BUTYL ANTHRANILATE

CAS: 7756-96-9 FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT

Butyl anthranilate is a synthetic ester used as a flavoring agent characterized by a mild fruity aroma and permitted as a synthetic flavoring substance under designated regulatory conditions.

What It Is

Butyl anthranilate is an organic chemical compound belonging to the class of esters formed from anthranilic acid and butanol, widely used for its fruity and floral sensory properties in flavor formulations. It is identified chemically with the CAS number 7756-96-9 and is recognized under flavoring additive regulations such as 21 CFR 172.515 in the United States. The compound is also catalogued in flavor and fragrance industry references such as FEMA with assigned identifier 2181 and has a JECFA number of 1536 for international additive evaluations. Structurally, it is the butyl ester of 2-aminobenzoic acid, combining a benzene ring with an amine and ester functional group, which contributes to its olfactory characteristics in food systems. Butyl anthranilate appears as a colorless or pale straw-colored liquid at room temperature, with a molecular profile that confers a mild sweet and fruity aroma reminiscent of grape or berry notes. This sensory quality underpins its use as a flavor enhancer and adjuvant in a variety of formulations. Due to its chemical nature, it is categorized not as a nutrient but as a functional additive intended to influence flavor perception and complement other flavor components within complex food matrices. When described within regulatory frameworks, butyl anthranilate is listed among synthetic flavoring substances and adjuvants that may be safely used in foods when applied according to good manufacturing practice and in minimum quantities necessary to achieve intended sensory effects under sections such as 21 CFR 172.515. The regulatory listing signifies recognition of its intended functional role rather than endorsement of specific health outcomes.

How It Is Made

Butyl anthranilate is generally produced through an organic esterification reaction between anthranilic acid and butanol, often facilitated by an acid catalyst, in which the carboxyl group of anthranilic acid reacts with the hydroxyl group of butanol to form the ester bond and release water. This classic esterification process yields the butyl ester derivative that exhibits the desired organoleptic properties for flavoring use. In industrial practice, synthesis and purification are conducted under controlled conditions to achieve a product with consistent identity and purity suitable for its intended technical function. The manufacturing environment typically involves reflux systems, phase separation, and careful control of temperature and catalysts to optimize yield and minimize by-products. Resulting batches are characterized for key physical properties such as refractive index and density, as well as compliance with defined purity criteria in chemical additive specifications. Consistent quality and identity are crucial for uses in food and flavor systems, where variability in composition could influence sensory outcomes or compliance with regulatory requirements. Specifications developed by expert bodies such as JECFA include parameters that help ensure that the synthesized compound meets defined analytical and sensory benchmarks appropriate for its role as a flavoring agent.

Why It Is Used In Food

Butyl anthranilate is incorporated into food formulations principally to enhance or impart specific sensory experiences associated with fruity and floral profiles. In food science, an additive classified as a flavor enhancer or flavoring agent is selected to complement natural or other synthetic flavors, contributing depth and nuance to product taste without altering the fundamental nutritional composition. Manufacturers integrate butyl anthranilate in carefully calibrated amounts because of its capacity to convey subtle fruit-like notes, which can balance or elevate other elements in a flavor blend. It is particularly useful in complex flavor systems where a hint of berry, grape, or floral nuance enhances the consumer perceivable profile. Its volatility and solubility characteristics influence how it interacts within different food matrices, supporting integration into beverages, confectionery, and bakery flavors when used appropriately. The technical rationale for using butyl anthranilate over other potential flavoring substances often relates to its specific aromatic signature and compatibility with other commonly used flavor constituents. When deployed as a component of a broader flavor composition, it can help achieve targeted sensory objectives without dominating the overall flavor impression.

Adi Example Calculation

As an illustrative example, if a hypothetical ADI were established at a value derived by an expert committee for a flavoring agent, a body weight-based calculation could be performed to estimate safe intake. For instance, if an expert panel established that typical daily consumption of a flavoring agent posed no safety concern at an estimated exposure level, one could calculate that exposure relative to body weight to illustrate the magnitude of intake. However, in the case of butyl anthranilate, expert evaluations conclude no safety concern at current levels of intake when used as a flavoring agent, and a specific numeric ADI is not established in that context. Any numerical example would therefore be hypothetical rather than reflective of a defined regulatory numeric ADI.

Safety And Health Research

Scientific evaluations of butyl anthranilate, such as those conducted by JECFA, focus on assessing toxicological data and exposure estimates to determine whether typical levels of intake via food use raise safety concerns. Expert committee reviews integrate available chemical and toxicological information to ascertain whether observed effects in relevant studies, when considered alongside probable human exposure, fall within margins considered acceptable by international food safety authorities. A key component of safety assessment in this context is examining endpoints such as acute toxicity, repeated-dose studies, and any indications of adverse effects at levels significantly higher than expected human exposure. Flavoring agents like butyl anthranilate are generally used at low concentrations in food, and evaluations that conclude no safety concern at these levels provide assurance that routine applications do not pose undue risk. Expert assessments also consider metabolism and elimination pathways to understand how the compound behaves in biological systems. It is important to note that regulatory safety assessments are based on available evidence and are periodically reevaluated as new data emerge. Statements about safety reflect consensus within expert panels regarding acceptable use levels rather than absolute guarantees of physiological effects. Consequently, safety characterization emphasizes the margin between potential effect thresholds identified in studies and typical consumer exposure levels.

Regulatory Status Worldwide

In the United States, butyl anthranilate is included within the provisions of 21 CFR 172.515, a listing that identifies synthetic flavoring substances and adjuvants permitted for direct addition to food when used in accordance with good manufacturing practice and minimum required quantities to achieve intended flavor effects. This regulatory listing reflects a formal recognition of its functional role as a flavoring agent under the U.S. Food and Drug Administration’s food additive regulations. Source documents such as the eCFR section confirm its inclusion in the flavoring agents category under Part 172 of the food additive regulations. Internationally, evaluations by expert bodies such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA) assign a JECFA number (1536) for butyl anthranilate and provide safety assessments indicating no safety concern at current intake levels when used as a flavoring agent. These expert evaluations inform regulatory decisions in various countries and contribute to international consensus on acceptable use practices and specifications for identity and purity. While butyl anthranilate does not have a designated E-number assigned by the European Food Safety Authority (EFSA), the JECFA evaluation and food additive specifications database entries provide context for its consideration in global regulatory environments. Regulatory frameworks in additional regions may reference international expert assessments and codified standards such as Codex Alimentarius when assessing the appropriateness of flavoring substances in food products.

Taste And Functional Properties

Butyl anthranilate is noted for its mild fruity and floral sensory attributes, which are leveraged in flavor formulation to evoke familiar fruit profiles without excessive intensity. Sensory descriptors associated with this compound often include grape and berry-like notes, which can be tailored in terms of concentration to achieve the desired impact in a finished food product. From a functional perspective, the solubility behavior of butyl anthranilate favors integration into lipid-rich or alcohol-containing systems, consistent with many beverage and confectionery applications where flavor solubility is key. Its stability under typical processing conditions, such as moderate heat and pH ranges encountered in food manufacture, supports its utility across a range of product categories, although formulation scientists consider its performance relative to other esters to balance volatility and persistence. The compound’s aroma characteristics and functional properties together make it a useful tool for flavorists seeking to build complexity in a flavor profile while maintaining control over sensory outcomes. Its interaction with other volatile compounds influences how flavors evolve over time, particularly in aroma release and perception during consumption.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a metric used by food safety authorities to express the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, based on available toxicological data and conservative uncertainty factors. ADIs are typically derived through expert review processes that identify a no-observed-adverse-effect level (NOAEL) in relevant studies and apply safety factors to account for uncertainties in extrapolating from experimental models to human populations. In the case of flavoring agents like butyl anthranilate, expert assessments such as those performed by JECFA may conclude that there is no safety concern at current intake levels when used as intended, indicating that a formal numeric ADI may not be necessary or that exposure estimates fall well below levels of toxicological concern. This type of conclusion informs regulatory decisions and helps guide manufacturers in making use level decisions consistent with safety benchmarks. It is important to understand that the ADI is a theoretical construct intended to support risk management, and it does not imply a recommended consumption level for individual consumers. Rather, it provides a basis for regulators and industry to ensure that cumulative exposure from food uses remains within bounds considered protective of public health.

Comparison With Similar Additives

Butyl anthranilate can be compared with other ester-based flavoring agents such as ethyl anthranilate and methyl anthranilate, which are also used to impart fruity and floral sensory characteristics. These compounds differ in their alkyl chain lengths, which influence volatility, solubility, and sensory nuance, leading to different applications in flavor design. Ethyl anthranilate, with a shorter alkyl chain than butyl anthranilate, may contribute a slightly sharper or more volatile profile, whereas the longer chain in butyl anthranilate can support more lingering fruit-like notes. When formulating flavor systems, flavorists consider how these esters interact with other components to achieve cohesive sensory outcomes, and the choice among related compounds often reflects a balance between intensity, persistence, and how the additive complements other flavor constituents. Comparisons also extend to stability under processing conditions, where structural differences affect how each compound responds to heat or pH changes.

Common Food Applications Narrative

In the development of flavored foods and beverages, a broad spectrum of sensory characteristics is often desired to meet consumer preferences. Butyl anthranilate serves a role in this context by contributing fruity and floral notes that help round out or accentuate overall flavor profiles. Its use aligns with the practice of blending multiple flavoring agents to achieve a cohesive taste experience, particularly when the target is to evoke nuances reminiscent of grapes, berries, or other fruit derivatives. For example, beverage formulations that aim for a refreshing, fruit-forward character may incorporate trace levels of butyl anthranilate as part of a composite flavor ingredient strategy. Similarly, confectionery products such as hard candies, chewable sweets, and gum bases frequently utilize esters with complementary sensory qualities to bolster fruit-related flavor impressions. In bakery applications, where discrete fruit notes can elevate the sensory appeal of fillings or frostings, flavorists may include butyl anthranilate alongside other esters and aldehydes to achieve a balanced profile that resonates with consumer expectations. Across these applications, the unifying theme is the role of butyl anthranilate as a supportive flavoring component, enhancing the perception of desirable sensory attributes without introducing off-notes. Its deployment is guided by principles of flavor design and regulatory compliance, ensuring that usage levels are appropriate to both technical function and adherence to applicable food additive standards.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: No specific EFSA approval or E-number directly verified for this compound

JECFA

  • Year: 2005
  • Notes: JECFA concluded no safety concern at current intake levels when used as a flavouring agent

Sources

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