CYCLOHEXYL ANTHRANILATE

CAS: 7779-16-0 FLAVORING AGENT OR ADJUVANT

**Cyclohexyl anthranilate** is a synthetic flavoring ingredient used to impart or modify taste in food and beverage formulations. It is identified by CAS number 7779-16-0 and functions as a flavoring agent or adjuvant, providing a fruit-like sensory character in formulations. Regulatory listings include 21 CFR 172.515 in the United States, indicating permissive conditions of use as a synthetic flavoring substance and adjuvant. The compound has been evaluated by international safety bodies and appears on flavor ingredient lists with assigned FEMA and JECFA identifiers. Its use in foods is generally in very low concentrations consistent with good manufacturing practice. This summary is intended to provide a clear factual snapshot of this flavoring ingredient’s identity, regulatory context, and typical application.

What It Is

Cyclohexyl anthranilate is a synthetic chemical used as a flavoring agent in food and beverage products. It is recognized by its Chemical Abstracts Service registry number 7779-16-0 and is generally classified among synthetic flavoring substances and adjuvants permitted for use under specific regulatory frameworks. As a compound, it belongs to the class of organic esters derived from anthranilic acid and cyclohexanol, producing a structure that carries both an aromatic ring and an ester linkage. This structural profile contributes to its organoleptic characteristics, including a fruity or citrus-like odor and taste profile when used in trace amounts in flavor formulations. Cyclohexyl anthranilate is also referred to by other systematic names that reflect its chemical structure, such as a benzoic acid derivative with an anthranilate moiety esterified to a cyclohexyl alcohol component. Within the context of food flavoring, its primary technical function is to enhance or modify taste and aroma in complex flavor blends. The compound’s role as a flavoring agent has been documented within regulatory inventories and flavor industry assessments, which typically categorize it under flavor and extract ingredient libraries with assigned FEMA and JECFA identifiers. These references serve as cross‑validation of the ingredient’s identity and its considered safety in use at low levels under prescribed conditions of good manufacturing practice. Exposure from food use is generally low due to its potent sensory properties, meaning that only minimal quantities are incorporated to achieve the desired flavor effect. The chemical’s identity, classification, and regulatory labeling requirements are important for formulators, regulatory specialists, and quality assurance teams working with flavor systems in food and beverage development.

How It Is Made

Cyclohexyl anthranilate can be produced through chemical synthesis involving the esterification of anthranilic acid or its derivatives with cyclohexanol. In such a reaction, an activating agent or dehydrating reagent facilitates the formation of the ester bond between the carboxylic acid group of the anthranilic acid and the hydroxyl group of cyclohexanol. Industrial or laboratory production of this compound generally adheres to standard organic chemistry practices for ester synthesis. Reaction conditions, catalysts, and purification steps are selected to yield a product of sufficient purity for its intended technical use, especially if the target application is in food flavoring contexts. High purity is essential for flavor applications to avoid off‑notes and to comply with applicable regulatory standards. In practice, the final product often undergoes distillation, filtration, or chromatographic purification to meet established specifications. The availability of cyclohexyl anthranilate as a commercial flavoring ingredient also depends on adherence to regulatory inventories and specifications. For instance, recognized flavor ingredient libraries and flavor industry assessments maintain records of this compound’s identity and use conditions. Manufacturers intending to include cyclohexyl anthranilate in food products must ensure compliance with relevant regulations, such as using it in the minimum amount necessary to achieve the intended sensory effect, as described in regulatory frameworks like 21 CFR 172.515 in the United States. These production and regulatory compliance considerations help ensure that the ingredient meets safety and quality expectations in food applications. While specific proprietary production processes may vary by supplier, the underlying esterification route remains the primary method to synthesize cyclohexyl anthranilate in commercial and research contexts.

Why It Is Used In Food

Cyclohexyl anthranilate is used in food primarily for its flavor‑modifying properties. As a flavoring agent or adjuvant, it contributes distinct sensory characteristics such as a fruity or citrus‑like aroma and taste when incorporated into flavor blends. Food scientists and flavor formulators select this compound to achieve specific flavor profiles that enhance the palatability or complexity of products. Its use is typically in trace amounts because flavor compounds often exhibit strong sensory effects at very low concentrations. The objective in using cyclohexyl anthranilate is to leverage its sensory attributes to complement or round out other components in a flavor system, thereby creating a more balanced and appealing overall taste experience. This role is particularly relevant in complex formulations such as beverages, confectionery, or bakery products where nuanced flavor contributions can affect consumer perception. In addition to direct flavor contribution, cyclohexyl anthranilate may act synergistically with other flavoring substances to achieve targeted sensory outcomes. Flavor systems often combine multiple compounds that together mimic natural flavors or create novel taste impressions. The inclusion of cyclohexyl anthranilate can help adjust floral, fruity, or sweet sensory dimensions in these blends. Flavor formulators rely on ingredient libraries and sensory evaluation data to determine optimal inclusion levels that achieve desired effects without overpowering the flavor profile. Because of its potency and specific sensory characteristics, careful dose‑response assessment is part of the formulation process to ensure that the ingredient enhances rather than detracts from the product’s intended flavor. Regulatory frameworks emphasize that such ingredients be used in good manufacturing practice amounts, meaning just enough to achieve the intended technical effect without unnecessary excess. This approach aligns with principles of ingredient safety and quality in food development.

Adi Example Calculation

To illustrate how Acceptable Daily Intake considerations are applied in practice, consider a hypothetical individual weighing 70 kilograms. If a flavoring compound had a defined numeric ADI of X milligrams per kilogram body weight per day, one would multiply that ADI by the body weight to estimate the daily amount that could be consumed without appreciable health risk. For example, if an ADI were established at 10 milligrams per kilogram body weight per day, a 70‑kilogram person could consume up to 700 milligrams per day. In the case of cyclohexyl anthranilate, regulatory evaluations have concluded qualitatively that typical use levels pose no safety concern without establishing a numeric ADI. As such, rather than applying a numeric multiplier, the focus is on ensuring that use in formulations aligns with good manufacturing practice and that exposure remains low relative to any levels at which adverse effects were not observed in safety studies. This hypothetical calculation illustrates general ADI application but does not assign a specific numeric threshold to cyclohexyl anthranilate because regulatory evaluations did not specify one.

Safety And Health Research

Safety assessments for flavoring agents typically consider potential effects based on exposure levels associated with intended use in food products. Cyclohexyl anthranilate has been evaluated by expert bodies that examine toxicological data, exposure assessments, and relevant studies to determine whether typical use levels raise safety concerns. For example, international evaluations by the Joint FAO/WHO Expert Committee on Food Additives concluded that there was no safety concern at current levels of intake when used as a flavoring agent, based on available data and the context of typical use. Such evaluations consider factors like estimated daily intake, metabolic fate, and toxicological endpoints to determine whether typical exposure poses any identifiable risk. These assessments provide a basis for regulatory inclusion in inventories that permit use under defined conditions. Laboratory data relevant to flavor compounds often include information on acute toxicity, genotoxicity, and other endpoints that help regulators characterize potential hazards. For many synthetic flavoring agents, including cyclohexyl anthranilate, comprehensive toxicological data may be limited, and expert committees rely on a combination of available studies, structural analogy to other compounds, and exposure considerations to draw conclusions. Flavor industry resources and regulatory filings also consolidate safety information to support the documented evaluations. In general, the safety profiles of flavoring agents used at low concentrations in food reflect both their low exposure and the lack of evidence for significant adverse effects at these levels. A key component of safety assessments is consideration of how a compound is metabolized and eliminated in the body. Many ester‑based flavor compounds are hydrolyzed to constituent acids and alcohols, which are further metabolized via common biochemical pathways. The metabolic handling of such compounds at low dietary exposure levels contributes to the conclusion that typical use does not pose significant toxicological concerns. Regulatory bodies also emphasize good manufacturing practice, meaning that ingredients should be used only in amounts necessary to achieve the intended sensory effect, which inherently limits exposure. Overall, safety evaluations for cyclohexyl anthranilate focus on ensuring that typical use scenarios in food and beverage products do not lead to exposures associated with potentially adverse effects, consistent with the qualitative conclusions of international expert committees.

Regulatory Status Worldwide

Cyclohexyl anthranilate is listed in regulatory inventories that track flavoring substances permitted for use under specified conditions. In the United States, it appears under the category of synthetic flavoring substances and adjuvants in 21 CFR 172.515, which sets conditions that allow the safe use of such substances when used in the minimum quantity required to achieve their intended effect and in accordance with principles of good manufacturing practice. This regulatory section provides a permissive framework that encompasses many synthetic flavoring agents, including cyclohexyl anthranilate, as identified by its CAS number and name in the inventory. The regulatory allowance does not include specific quantitative use limits for each substance but rather requires adherence to good manufacturing practice in formulation and use. The listing in this part of the Code of Federal Regulations confirms that the ingredient’s use is subject to regulatory oversight in the United States under food additive provisions. The FDA’s Substances Added to Food Inventory also lists cyclohexyl anthranilate with its technical effect and regulatory reference, reinforcing its documented role and conditions of use. Internationally, flavor ingredient libraries maintained by industry organizations such as the Flavor and Extract Manufacturers Association assign identifiers like FEMA number 2350 to this compound, indicating its evaluation and listing within flavor industry contexts. These industry lists often collate safety assessment information from authoritative sources and provide cross‑references to regulatory frameworks. At the global level, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated cyclohexyl anthranilate under JECFA number 1541 and concluded that there was no safety concern at current levels of intake when used as a flavoring agent, as indicated in its summary evaluations. Such international assessments contribute to a broader understanding of safety and support regulatory decisions in various jurisdictions. While specific numeric Acceptable Daily Intake values are not established, the qualitative conclusion of no safety concern at typical use levels informs regulatory acceptance and ongoing use in flavor applications. Regulatory status in other regions, such as the European Union, may also reference international evaluations and local assessments to determine permissible use conditions, reflecting a global landscape where food additive safety is assessed through multiple authoritative channels.

Taste And Functional Properties

Cyclohexyl anthranilate is characterized by sensory properties that include fruity, floral, and citrus‑like notes when used in appropriate concentrations within flavor blends. The compound’s organoleptic profile makes it valuable in formulations where these sensory cues contribute to the overall flavor experience. In sensory evaluation terms, such compounds are often described based on descriptors like citrus, berry, or soft fruity impressions, which help flavorists communicate and select ingredients that fit target profiles. Its effect on taste perception is primarily through olfactory pathways, as many flavor compounds act via aroma receptors as well as taste receptors, contributing to the integrated sensory perception of flavor. From a functional perspective, cyclohexyl anthranilate has physical and chemical properties typical of aromatic esters. It is relatively low in water solubility but can be readily incorporated into flavor oil systems and compatible with ethanol or other carriers used in flavor formulations. Its stability under typical processing conditions—such as heat encountered in baked goods or thermal processing of beverages—is an important consideration. While detailed stability data may vary by formulation and processing environment, compounds in this class are generally selected for their ability to withstand formulation and processing conditions without significant degradation that would alter the intended flavor impact. Functional considerations also include interactions with other flavor compounds; the presence of multiple components in a flavor blend can influence volatility, perception thresholds, and persistence of sensory effects. Because sensory impact occurs at low concentrations, cyclohexyl anthranilate and similar flavoring agents are evaluated for their effective sensory thresholds, meaning the minimum level at which users perceive a consistent sensory effect. Flavorists balance these thresholds against other ingredients to achieve a seamless sensory experience. In practical flavor design, cyclohexyl anthranilate’s role is never in isolation but as part of a carefully constructed profile that satisfies product objectives while complying with relevant regulatory and safety guidelines.

Acceptable Daily Intake Explained

The concept of an Acceptable Daily Intake (ADI) is used by regulatory and expert bodies to express the amount of a substance that can be consumed daily over a lifetime without appreciable health risk, based on toxicological data and safety factors. For many flavoring agents, including cyclohexyl anthranilate, expert evaluations may conclude qualitatively that there is no safety concern at current levels of intake rather than establishing a specific numeric ADI. In such cases, regulatory and safety assessments consider typical exposure from intended uses in food products and conclude that these exposures are well below levels associated with any identified adverse effects. This qualitative conclusion effectively serves the same regulatory purpose as a numeric ADI, indicating that typical exposure is considered safe under prescribed conditions of good manufacturing practice. For consumers and stakeholders, understanding ADI involves recognizing that it is not a recommended level of consumption but rather a safety threshold derived from toxicological data and uncertainty factors. When an expert body states that a flavoring agent presents no safety concern at current intake levels, it implies that the compound’s typical use in food does not approach levels that would raise safety flags in formal risk assessments. This context underscores why compounds like cyclohexyl anthranilate can be included in regulatory food additive inventories without specific numeric ADI values; the qualitative safety judgement reflects confidence that exposure under intended use conditions is sufficiently low and not associated with health risk.

Comparison With Similar Additives

Flavoring agents used in food products often share similar structural or sensory properties. For example, methyl anthranilate and ethyl anthranilate are related ester compounds that also contribute fruity or floral sensory notes and are used in flavor formulations. Compared with cyclohexyl anthranilate, methyl and ethyl anthranilate have smaller alkyl groups, which influence their volatility and sensory thresholds. These compounds are often selected for specific applications where their volatility and aroma profiles match product objectives. Another comparable additive is allyl anthranilate, which also belongs to the anthranilate class but differs in its alkyl substituent. The specific sensory and physicochemical properties of each compound guide formulators in choosing the most appropriate ingredient for a given flavor profile. When comparing across similar additives, formulators consider factors such as odor intensity, solubility in different carriers, and compatibility with other flavor components. Cyclohexyl anthranilate’s distinctive sensory impressions may complement or contrast with the attributes of other anthranilate derivatives. These comparisons help explain why a particular compound is chosen for certain flavor systems rather than others. The relative sensory impact, stability, and regulatory status of each additive inform decisions in product development, ensuring that selected flavoring agents achieve desired outcomes while complying with safety and quality standards.

Common Food Applications Narrative

Food and beverage products incorporate a wide array of flavoring agents to achieve desired sensory experiences that appeal to consumers. Cyclohexyl anthranilate is one such ingredient that may be included in carefully controlled trace amounts to contribute fruity, floral, or citrus‑like sensory cues in complex flavor systems. In product categories such as soft drinks, fruit‑flavored beverages, confectionery, and bakery items, flavor formulators often build layered profiles by combining multiple compounds, each adding specific sensory notes. Cyclohexyl anthranilate’s contribution lies in its ability to support and enhance fruity impressions without dominating the overall flavor profile when deployed judiciously in line with good manufacturing practice. Because flavor development is both art and science, such ingredients are selected based on sensory evaluation studies and compatibility with other components in the formulation. Product development teams use ingredients like cyclohexyl anthranilate as part of a broader palette of flavoring substances. For example, in fruit‑flavored beverages, it may be used alongside other esters and natural extracts to create a balanced flavor characteristic that aligns with consumer expectations for freshness and complexity. In confectionery, where sweetness and aroma interplay significantly in taste perception, fruity‑note contributors help round out profiles and combat flatness or one‑dimensional sweetness. Similarly, in bakery products or cereals with added flavor, such compounds can enhance the perception of fruit or floral notes without adding substantive caloric or ingredient mass. These applications underscore the role of cyclohexyl anthranilate as a supporting sensory ingredient rather than a principal nutritional component. The use of flavoring agents in food products is governed by specific regulatory frameworks that emphasize safety and appropriate application levels. Flavorists and regulatory professionals work together to ensure that each ingredient, including cyclohexyl anthranilate, is used in ways consistent with safety evaluations and regulatory permissions. Consumers rarely encounter these substances listed prominently on packaging because flavoring agents often fall under general flavor or natural/artificial flavor declarations. Nonetheless, knowledge of their usage helps explain how nuanced sensory profiles in modern food products are achieved through a combination of ingredients chosen for targeted sensory contributions.

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Safety & Regulations

FDA

  • Notes: Listed under synthetic flavoring substances and adjuvants allowing use under conditions of good manufacturing practice without specific numeric approval status.
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: EFSA evaluation status reported in industry reference lists but no direct linking authoritative numeric opinion was found.

JECFA

  • Notes: JECFA concluded no safety concern at current intake levels without a numeric ADI, based on the evaluation report.

Sources

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