CIS-4-HEPTENAL

CAS: 6728-31-0 FLAVORING AGENT OR ADJUVANT

CIS-4-HEPTENAL is an unsaturated aldehyde used in food and beverage flavorings to impart green, creamy, and fatty sensory notes.

What It Is

CIS-4-HEPTENAL is a chemical compound classified as a flavoring agent or adjuvant with the Chemical Abstracts Service Registry Number 6728-31-0. It is an unsaturated aldehyde with a seven-carbon chain featuring a cis-configured double bond that contributes to its distinct organoleptic properties, often described as green, fatty, creamy, and sometimes reminiscent of fried fats. This structure places it among aldehydes that are valued in flavor chemistry for their ability to deliver nuanced sensory effects in food formulations. The compound is known by multiple synonymous names, including 4-HEPTENAL and (Z)-4-Heptenal. It is not assigned a specific food additive number in the International Numbering System (INS) but is recognized in flavoring industry inventories and evaluations, such as those of the Flavor and Extract Manufacturers Association (FEMA) and the Joint FAO/WHO Expert Committee on Food Additives (JECFA). Its functional class is that of a flavoring agent, meaning it is used to enhance or modify the sensory profile of foods and beverages. CIS-4-HEPTENAL is a volatile organic compound that naturally occurs in various food matrices where lipid oxidation processes take place or where certain fermentation pathways are active. For example, it can be detected in dairy products, seafood, and plant-derived foods. Its presence contributes to sensory complexity, imparting characteristics that can enhance consumer perception of freshness or richness. The chemical’s classification as a flavoring agent or adjuvant reflects its role as a minor component in complex flavor systems rather than a primary nutrient or functional food ingredient. Its application in food systems is subject to regulatory frameworks governing flavoring substances. Understanding what CIS-4-HEPTENAL is also involves recognizing that it derives from broader structural classes of aldehydes that food scientists and flavorists manipulate to achieve targeted sensory outcomes. These outcomes may include enhancing creaminess in dairy analogs or adding green leafy notes to vegetable and herbal flavor profiles. Within the landscape of flavor additives, CIS-4-HEPTENAL is one of many specialized compounds that contribute to the nuanced sensory characteristics sought by product developers in the food industry.

How It Is Made

The production of CIS-4-HEPTENAL typically involves organic synthesis routes that generate the cis-configured double bond and aldehyde functional group with precision. Industrially, such unsaturated aldehydes can be synthesized through established organic reactions that build the carbon chain while controlling stereochemistry. These methodologies may include catalytic hydrogenation steps of precursor compounds, controlled olefin formation reactions, or rearrangement processes that yield the desired cis configuration. These synthetic approaches are rooted in classic organic chemistry techniques, enabling manufacturers to produce this compound at sufficient purity for use in flavor applications. Commercially available CIS-4-HEPTENAL is often supplied in a stabilized form that meets flavoring industry specifications. For example, flavor grade or food chemical codex (FCC) grade materials typically specify a minimum assay level (often reported at 98.0% as a sum of isomers) and limits on impurities, ensuring that the product delivers predictable sensory performance and conforms to technical quality standards. Such specifications are important in the flavor industry, where trace impurities or isomeric variations can significantly influence the sensory properties of the final formulation. In practical manufacturing settings, flavorists may work with CIS-4-HEPTENAL that has been produced under controlled reaction conditions and subsequently purified through distillation or chromatographic techniques. The purified compound is then incorporated into flavor blends at concentrations appropriate for the intended application. Unlike commodities such as sugar or salt, flavoring compounds like CIS-4-HEPTENAL are used at very low levels, often measured in parts per million or parts per billion, due to their potency and the risk of overpowering the product if used excessively. Because of its volatility and reactivity, handling and storage conditions for CIS-4-HEPTENAL require attention to solvent compatibility, temperature, and light exposure to preserve quality until use. These considerations are intrinsic to the processes by which flavoring chemicals are made and integrated into finished food products.

Why It Is Used In Food

CIS-4-HEPTENAL is used in food and beverage formulations because of its distinct sensory characteristics that enhance or modify flavor profiles. Particularly valued in dairy-related flavor systems, it can contribute green herbaceous effects, milky creamy nuances, and richness to caramel-like notes. These contributions allow flavorists to design complex sensory experiences that match consumer expectations for products such as flavored dairy beverages, confectionery, tea, and other prepared foods. The compound’s versatility also stems from its ability to blend with other flavor components to achieve balanced and harmonious profiles. Additionally, some of CIS-4-HEPTENAL’s flavor effects arise from its integration into systems where oxidative processes yield volatile aldehydes. In such contexts, it may serve as a desirable component that accentuates notes that align with product positioning, such as freshness in leafy or herbal flavors. Because flavor compounds act at very low concentrations compared with bulk ingredients, their use is carefully calibrated to meet desired sensory outcomes without significantly impacting nutritional or functional properties of the food. CIS-4-HEPTENAL’s inclusion in formulations therefore reflects its technical function as a potent sensory modifier rather than as a substantive ingredient. Flavoring agents like CIS-4-HEPTENAL are typically used under the principle of good manufacturing practice (GMP), meaning that they are incorporated at the minimum level needed to achieve the intended effect. This principle supports both consumer safety and cost-effective formulation. The rationale for using such agents is not to alter the nutritional profile of a food but to enhance consumer appeal by refining aroma and taste attributes. In complex flavor systems, multiple such agents are combined to simulate natural flavors, mask undesirable notes, or emphasize desirable characteristics. CIS-4-HEPTENAL’s green, creamy, and fatty sensory contributions make it a valuable tool for achieving nuanced flavor signatures in a broad range of food applications.

Adi Example Calculation

To illustrate how acceptable daily intake (ADI) considerations are applied, one might consider a hypothetical body weight for illustrative purposes only. For example, imagine a person with a body weight of 70 kilograms (kg). If a regulatory evaluation had assigned a numeric ADI of X milligrams per kilogram body weight per day for a given flavoring agent, the total daily exposure considered acceptable would be 70 times X milligrams. In such a scenario, a compound used at trace levels in food formulations would need to be consumed in quantities sufficient to reach that threshold before safety concerns would be implicated. However, for CIS-4-HEPTENAL, international evaluations have not assigned a specific numeric ADI; instead, regulatory bodies have concluded that typical use levels in flavor applications do not present safety concerns. In this context, the illustrative calculation underscores how numeric ADI values would be used if available but also highlights that such values are not always necessary to establish safe use when typical exposures are understood to be low. The key takeaway is that safety evaluations incorporate both toxicological data and realistic exposure estimates, focusing on ensuring that consumption through food use remains within boundaries that are considered safe over a lifetime. This example is for conceptual understanding only and does not provide personal health guidance.

Safety And Health Research

Regulatory evaluations of CIS-4-HEPTENAL focus on its safety when used as a flavoring agent in foods at levels consistent with good manufacturing practice. International bodies such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA) have reviewed this compound and determined that its use in flavor applications does not raise safety concerns at typical intake levels associated with such use. This assessment reflects consideration of available toxicological data and the compound’s functional role as a flavoring agent, which entails use at relatively low concentrations in food products. The absence of identified safety concerns at these exposure levels provides the basis for its continued inclusion in flavor inventories and regulatory frameworks that permit synthetic flavoring substances under defined conditions. Beyond regulatory evaluations, food chemistry research often investigates compounds like CIS-4-HEPTENAL in the context of their occurrence in natural food systems, including studies of lipid oxidation pathways that yield such aldehydes. Such research contributes to understanding how this compound and others influence sensory quality and how they may serve as markers of oxidative changes in foods. While these studies inform quality control and flavor science, they do not constitute direct safety evaluations but rather highlight the compound’s sensory and chemical behavior in complex matrices. Overall, safety and health research pertaining to CIS-4-HEPTENAL centers on its role as a flavoring substance used at low concentrations, with regulatory bodies evaluating its use within broader frameworks rather than establishing specific numeric thresholds for intake. This approach aligns with how many flavoring agents are managed internationally, where technical evaluations inform permissible use under principles of good manufacturing practice rather than fixed numerical limits. For consumers and formulators, this means that the compound’s incorporation into foods is governed by established regulatory and safety evaluation mechanisms that prioritize minimal effective use to achieve desired sensory outcomes.

Regulatory Status Worldwide

CIS-4-HEPTENAL is referenced in regulatory contexts as a synthetic flavoring substance allowed for use in foods under general provisions for flavoring agents. In the United States, flavoring substances that are classified as synthetic flavoring agents may be used in food according to the conditions set out in Title 21 of the Code of Federal Regulations, Part 172, Section 172.515, which permits synthetic flavoring substances and adjuvants to be safely used in food when employed at levels consistent with good manufacturing practice and the minimum needed to achieve the intended sensory effect. This regulatory framework establishes the conditions under which CIS-4-HEPTENAL may be incorporated into food products when used as a flavoring agent, though it does not assign a unique CFR listing specific to this compound by name. The regulation itself outlines a broader category of permitted synthetic flavoring substances under which CIS-4-HEPTENAL falls. Such inclusion reflects recognition that compounds evaluated and used in flavor technology may be integrated into food formulations under these general provisions, provided their use aligns with principles of good manufacturing practice. Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated this compound as a flavoring agent (JECFA Number 320) and does not identify safety concerns at current estimated levels of intake when used in flavor applications. This evaluation suggests that no specific acceptable daily intake (ADI) value was assigned numerically, but the compound’s use at typical levels in flavor formulations is not associated with identified toxicological risks under those conditions. Regulatory frameworks in other regions may also recognize CIS-4-HEPTENAL within lists of flavoring agents or fragrances subject to respective national or supranational standards, and food additive inventories may include it with reference to industry evaluation numbers such as the Flavor and Extract Manufacturers Association (FEMA) number. Overall, CIS-4-HEPTENAL’s regulatory status worldwide is guided by general provisions that permit synthetic flavoring agents under controlled conditions focused on safety and adherence to good manufacturing practice.

Taste And Functional Properties

CIS-4-HEPTENAL exhibits a potent sensory profile characterized by a combination of green, fatty, creamy, and sometimes vegetal or milky notes. At low concentrations, the compound can contribute subtle nuances that enhance perceived richness and freshness in food products. Its functional properties as a flavoring agent are rooted in the structure of its unsaturated aldehyde moiety, which interacts with olfactory receptors to produce distinct sensory impressions that are often associated with dairy or vegetal flavor components. These sensory effects can vary based on the food matrix, concentration used, and the presence of other flavoring compounds. The compound’s volatility and relative solubility in fats and alcohols influence how it performs in different food systems. Because it is insoluble in water but more soluble in ethanol and oils, CIS-4-HEPTENAL is particularly effective in applications where it can partition into fat or lipid phases, such as in dairy analogs, sauces, or flavored oils. Its volatility also means that it contributes to aroma perception, which is a critical component of overall flavor. However, this volatility necessitates careful consideration of processing conditions; excessive heat or prolonged exposure to air can lead to losses or transformations that affect the sensory profile. From a functional perspective, flavoring agents like CIS-4-HEPTENAL do not significantly contribute to the technological properties of foods such as texture or shelf stability. Their effect is largely perceptual, shaping how consumers experience the taste and aroma of a product. As with many aldehydes, the compound’s reactive nature means it must be handled with appropriate stability measures to maintain performance until consumption. In practice, this may include storage under controlled temperatures and protection from light and oxidation. Overall, CIS-4-HEPTENAL’s taste and functional properties center on its ability to deliver specific sensory impressions that enrich flavor formulations in a targeted manner.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a safety threshold established by scientific committees to indicate the amount of a substance that can be consumed daily over a lifetime without appreciable risk, based on toxicological data. For flavoring agents such as CIS-4-HEPTENAL, specific numeric ADI values are not always assigned when regulatory evaluations conclude that typical use levels do not pose safety concerns. In such cases, bodies like the Joint FAO/WHO Expert Committee on Food Additives (JECFA) may conclude that no safety concerns exist at current expected intakes, which effectively serves a similar purpose by assuring that ordinary consumption through food use is considered safe. It is important to emphasize that the concept of ADI applies to lifelong exposure and incorporates significant safety margins to account for variability among individuals and uncertainties in data. An ADI is not a recommended intake but rather a conservative benchmark used by regulators and food scientists to assess safety. When a compound like CIS-4-HEPTENAL is evaluated and found not to raise safety concerns at expected use levels, it means that exposure from normal food consumption is within bounds that regulatory bodies consider acceptable. In practical terms, flavoring agents are used at very low levels, and total dietary exposure to any single compound of this class is typically a small fraction of quantities associated with safety thresholds, thereby supporting their regulated use in food products. For consumers and those involved in product formulation, understanding ADI helps contextualize how regulatory evaluations support the safe use of flavoring agents. The lack of a specific numeric ADI for CIS-4-HEPTENAL reflects a determination that typical use leads to exposures that do not warrant a defined numeric limit, rather than an indication of uncertainty about safety. This approach is consistent with international practices for evaluating flavoring substances.

Comparison With Similar Additives

CIS-4-HEPTENAL can be compared to other flavoring agents that contribute distinct sensory notes while being used at low concentrations. For example, hexanal is another aldehyde used in flavor applications, often imparting grassy or green notes, similar to CIS-4-HEPTENAL but with a slightly different sensory profile weighted toward fresh cut grass. Both compounds are volatile and contribute to aroma formation in food products, yet they differ in chain length and specific odor characteristics, which influences how they are used in flavor design. Such comparisons help flavorists choose among multiple aldehydes to achieve desired sensory nuances. Another related compound is trans-2-heptenal, which also belongs to the class of unsaturated aldehydes used in flavor chemistry. While trans-2-heptenal shares some sensory attributes with CIS-4-HEPTENAL, its geometric configuration alters how olfactory receptors perceive its aroma, often yielding more fatty, green, or citrus undertones. These differences illustrate how slight changes in molecular structure can have meaningful impacts on sensory perception. Less closely related but still within the realm of flavoring agents is ethyl butyrate, an ester that imparts fruity notes and is widely used in beverage and confectionery formulations. Unlike aldehydes, esters tend to provide sweet, fruity characteristics rather than the green or creamy notes associated with unsaturated aldehydes. Comparing CIS-4-HEPTENAL with an ester such as ethyl butyrate highlights the diversity of functional roles within the flavor additive space, where distinct classes of compounds are selected based on sensory targets. Such comparisons support targeted formulation strategies that leverage the unique properties of each additive to craft balanced and appealing flavor profiles.

Common Food Applications Narrative

In the food and beverage industry, CIS-4-HEPTENAL finds niche applications where nuanced sensory enhancement is desired. It is most commonly encountered in formulations designed to replicate or emphasize dairy-related flavors, such as in flavored milks, creams, or yogurt-inspired beverages. In these systems, CIS-4-HEPTENAL’s green and creamy notes support the perception of freshness and richness, allowing product developers to achieve sensory profiles that align with consumer expectations for indulgent dairy flavors. The compound may also be used in confections where caramel or buttery nuances are targeted, such as in candies or dessert sauces. Beyond dairy-inspired products, CIS-4-HEPTENAL can be incorporated into tea flavors, especially those aiming to capture the character of freshly brewed teas. Its ability to subtly influence aromatic perception makes it a tool for enhancing complexity in beverage applications. In savory contexts, flavorists may leverage its green or herbal aspects to complement vegetable or plant-based flavor systems, contributing to balanced sensory profiles that resonate with broader consumer trends toward natural flavor experiences. CIS-4-HEPTENAL’s integration into these applications illustrates how flavoring agents operate behind the scenes to refine and elevate product character. In practical use, food manufacturers do not add CIS-4-HEPTENAL in isolation; rather, it is blended with other flavor ingredients to create cohesive and desirable flavor constructs. This collaborative use of multiple flavor agents allows for the replication of complex sensory signatures that mirror natural foods or evoke specific taste memories. The compound’s presence in these flavor blends underscores the multifaceted nature of modern flavor design, where technical understanding of sensory chemistry guides ingredient choice. For consumers, the result is a product that delivers a rich and satisfying sensory experience, even though the specific contribution of any single compound like CIS-4-HEPTENAL may be subtle within the broader flavor profile.

Safety & Regulations

FDA

  • Notes: Included under general synthetic flavoring substances provisions without a unique CFR listing specific to this compound.
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: No specific EFSA evaluation with numeric values found.

JECFA

  • Notes: JECFA evaluation did not assign a numeric ADI; typical use considered safe.
  • Adi Display: No safety concerns at typical use levels per JECFA evaluation

Sources

Comments

No comments yet. Be the first to share!