BUTYL 10-UNDECENOATE

CAS: 109-42-2 FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT

Butyl 10-Undecenoate is an ester used as a flavor enhancer and flavoring agent permitted in foods under regulated conditions. It has been evaluated by international expert committees for safety at current intake levels.

What It Is

Butyl 10-Undecenoate is a specific chemical compound belonging to the class of fatty acid esters, characterized by a long carbon chain attached to a butyl alcohol moiety that forms an ester linkage with an unsaturated acid portion. This compound is recognized in regulatory references and scientific databases by its CAS Registry Number 109-42-2 and the technical function classification as a flavor enhancer, flavoring agent, or adjuvant. It is documented under flavoring regulations including a designation in the U.S. Code of Federal Regulations at section 21 CFR 172.515 for synthetic flavoring substances and adjuvants. The compound is also listed with identifiers such as a FEMA GRAS number and a JECFA number in international evaluations, indicating that expert panels specializing in flavoring agents have reviewed it for food use. Butyl 10-Undecenoate may be referred to by alternate names such as butyl undecylenate, reflecting historical naming conventions in flavor chemistry, but for regulatory and safety contexts, its systematic identification by CAS number and technical function classification is central to how food scientists, regulators, and ingredient suppliers refer to it. In its chemical identity, this ester is a derivative of undecenoic acid in which a butyl group is esterified at the carboxyl position of the unsaturated fatty acid chain. This structure imparts certain properties that influence its sensory characteristics and how it behaves in food applications. It is typically a colorless to pale yellow liquid under ambient conditions and presents a subtle organoleptic profile that can include fatty, buttery, and wine-like notes, as documented in flavor chemistry references. The specific combination of its molecular structure and sensory properties makes it suitable for enhancing or imparting particular flavor attributes in food formulations where regulated flavoring agents are used, such as in beverages, confectionery, and baked goods.

How It Is Made

The manufacturing of butyl 10-Undecenoate generally follows classical esterification chemistry, where an unsaturated fatty acid, specifically 10-undecenoic acid, reacts with an alcohol, here n-butanol, in the presence of an acid catalyst to form the ester linkage characteristic of butyl 10-Undecenoate. Acid catalysts such as concentrated sulfuric acid are commonly used to facilitate this reaction and drive the equilibrium toward ester formation. The process typically involves heating the reactants under reflux to promote efficient conversion of the acid to its ester form. This general method of esterification is well established in organic chemistry and is widely applied in flavor and fragrance manufacturing to produce a range of ester-based compounds with desired sensory profiles. Once the reaction is complete, the crude ester product is subjected to purification steps that may include washing with water to remove residual acids and catalysts, phase separation, and distillation to isolate the target compound at high purity. In commercial contexts, reagents are selected and process parameters optimized to achieve a purity grade suitable for flavor use, often indicated by specifications such as "food grade" or meeting specific standards. The resulting butyl 10-Undecenoate is then evaluated for compliance with regulatory specifications, including identity and purity criteria outlined by expert bodies such as JECFA and relevant food safety authorities. Because many specialized aspects of production, such as reaction conditions and catalyst handling, are proprietary to manufacturers, publicly available sources focus on the general chemical principles at play. Nonetheless, the core synthetic approach relies on the well-understood esterification mechanism that has been a foundation of flavor and fragrance chemistry for decades. Quality control in the production process is designed to ensure that the product meets analytical criteria for use in food, and that residual reactants or by-products are minimized to acceptable levels. This common chemical route also allows for scale-up in commercial flavor ingredient production, enabling consistent supply to food formulators who rely on regulated flavor enhancers and flavoring agents.

Why It Is Used In Food

Butyl 10-Undecenoate is used in food primarily for its role as a flavor enhancer and flavoring agent. In this capacity, it contributes nuanced sensory attributes that can improve or modify the taste experience of food products without imparting significant nutritional content. The ester linkage and unsaturated fatty acid backbone contribute to the compound's organoleptic profile, which can be described in literature references as having fatty, buttery, and slight wine-like notes. These sensory qualities make it useful for blending into flavor formulations to achieve a balanced taste profile or to reinforce specific notes in complex food matrices. Functional considerations also play a role in why this compound is selected by flavorists. Esters such as butyl 10-Undecenoate tend to have sufficient volatility to contribute to aroma perception, a key component of flavor, while remaining stable enough under typical food processing and storage conditions. Their compatibility with other flavor compounds allows them to be integrated into multi-component flavor blends that target consumer preferences for particular sensory experiences. For example, in confections, beverages, or bakery products where a creamy or rounded note is desired, esters with subtle fatty and green nuances can support the overall profile formulated by flavor professionals. In food science, such compounds are not used for direct nutritional value but rather for their ability to shape consumer perception of taste and aroma. Their incorporation into food products aligns with principles of good manufacturing practice and regulated use levels, as stipulated by food additive regulations. Regulatory frameworks ensure that flavoring agents are used in quantities appropriate to achieve their intended sensory function while maintaining safety. Thus, the use of butyl 10-Undecenoate in food formulation reflects both its sensory contributions and adherence to regulatory guidelines that govern flavoring agent use in various regional markets.

Adi Example Calculation

While butyl 10-Undecenoate does not have a specific numeric ADI assigned in major regulatory evaluations, an illustrative example of how ADI calculations would work can help clarify the concept for lay readers. Suppose for a hypothetical compound that a safety evaluation identified a no-observed-adverse-effect level (NOAEL) of 100 mg per kilogram of body weight per day from animal studies. Regulators typically apply uncertainty factors, often 100-fold, to account for differences between animal and human biology and variations within human populations. Dividing the NOAEL by 100 would yield an ADI of 1 mg per kilogram of body weight per day. For a person weighing 60 kg, this hypothetical ADI would translate to 60 mg per day as an upper boundary considered safe for lifelong daily exposure. In the case of butyl 10-Undecenoate, because expert evaluations indicate no safety concern at expected use levels, a numeric ADI is not designated, and typical exposures from food flavor use are orders of magnitude below what would raise safety questions.

Safety And Health Research

Safety evaluations concerning butyl 10-Undecenoate focus on its use as a flavoring agent and the potential for adverse effects at intake levels typical of food applications. Expert committees review available toxicological and exposure data to determine whether a substance presents safety concerns under intended conditions of use. For butyl 10-Undecenoate, JECFA evaluations concluded that there is no safety concern at current levels of intake when used as a flavoring agent, providing a scientific basis for regulatory acceptance. Such assessments consider factors including toxicological endpoints, potential genotoxicity, and overall exposure relative to thresholds of concern. In addition to formal regulatory evaluations, independent scientific assessments may evaluate specific toxicological endpoints for related compounds or read-across analogs. These assessments explore aspects such as genotoxicity and repeated dose toxicity, using available data, computational toxicology models, and analog information to fill data gaps where direct studies may be limited. Overall, the body of evidence supports that, within the context of regulated flavoring use, butyl 10-Undecenoate does not present inherent health risks at established intake levels, aligning with JECFA conclusions.

Regulatory Status Worldwide

Butyl 10-Undecenoate is recognized within key regulatory frameworks governing flavoring agents and synthetic flavoring substances permitted for use in food. In the United States, the compound is listed under the Code of Federal Regulations at 21 CFR 172.515, which covers synthetic flavoring substances and adjuvants that may be safely used in food in accordance with good manufacturing practice, indicating that its use is permitted under regulated conditions when used at the minimum level required to achieve its intended flavoring effect and otherwise consistent with good manufacturing practice. This regulatory reference reflects the outcome of safety assessments and reviews conducted to support its inclusion in the spectrum of permissible flavoring agents. Internationally, butyl 10-Undecenoate has been evaluated by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), an authoritative body that reviews food additives for safety. JECFA assigns numbers to substances it has evaluated, and butyl 10-Undecenoate is associated with JECFA number 344. According to expert committee evaluations, when such compounds are used as flavoring agents at current levels of intake, they do not pose safety concerns, providing a basis for their continued regulated use in food applications. These evaluations take into account available toxicological data and expected exposure levels from typical use patterns. Other jurisdictions often reference expert evaluations such as those by JECFA or align with established lists of permitted flavoring agents through regional regulatory processes. In Europe, similar flavoring substances are included in flavor inventories and regulated under relevant flavoring substances regulations, reflecting shared principles of safety assessment and permitted use. The presence of butyl 10-Undecenoate on these lists underscores its recognition by multiple authoritative bodies that review flavoring agent use in food.

Taste And Functional Properties

Butyl 10-Undecenoate exhibits sensory characteristics that are typical of many medium-chain fatty acid esters, combining subtle taste and aroma elements that influence overall flavor perception when used in food formulations. Its organoleptic profile is generally described as presenting fatty, buttery, and mild wine-like notes, which can complement or enhance specific flavor nuances in food products. These properties arise from the ester’s chemical structure, where the combination of a long carbon chain and an unsaturated bond contributes volatility and interaction with human olfactory receptors in ways that are distinct from short-chain esters, which are often more fruity or sharp. In functional terms, this compound’s sensory contributions are balanced and not overwhelming when used at regulated levels, allowing it to integrate harmoniously with other flavor components. Its volatility profile supports aroma perception without excessive retention, making it suitable for applications where both aroma and mouthfeel impressions are important. Stability considerations are also relevant: while esters can be sensitive to hydrolysis under extreme pH or heat conditions, properly formulated products account for such factors to preserve desired sensory attributes during processing and shelf life. From a formulator’s perspective, understanding both taste and functional properties is essential when incorporating butyl 10-Undecenoate into a flavor system. Tasting evaluations and instrumental analysis help determine optimal use levels that achieve the intended sensory effect without dominating a blend. As a result, this ester is valued for its ability to contribute depth and complexity to flavor formulations, supporting the creation of balanced sensory experiences in finished food products.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a concept used by food safety authorities to describe the amount of a substance that can be consumed every day over a lifetime without appreciable health risk. ADIs are typically derived from toxicological studies and include safety factors to account for uncertainties in data and variability among populations. For flavoring agents like butyl 10-Undecenoate, expert committees such as JECFA evaluate available toxicological data and exposure estimates to determine whether specific intake limits are warranted. In the case of butyl 10-Undecenoate, expert evaluations have concluded that there is no safety concern at current intake levels when used as a flavoring agent, meaning that formal numeric ADI values have not been established because typical use levels are far below thresholds of concern. It is important to emphasize that an ADI, when established, differs from a recommended intake; it does not represent a target level to achieve but rather a boundary below which exposure is expected to be without appreciable risk. The absence of an explicit numeric ADI for a flavoring compound like butyl 10-Undecenoate in regulatory references reflects a determination that, based on existing data and exposure estimates, ordinary consumption within permitted use patterns does not raise safety concerns.

Comparison With Similar Additives

In the broader category of flavoring agents and esters, compounds such as ethyl esters, methyl esters, and other medium-chain fatty acid esters are often compared to butyl 10-Undecenoate in terms of their sensory contributions and functional uses. For example, ethyl butyrate and methyl butyrate are commonly used to impart fruity and sweet notes in flavor systems, while butyl 10-Undecenoate provides subtler background notes that complement other esters. Although these compounds differ in specific sensory profiles, they share a common functional role in modulating aroma and taste. Another similar additive is butyl acetate, an ester with a fruity note used in various beverage and confectionery applications. Compared with these more volatile and pronounced esters, butyl 10-Undecenoate’s longer carbon chain and unsaturated structure contribute to a more restrained sensory impact, making it useful in different blending contexts. Such comparisons illustrate the range of functional properties among flavoring esters and how formulators select specific agents to achieve desired sensory outcomes in food products.

Common Food Applications Narrative

Butyl 10-Undecenoate finds its place in a wide range of food applications where flavor quality and consumer sensory experience are priorities. In the context of beverages, the compound can be part of flavor blends designed to provide subtle background notes that support primary taste attributes such as sweetness or fruitiness. In sugar confectionery and chewable candies, it may be included to enhance creamy, rounded nuances that contribute to a more satisfying flavor impression. Similarly, in baked goods, esters with gentle fatty and aromatic characteristics can help achieve a harmonious balance between sweetness and richness. In products such as dairy analogs, flavored milks, or dessert items, butyl 10-Undecenoate may be used as part of a suite of flavoring agents to mimic or enhance natural flavor profiles. Because it does not contribute caloric value or nutritional content, its role remains squarely in the realm of taste modulation. Flavor professionals often combine this ester with others to create composite flavors that align with consumer expectations for certain product categories. For example, in fruit-flavored beverages or snacks, it can support underlying notes that round out sharp acidity or deliver a perception of fuller body. Across these applications, the use of butyl 10-Undecenoate is guided by regulated frameworks that stipulate permitted use conditions, ensuring that it contributes to the sensory profile without exceeding levels necessary to achieve the desired effect. This balance between functional contribution and regulatory compliance underpins its application in diverse food product categories.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: No specific EFSA numeric ADI established based on available data

JECFA

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

Sources

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