CIS-3-HEXENOIC ACID

CAS: 1775-43-5 FLAVORING AGENT OR ADJUVANT

CIS-3-HEXENOIC ACID is an unsaturated aliphatic acid used as a flavoring agent in food and beverage formulations, characterized by a green, fruity aroma profile.

What It Is

CIS-3-HEXENOIC ACID is an organic compound defined by the CAS Registry Number 1775-43-5 and classified in technical contexts as a flavoring agent or adjuvant. It belongs to a class of unsaturated aliphatic carboxylic acids with a cis double bond at the 3-position of a six-carbon chain. This structural arrangement differentiates it from its trans counterpart and other isomers. The compound’s identity is supported in scientific chemical databases, which list its stereochemical InChIKey and molecular formula (C6H10O2). It is recognized for its sensory properties, often contributing green and fruity notes in flavor profiles. The scientific name and multiple synonyms reflect its presence in flavor chemistry literature, where it is discussed as a functional ingredient in aroma and taste formulations. In flavor science, CIS-3-HEXENOIC ACID is considered within the broader category of volatile organic acids that contribute to complex sensory perceptions in food products. Beyond its technical use, it also appears in research contexts where its physical properties, such as volatility and partition coefficients, are characterized. While it is not universally familiar outside flavor chemistry and related industries, its inclusion in international flavoring evaluations highlights its relevance in regulatory and safety assessments. Chemical databases such as the JECFA listing provide authoritative classification for this substance. The compound’s inclusion in flavoring inventories indicates its potential incorporation in food systems subject to evaluation under food additive guidelines. It should be noted that detailed chemical attributes such as its odor profile, molecular weight, and structural identifiers are consistently documented across reputable sources.

How It Is Made

The production of CIS-3-HEXENOIC ACID involves chemical synthesis routes that start from simpler organic precursors. Industrial and laboratory synthesis approaches leverage well-established organic reactions to assemble the six-carbon backbone and introduce the unsaturated cis double bond. Common synthetic strategies include oxidation of the corresponding cis-3-hexenol or hydrolysis of cis-3-hexenyl derivatives. These pathways are typical for preparing unsaturated carboxylic acids with defined stereochemistry. In research and industrial settings, the stereoselective formation of the cis double bond is a critical quality consideration, as configuration influences both sensory properties and regulatory classification. For laboratory-scale preparations, oxidation reactions of alcohol intermediates can yield the desired acid with controlled stereochemistry. In larger-scale or commercial synthesis, processes that start from selectively functionalized precursors are often optimized to improve yield and minimize by-products. Purity specifications for flavoring agents such as CIS-3-HEXENOIC ACID are developed in part through international compendia that outline analytical requirements for identity and quality. These specifications focus on chromatographic purity, residual solvents, and other chemical attributes relevant to food-grade applications. In practical terms, manufacturers producing this compound for use in flavor formulations must adhere to quality control measures appropriate for food ingredients, whether sourced from natural materials or synthesized chemically. The compound’s stability, handling, and storage implications derive from its organic acid nature and need to be managed consistently in manufacturing environments.

Why It Is Used In Food

CIS-3-HEXENOIC ACID is utilized in food applications primarily for its flavoring properties. As a volatile organic acid, it contributes distinct sensory attributes that can enhance the complexity of flavor profiles, particularly in formulations seeking green, fruity, or slightly acidic nuances. Flavors in foods and beverages are often carefully blended from multiple such compounds to achieve a balanced and appealing sensory experience for consumers. In technical terms, flavoring agents like CIS-3-HEXENOIC ACID are chosen because they interact with olfactory receptors in ways that complement other aromatic ingredients. Their inclusion in formulations allows flavorists to fine-tune the bouquet of a product, whether to emphasize freshness, fruitiness, or other descriptive characteristics. These functional contributions are valuable in products ranging from beverages and confectionery to dairy and savory applications. The decision to use a specific flavoring compound reflects both sensory goals and regulatory acceptance within food systems. Flavoring agents are evaluated for safety in the context of anticipated dietary exposure, and decisions about their incorporation hinge on such evaluations. CIS-3-HEXENOIC ACID’s assessment by international expert committees underscores its role as a technically useful ingredient when used within established guidelines and current use levels. Such evaluations support informed use by formulators while ensuring that sensory quality does not compromise food safety.

Adi Example Calculation

To illustrate how an acceptable daily intake (ADI) might be applied, consider a hypothetical compound with an ADI of X mg/kg body weight per day. For a person weighing 70 kg, the daily intake corresponding to the ADI would be calculated as 70 multiplied by X. This hypothetical calculation shows how regulators translate a per-body-weight safety threshold into a daily intake figure for an individual. In the case of CIS-3-HEXENOIC ACID, regulatory evaluations have not established a numeric ADI because the conclusion was that there is no safety concern at current intake levels when used as a flavoring agent. Therefore, the illustration above is generic and not specific to this compound. It demonstrates the underlying principle of ADI calculations rather than prescribing a value for this particular substance. Such illustrative examples are useful for understanding risk assessment frameworks, but they do not replace regulatory determinations or personal dietary planning. Actual intake levels and safety evaluations depend on compound-specific data and regulatory guidance.

Safety And Health Research

Safety and health research concerning food flavoring agents like CIS-3-HEXENOIC ACID focuses on evaluating potential toxicity, metabolism, and exposure at levels anticipated from normal dietary use. International expert committees such as JECFA undertake systematic reviews of available data related to chemistry, toxicology, and intake estimates. Such evaluations consider endpoints including general toxicity, organ-specific effects, and any indications of genotoxicity or carcinogenicity in available studies. In the case of CIS-3-HEXENOIC ACID, JECFA’s assessment concluded that, at current levels of intake in food, there is no safety concern when the compound is used as a flavoring agent. This type of conclusion reflects a balance of available evidence where adverse effects are not anticipated at levels typical of flavoring use. It should be noted that the absence of a formal numeric acceptable daily intake (ADI) value in JECFA’s report reflects a safety determination rather than an absence of data; in many flavoring evaluations, safety is inferred from a body of evidence showing that exposures are orders of magnitude below levels associated with toxicity. Research beyond formal regulatory evaluations may explore additional aspects of a compound’s biological interactions, but such work does not necessarily change regulatory conclusions unless it identifies specific risks at realistic exposure levels. It is also important to recognize that most flavoring agents are used in relatively low concentrations compared to bulk food ingredients, which further limits potential exposure. Safety evaluations are periodically revisited as new data emerge, ensuring that regulatory positions remain aligned with current scientific understanding.

Regulatory Status Worldwide

The regulatory status of CIS-3-HEXENOIC ACID reflects evaluation by international expert bodies responsible for assessing flavoring agents in food. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated the compound and assigned it a functional classification as a flavoring agent under the JECFA number 2181. In its evaluation, JECFA concluded that there is no safety concern at current levels of intake when used as a flavoring agent. This assessment provides a scientific basis for its use in food systems where flavoring agents are permitted under applicable national frameworks (see sources). In the United States, the compound is listed in the FDA’s Substances Added to Food inventory (formerly EAFUS) as a flavoring substance. Inclusion in this inventory indicates recognition of the substance in the context of food ingredient inventories, but it does not in itself constitute an affirmative statement of approval under specific Code of Federal Regulations sections. Regulatory oversight in different regions varies, and individual jurisdictions may have specific labeling or usage requirements tied to their food laws. In other jurisdictions, similar inventories and flavoring evaluations are maintained by competent authorities, with reference to international standards where appropriate. The regulatory acceptance of CIS-3-HEXENOIC ACID is tied to expert safety evaluations and its use at levels consistent with customary practice in flavoring. Manufacturers and formulators must ensure that their use aligns with the applicable regulatory framework in each market where products are sold.

Taste And Functional Properties

CIS-3-HEXENOIC ACID exhibits sensory properties that are described in flavor science as green, fruity, and slightly acidic. These descriptive terms reflect how the compound interacts with human olfactory and gustatory receptors, contributing nuanced aromatic complexity to food products. Because of its volatility and aromatic profile, it is typically considered part of a broader portfolio of flavoring substances rather than a dominant flavor on its own. From a functional standpoint, compounds of this chemical class often exhibit limited water solubility but can be readily incorporated into emulsions, alcohol-based flavor systems, or encapsulated flavor delivery vehicles. Their behavior in food matrices depends on factors such as pH, temperature, and interaction with other ingredients. The compound’s stability under processing conditions is also an important consideration; while some flavoring agents are stable across a range of temperatures, others may degrade or transform during heating or prolonged storage, affecting both safety and sensory outcomes. Understanding the balance between sensory contribution and functional performance is central to flavor formulation. Compounds like CIS-3-HEXENOIC ACID are selected based on their ability to complement other ingredients without overwhelming the overall profile. The strength of aroma, threshold of perception, and compatibility with matrix components all play into decisions about when and how much to include. In practice, flavorists rely on sensory panels and analytic chemistry to gauge the performance of such compounds and optimize their use for desired product characteristics.

Acceptable Daily Intake Explained

The concept of an acceptable daily intake (ADI) is central to regulatory toxicology and food safety assessment. An ADI represents an estimate of the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, based on available toxicological data. It is expressed relative to body weight, typically as milligrams per kilogram of body weight per day. An ADI is often derived by identifying the highest dose in animal studies that does not produce adverse effects and applying uncertainty factors to account for differences between species and human variability. For flavoring agents such as CIS-3-HEXENOIC ACID, regulatory evaluations sometimes conclude that anticipated intake levels from food use are so low that a formal numeric ADI is not necessary. In such cases, expert bodies may state that there is no safety concern at current levels of intake. This type of conclusion does not imply that the compound is without any potential toxicity at high doses; rather, it reflects a judgment that typical dietary exposure is far below any level associated with adverse effects based on available evidence. Understanding the ADI concept helps consumers and professionals interpret regulatory decisions. When an ADI is established, it provides a quantitative benchmark for safety assessments. When a formal ADI is not specified, as in the case of certain flavoring agents, the regulatory conclusion of no safety concern at current levels serves a similar purpose by indicating that normal use does not raise safety issues.

Comparison With Similar Additives

When comparing CIS-3-HEXENOIC ACID with other flavoring agents, it is helpful to look at compounds that share functional roles or sensory characteristics. For example, other organic acids and volatile aroma compounds may also contribute green, fruity, or slightly acidic notes in flavor formulations. Differences among such compounds can include volatility, intensity of aroma, solubility in food matrices, and sensory threshold values. Another comparison is with related unsaturated acids that might have similar structural features but different sensory outcomes. The specific configuration of cis double bonds often alters how a compound interacts with olfactory receptors compared to trans isomers or saturated analogs. Formulators select particular compounds based on these nuanced differences to achieve a desired balance of aroma and taste. From a regulatory perspective, many flavoring agents undergo similar evaluations by expert committees such as JECFA or are listed in flavor inventories maintained by food safety authorities. While the safety conclusions may be comparable for substances with low anticipated intake, variations in regulatory decisions can arise due to differences in available toxicological data or in how widely a compound is used. Comparing CIS-3-HEXENOIC ACID with other well-characterized flavoring agents highlights the importance of context in both sensory application and safety evaluation.

Common Food Applications Narrative

CIS-3-HEXENOIC ACID finds its way into a wide range of food applications where nuanced flavoring is desired. In beverage formulations, particularly fruit-flavored drinks and mixers, its green and fruity nuances can accentuate freshness and aromatic complexity. These sensory enhancements are especially valuable in products that aim to mimic or amplify natural fruit notes without resorting to high levels of sugar or artificial sweeteners. In confectionery and bakery products, ingredients that deliver subtle aromatic depth are often blended with other flavoring agents to create multi-dimensional sensory experiences. CIS-3-HEXENOIC ACID can contribute complementary green or fruity facets that round out sweetness or other dominant flavor components. Its use in dairy-based desserts and fermented products reflects a similar logic: augmenting the perceived naturalness of flavor without compromising texture or mouthfeel. Savory products, including sauces and dressings, sometimes employ green or fruity acid notes to balance fat and salt, providing a refreshing contrast. The compound’s role in these systems underscores the versatility of selected flavoring acids in meeting consumer expectations for sensory balance and complexity. Across all these applications, the compound is part of carefully curated blends where technical function and sensory outcome converge. Its contribution is calibrated to the overall product profile and regulatory considerations, ensuring that the final food experience aligns with both quality and safety expectations.

Safety & Regulations

FDA

  • Notes: Inclusion in the FDA Substances Added to Food inventory does not by itself confirm approval under specific CFR sections; specific regulatory status must be confirmed with current CFR listings.

EFSA

  • Notes: No specific EFSA evaluation reference found for numeric ADI; regulatory assessment by EFSA not identified in sources.

JECFA

  • Notes: JECFA conclusion indicates no safety concern rather than a numeric ADI; year of evaluation not explicitly shown on the d entry.
  • Adi Display: No safety concern at current intake levels when used as a flavouring agent

Sources

Comments

No comments yet. Be the first to share!