N-BENZOYLANTHRANILIC ACID

CAS: 579-93-1 FLAVORING AGENT OR ADJUVANT

N-Benzoylanthranilic acid is an aromatic organic compound used in the flavor and fragrance industry with a fruity odor and is evaluated as a flavouring agent by JECFA.

What It Is

N-Benzoylanthranilic acid is a synthetic aromatic compound identified by the Chemical Abstracts Service Registry Number 579-93-1 where it functions as a flavoring agent or adjuvant. This chemical belongs to the class of benzoic acid derivatives that contain an amide linkage between an anthranilic acid moiety and a benzoyl group. In flavor chemistry, N-Benzoylanthranilic acid is recognized by both industrial flavor authorities and international committees, including the Flavor and Extract Manufacturers Association (FEMA) which assigns it FEMA number 4078, and the Joint FAO/WHO Expert Committee on Food Additives (JECFA) which assigns it JECFA number 1552, confirming its classification as a flavouring agent. Its other systematic names include 2-(benzoylamino)benzoic acid and N-(2-carboxyphenyl)benzamide, reflecting standard IUPAC nomenclature and illustrating its chemical structure as an amidobenzoic acid derivative with a carboxylic acid functional group attached to an aromatic ring system. The compound typically appears as a white to off-white solid with a characteristic fruity aroma, which underpins its use in flavor formulations. The systematic categorization by regulatory and flavor industry bodies underscores its role as a technical flavoring ingredient rather than a nutritional or color additive, and it is evaluated specifically for its sensory contributions in foods and beverages (JECFA; FEMA).

How It Is Made

N-Benzoylanthranilic acid is synthesized through standard organic chemistry reactions that form an amide bond between anthranilic acid and benzoyl chloride or equivalent benzoyl donors under controlled conditions. A typical laboratory-scale or industrial preparation involves activating benzoic acid derivatives (such as benzoyl chloride) to react with the amino group of anthranilic acid, forming the benzoylamino linkage characteristic of this compound. The process is carried out in a solvent medium at temperatures and stoichiometries optimized to minimize side products and maximize yield. Following synthesis, the crude product is purified using crystallization and other separation techniques to achieve a solid product with high purity suitable for flavor or fragrance use, often specified at 95–99% purity for analytical or industrial applications. Because N-Benzoylanthranilic acid is not naturally abundant in food matrices, controlled synthesis ensures consistent sensory and chemical properties for its formulation in flavor blends. The manufacturing process aligns with good laboratory and manufacturing practices, including adherence to safety data sheet (SDS) guidelines for handling, since the raw materials and intermediate reagents are typically corrosive or irritant in their own right. Given the compound’s intended use in flavor applications, manufacturers also ensure compliance with relevant standards and specifications established by international bodies, though detailed proprietary synthesis routes are often confidential and optimized by individual chemical producers (ChemicalBook; Sigma-Aldrich).

Why It Is Used In Food

N-Benzoylanthranilic acid is incorporated in flavor formulations because it contributes specific aromatic characteristics that can enhance fruity or complex notes in food products. Flavoring agents such as N-Benzoylanthranilic acid are used to create, modify, or enhance the sensory profile of foods and beverages, adding depth and character beyond what can be achieved through primary food ingredients alone. The use of such compounds is grounded in sensory science, where small amounts of a chemical with a particular odor threshold can significantly influence the overall flavor perception of a product. By functioning as a flavoring adjuvant, N-Benzoylanthranilic acid interacts with other components of a flavor blend to achieve a balanced and desirable profile that meets consumer expectations for taste and aroma. This is common in complex flavor systems such as fruit-flavored products, confectioneries, beverages, and other prepared foods where layered sensory effects are desired. Its inclusion is carefully calibrated based on its odor impact and relative potency, ensuring it enhances flavor without overwhelming other key aromatic notes. The technical purpose of such flavoring substances is to support product consistency, appeal, and differentiation in competitive food markets, always within regulatory frameworks governing the use of flavoring agents in food. The JECFA and FEMA evaluations focus on both the sensory function and safety profile of N-Benzoylanthranilic acid under anticipated conditions of use, reflecting its role as a specialized flavor additive rather than a nutritive component (JECFA; FEMA).

Adi Example Calculation

Because N-Benzoylanthranilic acid does not have a specific numeric ADI assigned by JECFA or other regulatory bodies in the available evaluations, an illustrative calculation with a hypothetical numeric ADI cannot be provided. In typical ADI example calculations for substances with assigned numeric ADIs, one would multiply a hypothetical mg per kg body weight ADI by an example body weight (for example 60 kg for an average adult) to estimate a lifetime daily intake threshold in milligrams. For example, a hypothetical ADI of "X mg per kg body weight" times "Y kg body weight" yields "X * Y mg per day" as a lifetime exposure estimate. Because a defined numeric ADI is not established for N-Benzoylanthranilic acid in the available regulatory evaluations, and the JECFA evaluation focused on "no safety concern at current levels of intake," a numeric example cannot be confidently constructed without speculative assumptions.

Safety And Health Research

Evaluations by authoritative bodies have focused on the safety profile of N-Benzoylanthranilic acid in the context of its intended use as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) conducted a formal evaluation and concluded that there is no safety concern at estimated current intake levels from flavor use, a common benchmark for flavoring substances that are used at low concentrations in food products (JECFA). These evaluations consider toxicological endpoints relevant to chronic exposure, including acute toxicity, potential irritancy, and general systemic effects observed in animal studies, although explicit toxicological metrics such as LD50 values or detailed mechanistic data may not be extensively published in regulatory monographs. Because flavoring agents are typically present in foods at trace levels, safety assessments prioritize ensuring that typical exposures remain far below thresholds that could pose health risks. In addition to formal JECFA evaluations, industrial ingredient libraries such as those maintained by FEMA reflect considerations of sensory use and safety information, reinforcing the technical context in which this compound is applied (FEMA). Research published in scientific literature often explores structural analogs or derivatives for pharmacological or biochemical properties, but such studies do not directly translate to food safety assessment without specific exposure data. Overall, safety research for N-Benzoylanthranilic acid emphasizes its low-level use in food flavorings and the absence of identified hazards at those use levels, consistent with regulatory evaluations.

Regulatory Status Worldwide

The regulatory status of N-Benzoylanthranilic acid varies by jurisdiction and is framed around its evaluation as a flavoring agent rather than a nutritive additive. In the United States, this compound appears in the FDA "Substances Added to Food" inventory with identification and associated FEMA number 4078, indicating its recognition as a flavoring ingredient in that context (FDA Substances Added to Food). However, the FDA does not list a specific Code of Federal Regulations (CFR) section that individually authorizes this compound, and therefore formal "approved" labeling in CFR sections cannot be ascribed without direct citation; accordingly, the FDA approval status is set to null pending specific regulatory text verification. Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated N-Benzoylanthranilic acid and assigned it JECFA number 1552, concluding that “no safety concern at current levels of intake when used as a flavouring agent” based on its evaluation documents, though this evaluation may carry conditional context regarding intake data and is not an explicit numeric acceptable daily intake (ADI) (JECFA). In the European Union and other regions, flavoring agents are typically regulated as part of broader flavoring substances frameworks, where individual compounds are assessed for safety and allowed in food under specified conditions; specific E-number assignment for this compound is not established in EU flavoring regulations, and as such that field remains empty. Across jurisdictions, flavor regulatory authorities emphasize use levels consistent with good manufacturing practices and safety evaluations rather than enumerating broad permitted uses, reinforcing the technical specificity of evaluation rather than a universal numeric authorization.

Taste And Functional Properties

N-Benzoylanthranilic acid possesses a fruity aromatic profile that can contribute characteristic sensory notes to flavor formulations. Compounds with this type of aromatic structure often exhibit a balance of sweet and fruity odor nuances, which can complement or enhance other flavoring ingredients in a blend. The sensory impact of N-Benzoylanthranilic acid is dependent on its concentration relative to its odor threshold, which is typically low for effective flavor compounds, making even small amounts significant in the overall flavor architecture. Functionally, the compound is a solid at room temperature, moderately lipophilic due to its aromatic structure, and sparingly soluble in water but more soluble in organic solvents, a behavior consistent with many aromatic flavoring agents. Its stability across typical food processing conditions, such as moderate heat or pH changes, supports its utility in a range of applications where sensory attributes must withstand formulation and storage processes. Because it is used at low concentrations for sensory effects, its contribution to overall matrix properties such as texture or viscosity is negligible, and its main functional role remains within the olfactory and taste dimensions of the consumer experience. These characteristics align with the industry practice of using specialized flavoring agents judiciously to achieve targeted sensory outcomes while maintaining product quality and consistency (ChemicalBook; Sigma-Aldrich).

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory concept that represents an estimate of the amount of a substance that can be consumed every day over a lifetime without appreciable health risk, based on available toxicological data and conservative safety factors. For many flavoring agents, including N-Benzoylanthranilic acid, formal ADI values are not always established as fixed numeric benchmarks, especially when exposure from use in food is low and safety evaluations conclude no concern at estimated intake levels. In the case of N-Benzoylanthranilic acid, the JECFA evaluation did not assign a specific numeric ADI but concluded that there was no safety concern at current levels of intake when used as a flavoring agent; this reflects a context where anticipated exposures derived from typical use are considered acceptable within safety margins. It is important to emphasize that an ADI is not a recommended consumption level or a target to achieve, but rather a conservative upper bound for safety planning and regulatory assessment. When numeric ADIs are established, they provide a reference for risk assessors and manufacturers to compare estimated dietary exposures against accepted safety thresholds, ensuring that use levels are consistent with public health protection. In practice, for flavoring agents, adherence to good manufacturing practices and minimal effective concentrations helps ensure that daily exposure remains well below any levels of toxicological concern.

Comparison With Similar Additives

N-Benzoylanthranilic acid shares its functional role as a flavoring agent with many other aromatic compounds used to enhance food sensory profiles. For example, ethyl maltol, another flavoring agent, is widely used for its sweet and caramel-like aroma properties and is evaluated under flavor additive frameworks with established safety assessments. Similarly, benzyl acetate is used for fruity aromatic notes in flavor formulations and is also evaluated by JECFA and FEMA for safety at low exposure levels. While N-Benzoylanthranilic acid contributes a distinctive aromatic profile that can support fruit-like or complex notes, ethyl maltol tends toward sweet and sugary nuances and benzyl acetate toward pear or apple-like aromas, illustrating how different flavoring agents are selected based on their sensory characteristics rather than a single common profile. Each of these compounds undergoes safety evaluations appropriate to their use levels; the absence of a numeric ADI in contexts where exposure is low and deemed safe reflects a regulatory approach similar to that for other specialized flavor additives. Comparisons among flavoring agents underscore the importance of sensory function, sensory thresholds, and regulatory evaluations that align with anticipated dietary exposure patterns rather than broad generalized classifications.

Common Food Applications Narrative

N-Benzoylanthranilic acid finds application in a variety of flavored products where nuanced aromatic enhancement is desired. In beverage formulations, especially fruit-flavored drinks or sparkling waters, specialized aromatic compounds like N-Benzoylanthranilic acid can help emphasize or round out specific fruity notes that might otherwise be muted. In confectionery, such flavoring agents are useful for adding distinctive odor facets to gummies, hard candies, or chewing gums, where consumer expectations for complex and memorable flavor profiles are high. Bakery products and ready-to-eat snacks also sometimes incorporate such compounds within proprietary flavor blends to differentiate products in a crowded marketplace, enhancing the perceived intensity or authenticity of flavors such as citrus or berry under specific processing conditions. Dairy-based treats like flavored yogurts or ice creams can also benefit from the subtle sensory contributions provided by this compound, where it supports the primary flavoring agents to achieve a balanced profile. Alcoholic beverages with fruity character or low-alcohol refreshers may similarly employ it in controlled amounts to modulate aroma impact and complement natural or artificial flavor sources. In all these contexts, the use of N-Benzoylanthranilic acid is calibrated to achieve consistent sensory results that meet consumer preferences for taste quality, with its fruity aromatic tendencies providing a complementary sensory dimension. The application across these food categories reflects broader industry practices for flavoring agents, which prioritize controlled sensory outcomes alongside regulatory compliance and quality assurance (ChemicalBook; Sigma-Aldrich).

Safety & Regulations

FDA

  • Notes: The FDA does not provide a specific CFR section for this compound within flavoring agents, and direct authorization text was not found in the reviewed sources.

EFSA

  • Notes: No specific EFSA numeric ADI or E-number assignment was identified in the available sources.

JECFA

  • Year: 2008
  • Notes: JECFA concluded no safety concern at current intake levels for use as a flavouring agent but did not assign a numeric ADI.

Sources

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