ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL

CAS: 28069-74-1 FLAVORING AGENT OR ADJUVANT

ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL is a synthetic flavouring compound found in some foods and flavour formulations; it has been evaluated by JECFA with no safety concern at current levels of intake.

What It Is

ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL is an organic chemical compound classified as a flavouring agent or adjuvant used in food and beverage applications to impart specific aroma and taste characteristics. It carries the CAS Registry Number 28069-74-1 and belongs to the acetal class of compounds, which are characterized by two alkoxy groups attached to the same carbon atom. This additive may be referred to by a variety of synonyms reflecting its structure and sensory role, such as ethyl cis-3-hexenyl acetal and leaf acetal, with the cis configuration indicating the geometric orientation of the hexenyl portion of the molecule. As a flavouring agent, it is often used to provide green, herbaceous and leafy notes in formulations where subtle vegetal or fresh notes are desirable, enhancing the sensory profile of a product without introducing off-flavours. This compound has been identified and characterized in flavour chemistry databases and by suppliers of analytical standards. Its role as a flavouring agent is supported by evaluations from expert scientific panels that consider both naturally occurring and synthetic flavour components. The flavour perception associated with ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL reflects its chemical structure and the interaction of its functional groups with olfactory receptors, giving rise to sensory descriptors such as fresh, green and leafy, which are commonly used in flavour creation and matching. Because flavouring agents are used at trace levels, their sensory impact typically arises even at small concentrations in food or beverage matrices. The flavouring functions of this compound are distinguished from other roles such as preservatives, emulsifiers or colourants. It does not impart colour or structural stability to food products; rather, its primary function is sensory enhancement. In regulatory frameworks, flavouring agents are generally evaluated for safety based on exposure estimates and toxicological profiles, with organisations such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA) providing independent assessments to support the safe use of such substances in foods and beverages.

How It Is Made

The production of ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL generally involves an acetalisation reaction, in which acetaldehyde or a suitable aldehyde derivative reacts with an alcohol in the presence of an acid catalyst. For this specific compound, the cis-3-hexenyl alcohol moiety is combined with ethylaldehyde under controlled conditions to form the acetal linkage. Acetalisation reactions are widely used in organic synthesis to protect aldehyde functional groups or to produce stable flavouring compounds with defined sensory properties. Commercial production methods typically emphasise high purity and controlled reaction conditions to minimise by-products and ensure the resulting material meets appropriate quality specifications for flavour applications. The reaction parameters, such as temperature, catalyst selection and reaction time, are optimised to maximise yield while maintaining the desired stereochemistry (cis configuration) of the hexenyl substituent. Following synthesis, purification steps such as distillation or chromatography may be used to achieve the purity levels required for food flavour applications. These processes must conform to good manufacturing practices, particularly when the product is intended for use in consumable goods. Manufacturers of flavouring agents often provide analytical documentation, such as certificates of analysis and safety data sheets, detailing the identity, purity and physical properties of the compound, including molecular weight, boiling point and appearance. Quality control in the production of flavouring compounds is essential, as impurities or unwanted isomers can affect both the sensory performance and safety profile of the additive. Suppliers typically offer this compound with a stated purity (e.g., greater than 97 percent) based on gas chromatography or similar analytical techniques, ensuring that the material supplied to flavour houses or food formulators is consistent with industry expectations.

Why It Is Used In Food

ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL is used in food and beverage formulations primarily for its role as a flavouring agent that contributes specific sensory characteristics. Flavouring agents are integral to creating appealing taste profiles, and this compound is selected for applications where a green, fresh or leafy aromatic note is desirable. These sensory attributes can enhance consumer perception of products such as beverages, sweets or processed foods by adding complexity, balance or harmony to the flavour profile. In food science and formulation, flavouring agents like ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL are used to fine-tune the organoleptic properties of products without significantly altering other technological characteristics such as texture or appearance. Because this compound has a distinctive herbaceous note, it can complement fruity, floral or vegetal flavour systems, making it useful in confections, fruit preparations, beverages and savoury applications that benefit from a natural-green character. Its use may also support the masking of off-notes or the enhancement of other flavour ingredients present in a formulation. Flavouring agents are typically used in very small quantities, often at levels measured in parts per million, to achieve the desired sensory effect. The decision to include a specific flavouring agent is guided by sensory evaluation and consumer testing, ensuring that the final product meets the desired taste profile and market expectations. Food formulators select compounds like ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL based on both sensory attributes and compatibility with other ingredients in the formulation, balancing intensity, longevity and overall flavour perception.

Adi Example Calculation

To illustrate how intake might be considered in a hypothetical scenario, consider a food product consumed daily that contains a flavouring formulation with ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL at trace levels. If the average daily intake of the compound from all foods were estimated to be a few micrograms per person per day, that amount would be far below the levels at which toxicological effects might be observed in studies. Because expert evaluations conclude that there is no safety concern at typical intake levels, this example underscores that dietary exposure to flavouring agents is generally orders of magnitude lower than doses associated with toxicological endpoints in laboratory studies. It is important to emphasise that this calculation is illustrative and not a specific guidance for consumers. The actual exposure depends on the types of foods consumed, their flavouring compositions and individual consumption patterns. However, the principle in safety evaluation is that flavouring agents used in accordance with good manufacturing practices result in low exposures that remain within the bounds of safety identified by expert committees.

Safety And Health Research

Safety and health research related to ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL focuses on toxicological evaluations and exposure assessments conducted by international expert committees. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) reviewed this compound, along with a range of structurally related aliphatic acetals, and concluded that there is no safety concern at current levels of intake when used as a flavouring agent, reflecting a comprehensive review of available toxicological data, metabolic considerations and exposure estimates. These evaluations consider how the compound is metabolised, expected levels of dietary exposure and potential toxicological endpoints, guiding risk assessment for human consumption. Aliphatic acetal compounds such as this one are expected to hydrolyse in the acidic environment of the stomach to yield component alcohol and aldehyde fragments, which are further metabolised by normal physiological processes. Toxicological studies generally assess acute toxicity, repeated dose toxicity, genotoxicity and other end points relevant to food safety, with findings informing expert committee conclusions about acceptability at current exposure levels. It is also important to distinguish between flavouring agents used at very low concentrations and compounds present at higher levels in food additives where different safety considerations may apply. Regulatory and scientific reviews emphasise that toxicological risk is dependent on both dose and exposure; available evaluations for this flavouring agent indicate that intake from food use is well below levels of concern. These assessments are documented in publications and compendia prepared by JECFA, which provide detailed context about the basis for safety conclusions. While ongoing research continues to refine understanding of flavouring agent metabolism and effects, current evidence from authoritative evaluations supports the compound's continued use in flavour applications.

Taste And Functional Properties

ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL is known for its distinctive sensory qualities that can influence the overall flavour profile of a food or beverage product. Sensory descriptors often associated with this compound include green, herbaceous, leafy and fresh notes, which contribute a natural character to flavour systems. These sensory impressions are an important part of how the compound is perceived in complex mixtures, allowing it to complement or enhance other aromatic ingredients in a formulation. The functional behaviour of this compound in food systems is largely determined by its chemical structure and physical properties. As an acetal, it tends to be relatively stable under neutral to slightly alkaline conditions, though acetal linkages can hydrolyse in strongly acidic environments. This property influences how the compound is used in different food matrices, requiring formulators to consider pH and processing conditions to maintain sensory performance. Its solubility in organic phases means it can be incorporated effectively into flavour oils or emulsions used in various applications. Because flavouring agents are used at very low concentrations, their impact on texture or nutritional properties of the food is negligible. The intensity of the sensory effect depends on factors such as the concentration used, the nature of the food matrix and the presence of other flavour components. Taste and aroma perception also vary among individuals, meaning formulators must evaluate the compound in sensory panels to calibrate its use. It is also important to consider volatility; compounds with volatile characteristics may contribute to top-notes in aroma, influencing how consumers experience the product upon opening or initial consumption.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) represents a level of a substance that can be consumed daily over a lifetime without appreciable health risk, based on expert toxicological evaluation. For many flavouring agents, including ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL, formal numeric ADI values are not established because expert committees conclude that there is no safety concern at current levels of intake when used as intended. In such cases, the compound is considered acceptable for flavour use at levels that result in typical dietary exposure, with evaluations focusing on risk assessment methodologies and conservative exposure estimates rather than numerical ADI limits. For regulatory purposes, expert panels such as JECFA review toxicological data and expected intake from food use to determine whether there is a reasonable certainty of no harm. Because flavouring agents are used at very low concentrations and dietary exposure is correspondingly low, the conclusion of no safety concern implies that the estimated intake is below any threshold associated with potential adverse effects. This approach recognises that flavouring agents differ from nutrients or food additives with technological roles requiring specific numerical limits.

Comparison With Similar Additives

ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL can be compared with other flavouring agents in the class of aliphatic acetals, such as acetal (ethanal diethyl acetal) and other alkyl acetals used for green or fruity notes in food formulations. These compounds share structural features that influence their sensory properties and metabolic pathways. Like other acetals, they tend to be hydrolysed to corresponding alcohols and aldehydes during digestion, and expert evaluations often group them structurally for safety assessments. Comparisons among these compounds highlight similarities in sensory characteristics and exposure profiles, supporting the conclusion that they pose no safety concern at typical use levels. Flavouring agents outside the acetal class, such as esters (e.g., ethyl butyrate) or aldehydes (e.g., citral), offer different sensory profiles and metabolic features but are evaluated according to similar principles of toxicology and exposure assessment. Understanding the relative functional properties of different classes of flavour molecules helps formulators select appropriate agents for specific sensory goals while considering safety evaluations conducted by expert panels. The broader context of flavour chemistry encompasses diverse compounds with varied sensory impacts, all assessed within frameworks that consider both exposure and toxicological data to ensure consumer safety.

Common Food Applications Narrative

In flavour formulation and food product development, ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL finds application in a variety of categories where a bright, green or leafy note enhances overall sensory appeal. For example, in confectionery applications such as gummy candies, hard candies and fruit-flavored sweets, this compound can contribute nuanced aroma and taste components that round out the flavour profile and support the primary notes of fruits or botanicals. Similarly, in non-alcoholic beverages like fruit punches, iced teas and soft drinks, carefully calibrated amounts of this flavouring agent help achieve fresh, clean aromatic accents that elevate the perceived quality of the drink. In dairy-based desserts and gelled desserts, the inclusion of ACETALDEHYDE ETHYL CIS-3-HEXENYL ACETAL may be used to complement fruit or botanical flavours, adding a subtle layer of complexity without distracting from the core taste. Its use must be balanced with other sensory elements to ensure that the final product delivers a harmonious flavour profile that resonates with consumer expectations. Although not a primary flavour component in most applications, its role as a supporting aromatic accent makes it valuable in tailored formulations where the sensory objective is a refined, multi-dimensional profile. Food flavourists often describe this compound as contributing top-notes that are perceived early in the sensory experience, making it particularly useful in products where first impressions of aroma and taste are important. Given its botanical character, it may also be found in flavour systems designed to mimic natural fruit or plant extracts. These applications illustrate how additive flavouring agents are used to achieve specific consumer-desired sensory effects in a wide range of food products.

Safety & Regulations

FDA

  • Notes: No specific FDA approval indicated in the Substances Added to Food inventory; inclusion does not confirm formal regulation.

EFSA

  • Notes: No specific EFSA numerical ADI verified from authoritative sources.

JECFA

  • Year: 2001
  • Notes: JECFA concluded no safety concern at current intake levels; no numeric ADI given.

Sources

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