esters such as ethyl butyrate, isoamyl acetate, and ethyl hexanoate are among the widely used flavoring agents known for their fruity and sweet characteristics. Like these esters, citronellyl trans-2-methyl-2-butenoate contributes aromatic and flavor nuances that can enhance sensory complexity. The structure of esters generally confers volatile aromatic profiles that interact with olfactory receptors, making them valuable in creating characteristic taste and aroma sensations in foods and beverages. However, differences arise in the specific sensory notes each compound provides. For example, ethyl butyrate is commonly associated with pineapple-like notes and is frequently used in fruit-flavored beverages and confectionery. In contrast, citronellyl trans-2-methyl-2-butenoate’s floral and leafy attributes make it more suitable for nuanced applications where subtle botanical or floral accents are desired. This distinction influences how formulators select from a palette of esters to achieve targeted flavor outcomes. The relative volatility and solubility of each compound also affect how they perform in different food matrices, with some esters being more stable under heat or in lipid-rich environments than others. By understanding these differences, product developers can choose flavoring agents strategically to balance sensory attributes and achieve specific consumer experiences. The interplay of multiple flavoring compounds, each contributing distinct notes, results in richer and more appealing flavor profiles. In this context, citronellyl trans-2-methyl-2-butenoate occupies a niche among flavoring esters, valued for its unique floral and herbaceous contributions.

Common Food Applications Narrative

CITRONELLYL TRANS-2-METHYL-2-BUTENOATE finds its way into a variety of food and beverage applications where a refined, nuanced aromatic profile is sought. Flavorists and product developers often incorporate it into beverage concentrates, confectionery products, and dairy alternatives to provide delicate floral and fruity accents that contribute to a more layered and appealing sensory experience. For example, in specialty beverages aimed at adults who enjoy complex flavor profiles, the subtle floral and leafy nuances of this compound help support botanical or herbal notes without dominating the overall flavor. In confectionery, it can contribute a hint of sophistication to fruit-flavored or floral-infused candies and sweets, making them stand out in a crowded market. Beyond beverages and confectionery, this compound can be used in savory applications that benefit from a gentle herbaceous overlay. Ready-to-eat sauces and dressings that aim to evoke natural botanical flavors can employ small amounts of such esters to reinforce the perception of freshness or complexity, particularly when paired with natural extracts. Similarly, dairy analogues such as plant-based yogurts and desserts sometimes incorporate flavoring agents like this one to round out flavor profiles that might otherwise lack depth when compared to traditional dairy products. In each application, product developers consider how the compound interacts with other ingredients and the specific food matrix. Intricate flavor compositions often rely on a symphony of components, with each playing a role in achieving the desired consumer experience. While CITRONELLYL TRANS-2-METHYL-2-BUTENOATE is only one of many flavoring agents used in the industry, its unique sensory attributes make it a valuable ingredient in the toolkit of flavor professionals seeking to create differentiated and memorable products.

Safety & Regulations

FDA

  • Notes: No specific CFR section listing found; used as a flavoring agent consistent with general flavor use provisions.

EFSA

  • Notes: Specific EFSA numeric ADI not identified in available evaluations.

JECFA

  • Notes: JECFA noted no safety concern at typical intake but did not define numeric ADI on the summary page.
  • Adi Display: No safety concern at typical intake levels

Sources

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