CYCLOHEXYL BUTYRATE

CAS: 1551-44-6 FLAVORING AGENT OR ADJUVANT

Cyclohexyl butyrate is a synthetic flavoring ingredient used to impart fruity and floral notes in foods. It is permitted as a flavoring agent under specific regulatory provisions.

What It Is

Cyclohexyl butyrate is a chemical compound in the class of esters that combines a cyclohexyl ring with a butyrate moiety. Esters like cyclohexyl butyrate are commonly found in nature and in manufactured flavorings because they can produce pleasant sensory perceptions. In the context of food science, cyclohexyl butyrate is characterized as a flavoring agent or adjuvant, meaning it contributes to the composition of flavors in processed foods. The chemical is identified by the CAS number 1551-44-6, a unique numeric identifier assigned to chemical substances for regulatory and scientific communications. Cyclohexyl butyrate is described in supplier and industry literature as a stable, colorless liquid with a fruity or floral odor profile. It is associated with sensory descriptors such as apple, pineapple, or other sweet fruit-like characteristics when used in flavor formulations. Although this compound can be detected at very low concentration levels in foods, its presence can significantly influence taste and aroma profiles. The molecular structure reflects a cyclohexane ring linked via an ester bond to a butyric acid derivative, a configuration that contributes to its volatility and scent properties. Functionally, cyclohexyl butyrate falls into the broader category of aroma esters, which are widely used in the flavor industry to mimic or enhance natural fruit flavors. The class of esters to which it belongs is often selected for applications where a bright, sweet, fruit-associated note is desirable. Its use in food products aligns with the flavoring principles of eliciting desirable sensory responses without imparting nutritive value on its own.

How It Is Made

The synthesis of cyclohexyl butyrate typically involves an organic chemistry process known as esterification. In esterification, an alcohol and a carboxylic acid are reacted under controlled conditions in the presence of a catalyst to produce an ester and water. For cyclohexyl butyrate, the starting materials are cyclohexanol and butyric acid. Under acidic conditions—often with a strong acid catalyst such as sulfuric acid—the hydroxyl group of cyclohexanol reacts with the carboxyl group of butyric acid to form the ester link that defines cyclohexyl butyrate. After the reaction, purification steps such as distillation or solvent extraction are commonly employed to isolate the cyclohexyl butyrate product from unreacted starting materials and byproducts. Commercial preparations of the compound are typically formulated to high purity standards (often greater than 98 percent) to ensure consistent sensory properties and predictable performance as a flavoring ingredient. The resulting product is a clear, colorless liquid with characteristic aromatic properties. Since flavor compounds must meet stringent quality and safety criteria, manufacturers maintain good manufacturing practice (GMP) protocols throughout production. These practices encompass controlled reaction conditions, rigorous analytical testing, and appropriate documentation to ensure traceability and compliance with regulatory expectations. Although the specific operational details can vary among producers, the general steps of esterification, purification, and quality assurance are standard in the manufacture of aroma esters like cyclohexyl butyrate.

Why It Is Used In Food

Cyclohexyl butyrate is used in foods because of its ability to contribute specific fruity and floral sensory characteristics that enhance flavor complexity. Many processed foods, especially those with fruit-forward profiles, rely on carefully balanced flavoring agents to mimic or reinforce the sensory cues consumers associate with natural ingredients. As an ester, cyclohexyl butyrate exhibits volatility and aroma characteristics that can complement other flavor components in a formulation. Food technologists select flavoring agents like cyclohexyl butyrate to achieve consistent taste and aroma profiles across batches of products. Because natural fruit flavors can vary due to seasonal or sourcing differences, synthetic or semi-synthetic esters offer a predictable and stable alternative that can be blended in precise quantities. Its inclusion helps create or enhance notes reminiscent of apple, pineapple, berry, or other fruit impressions, contributing to overall sensory appeal. The functional role of cyclohexyl butyrate is primarily sensory rather than nutritive or preservative. It does not significantly affect the nutritional composition of the foods in which it is used but serves to shape the consumer’s perception of flavor. Manufacturers often pair it with other esters and aroma compounds to create complex flavor profiles that align with specific product concepts, such as tropical fruit drinks, confectioneries, or dairy-based desserts. Its compatibility with other flavor ingredients and its stability under typical food processing conditions make it a useful component in flavor design.

Adi Example Calculation

To illustrate how an ADI concept might be applied in a hypothetical scenario, imagine a generic flavoring compound with an ADI of X mg/kg body weight per day. For a 70 kg adult, the total allowable intake would be calculated by multiplying the ADI by body weight (e.g., X mg times 70 kg). This theoretical number would represent the maximum amount that, according to toxicological evaluations and safety factors, could be consumed daily over a lifetime without appreciable risk. In the case of cyclohexyl butyrate, where expert evaluations indicate no safety concern at current intake levels and a numeric ADI is not established, such a calculation is not directly applicable. Rather, the concept emphasizes that expected food use levels lead to exposures far below thresholds of toxicological concern.

Safety And Health Research

Evaluations of flavoring agents like cyclohexyl butyrate typically focus on toxicological profiles, anticipated exposure levels from food use, and mechanistic toxicity data. Regulatory agencies and expert committees assess such compounds for potential genotoxicity, chronic toxicity, reproductive toxicity, and other endpoints relevant to human health. In the case of cyclohexyl butyrate, findings from authoritative reviews—including those summarized by JECFA—have concluded that there is no safety concern at current intake levels when used as a flavoring agent. These conclusions generally reflect structural considerations (e.g., rapid metabolic hydrolysis to constituent alcohol and acid), expected low exposure based on usage levels, and absence of evidence for adverse effects at anticipated intake. (See JECFA evaluation link below.) Although comprehensive toxicology data for every flavoring compound are not always publicly available in full detail, expert committee evaluations consider all relevant studies submitted by industry or included in scientific assessments. In these contexts, safety research emphasizes potential hazard identification and exposure estimation rather than direct health benefits or nutritional effects. For cyclohexyl butyrate, the body of evidence considered in regulatory evaluations supports its use within the scope of flavoring functions without evidence of significant hazards at intended use levels, consistent with the principles applied to similar flavoring esters.

Regulatory Status Worldwide

Regulatory frameworks for flavoring agents vary by jurisdiction, reflecting the need to balance functional utility with consumer safety. In the United States, the Food and Drug Administration (FDA) includes cyclohexyl butyrate in the list of synthetic flavoring substances and adjuvants that are permitted for use in food when employed in accordance with good manufacturing practice. This is reflected in the regulatory text of 21 CFR 172.515, which outlines conditions under which such synthetic flavoring agents may be safely used in food formulations. Inclusion in this regulatory section indicates that cyclohexyl butyrate is recognized within the parameters of existing federal regulations governing direct food additives rather than requiring a separate food additive petition or specific numeric use limits beyond general good manufacturing practice provisions. The regulation emphasizes usage at minimum quantities necessary to achieve intended sensory effects and compliance with broader safety principles. (See source below.) Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated cyclohexyl butyrate as a flavoring substance, assigning it a JECFA number 1094 and concluding that there is no safety concern at current levels of intake when used as a flavoring agent. Such evaluations are documented in JECFA summaries, which reflect expert assessment of toxicological data and anticipated exposure from flavor use. Regulatory acceptance in other jurisdictions—such as those aligned with FAO/WHO evaluations or with comparable food additive frameworks—often mirrors JECFA’s conclusions within national or regional standards. This global perspective underscores a regulatory pathway wherein cyclohexyl butyrate is recognized for its intended functional use in foods, subject to appropriate quality controls and adherence to specified regulatory provisions in each jurisdiction.

Taste And Functional Properties

Cyclohexyl butyrate is valued for its aromatic and taste-enhancing properties rather than its contribution to basic taste modalities like sweet, salty, bitter, sour, or umami on its own. As an ester, it is inherently volatile, meaning it readily transitions into the gas phase, where it can interact with olfactory receptors to contribute to perceived aroma. Sensory descriptions of cyclohexyl butyrate frequently include terms such as fruity, floral, sweet, apple-like, or pineapple-like—notes that help reinforce fruit-forward flavor profiles in foods and beverages. From a functional perspective, flavoring agents such as cyclohexyl butyrate must balance volatility with stability. Too high volatility can lead to rapid loss of aroma during processing or storage, while insufficient volatility may minimize sensory impact. Esters like cyclohexyl butyrate typically exhibit moderate volatility, allowing them to persist in aroma release yet maintain stability under standard food handling conditions. They also tend to be compatible with other common food ingredients, including sugars, acids, and lipids, which influence how flavor molecules interact in complex matrices. Although esters do not directly contribute caloric energy in significant amounts, they influence taste perception through synergistic interactions with sweet and fruity flavor notes. Their functional behavior is influenced by factors such as pH, temperature, and the presence of other aroma compounds. Cyclohexyl butyrate must be used at concentrations that are sufficient to contribute desired sensory notes without overpowering other components in the flavor profile.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a regulatory concept used by expert committees to define a level of daily exposure to a substance that is considered safe over a lifetime without appreciable risk. ADIs are typically derived from toxicological studies and include safety factors to account for uncertainties in data and differences between experimental models and humans. For many flavoring agents such as cyclohexyl butyrate, expert evaluations such as those conducted by JECFA conclude that there is no safety concern at current levels of intake from food use, which is functionally interpreted as not requiring a numeric ADI because exposures are orders of magnitude lower than levels that have raised toxicological concerns. The absence of a numeric ADI in such evaluations reflects confidence in safety at expected usage concentrations rather than a determination that an ADI is irrelevant. It is important to understand that an ADI is not a recommended intake level for consumers but rather a regulatory tool to inform safety assessments. When regulators state that a compound presents no safety concern at typical intake levels, they are indicating that everyday dietary exposure to the compound—as reflected in its use patterns—is well within safety margins established by scientific evaluation.

Comparison With Similar Additives

Esters used as flavoring agents share structural and functional characteristics that influence sensory perception. For example, ethyl butyrate is an ester with a fruity aroma commonly used to evoke pineapple or orange notes in food and beverage formulations. Compared with ethyl butyrate, cyclohexyl butyrate incorporates a larger cyclohexyl ring, which can modify volatility and odor thresholds, leading to different nuances in aroma profiles. Similarly, methyl butyrate offers a lighter fruity note with higher volatility, making it useful for top-note effects in flavor blends, whereas cyclohexyl butyrate’s profile may persist longer in complex matrices. Other related additives include butyl butyrate and hexyl acetate, each contributing distinctive fruity or floral characteristics that food formulators select based on desired flavor outcomes. These compounds are all esters that can be metabolized by the body to constituent alcohols and acids, a feature that generally supports their safety profiles when used appropriately. The choice among these agents depends on factors such as intensity, volatility, and compatibility with other flavoring components. In this context, cyclohexyl butyrate occupies a niche within flavor design where the sensory impact aligns with specific fruit-associated notes that complement other esters in blended profiles.

Common Food Applications Narrative

In the realm of food formulation, cyclohexyl butyrate finds its place in flavor systems designed to evoke fruity, sweet, and floral sensations. Products that aim to deliver a strong fruit character—whether a tropical beverage or a creamy dessert—often incorporate a tailored mix of flavoring esters to achieve the desired sensory experience. Cyclohexyl butyrate’s profile aligns well with applications where an apple, pineapple, or general fruit impression supports the product’s identity. Beverages are a common category where cyclohexyl butyrate may be incorporated. Fruit-flavored drinks, whether carbonated sodas or still juice blends, rely on carefully selected aroma compounds to create a sensory impression that aligns with consumer expectations for fruit. Confectionery items, such as candies and chewing gums, also benefit from esters that provide persistent fruity notes that complement sweetness. Dairy desserts, including flavored ice creams or frozen treats, use aroma components to reinforce fruit or dessert notes without detracting from the creamy base. Bakery products and snack foods can also incorporate fruity esters in frostings, fillings, or coatings where aroma is critical to perceived flavor quality. In each case, cyclohexyl butyrate plays a supporting role within a broader flavor formulation, contributing specific aromatic cues that enhance the complexity, depth, and overall appeal of the finished product. The use of such compounds allows food developers to replicate familiar natural flavors while maintaining consistency, stability, and consumer appeal across production runs.

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Safety & Regulations

FDA

  • Notes: Cyclohexyl butyrate is listed under 21 CFR 172.515 as a synthetic flavoring substance permitted for use in food when consistent with good manufacturing practice; specific numeric use limits are not defined in the d regulation.
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: EFSA regulatory evaluation specific to cyclohexyl butyrate was not found in the available authoritative sources.

JECFA

  • Notes: JECFA concluded no safety concern at current intake levels; a numeric ADI was not established in the accessible evaluation summary.
  • Adi Display: No safety concern at current intake levels

Sources

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