ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL

CAS: 63449-64-9 FLAVORING AGENT OR ADJUVANT

ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL is a synthetic flavoring compound used to impart green, leafy, and herbal notes in food and beverage formulations. It has been evaluated by international expert bodies for safety at typical levels of intake.

What It Is

ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL is an organic acetal compound belonging to a class of flavoring agents used in food and beverage formulations. This compound is identified by the CAS registry number 63449-64-9 and is characterized chemically as an acetal formed from acetaldehyde and cis-3-hexenyl alcohol. In flavor chemistry, it is often included in lists of synthetic flavoring substances for its distinctive aromatic profile, which is described as green, fresh, and herbaceous. Its functional role in food formulations is to contribute specific sensory notes without significantly altering other organoleptic properties. In industrial and regulatory contexts, flavoring agents are substances added to food products specifically to impart taste or aroma rather than to provide nutritional value. Flavoring agents can be derived from natural sources, synthesized chemically, or produced via fermentation, and they are subject to evaluation by food safety authorities. An acetal such as this one functions at low concentrations, where it interacts with olfactory receptors to enhance the perception of certain flavor profiles. It is typically used alongside other flavor compounds in complex mixtures designed to achieve a desired sensory effect. Synonyms and systematic identifiers include variants of the IUPAC name and structural descriptors that reflect its molecular configuration. The compound’s molecular formula is C14H26O2, and although structurally it is stable under specific conditions, it can undergo hydrolysis in acidic environments, reverting to its precursor aldehyde and alcohol components. This structural behavior is common for acetal linkages and factors into considerations for processing and storage in food systems.

How It Is Made

The production of ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL typically follows principles of acetal formation in organic synthesis. At its core, an acetal is formed by the reaction between an aldehyde and an alcohol under acid-catalyzed conditions. In this case, acetaldehyde, a simple aldehyde, is reacted with two equivalents of cis-3-hexen-1-ol, a primary alcohol, in the presence of an acid catalyst. The catalyst activates the carbonyl group of the acetaldehyde, enhancing its electrophilicity and facilitating nucleophilic attack by the alcohol. During the reaction, a hemiacetal intermediate forms, which then undergoes further transformation to yield the acetal product. This synthetic pathway is typical for generating stable acetal linkages, where the reaction conditions are controlled to favor complete conversion of the intermediate hemiacetal to the final acetal product. Factors such as temperature, catalyst strength, solvent choice, and stoichiometric balance influence yield and purity. After synthesis, purification steps such as distillation or chromatography are used to isolate the target compound and remove residual starting materials or byproducts. In practical settings, industrial-scale syntheses of flavoring agents involve rigorous quality control measures to ensure consistency and compliance with food safety standards. These measures include verification of structural identity, monitoring purity levels, and testing for residual catalysts. Synthetic routes are designed to be efficient and reproducible, and they may be adapted to minimize environmental impact by optimizing reagent use and waste management. Although the core chemistry is well understood, proprietary variations in catalysts and process parameters may be employed by manufacturers to improve production efficiency.

Why It Is Used In Food

Flavoring agents like ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL are used in food and beverage products to enhance or impart specific sensory qualities that contribute to the consumer’s overall taste experience. In the competitive landscape of food product development, achieving a desirable flavor profile is crucial for differentiating products, maintaining consistency, and meeting consumer expectations. This compound’s green and herbal aromatic characteristics can complement fruit, vegetable, and botanical flavor profiles, particularly in applications where freshness or natural notes are desired. The use of such synthetic flavoring agents allows food formulators to achieve consistent sensory attributes that may be difficult to obtain solely from natural ingredients due to variability in natural sources. For example, the intensity of natural green notes from botanical extracts can vary seasonally or by geographic origin. Incorporation of well-characterized synthetic flavorants provides stability across production batches. Additionally, synthetic agents are often used in reduced-calorie or reformulated products where traditional flavor sources may contribute unwanted calories or complexity. Importantly, flavoring agents serve solely to modify sensory perception; they do not provide nutritional value and are typically effective at very low concentrations. Their selection in a formulation is based on sensory evaluation, compatibility with other ingredients, stability under processing conditions, and regulatory approval status. ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL, with its characteristic aroma, is chosen when a formulation benefits from green, leafy, or fresh aromatic notes without overwhelming other flavors in the product.

Adi Example Calculation

To illustrate how an ADI would be used if it were established, imagine a hypothetical ADI of X mg/kg body weight per day for a flavoring agent. For a person weighing 70 kilograms (approximately 154 pounds), the calculated ADI would be 70 X mg per day. This calculation would represent the upper limit of daily intake considered safe over a lifetime. If typical use levels in flavored foods result in an estimated daily intake below that number, then exposure would be considered acceptable. In the case of ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL, a numeric ADI was not specified by JECFA, but this kind of calculation framework helps contextualize how regulators and risk assessors think about exposure and safety.

Safety And Health Research

Regulatory evaluations of flavoring agents like ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL focus on toxicological endpoints relevant to human exposure through food. These assessments consider factors such as acute toxicity, metabolism, potential for genotoxicity, and chronic effects observed in laboratory studies. The JECFA evaluation in 2007 concluded that there was no safety concern at typical levels of intake for this compound when used as a flavoring agent, which reflects a comprehensive review of relevant safety data available at that time. This type of evaluation typically integrates data from animal studies, in vitro tests, and knowledge of metabolic pathways to assess potential risks. In general, food flavoring agents are used at very low concentrations relative to total food intake, and their systemic exposure is correspondingly low. Expert panels consider both the potency of the flavoring compound and typical use levels across different food categories when assessing safety. Because ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL is an acetal, it has the potential to hydrolyze into constituent molecules under certain conditions, and understanding the toxicity and metabolism of those products can be part of the safety assessment. Evaluators also consider whether metabolites or degradation products have known toxicological concerns. When comprehensive data support a conclusion of no safety concern at typical intake levels, regulatory bodies may permit use within the context of good manufacturing practices.

Regulatory Status Worldwide

ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL has been evaluated by international expert bodies for its safety when used as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) assigned this compound a JECFA number (1747) and reviewed it in 2007, concluding that there was no safety concern at current levels of intake when used as a flavoring agent, based on the available toxicological data. This evaluation provides a basis for its consideration in flavor formulations in markets that reference JECFA evaluations as part of their food additive regulations. However, JECFA did not establish a numerical acceptable daily intake, and the evaluation language indicates a no-safety-concern finding at typical exposure levels rather than a specific numeric limit. In the United States, the Food and Drug Administration (FDA) maintains inventories of substances added to food, including flavoring agents evaluated by expert bodies such as the Flavor and Extract Manufacturers Association (FEMA) and JECFA, but inclusion in such inventories does not itself constitute direct regulatory approval for specific uses under the Code of Federal Regulations. ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL does not appear explicitly in the CFR sections that list permitted flavoring substances, and therefore its regulatory status in the U.S. may depend on whether it is recognized through FEMA GRAS determinations or other pathways. In the European Union, flavoring substances are subject to regulation under EU flavoring legislation, and specific authorizations would depend on evaluation by the European Food Safety Authority (EFSA). As of this writing, there is limited publicly available EFSA-specific authorization information for this compound.

Taste And Functional Properties

The sensory profile of ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL is described in industry references as possessing green, leafy, and fresh aromatic qualities. These sensory attributes make it particularly useful for enhancing herbal or vegetal notes in flavor formulations. Unlike primary taste stimuli such as sweet, sour, salty, bitter, or umami, flavoring agents primarily influence aroma, which is closely tied to perceived taste through retronasal olfaction. The specific odor profile of this compound is leveraged in applications where subtle green or fresh nuances are desired. Functionally, the behavior of the compound in food systems depends on several factors, including its solubility, volatility, and stability. Acetals such as this are generally more soluble in organic matrices and less soluble in water, which can influence how they partition between phases in complex food products. In many beverage systems, for example, the interaction between flavor compounds and ethanol or other solvents affects the release and perception of aroma. The stability of the acetal linkage under neutral to mildly acidic conditions contributes to its persistence in many formulations, although under strongly acidic environments, hydrolysis back to its precursor aldehyde and alcohol may occur. Processing parameters such as heat and pH adjustments can impact the functional properties of flavoring agents. ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL, like many volatiles, may be subject to volatilization during high-temperature processing, which can reduce its effective contribution if not properly accounted for during formulation. Additionally, interactions with other ingredients such as fats, proteins, and carbohydrates can influence the release and perception of aroma compounds. Understanding these functional properties helps food scientists design formulations that deliver the desired sensory experience consistently.

Acceptable Daily Intake Explained

The concept of an acceptable daily intake (ADI) is fundamental in regulatory toxicology and food safety assessments. An ADI represents an estimate of the amount of a substance that can be consumed every day over a lifetime without appreciable health risk. ADIs are typically expressed in milligrams of substance per kilogram of body weight per day and are derived from toxicological studies where the highest exposure level that does not produce adverse effects is identified. A safety factor is then applied to account for uncertainties, such as differences between animals and humans or variability among individuals. For ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL, the JECFA evaluation did not establish a specific numeric ADI. Instead, the committee concluded that there was no safety concern at current levels of intake when used as a flavoring agent. This type of conclusion means that based on available data and typical use levels, routine consumption through flavored foods is not expected to pose health risks. In the absence of a numeric ADI, regulatory authorities and food industry stakeholders rely on expert evaluations and principles of good manufacturing practice to guide usage. The absence of a numeric ADI does not imply that the substance is unrestricted, but rather that current scientific evidence supports its safe use at intended levels.

Comparison With Similar Additives

ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL can be compared with other synthetic flavoring agents that impart specific aromatic nuances. For example, acetaldehyde diethyl acetal is another acetal used for fruit and nut flavor profiles, which contributes sweet and alcoholic notes in formulations. Both compounds share an acetal functional group, but their sensory profiles differ due to the nature of their alcohol-derived moieties. Another related compound is cis-3-hexenyl acetate, a naturally occurring ester with a green, fruity aroma commonly found in many fruits and vegetables. While acetals and esters differ structurally, both contribute green or fresh notes, and formulators choose between them based on desired sensory outcomes and stability under processing. Additionally, some terpenoid-based flavoring agents provide herbal or botanical notes, such as linalool or geraniol. These compounds are structurally distinct from acetals but serve overlapping sensory purposes in complex flavor blends. When formulating products, food scientists consider volatility, perception thresholds, and compatibility with other ingredients. ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL’s acetal structure provides a balance of green note intensity and chemical stability, which can complement other aroma compounds in multifaceted flavor systems.

Common Food Applications Narrative

ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL finds application in a wide range of food and beverage categories where specific green and fresh aromatic nuances are desired. In beverages, it may be used to enhance fruit-based flavors such as apple, pear, or citrus profiles by contributing a subtle vegetal note that complements the primary fruit character. Its presence can lend complexity and freshness, especially in low-alcohol or alcohol-free formulations where traditional cues of freshness are more challenging to achieve. In bakery and confectionery products, the compound may be used to support herbal or botanical flavor themes, particularly when paired with other flavorants that accentuate floral, citrus, or spice notes. Its green character can provide contrast and balance in complex flavor systems, contributing to the overall sensory richness without dominating the profile. In dairy-based products, such as flavored yogurts or frozen desserts, it may be used alongside fruit or herb extracts to enhance the perception of freshness. Savory applications can also benefit from green aromatic notes, especially in dressings, sauces, and seasonings that aim for a garden-fresh or herbaceous quality. In such contexts, the compound’s green profile complements ingredients like basil, parsley, or cilantro. Across all applications, formulators consider factors such as processing conditions, ingredient interactions, and sensory goals when incorporating flavoring agents. The nuanced contribution of ACETALDEHYDE DI-CIS-3-HEXENYL ACETAL enhances consumer experiences by adding depth and complexity to flavor profiles in diverse food categories.

Safety & Regulations

FDA

  • Notes: Specific FDA CFR approval for this compound as a direct food additive was not identified; its status may depend on FEMA GRAS evaluations.

EFSA

  • Notes: EFSA specific authorization and numerical ADI data were not found.

JECFA

  • Notes: JECFA concluded no safety concern at current intake levels but did not assign a numeric ADI.

Sources

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