METHYL ANTHRANILATE

CAS: 134-20-3 FLAVORING AGENT OR ADJUVANT, SOLVENT OR VEHICLE

**Methyl anthranilate** is a synthetic and naturally occurring ester used primarily as a flavoring agent in food and beverages, notable for contributing a fruity grape-like aroma and flavor. It has been evaluated by international bodies and appears on official additive inventories.

What It Is

Methyl anthranilate is a chemical compound defined as the methyl ester of anthranilic acid. This ester, identified by the CAS number 134-20-3 and known by several synonyms including methyl 2-aminobenzoate and o-methyl o-aminobenzoate, belongs to the class of organic aromatic esters that are used for their organoleptic properties. As an ingredient, it functions as a flavoring agent or adjuvant and may serve as a solvent or vehicle in formulations where it is added for its sensory profile. Its inclusion in food and beverage formulations is based on its ability to impart characteristic fruity or grape-like notes that enhance the consumer perception of products. The compound exists as a clear to slightly colored liquid under typical storage conditions and is recognized in regulatory listings for food use in certain jurisdictions. It is commonly listed in food additive inventories under flavoring categories and has been the subject of formal evaluations for safety in human consumption by international expert committees. The range of names and identifiers associated with methyl anthranilate reflects its diverse presence in both natural extracts and industrially synthesized aroma chemicals.

How It Is Made

The manufacture of methyl anthranilate involves classical organic esterification reactions. At a basic level, this compound can be synthesized by reacting anthranilic acid with methanol in the presence of an acid catalyst, often a strong protic acid, under controlled temperature to promote the formation of the methyl ester. Alternative industrial routes may employ activated intermediates or use of isatoic anhydride as a precursor that, upon reaction with methanol, yields the methyl ester with removal of byproducts. These esterification processes highlight a fundamental transformation in organic chemistry where a carboxylic acid derivative (anthranilic acid) and an alcohol (methanol) form an ester link, releasing water as a byproduct. Post-reaction steps typically include purification such as distillation to achieve the desired level of chemical purity appropriate for flavor industry specifications. The resulting product must meet defined specifications, which may include limits on impurities, water content, and sensory performance, to conform to food additive standards. In natural contexts, methyl anthranilate can also be extracted from essential oils of plants where it occurs at low concentrations, although industrial production for commercial applications generally relies on synthetic methods due to yield and consistency considerations. The production and formulation are conducted with attention to standard safety protocols for handling flammable organic liquids and ensuring batch-to-batch consistency for commercial use.

Why It Is Used In Food

Methyl anthranilate is used in food because of its distinctive aromatic profile that contributes to the sensation of fruit-like or grape-flavored notes in edible products. Its role as a flavoring agent involves interacting with the complex matrix of food ingredients to modify or enhance the sensory perception experienced by consumers. Flavor chemists select methyl anthranilate to highlight or amplify specific taste impressions, especially in products where a grape or berry character is desired. It is compatible with other flavor compounds and can be blended in precise quantities to achieve a target flavor bank that aligns with consumer expectations. The utility of methyl anthranilate extends to confections, beverages, chewing gums, dairy analogues, and other foods where fruit flavor appeal is a priority. Beyond its straightforward sensory contribution, it can also function as a solvent or vehicle for delivering other aromatic components due to its moderate solubility in alcohol and organic phases, supporting effective distribution of flavor profiles within a product. Manufacturers value its relatively strong aroma at low concentrations, which allows formulators to achieve desired sensory effects without adding excessive amounts of additive. The selection of methyl anthranilate in a formulation strategy is grounded in its performance characteristics in sensory trials and its established use history within flavoring systems recognized by regulatory listings.

Adi Example Calculation

To illustrate how an ADI concept might be applied in a simplified, hypothetical scenario, consider a value at the upper end of the established acceptable intake range for methyl anthranilate. For a hypothetical adult weighing a defined body weight, multiplying the ADI value by the body weight yields an estimated allowable daily intake amount. This exercise shows how regulators translate a per-body-weight benchmark into an absolute intake figure that can be used in exposure modeling. It is important to emphasize that such examples do not constitute personalized guidance and are intended solely to demonstrate how the ADI framework operates conceptually. Actual exposure assessments consider average consumption patterns across product categories where the ingredient is used. By comparing these exposure estimates to the ADI threshold, regulators can determine whether use levels in the marketplace are consistent with safety objectives. This form of calculation supports risk managers in making informed decisions about allowable use levels and helps ensure that consumers remain protected across typical dietary scenarios.

Safety And Health Research

Safety assessments of methyl anthranilate have been conducted by recognized scientific committees that review available toxicological studies to characterize hazard potential and inform regulatory decisions. Toxicology data often include evaluations of acute toxicity, metabolism, and chronic exposure in laboratory models, focusing on endpoints relevant to health risk characterization. For methyl anthranilate, evidence indicates that it undergoes metabolic transformation in biological systems, and studies have explored its hydrolysis and subsequent clearance. Expert committees review studies addressing potential carcinogenicity, genotoxicity, and other systemic effects to determine the margins of safety when used as intended in food. Regulatory frameworks rely on a weight-of-evidence approach that considers study design quality, reproducibility, and relevance to human exposure scenarios. Findings from such evaluations support the categorization of methyl anthranilate for use at specific levels where consumer exposure is not expected to exceed established safety benchmarks. It is important to distinguish between the technical evaluation of hazard endpoints and the actual exposure consumers experience when additives are used within defined regulatory parameters. Safety research informs acceptable use practices, and ongoing monitoring by regulators ensures that new data can be incorporated into risk assessments over time. Risk communication emphasizes that evaluations are based on scientific methods to protect public health and do not imply inherent hazard at regulatory-compliant use levels.

Regulatory Status Worldwide

Methyl anthranilate is listed in regulatory inventories for use as a flavoring agent in certain jurisdictions. In the United States, it appears on the Food Additive Status List under Section 182.60 of Title 21 of the Code of Federal Regulations, where it is recognized for use as a synthetic flavoring substance permitted in foods, reflecting its established history of safe use under defined conditions. Internationally, expert panels such as the Joint FAO/WHO Expert Committee on Food Additives have evaluated methyl anthranilate and assigned it a category and acceptable intake ranges, indicating systematic review of available toxicological data. Such evaluations often consider metabolism, toxicology, and dietary exposure patterns in determining appropriate use levels. In Europe, chemical group assessments including anthranilate derivatives have been undertaken by scientific bodies that provide opinions on their safety and efficacy in animal nutrition and, by extension, inform considerations for food applications in human consumption contexts. The regulatory status in various countries may include specific labeling requirements or restrictions that guide manufacturers in compliant use. In all cases, inclusion in regulatory listings indicates that competent authorities have mechanisms to monitor its application within food systems, and compliance with local regulations is a prerequisite for market placement. As with all flavoring agents, adherence to stipulated use levels and documentation in ingredient statements ensures transparency for regulators and consumers.

Taste And Functional Properties

The taste profile of methyl anthranilate is predominantly described as having a fruity, grape-like character that can contribute a sweet and floral nuance to a flavor blend. Sensory evaluators often describe it as evoking the typical aroma and taste associated with ripe grapes, making it a valuable tool in creating grape-flavored products and other fruit-concept flavors. Functionally, methyl anthranilate’s volatile nature allows it to contribute aroma impact in the headspace above a food matrix, thereby influencing the overall perception of flavor even at low inclusion rates. It has differential solubility properties, being relatively soluble in ethanol and certain organic solvents while having limited water solubility, which informs how it is incorporated into complex flavor systems. These physical and functional properties allow it to work in synergy with other flavoring ingredients to build layered sensory experiences. Formulators must consider matrix effects, such as fat content and temperature conditions, which can affect the volatility and release of methyl anthranilate’s aroma. Its stability under various processing conditions is managed by selecting appropriate use levels and combining it with stabilizers or encapsulation techniques where extended shelf-life or controlled release is desired. As with many aroma chemicals, interaction with packaging materials and storage conditions can influence performance, requiring careful consideration in product development. The result is a flavor component that can reliably contribute a characteristic and recognizable sensory attribute when used within recommended use levels.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory concept that represents the amount of a substance, expressed per unit of body weight, that can be ingested daily over a lifetime without appreciable health risk. The ADI is determined by expert committees reviewing toxicological data and applying safety factors to account for uncertainties when extrapolating from experimental systems to humans. For methyl anthranilate, international evaluations have assigned a range for the ADI, reflecting a conservative approach that encompasses available evidence on metabolism and toxicity. The ADI is not a recommended intake level but serves as a benchmark for regulators and manufacturers when assessing the safety of cumulative exposure from all food sources. Use of methyl anthranilate in food formulations is managed so that estimated daily exposure stays well below the upper bound of the ADI, ensuring a wide margin of safety. The ADI allows public health authorities to set policies and guidance that prevent excessive exposure, while enabling industry to use flavoring agents within safe and approved limits. Consumers typically encounter methyl anthranilate at very low levels in flavored products, contributing a fraction of the ADI when consumed as part of a varied diet. Understanding the ADI helps contextualize regulatory decisions and supports confidence in ingredient safety frameworks that prioritize protecting human health.

Comparison With Similar Additives

Methyl anthranilate can be compared with other ester-based flavoring agents that contribute fruity notes, such as ethyl butyrate and propyl acetate. Ethyl butyrate is widely used to generate pineapple-like or tropical fruit flavors in beverages and confectionery, while propyl acetate delivers a pear-like aroma. In contrast, methyl anthranilate uniquely imparts a grape-like character that distinguishes it within the flavor palette. Functional similarities include their roles in enhancing fruit concept flavors and their incorporation at low use levels due to strong sensory impact. Each of these esters has distinct physicochemical properties that influence volatility and solubility, affecting how they perform in specific food matrices. In formulation practice, the choice among such flavoring agents depends on the target sensory profile and product matrix characteristics. Like methyl anthranilate, other flavoring esters undergo regulatory review and have defined status in food additive inventories. Comparing these additives highlights how flavor chemists leverage structural diversity to achieve tailored sensory outcomes while adhering to safety and regulatory standards.

Common Food Applications Narrative

Methyl anthranilate finds application across a spectrum of food categories where its sensory characteristics align with product positioning and consumer expectations. In confectionery, it is frequently a component of fruit-flavored candies, sugar confections, and gummies where grape notes are central to the flavor profile. Beverage manufacturers may incorporate methyl anthranilate in soft drinks, flavored waters, and carbonated beverages to evoke fruit character, particularly where a natural grape nuance is sought. The dairy and frozen dessert sector also uses it in flavored milk products, ice creams, and sherbets to reinforce fruit-themed varieties. Bakery applications include fillings, frostings, and icings that leverage its aroma to complement fruit-based fillings or toppings. Chewing gum and breath freshening products use methyl anthranilate to deliver long-lasting fruit impressions that resonate with consumer taste memories associated with grape flavors. Additionally, non-alcoholic cocktails and syrups may use it to bolster complex fruit blends, while snack producers incorporate it into coated nuts or cereal bars with fruit flavor accents. In each of these categories, the ingredient is blended with other flavoring agents to construct a balanced and appealing sensory profile. Its versatility allows it to be part of multi-dimensional flavor constructs that satisfy varied consumer segments in both mainstream and niche markets.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 182.60

EFSA

  • Notes: EFSA evaluation available for related use in feed but specific human ADI numeric not verified

JECFA

  • Year: 1979
  • Adi Display: 0-1.5 mg/kg bw
  • Adi Mg Per Kg: 1.5

Sources

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