CINNAMYL ISOVALERATE

CAS: 140-27-2 FLAVORING AGENT OR ADJUVANT

Cinnamyl isovalerate is a synthetic flavoring agent permitted in food under 21 CFR 172.515 and evaluated by flavor expert committees for use in enhancing sensory profiles.

What It Is

Cinnamyl isovalerate is a defined chemical compound used as a flavoring agent intended to impart specific sensory qualities to food products. It is identified by the Chemical Abstracts Service (CAS) number 140-27-2 and is recognized in regulatory listings as a synthetic flavoring substance permitted under U.S. food additive regulations (21 CFR 172.515). The chemical belongs to the class of esters, which are organic compounds formed through the reaction of an acid and an alcohol. In this case, cinnamic alcohol and isovaleric acid are combined to form the ester known as cinnamyl isovalerate. It is often encountered in flavor and fragrance industry listings as having a fruity, floral, or apple-like taste and odor profile, which makes it suitable for use in a variety of applications where such sensory notes are desired. The compound can appear as a colorless to pale yellow liquid under typical conditions and has physical properties consistent with other flavor esters. In the context of food technology, cinnamyl isovalerate is categorized under flavoring agents or adjuvants, indicating its role is primarily to enhance, modify, or contribute to the flavor profile of a product rather than to provide nutritional value. Regulatory frameworks around the world, including in the United States under the Federal Food, Drug, and Cosmetic Act (FD&C Act), include this compound in specified sections of the Code of Federal Regulations (CFR) that list synthetic flavoring substances allowed for direct addition to food. These frameworks require that such substances be used in accordance with good manufacturing practices and under conditions that ensure safety for intended use. The classification as a flavoring agent reflects its functional use in formulations and distinguishes it from other additive categories such as preservatives or colorants. Other names for cinnamyl isovalerate reflect its chemical structure and synonyms used in industry and scientific literature. These synonyms include systematic names based on IUPAC nomenclature as well as trade or catalog names. Awareness of these alternate names is essential for regulatory compliance and for professionals interpreting ingredient lists on product specifications or safety data sheets.

How It Is Made

The manufacture of cinnamyl isovalerate typically involves an esterification reaction between an alcohol and an acid, which is a fundamental organic chemistry process. In the case of cinnamyl isovalerate, the alcohol component is cinnamic alcohol (which features a phenyl group attached to a propenyl chain) and the acid component is isovaleric acid (a branched-chain carboxylic acid). In the presence of a catalyst and under controlled reaction conditions, these two reactants form the ester bond that characterizes cinnamyl isovalerate. This esterification process is similar in principle to the synthesis of many other flavor and fragrance esters, which are often produced at scale for industrial use. Producers of cinnamyl isovalerate operate in facilities equipped to handle organic chemical synthesis and purification. After the initial esterification reaction, the product undergoes purification steps to achieve the desired level of purity for its intended application. Such purification may involve distillation or other separation techniques that remove unreacted starting materials, catalysts, and byproducts. The final material is typically characterized to confirm that it meets relevant purity specifications and quality standards appropriate for flavoring use. Specifications may include parameters such as the percentage of the desired isomeric forms and limits on impurities. High standards for purity and consistency are particularly important when producing compounds intended for use in food applications. Manufacturers often adhere to Good Manufacturing Practices (GMP) and internal quality control protocols to ensure batch-to-batch consistency. Additionally, suppliers may provide material with documented certificates of analysis (COA) and safety data sheets that describe the chemical and physical properties, handling precautions, and composition. The commercial availability of cinnamyl isovalerate from chemical suppliers reflects its established role in flavor and fragrance formulation. The compound’s production process underscores its classification as a synthetic ingredient. While naturally occurring esters can be extracted from botanical sources, industrial-scale supply for food additive applications often relies on synthetic synthesis to ensure availability and consistency. The strategic selection of starting materials and controlled reaction conditions enables manufacturers to produce cinnamyl isovalerate in a form suitable for further use by flavor houses, formulators, and food manufacturers.

Why It Is Used In Food

Cinnamyl isovalerate is used in food primarily for its capacity to contribute specific flavor characteristics that are desirable in many formulations. The human sensory perception of food includes detection of sweet, sour, salty, bitter, and umami tastes, but much of the nuance in flavor experience arises from volatile compounds that interact with olfactory receptors. Esters such as cinnamyl isovalerate are known for their fruity and floral notes, and they can mimic or enhance flavor profiles reminiscent of fruits such as apple or pear. For this reason, manufacturers of confections, beverages, baked goods, and other products may include cinnamyl isovalerate at the formulation stage to achieve a balanced and appealing sensory outcome. Flavoring agents like cinnamyl isovalerate are selected based on the target flavor profile of a product. For example, in fruit-flavored beverages or candies, an ester with a fruity note can add depth and complexity to the overall taste composition. Such compounds do not typically contribute sweetness in the way sugar does, but their odor and taste characteristics influence the perception of sweetness and fruitiness when combined with other ingredients. In more complex formulations, flavor chemists may blend multiple esters and flavor components to approximate a particular natural flavor or to create a novel sensory experience. The versatility of cinnamyl isovalerate in contributing to fruity, floral, or slightly spicy notes makes it a useful tool in the flavorist’s repertoire. Another reason for its use is the compound’s compatibility with other flavor components and processing conditions. In many food manufacturing processes, ingredients are subjected to heat, mixing, and storage conditions that can alter flavor profiles over time. A compound like cinnamyl isovalerate can be formulated to remain stable under typical processing environments and still deliver the intended sensory effects in the finished product. Additionally, regulatory frameworks in markets that permit its use provide guidance on conditions of use, which inform formulators about compliance requirements and acceptable practices. The purposeful use of flavoring agents such as cinnamyl isovalerate reflects the broader objectives of food formulation: to deliver a consistent and enjoyable sensory experience while meeting regulatory and quality standards. These compounds are one among many tools available to flavorists and product developers working in competitive food and beverage markets.

Adi Example Calculation

An illustrative example can help clarify the concept of acceptable daily intake (ADI) and how it relates to real-world exposure, even when a specific numeric ADI is not established for a given compound such as cinnamyl isovalerate. Suppose a hypothetical flavoring agent were assigned an ADI of X mg per kilogram of body weight per day based on toxicological data. For an adult weighing 70 kilograms (approximately 154 pounds), the total amount of that flavoring that could be consumed daily without exceeding the ADI would be 70 multiplied by X. This multiplication provides a reference point against which estimated dietary exposures can be compared. If a compound like cinnamyl isovalerate is used at very low concentration levels in food products — for example, fractions of a milligram per kilogram of product — actual intake for most consumers is likely orders of magnitude below hypothetical ADI levels. This is because food flavorings are designed to be potent in sensory impact, requiring only trace amounts to contribute to overall flavor profiles. In normal consumption scenarios, the amount of flavoring agent ingested from flavored beverages or confections is minimal relative to body weight. Importantly, this illustrative calculation is not a recommendation or indication of safe intake for cinnamyl isovalerate specifically, but rather a demonstration of how ADI concepts are used in regulatory science. An ADI, when established, provides a cautious, science-based reference that accounts for uncertainties and variability across populations. It aids regulators in ensuring that typical dietary exposures through permitted uses of flavoring agents and other food additives remain within ranges that expert evaluations consider safe. By applying ADI principles and considering typical food use patterns, regulatory agencies and committees help ensure that consumer exposure to flavoring agents like cinnamyl isovalerate remains consistent with established safety frameworks. Illustrative calculations reinforce the idea that actual intake under normal usage conditions is a fraction of the intake levels associated with potential toxicological thresholds.

Safety And Health Research

Research related to cinnamyl isovalerate and structurally similar flavoring agents encompasses assessments of toxicological endpoints and exposure scenarios relevant to food use. Regulatory agencies and scientific committees often consider data on absorption, distribution, metabolism, and excretion (ADME) of flavoring compounds, as well as results from acute and chronic toxicity studies, to evaluate safety in the context of human consumption. These evaluations help determine whether typical levels of intake through diet are likely to pose concerns for consumers. Many flavoring esters, including cinnamyl isovalerate, are rapidly metabolized in the body, with enzymatic processes breaking the ester bond to yield constituent alcohols and acids. This metabolic pathway is one reason why structurally related esters undergo similar safety assessments as groups rather than as isolated chemicals in some cases. Expert committees consider available data from animal studies and in vitro research to identify no-observed-effect levels (NOELs) and to assess whether any potential adverse effects might be associated with typical dietary exposures. In the case of cinnamyl isovalerate, summary evaluations have indicated no safety concern at current levels of intake when used as a flavoring agent, reflecting a consensus that exposures arising from approved uses do not raise adverse health signals. It is important to recognize that scientific evaluations account for conservative assumptions about exposure and sensitivity across populations. These evaluations do not typically provide direct measures of health effects in humans but rather interpret data from controlled studies and apply safety factors to account for uncertainty. The absence of identified safety concerns at normal exposure levels does not imply that extremely high doses would be without effect; instead, it indicates that within the expected range of use in food, the compound does not present measurable risk. Ongoing monitoring of scientific literature and regulatory updates ensures that new evidence can be incorporated into safety considerations as needed. In addition to evaluations by expert committees, manufacturers may conduct or reference toxicity studies specific to compounds like cinnamyl isovalerate to support regulatory submissions or internal safety assessments. Such studies can include acute toxicity tests, skin or eye irritation assessments for handling safety data, and evaluations of stability and breakdown products that may form under processing conditions. Collectively, these research efforts contribute to a body of evidence that informs regulatory determinations and industry practices regarding the safe use of flavoring agents in food.

Regulatory Status Worldwide

The regulatory status of cinnamyl isovalerate reflects its recognition as a flavoring agent permitted for direct addition to food in specific jurisdictions under defined conditions. In the United States, cinnamyl isovalerate is listed under 21 CFR 172.515, which enumerates synthetic flavoring substances and adjuvants that may be safely used in food when employed in the minimum quantity necessary to achieve the intended effect and in accordance with good manufacturing practices. The presence of this compound in that section signifies that the U.S. Food and Drug Administration has determined it can be used in food within those parameters. The regulation itself sets a framework for allowable use but does not specify a numerical limit for every permitted compound; instead, it emphasizes appropriate usage conditions that align with safety and quality expectations in food production. Internationally, expert panels and committees contribute to the safety evaluation of flavoring agents. For example, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated cinnamyl isovalerate as part of a group of structurally related flavoring agents. In a summary of evaluations, the committee concluded there was no safety concern at current levels of intake when used as a flavoring agent, highlighting that the compound’s typical exposure through food use did not raise safety issues for general consumption. This conclusion informs regulatory bodies and industry stakeholders about the relative safety of the substance in its functional context. Additionally, the Flavor and Extract Manufacturers Association (FEMA) assigns a unique reference number (FEMA 2302) to cinnamyl isovalerate in its flavor library, indicating it has been assessed for use as a flavor ingredient. Such listings are often used by industry professionals as part of internal compliance and formulation decisions. In regions beyond the United States and international expert committees, individual countries or economic blocs may have their own regulatory frameworks governing the use of flavoring agents. These frameworks typically consider safety evaluations, exposure assessments, and international standards when determining permissible use conditions. Overall, the regulatory landscape for cinnamyl isovalerate emphasizes controlled and informed usage in food products. By situating the compound within recognized regulatory and expert evaluation contexts, manufacturers can align formulation practices with established safety and compliance expectations.

Taste And Functional Properties

Cinnamyl isovalerate contributes distinct sensory attributes that are valued in flavor formulation. Sensory descriptions from industry references note that this compound may impart fruity, floral, and apple-like notes when present in low concentrations in a flavor mixture. These descriptors help illustrate how the molecule interacts with human olfactory and taste receptors to influence flavor perception. Esters generally possess high volatility relative to many other organic compounds, which means they readily evaporate and reach the olfactory epithelium where smell perception occurs. This characteristic is central to why esters are often perceived as fruity or floral: their volatility and molecular structure combine to evoke specific sensory impressions. In functional terms, cinnamyl isovalerate is not used for nutritional purposes but rather as a sensory modifier. It does not provide macronutrients such as proteins, carbohydrates, or lipids, nor does it act as a preservative or coloring agent. Instead, its principal role is to enhance or complement other flavor notes in a formulation. The functional properties of a flavoring agent are influenced by its solubility in various media, its stability under processing conditions, and its interaction with other ingredients. For example, an ester may be more soluble in ethanol or other organic solvents than in water, which can influence how it is incorporated into liquid flavor blends or emulsions. The stability of cinnamyl isovalerate can vary with temperature and pH. Like many esters, prolonged exposure to high temperatures or extreme pH conditions can promote hydrolysis, which would break the ester bond and reduce the compound to its constituent alcohol and acid. In typical food processing environments where temperatures and pH levels are controlled, formulators account for such factors to ensure the compound maintains its functional properties through production, storage, and consumption. The compound’s sensory impact is thus a function not only of its inherent odor and taste characteristics but also of its resilience in the product matrix. Understanding the sensory and functional properties of cinnamyl isovalerate helps product developers integrate it effectively into food systems. By balancing its contribution with other ingredients and adjusting for processing variables, formulators can achieve desired sensory outcomes without compromising product integrity.

Acceptable Daily Intake Explained

The concept of an acceptable daily intake (ADI) is central to how regulatory agencies and expert panels approach the safety assessment of food additives, including flavoring agents such as cinnamyl isovalerate. An ADI represents an estimate of the amount of a substance that can be consumed daily over a lifetime without appreciable risk, based on current scientific evidence. It is typically expressed in terms of milligrams of the substance per kilogram of body weight per day. Establishing an ADI involves evaluating toxicological data from studies in animals and humans, identifying a no-observed-effect level (NOEL), and applying safety or uncertainty factors to account for differences between study conditions and real-world human exposures. For many flavoring agents evaluated by expert committees like the Joint FAO/WHO Expert Committee on Food Additives (JECFA), the data support conclusions that typical intake levels do not pose safety concerns. In the case of cinnamyl isovalerate, the available evidence summarized by JECFA indicates no safety concern at current levels of intake when used as a flavoring agent. This type of conclusion reflects the committee’s assessment that exposures arising from normal food use fall well below thresholds associated with adverse effects in toxicity studies. It is important to understand that an ADI, when established, does not serve as a recommended intake level or a nutritional requirement. Instead, it provides a safety benchmark that regulators use to evaluate whether estimated exposures through the diet are likely to remain within safe bounds. For compounds where a numeric ADI is not explicitly identified, expert assessments may rely on qualitative evaluations of safety at typical use levels, indicating that exposures are not expected to reach levels of toxicological concern. Consumers and professionals should recognize that the presence of an ingredient like cinnamyl isovalerate on a food label does not imply that it is consumed at levels near any safety threshold. Flavoring agents are used in minute quantities, often in parts per million or less within finished products, contributing sensory character without significant bulk. Regulatory frameworks require that such substances be used in accordance with good manufacturing practices, which include using the minimum effective amount necessary to achieve the intended flavor effect. By situating usage within these frameworks and informed by expert evaluations, manufacturers help ensure that daily intake from typical consumption patterns remains consistent with safety considerations.

Comparison With Similar Additives

Flavoring agents encompass a broad class of compounds used to enhance or modify sensory characteristics in food products. Cinnamyl isovalerate can be compared with other ester-type flavoring agents, such as ethyl butyrate or isoamyl acetate, which also contribute fruity or floral notes to flavor formulations. While all these esters share a common functional purpose of imparting specific sensory impressions, they differ in their particular odor profiles. Ethyl butyrate, for instance, is often described as having a pineapple-like aroma, whereas isoamyl acetate may evoke banana notes. Cinnamyl isovalerate’s sensory profile is typically associated with fruitiness and floral nuances, making it suitable for certain applications where its specific character complements the overall flavor design. In terms of chemical structure, these esters vary by the length and branching of their carbon chains, which influences volatility and odor perception. Volatility plays a significant role in how quickly and intensely a flavor compound is perceived: more volatile molecules tend to reach olfactory receptors rapidly, contributing to immediate sensory impressions. Structural differences among esters also affect solubility in aqueous and lipid phases of food systems, which can influence how they are integrated into formulations. For example, an ester with higher solubility in lipids might be more suitable for fat-rich products. Another point of comparison is regulatory status. Many commonly used flavoring esters are recognized under similar regulatory provisions that emphasize use in minimal quantities consistent with good manufacturing practices. The frameworks governing these compounds often rely on expert evaluations that consider metabolism, exposure, and toxicological data to determine whether typical use patterns are consistent with safety. While specific numeric acceptable daily intake values may vary or remain unspecified for certain compounds, expert panels often conclude that typical exposures do not pose safety concerns. By comparing cinnamyl isovalerate with other ester flavoring agents, it becomes clear that while the functional role — contributing specific olfactory and taste-driven nuances — is shared across the class, individual compounds offer unique sensory contributions and must be selected based on target flavor profiles. Understanding these differences helps formulators create balanced and appealing flavors while ensuring compliance with regulatory expectations and safety considerations.

Common Food Applications Narrative

Cinnamyl isovalerate is incorporated into a variety of food products where specific fruity or floral sensory profiles are desirable. In the realm of confectionery, for example, fruit-flavored candies and sweets often include a blend of esters and other flavoring agents to emulate natural fruit essence. The nuanced combination of these compounds, including cinnamyl isovalerate, can contribute to an overall profile that consumers associate with apple, pear, or other fruit notes. Similarly, in beverages that aim to deliver a refreshing fruit taste, flavor chemists may select cinnamyl isovalerate as part of a broader flavor blend to enhance perceived sweetness and complexity. In such formulations, the compound’s volatility and odor characteristics work in concert with other ingredients to deliver a consistent flavor experience when the beverage is consumed. Baked goods and desserts also represent categories where cinnamyl isovalerate can play a role. In products such as pastries, cakes, or fruit-flavored fillings, the careful integration of flavoring agents helps achieve sensory attributes that complement the base recipe. The compound may be combined with natural extracts, sugar, and other esters to achieve a balanced flavor that resonates with consumer expectations. Its use in dairy-based desserts or puddings follows a similar logic: as part of a carefully calibrated mixture of flavoring materials, it contributes to an appealing aroma and taste profile that enhances the overall product experience. The inclusion of cinnamyl isovalerate in chewing gum and breath fresheners reflects another application where fruity or floral esters are prized. In these categories, flavor duration and immediacy are important attributes, and esters with distinct sensory impacts can help achieve those goals. By combining multiple flavor components, manufacturers aim to deliver a pleasant initial impression followed by sustained sensory perception. In addition, flavored syrups and toppings used in frozen desserts or breakfast foods may incorporate such esters to enrich the product’s flavor landscape. Across these diverse food applications, the decision to use cinnamyl isovalerate is guided by sensory objectives, regulatory compliance, and production considerations. While it is only one component among many in a flavor formulation, its contribution can be significant in shaping the consumer’s sensory experience.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: No authoritative EFSA evaluation URL found for numeric ADI

JECFA

  • Year: 2001
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent

Sources

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