ALLYL CYCLOHEXANEACETATE

CAS: 4728-82-9 FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT

ALLYL CYCLOHEXANEACETATE is a synthetic flavoring agent and enhancer permitted for use in food under 21 CFR 172.515 with a fruity aroma profile.

What It Is

ALLYL CYCLOHEXANEACETATE is a synthetic food flavoring substance classified as a flavor enhancer, flavoring agent or adjuvant used to impart or enhance fruity and mixed-fruit notes in food products. It is a member of the ester family of compounds characterized by a cyclohexane ring bonded to an acetic acid ester group and an allyl moiety. It is identified by the CAS number 4728-82-9 and appears in regulatory lists such as 21 CFR 172.515 under synthetic flavoring substances and adjuvants. The compound has been evaluated by international bodies and is included in expert panel evaluations as a flavoring agent. Its other chemical names include variations on allyl cyclohexaneacetate and cyclohexaneacetic acid esters, reflecting its structural identity and synonyms reported in flavoring ingredient libraries and chemical registries. ALLYL CYCLOHEXANEACETATE is not naturally occurring to any significant extent in foods but is instead manufactured for use in formulated flavor blends. It is often used by flavorists and food scientists to achieve specific sensory profiles in confections, beverages, and other processed food applications where fruity notes or mouthfeel enhancement is desired. The technical function of this ingredient centers on modulation of flavor perception and reinforcement of desired taste characteristics, rather than providing nutritive value. Its use in food is tightly controlled by regulatory frameworks that specify conditions under which it can be incorporated into food products, focusing on minimal effective usage consistent with good manufacturing practices. As a defined flavoring agent, ALLYL CYCLOHEXANEACETATE provides a chemical solution for achieving flavor complexity in food formulations. In regulatory inventories, it is listed alongside other synthetic flavoring esters with similar aromatic contributions. While it shares a common presence in flavor chemistry with other fruit‑type esters, it remains distinct in its cyclohexane backbone and allyl group, contributing to its unique sensory profile. This specificity in chemical structure is a key factor in understanding its behavior in food matrices and why it is selected for particular flavor roles.

How It Is Made

The production of ALLYL CYCLOHEXANEACETATE involves an esterification reaction between cyclohexaneacetic acid and allyl alcohol under controlled chemical synthesis conditions. The reaction typically takes place in the presence of an acid catalyst such as sulfuric acid or phosphoric acid to facilitate the formation of the ester bond, resulting in a compound with both hydrophobic (cyclohexane) and unsaturated (allyl) components. The synthesis route mirrors esterification pathways used for many flavor esters, adapted to achieve high purity and yield for food‑grade applications, though proprietary variations in industrial practice may include solvent choices and catalyst systems tailored to efficiency and regulatory compliance. In commercial production, after the initial esterification, the reaction mixture undergoes purification steps to remove unreacted starting materials and by‑products. These purification steps may include distillation under reduced pressure or chromatographic techniques to ensure that the final product meets flavor industry standards for identity and purity. The resulting material is typically a colorless to pale liquid with a characteristic fruity aroma. Control of reaction conditions such as temperature, catalyst concentration, and reaction time is essential to minimize side reactions and to achieve consistent quality appropriate for food flavor applications. Manufacturers engaging in production for food use must adhere to applicable regulatory requirements for food‑grade chemicals, including documentation of raw material sources, process controls, and analytical verification of composition. The identity of this substance is confirmed through analytical methods such as gas chromatography and mass spectrometry to ensure conformity with specifications. While detailed industrial methods are often proprietary, the general principle of esterification and purification remains consistent with standard organic chemistry practices employed across flavoring substance manufacture. This fundamental chemistry underpins the availability of the substance for inclusion in flavor blends used in diverse food matrices.

Why It Is Used In Food

The principal reason ALLYL CYCLOHEXANEACETATE is used in food is to enhance or impart desirable flavor characteristics. In food science and flavor formulation, esters like this one are prized for their ability to evoke fruity sensory perceptions, often described as pineapple, apricot, peach, or mixed fruit nuances. These sensory properties are leveraged in product categories where a specific fruity character adds consumer appeal, such as in beverages, confections, dairy desserts, and certain baked goods. The inclusion of such compounds allows food developers to achieve complex flavor profiles that would be difficult to obtain exclusively from natural ingredients or raw food components. In addition to imparting specific tastes, flavoring agents such as ALLYL CYCLOHEXANEACETATE may interact synergistically with other aromatic compounds to create balanced and consistent flavor impressions. This synergism is particularly valuable in processed foods where heat, pH changes, and storage conditions can diminish flavor potency or alter perception. By judiciously combining flavoring agents with complementary sensory attributes, food formulators can stabilize and prolong the desired aroma and taste experiences in finished products. Another reason for its use lies in the cost‑effective delivery of flavor. Natural sources of certain fruit notes may be expensive, seasonally variable, or unsustainable at scale. Synthetic flavoring agents provide predictable, scalable options that enable manufacturers to maintain product consistency year‑round. When used in accordance with regulatory allowances and industry good manufacturing practices, these agents contribute to product quality without introducing nutritive components or functional changes unrelated to flavor. The regulatory framework, such as 21 CFR 172.515, defines conditions under which such substances can be included in foods, emphasizing minimal effective usage that achieves intended sensory effects without compromising safety or quality.

Adi Example Calculation

An illustrative example of an ADI calculation shows how experts use available toxicological data to determine safety margins. Suppose a flavoring agent had a no‑observed‑adverse‑effect level (NOAEL) identified in animal studies at a certain dose, such as X mg/kg body weight per day. Regulatory scientists would apply uncertainty factors to account for differences between animals and humans, and variations within human populations, resulting in an ADI that is a small fraction of the NOAEL. For instance, applying an uncertainty factor of 100 would yield an ADI of X divided by 100. For ALLYL CYCLOHEXANEACETATE, expert evaluations have concluded there is no safety concern at current levels of intake, meaning that typical intake through food flavor use is far below levels associated with adverse effects in experimental settings. While a specific numeric ADI has not been promulgated for this compound, the principle of deriving an ADI through NOAEL and uncertainty factors illustrates how safety margins are established. This example is hypothetical and serves to explain the methodology rather than provide a numeric benchmark for this specific additive.

Safety And Health Research

Regulatory evaluations of ALLYL CYCLOHEXANEACETATE focus on its safety when used as a flavoring agent at levels consistent with typical food use patterns. Agencies and expert committees assess information on chemical identity, metabolic pathways, and toxicological data to determine whether there are concerns related to genotoxicity, systemic toxicity, or other health endpoints. In the case of this compound, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) concluded that there is no safety concern at current levels of intake when used as a flavoring agent, indicating that available toxicological data and estimated exposures did not raise issues warranting quantitative limits or restrictions beyond good manufacturing practice. Safety assessments by expert panels consider a range of factors, including how a substance is metabolized in the body, whether it is rapidly broken down into innocuous components, and whether studies in experimental models show adverse effects at doses far exceeding human exposure. For many flavoring agents, metabolic studies demonstrate that ester bonds are cleaved by ubiquitous esterases, leading to metabolites that are common and readily handled by normal metabolic processes. While detailed toxicological data may be limited for some specific flavoring compounds, the body of evidence supports their safe use in foods at low levels typical of flavoring applications. It is important to distinguish between safety under intended conditions of use and assertions about pharmacological or health benefits; the safety evaluations for ALLYL CYCLOHEXANEACETATE are specific to its role as a flavoring agent. Expert committees like JECFA and industry panels like FEMA review available data and consider margins of exposure when concluding there is no safety concern. These conclusions are based on comprehensive review of relevant studies, chemical identity, and patterns of use, reflecting a risk assessment approach rather than therapeutic or health claims.

Regulatory Status Worldwide

In the United States, ALLYL CYCLOHEXANEACETATE is listed in 21 CFR 172.515 among synthetic flavoring substances and adjuvants permitted for direct addition to food under specified conditions. This regulatory citation indicates that the compound is recognized as a flavoring agent that can be safely used in food when included in the minimum quantity necessary to achieve its intended sensory effect and otherwise in accordance with good manufacturing practice. The provisions of 21 CFR 172.515 provide a broad list of synthetic flavoring substances, including this one, that the Food and Drug Administration has identified as acceptable for food use under these conditions. At the international level, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated ALLYL CYCLOHEXANEACETATE as a flavoring agent. According to the JECFA database entry, it is assigned JECFA number 12 and was evaluated with the conclusion that there is no safety concern at current levels of intake when used as a flavoring agent, reflecting expert assessment of available toxicological information and usage patterns. This conclusion is based on historical evaluations documented in JECFA reports. The Flavor and Extract Manufacturers Association (FEMA) Expert Panel includes this substance in its flavor ingredient library, indicating that it has been assessed for safety under conditions of intended use as a flavoring substance and referenced with a FEMA number. These evaluations are part of ongoing expert review processes that consider available scientific data to determine whether substances can be used safely in food. Regulatory frameworks in other regions may have parallel provisions for flavoring agents, often aligned with international scientific assessments such as those from JECFA, though specific listings and conditions of use vary by jurisdiction.

Taste And Functional Properties

ALLYL CYCLOHEXANEACETATE is characterized by a distinctive fruity and sweet aroma profile that is often described as reminiscent of tropical fruits such as pineapple, peach, and apricot. These sensory attributes make it a useful ingredient in flavor formulation for food products seeking to achieve specific aromatic notes or to complement other flavor components in a blend. Its molecular structure—comprising a cyclohexane ring and an allyl ester moiety—contributes to both its volatility profile and how it interacts with olfactory receptors, translating chemical presence into perceived taste and aroma. Functionally, this substance exhibits solubility characteristics compatible with many food formulations. While it is not highly water‑soluble due to its hydrophobic cyclohexane segment, it demonstrates miscibility with alcohol, oils, and other flavoring matrices, which facilitates its integration into complex flavor systems. Its relative stability under typical processing conditions—such as moderate heat and standard pH ranges encountered in food production—allows it to retain aromatic integrity throughout manufacturing and storage. However, like many esters, extreme pH or prolonged high temperatures may lead to hydrolysis or volatility changes that alter sensory impact. The perceived intensity of its flavor contribution is concentration dependent. In flavor chemistry practice, formulators adjust usage levels to achieve the targeted sensory effect, mindful of the compound’s potent aromatic properties, so that it enhances rather than overwhelms the overall flavor profile. The compound’s compatibility with other flavoring substances also allows it to function as part of multi‑component systems where complex taste and aroma notes are needed. Its performance in these systems is a balance of chemical stability, olfactory impact, and interaction with other sensory constituents, and these properties guide its application in food products where specific taste outcomes are desired.

Acceptable Daily Intake Explained

Acceptable Daily Intake (ADI) is a concept used by regulatory bodies to indicate an estimate of the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, based on available toxicological data and exposure estimates. For many flavoring agents, including ALLYL CYCLOHEXANEACETATE, expert committees have concluded that typical intake levels from food use do not present a safety concern, and thus a formal numeric ADI value may not be assigned. In such cases, safety assessments indicate that there is no safety concern at current levels of intake when used as intended in food. The ADI framework helps regulators and risk assessors communicate about safety margins. When a numeric ADI is established for a compound, it is usually derived from toxicological studies identifying a no‑observed‑adverse‑effect level (NOAEL) in animal models, followed by application of uncertainty factors to account for interspecies and intraspecies differences. For flavoring agents evaluated by expert committees, the absence of adverse findings at levels of exposure far exceeding expected human intake often leads to conclusions of no safety concern without needing to specify numeric limits. Consumers should understand that an ADI or similar safety conclusion does not imply a recommendation to consume the additive at high levels. Instead, it reflects a risk assessment process in which regulatory scientists determine that the compound’s use in food at levels consistent with good manufacturing practice is not expected to harm human health. For ALLYL CYCLOHEXANEACETATE, existing evaluations conclude that intake from typical food use does not pose a safety issue, consistent with regulatory grants of use in specified contexts.

Comparison With Similar Additives

ALLYL CYCLOHEXANEACETATE can be compared to other ester‑type flavoring agents such as allyl butyrate or isoamyl acetate, which are also used to impart fruity notes in food products. Like ALLYL CYCLOHEXANEACETATE, these esters contribute characteristic sensory impressions—allyl butyrate often evokes pineapple and tropical fruit notes, while isoamyl acetate is associated with banana‑like aromas. The selection among these compounds depends on the specific aroma profile desired in a product formulation. In terms of functional properties, many ester flavoring agents share solubility characteristics that favor incorporation into oil‑based flavor systems and moderate stability under typical processing conditions. However, differences in volatility and odor threshold can influence how a particular compound is perceived; some esters may be more volatile and perceived at lower concentrations, while others require higher usage levels within regulatory allowances to achieve the same sensory impact. Compared to simple aliphatic esters like ethyl acetate, compounds with more complex cyclic structures such as ALLYL CYCLOHEXANEACETATE may exhibit nuanced aromatic characteristics that enhance complexity in flavor profiles. Another similar category includes fruit‑type lactones, which also provide creamy or fruitnotes but differ in chemical structure and sensory quality. When formulating flavors, food scientists often blend multiple compounds from these classes to achieve balanced and appealing profiles. While regulatory evaluations focus on safety at usage levels consistent with good manufacturing practice, the practical selection of one additive over another is driven by the targeted sensory outcome and functional performance in the specific food matrix.

Common Food Applications Narrative

ALLYL CYCLOHEXANEACETATE finds application across a range of food products where fruity and mixed fruit aromas are desirable. In beverage formulations, it contributes to tropical or orchard fruit notes in soft drinks, flavored waters, and ready‑to‑drink mixes, often blended with other esters and natural flavors to achieve a balanced sensory profile. In confectionery, it enhances the fruitiness of sweets, chews, and gummy candies, where consistent and pronounced flavor characteristics are essential to product identity. Similarly, in frozen desserts such as fruit‑flavored ice creams and sorbets, this flavoring agent can be part of a broader blend used to intensify perceived fruit quality without adding sugar or caloric content directly. In baked goods, the compound may be included in fillings, icings, or dough formulations to impart fruit notes that complement other ingredients like chocolate, vanilla, or nut flavors. Its use in dairy‑based products extends to yogurts and drinkable dairy beverages where a stable fruit character enhances consumer appeal. In non‑alcoholic beverage concentrates and syrups, it can be part of the flavor base that consumers expect when selecting fruit‑flavored options. Across these applications, formulators use ALLYL CYCLOHEXANEACETATE in small quantities tailored to the specific product matrix and desired sensory impact, consistent with regulatory allowances for food flavoring agents. Beyond these core categories, flavoring agents with fruity profiles also appear in snack seasonings, gelatin and pudding desserts, and culinary sauces, where a hint of fruit essence can modify or uplift the overall taste. The suitability of ALLYL CYCLOHEXANEACETATE for such diverse applications comes from its ability to contribute targeted sensory notes without altering nutritional composition or functional texture. Its inclusion in flavor systems exemplifies how synthetic flavoring agents support the creation of consistent and appealing food experiences across a broad food landscape.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: No specific EFSA evaluation found

JECFA

  • Year: 1996
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent

Sources

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