ALLYL ANTHRANILATE

CAS: 7493-63-2 FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT

Allyl anthranilate is a synthetic flavor enhancer and flavoring agent permitted for use under the US FDA food additive regulations and evaluated by international expert committees as a flavoring substance.

What It Is

Allyl anthranilate is a synthetic organic compound used primarily in the food industry as a flavor enhancer and flavoring agent. It is identified chemically by the CAS Number 7493-63-2 and referred to in flavor science and regulatory literature by multiple synonyms including allyl o-aminobenzoate and anthranilic acid allyl ester. As a member of the benzoate ester family, this substance contributes to flavor profiles in food and beverage applications where its olfactory characteristics are desirable. It is recognized in regulatory contexts such as the United States Code of Federal Regulations under section 172.515, which lists it among permitted synthetic flavoring substances and adjuvants. Its use is consistent with sound manufacturing practice in foods to impart or enhance specific sensory characteristics. The chemical structure of allyl anthranilate includes an allyl ester attached to an aminobenzoic acid backbone, lending the compound its functional properties in aroma formulation. In industry parlance, it is also referenced by a FEMA number—2020—indicating evaluation within the Flavor and Extract Manufacturers Association programs. While physical chemical databases record its fundamental identifiers and properties such as melting point and density, the regulatory context focuses on its role in flavoring food products and its safe use under defined conditions. Because it functions specifically to enhance or provide flavor, allyl anthranilate is classified under a subset of food additives defined for flavor purposes, distinguished from nutritional additives, preservatives, or coloring agents. Understanding these classifications helps formulators and regulatory professionals place it appropriately within ingredient inventories and label declarations.

How It Is Made

The production of allyl anthranilate typically involves esterification chemistry where an allyl alcohol moiety is reacted with an anthranilic acid derivative. In general, esterification to form allyl esters can be achieved through direct condensation of acids and alcohols in the presence of acid catalysts, or via transesterification processes where an ester precursor is modified to introduce the allyl group. Industrial flavor ingredient manufacturers employ controlled organic synthesis routes under conditions that aim to achieve high purity while minimizing byproducts. In commercial settings, manufacturing practices also integrate purification stages such as distillation to separate the target ester from reaction mixtures. Quality control measures assess parameters like identity, purity, and absence of undesirable contaminants to ensure compliance with food-grade specifications. Although precise proprietary synthesis recipes vary by producer, the underlying chemical transformations adhere to well-known organic reactions taught in advanced chemistry coursework. It is important that manufacturing environments maintain rigorous standards for food-grade chemical production, which include strict control of reaction conditions, appropriate handling of reagents, and validation of product consistency. While academic and chemical supply literature describe potential routes for ester synthesis, industrial production for food use follows good manufacturing practices and food safety requirements. The exact production processes are governed by manufacturer protocols and regulatory compliance frameworks rather than public regulatory mandates.

Why It Is Used In Food

Allyl anthranilate is used in food formulations because of its ability to contribute distinct flavor characteristics that enhance the sensory profile of products. Flavoring agents like this one are selected when a specific aromatic quality—such as fruity, floral, or wine-like cues—is desired to complement or round out natural and formulated flavor profiles. In food science, flavor enhancers and flavoring agents work by interacting with human sensory perception at low concentrations, delivering noticeable impact without contributing significant mass or nutritional value. Manufacturers often include such agents in confections, beverages, and other processed foods where nuanced aroma is critical to consumer acceptance. These substances do not generally function as nutrients or preservatives; rather, they serve to influence the hedonic and qualitative aspects of flavor. The choice of one agent over another depends on the desired sensory effect, compatibility with other ingredients, and stability under processing conditions like heat or pH changes. Because regulatory frameworks recognize their use within defined good manufacturing practices, food technologists can incorporate them into recipes with clear expectations for performance and labeling. Allyl anthranilate and similar compounds provide formulation options that allow product developers to achieve specific sensory goals while maintaining compliance with food safety and additive regulations. Its inclusion is justified not for broad nutritional impact but specifically to satisfy defined technical objectives in flavor creation.

Adi Example Calculation

An illustrative example of acceptable daily intake interpretation involves hypothetical exposure. Suppose an expert review establishes that a flavoring agent poses no safety concern at typical intake levels encountered in foods. If a person weighing 70 kg (about 154 pounds) consumes a variety of foods containing trace levels of a flavoring agent like allyl anthranilate throughout a day, the cumulative exposure is assessed relative to what is known about safety margins from toxicological studies. Because the expert review for this compound concluded there was no safety concern at current levels of intake, the implication is that exposures far below any threshold of concern have been considered safe. In practice, flavoring agents are used at parts per million or lower concentrations, and typical food consumption patterns result in exposure levels that remain considerably below conservative safety benchmarks. This example is illustrative and not a personalized recommendation, but it reflects how regulatory bodies consider consumer body weight and additive concentration when assessing potential exposure risks.

Safety And Health Research

Food additive safety assessment involves evaluation of potential hazards, exposure levels, and toxicological endpoints relevant to human health. In the case of flavoring agents like allyl anthranilate, expert review bodies consider available data on metabolism, acute toxicity, and long-term exposure to determine whether typical use levels present safety concerns. For allyl anthranilate, the Joint FAO/WHO Expert Committee on Food Additives evaluated the compound in the context of its intended use as a flavoring agent and reported that there was no safety concern at anticipated intake levels, based on available data up to the time of that evaluation. Regulatory frameworks also incorporate good manufacturing practices, which emphasize using the minimum effective quantity of flavoring agents to achieve the desired sensory effect. Limiting use to practical levels reduces overall exposure and contributes to maintaining safety margins. Toxicological evaluations generally focus on identifying endpoints such as organ toxicity, potential for irritation, or other adverse responses in experimental systems. These assessments inform expert panels when determining acceptability of use. Scientific research on specific flavoring agents may vary in depth depending on historical usage and data availability. For allyl anthranilate, historical evaluations by internationally recognized expert committees provide context for its safe use in food formulations, but ongoing research and monitoring mechanisms ensure that new evidence can be considered. As with all food additives, oversight continues through regulatory review and updates to scientific understanding.

Regulatory Status Worldwide

In the United States, allyl anthranilate is included in the Code of Federal Regulations under 21 CFR section 172.515, which lists synthetic flavoring substances and adjuvants that may be safely used in food when applied according to good manufacturing practice. This regulatory listing affirms that the compound is recognized within the framework that governs permitted flavoring agents in food products as of the most recent codification. The regulatory text specifies that substances in this category are to be used in the minimum quantity required to achieve their intended effect and in accordance with principles of good manufacturing practice, which aligns with general food additive safety policy in the United States. Internationally, the compound has been evaluated by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), an authoritative expert panel that reviews food additive safety. According to the JECFA evaluation, allyl anthranilate was reviewed with respect to its use as a flavoring agent, and the committee concluded that there is no safety concern at current levels of intake when used for its intended purpose. Regulatory frameworks outside the United States may reference JECFA evaluations when setting their own standards for flavoring agent use, contributing to broader international acceptance. Different jurisdictions maintain their own additive regulations, but many align with or consider internationally recognized assessments such as those from JECFA when determining allowable substances and use conditions. The presence of a JECFA evaluation alongside a US CFR listing provides a harmonized context for understanding its regulatory status in global food markets.

Taste And Functional Properties

Allyl anthranilate is noted for its sensory contribution described in the flavor industry literature as imparting fruity and floral notes, sometimes with a wine-like aspect. These sensory descriptors reflect human olfactory and taste perceptions when the compound is present in minute quantities, as typical for flavoring substances. Flavor chemists select these agents when the target profile aligns with the sensory cues that consumers associate with specific tastes or aromas. From a functional perspective, food scientists consider factors beyond mere sensory description, such as the compound's solubility characteristics and stability under processing conditions. Allyl anthranilate is reported to be poorly soluble in water but more amenable to solubilization in alcohols and oils, which influences how it is incorporated into aqueous or lipid-containing foods. Solubility behavior is a critical consideration because it affects homogeneous dispersion and consistency of flavor impact across batches. Stability under heat and varying pH can also influence performance. While specific data for this compound’s stability profiles under all processing conditions may be limited, formulators generally test flavoring agents in their intended application matrices to evaluate performance. Flavoring agents must also remain organoleptically stable, meaning they should not degrade into off-flavors during shelf life or under expected storage conditions. As a result, the functional properties of allyl anthranilate, combined with its sensory profile, guide its use in select food categories where those attributes align with product goals.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a concept used by food safety experts to describe the estimate of the amount of a substance that can be consumed every day over a lifetime without appreciable health risk, based on current scientific knowledge. In the context of flavoring agents like allyl anthranilate, expert committees such as JECFA may evaluate toxicological data and exposure estimates to determine whether an ADI can be established and whether use at intended levels is acceptable. For allyl anthranilate, the JECFA evaluation concluded there was no safety concern at current levels of intake when used as a flavoring agent, which reflects an assessment of exposure and toxicological data available at the time. This does not mean that an ADI with a specific numeric value was assigned; rather, it indicates that typical use levels are not expected to raise safety issues for consumers. The distinction between a defined numeric ADI and a conclusion of no safety concern is important: the latter conveys that safety margins were judged sufficient for the conditions of use evaluated. Consumers and professionals should understand that ADIs serve as protective benchmarks derived from scientific review and are not intended as recommended daily consumption targets. They provide a context for regulators to balance potential exposure against toxicological data, ensuring that food additive use remains within established safety margins.

Comparison With Similar Additives

Allyl anthranilate can be compared with other flavoring agents that serve similar roles in food formulations. For example, esters such as ethyl butyrate and methyl anthranilate are also used to impart fruity notes in beverages and confectionery products. These compounds, like allyl anthranilate, are selected for their sensory qualities and functional behavior in solution rather than for nutritional or preservative roles. Each compound’s specific odor profile—fruity, floral, or otherwise—informs its use in different product categories. Another comparison can be made with cinnamates and other allyl-derived esters used in flavor science. While allyl anthranilate may contribute floral or wine-like cues, compounds such as allyl cinnamate provide spicy or aromatic characteristics that suit different applications. The choice among these flavoring agents depends on the desired sensory outcome and how each interacts with the broader flavor matrix in a formulation. From a regulatory perspective, many of these compounds are addressed in similar sections of food additive regulations, which list permissible flavoring substances under good manufacturing practice conditions. Although regulatory status and permitted use conditions are similar, the specifics of sensory contribution and formulation compatibility distinguish one flavoring agent from another in practical use.

Common Food Applications Narrative

Allyl anthranilate finds application in a variety of flavored food products where its aromatic characteristics can enhance the overall sensory experience. In beverage categories, flavor specialists may use it to support or intensify fruit-forward or floral notes, especially in products designed to evoke wine-like profiles or complement fruit blends. The compound's contribution to nuanced flavor perception can help bridge gaps where natural flavor components alone might fall short, offering formulators another tool in their palette. In confectionery, particularly in candies and sweet treats, small quantities of specialized flavoring agents like allyl anthranilate can make a notable difference in consumer perception. For example, when combined with sugar and other flavor building blocks, such compounds can round out top notes and give complexity to otherwise simple sweet profiles. The aim is not merely to add flavor but to refine and elevate the eating experience with subtle aromatic cues. Product developers also consider the compatibility of flavoring agents with other ingredients and manufacturing processes. Because such agents are typically used at low concentrations, their effect on overall formulation stability or texture is minimal, allowing flexibility in use across baked goods, beverages, and other categories that benefit from enhanced sensory appeal. Ultimately, the decision to include such an ingredient arises from sensory evaluation, formulation objectives, and regulatory compliance considerations.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: EFSA specific evaluation data not found in authoritative sources searched

JECFA

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

Sources

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