CINNAMYL ANTHRANILATE--PROHIBITED

CAS: 87-29-6 FLAVORING AGENT OR ADJUVANT

Cinnamyl anthranilate is a synthetic flavoring agent formerly used in foods; it has been prohibited from use in food by the U.S. Food and Drug Administration and is not permitted as a food additive.

What It Is

Cinnamyl anthranilate is a synthetic chemical compound classified as a flavoring agent or adjuvant with CAS number 87-29-6. It is an ester formed from cinnamyl alcohol and anthranilic acid. Historically used to impart a fruity or balsamic taste profile in certain food formulations, it belongs to a class of aromatic esters once employed for their sensory properties in flavor systems. Its structure integrates a phenylpropene moiety with an anthranilic acid ester, giving rise to both olfactory and taste characteristics valued in flavor science. Despite its prior use, regulatory actions have led to the prohibition of cinnamyl anthranilate in food applications in many jurisdictions, signaling that its safety profile in foods does not meet modern regulatory standards. The compound also appears in fragrance applications, where its aromatic properties are of interest in products such as perfumes and scented preparations. The chemical is typically a solid at ambient conditions, exhibiting low water solubility and greater solubility in organic solvents. Its other names capture the chemical identity, such as cinnamyl ester of anthranilic acid and cinnamyl o-aminobenzoate, reflecting different naming conventions in chemical registries and literature. This overview introduces cinnamyl anthranilate as a compound of regulatory significance with a specific contextual history in flavoring science.

How It Is Made

The synthesis of cinnamyl anthranilate generally involves classical esterification chemistry. In this process, anthranilic acid, which contains a carboxylic acid functional group, reacts with cinnamyl alcohol, an allylic alcohol with an aromatic substitution, under dehydrating conditions. The esterification reaction often uses an acid catalyst to facilitate the formation of the ester bond, yielding cinnamyl anthranilate alongside water. This type of reaction is a fundamental transformation in organic chemistry and forms the basis of manufacturing for various esters used as flavor or fragrance compounds. In industrial or laboratory environments, careful control of reaction conditions such as temperature, catalysts, and reagent purity is important to obtain a product suitable for analytical or formulation purposes. Given its regulatory status, new production for food use has ceased, but the basic synthetic route remains relevant in research contexts where the compound is studied for chemical properties or mechanisms of biological interaction. The final product typically appears as a solid material with a characteristic odor and must be isolated and purified to remove unreacted starting materials or side products. Historically, analytical methods like chromatography have been used to confirm the identity and purity of cinnamyl anthranilate during or after synthesis. While the production pathway is standard for esters, the regulated and prohibited status of this compound in food underscores that its manufacture is largely limited to non-food scientific applications today.

Why It Is Used In Food

Cinnamyl anthranilate was incorporated in food formulations primarily for its sensory-modifying properties. As a flavoring agent, it was valued for providing fruity, balsamic, or aromatic notes, which could enhance or complement other flavor components in a complex formulation. Flavor chemists often seek compounds that deliver distinctive sensory cues at low concentrations, and cinnamyl anthranilate once fit that profile in experimental or applied flavor design. Its application in certain beverages, confectionery, or baked goods was aimed at broadening the palette of available flavor impressions without relying solely on natural extracts. However, the use of cinnamyl anthranilate in food was reevaluated as toxicological evidence emerged regarding its safety in long-term exposure studies. Regulatory agencies such as the U.S. Food and Drug Administration concluded that the risks associated with its inclusion in food were not acceptable, leading to its prohibition. Consequently, the compound is no longer used in food production, and modern flavor systems rely on other chemicals or natural extracts with well-documented safety profiles. The historical context underscores how the functional rationale for an additive can evolve alongside advancements in toxicological science and regulatory frameworks.

Adi Example Calculation

An illustrative example of how acceptable daily intake might be calculated is as follows: if an additive were assigned an ADI of X mg per kg of body weight per day by a regulatory body, a hypothetical calculation for a person weighing 70 kg would multiply X by 70 to estimate a lifetime daily intake that stays within the ADI. For example, if X were 0.1 milligrams per kilogram of body weight per day, then 0.1 mg/kg times 70 kg equals 7 mg per day as a reference point. It is important to emphasize that this example is generic and does not apply to cinnamyl anthranilate, as no ADI has been established for this compound for food use. Instead, the example demonstrates the general principle of how ADI values are applied in risk assessment and regulatory contexts, without implying a safe intake level for a specific prohibited additive.

Safety And Health Research

Scientific and regulatory evaluations of cinnamyl anthranilate have focused on its toxicological profile, particularly in the context of long-term exposure. Animal studies, including chronic bioassays in rodents, contributed to the evidence base that informed regulatory decisions. Such studies examined endpoints such as tumor incidence in rodent models, with certain bioassays indicating species-specific increases in liver tumors under test conditions. These findings, along with other toxicological data, influenced risk assessments by agencies such as the U.S. Food and Drug Administration and the Joint FAO/WHO Expert Committee on Food Additives. Based on these assessments, regulators concluded that cinnamyl anthranilate was not appropriate for use in food due to safety concerns identified in experimental settings. It is important to note that species differences in metabolism and response observed in these studies may not directly translate to humans, yet regulatory frameworks adopt precautionary approaches when evidence suggests potential adverse outcomes. The body of research reflects an emphasis on standard toxicological endpoints evaluated in the context of additive safety, including chronic toxicity and carcinogenicity studies, rather than direct observations in humans. Consequently, the safety research underpinning regulatory decisions is rooted in established scientific methodologies applied to food additive evaluation.

Regulatory Status Worldwide

Regulatory authorities have evaluated cinnamyl anthranilate and determined that it is not permitted as a food additive. In the United States, the Food and Drug Administration codified this prohibition in the Code of Federal Regulations under 21 CFR 189.113, which establishes that foods containing added cinnamyl anthranilate are deemed adulterated. This action followed regulatory assessment and reflects a policy that the compound should not be used in food products. Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) reviewed cinnamyl anthranilate and concluded that it should not be used as a food additive, indicating a global consensus on its unsuitability for food applications. Because of these determinations, food safety authorities in many regions, including jurisdictions that follow Codex recommendations, have not authorized cinnamyl anthranilate for use in food. As a result, its regulatory status worldwide is one of prohibition in food contexts, and manufacturers are expected to comply with these provisions in formulating food products.

Taste And Functional Properties

Cinnamyl anthranilate, as an ester of anthranilic acid and cinnamyl alcohol, exhibits olfactory and taste characteristics that were once described as fruity or balsamic. These sensory attributes made it of interest to flavor chemists seeking to replicate or enhance specific flavor notes in complex food matrices. However, esters such as cinnamyl anthranilate often present variability in sensory impact depending on concentration and the surrounding formulation environment, including the presence of other flavor compounds, pH levels, and processing conditions. Solubility considerations also play a role; cinnamyl anthranilate tends to be poorly soluble in water but more soluble in organic solvents or lipid phases. This limited aqueous solubility influences how it interacts with foods or beverages, especially those with higher water content. Additionally, compounds of this type can be sensitive to oxidation or hydrolysis over time, which affects both flavor integrity and stability. In practical terms, its functional profile reflects the dual nature of many aromatic esters: a combination of sensory appeal and specific physicochemical constraints that must be balanced in formulation. While these characteristics historically informed its use, contemporary regulatory context precludes its application in food, redirecting sensory formulation work toward alternative substances with established safety records.

Acceptable Daily Intake Explained

Acceptable daily intake (ADI) is a concept used by regulatory and scientific bodies to express an estimate of the amount of a substance that can be ingested daily over a lifetime without appreciable health risk. ADIs are typically established based on toxicological data, often from animal studies, with safety factors applied to account for uncertainty and interspecies differences. For cinnamyl anthranilate, evaluations by expert committees concluded that it should not be used as a food additive, and therefore no numerical ADI was established for food use. This reflects a regulatory determination that the compound does not meet safety criteria for food additive applications, rather than a quantitative assessment of safe exposure. In general, when an ADI is defined for an additive, it serves as a benchmark for regulatory limits and risk management decisions. Such values are derived by identifying a no-observed-adverse-effect level (NOAEL) in toxicological studies and applying uncertainty factors to protect public health. In the case of cinnamyl anthranilate, the absence of an authorized ADI underscores that its use in food is precluded on safety grounds.

Comparison With Similar Additives

Cinnamyl anthranilate can be compared with other aromatic ester flavoring agents, such as methyl anthranilate and ethyl anthranilate. Methyl anthranilate, for instance, is an ester used in flavor applications with documented sensory properties, often described as grape-like, and is authorized for food use in certain jurisdictions due to a favorable safety assessment. In contrast, cinnamyl anthranilate’s regulatory history reflects prohibition for food use, highlighting a key difference in how structurally related compounds are managed based on toxicological evidence. Another example is ethyl butyrate, an ester with fruity flavor notes that is widely accepted in food flavoring and has clear regulatory allowances supported by defined safety evaluations. These comparisons illustrate that while many ester-based compounds serve similar functional roles in flavor systems, each additive’s regulatory acceptability depends on a comprehensive assessment of safety data and risk management decisions by competent authorities. The divergence in regulatory status between these substances underscores the importance of evidence-based evaluation rather than assumptions based solely on structural similarity.

Common Food Applications Narrative

Historically, cinnamyl anthranilate found use in a limited range of flavor applications where its distinctive sensory properties were considered desirable. Flavor professionals experimented with this compound to introduce nuanced fruity or balsamic notes, particularly in beverage, confectionery, or baked goods formulations. In the landscape of flavor chemistry, compounds with unique aromatic and taste profiles are selected to broaden the palette of sensory impressions available to food developers. In such experimental contexts, cinnamyl anthranilate’s contribution would have been as a minor component alongside other flavor ingredients, offering complementary nuances rather than serving as a dominant taste source. The incorporation of flavoring agents into food formulations involves careful calibration of sensory impact relative to product type and consumer expectations. While cinnamyl anthranilate’s sensory attributes once supported its inclusion in such flavor systems, it is important to emphasize that current food products no longer contain this compound due to regulatory determinations that it is not suitable for food use. Modern practice in food formulation relies on approved flavoring agents that have undergone robust safety evaluations, ensuring that consumer products meet contemporary standards for both sensory quality and health protection.

Safety & Regulations

FDA

  • Notes: Use in food is prohibited; presence renders food adulterated per CFR.
  • Regulation: 21 CFR 189.113

EFSA

  • Notes: No EFSA authorization found; not included in EU flavoring lists.

JECFA

  • Notes: JECFA evaluation indicates the compound should not be used as a food additive.

Sources

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