2-BUTYL-5 OR 6-KETO-1,4-DIOXANE

CAS: 65504-95-2 FLAVORING AGENT OR ADJUVANT

2-BUTYL-5 OR 6-KETO-1,4-DIOXANE is a synthetic flavoring agent evaluated by JECFA with no safety concern at current levels of intake when used as a flavouring agent. Its detailed regulatory use and safety evaluations are provided by authoritative food additive bodies.

What It Is

2-BUTYL-5 OR 6-KETO-1,4-DIOXANE is a chemically defined synthetic compound used in the flavor industry. It is identified by the Chemical Abstracts Service number 65504-95-2 and belongs to the class of lactone derivatives characterized by a substituted 1,4-dioxane ring with a butyl side chain at the 5 or 6 position. This compound is recognized primarily for its function as a flavoring agent or adjuvant in food formulations, where it contributes specific sensory properties to enhance or support desired flavors in products. It is also known under a series of systematic and alternate names reflecting its structural variations and isomerism, including 5(OR 6)-BUTYL-P-DIOXAN-2-ONE and 1,4-DIOXAN-2-ONE, 5(OR 6)-BUTYL-. The substance is typically encountered as a mixture of isomers, reflecting the fact that the butyl substitution can occur at either the 5 or the 6 position on the dioxane ring. While its structural complexity may suggest specialized applications, in practical use it functions as an odor and flavor contributor at trace levels when formulated into food flavor systems. It is one of numerous lactone-based compounds evaluated and cataloged by expert panels that assess synthetic flavoring agents for safety and technical performance. The identification of this compound in flavor chemistry databases is indicative of its recognized role in flavor formulation rather than broad functional uses such as preservatives, emulsifiers, or texture modifiers.

How It Is Made

Manufacturing of 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE involves organic synthesis techniques typical of cyclic ester (lactone) compounds. While the specific proprietary methods used by individual chemical suppliers are not widely published, the high-level approach generally starts from precursors featuring the 1,4-dioxane ring or equivalent diol and carbonyl functional groups. These precursors are chemically manipulated, often via catalyzed ring formation or esterification reactions, to install the butyl side chain at the appropriate ring position. Controlled reaction conditions and downstream purification steps—such as distillation or chromatography—are employed to achieve the desired isomeric composition and purity suitable for use in flavor applications. Analytical verification of the resulting compound, including structure confirmation and isomer ratio determination, is carried out using standard spectroscopic methods such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. In industrial settings, specifications for flavoring agents are established to ensure consistency in sensory performance and compliance with regulatory or expert panel guidelines. Suppliers often provide a minimum purity level on product specifications to ensure that the material behaves as expected when incorporated into complex flavor blends. Even though the public literature lacks detailed step-by-step synthetic protocols, these general approaches align with accepted practices for producing cyclic lactones for industrial use in regulated sectors.

Why It Is Used In Food

In food and beverage formulation, flavoring agents such as 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE are incorporated to impart, enhance, or modify specific sensory impressions. Flavor chemists leverage such compounds for their distinct aromatic profiles, which can contribute to fruit, sweet, or complex background notes that complement primary ingredients. As a lactone derivative with a butyl substitution, this compound fits into a broader class of molecules valued for subtle and nuanced contributions to flavor systems, especially at the trace addition levels typical of flavorings. The reason for its inclusion in food products is not as a nutrient or preservative, but strictly for sensory modification—to achieve a more desirable taste or aroma that aligns with consumer expectations for specific product categories. In combination with other flavor ingredients, it may play a role in balancing, enhancing, or rounding out complex flavor profiles. Flavoring agents like this are often chosen based on their compatibility with other ingredients, stability under processing conditions (such as heat or mixing), and their ability to provide consistent sensory characteristics without overwhelming the overall flavor matrix.

Adi Example Calculation

To illustrate how ADI concepts work in general (not specific to this compound), consider a hypothetical flavoring agent with an established numeric ADI of X mg per kg body weight per day. For a person weighing 70 kg, the maximum acceptable daily intake would be X times 70. However, because 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE does not have a numeric ADI established by JECFA and is considered safe at current intake levels, such a calculation is illustrative of the broader methodology rather than applicable directly to this substance. Generally, ADI calculations emphasize conservative safety margins that ensure that even high-level consumption within realistic use scenarios remains well below thresholds of toxicological concern.

Safety And Health Research

Assessment of flavoring agents like 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE centers on understanding potential hazards relative to expected exposure from typical use levels. Expert committees such as JECFA review available experimental data on toxicology, including genotoxicity, subchronic and chronic toxicity, and reproductive or developmental endpoints, to determine whether use at flavor-relevant levels presents a risk. For this compound, the outcome of such assessment indicated that there were no safety concerns at anticipated intake levels when used in flavorings, based on the body of evidence available at the time of evaluation. While specific studies for every flavoring agent are not always publicly detailed, safety evaluation frameworks emphasize conservative assumptions and margins of exposure that are orders of magnitude below levels associated with any adverse effects observed in toxicological studies. This framework supports regulatory confidence that the use of such compounds at intended levels in food products does not pose appreciable risk to human health. It is important to note that comprehensive human clinical data are generally not required for flavoring agents due to their low levels of use and extensive review of animal toxicology data by expert panels.

Regulatory Status Worldwide

Regulatory evaluation of 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE has been conducted by international expert committees with a focus on safety when used as a flavoring agent. According to the Joint FAO/WHO Expert Committee on Food Additives (JECFA), the compound has been evaluated and no safety concern at current levels of intake when used as a flavouring agent was identified in its 2005 assessment, which is documented in JECFA’s report series. This evaluation reflects expert review of available toxicological data and anticipated exposure levels consistent with flavor use. In the United States, this substance appears in the Food Additives Status List (formerly EAFUS) maintained by the FDA, where flavoring agents assessed for safety by expert panels (such as the Flavor and Extract Manufacturers Association) are listed with relevant identifiers; however, it is not tied to a specific CFR allowance text that authorizes its use in defined food categories. According to FEMA documentation, a GRAS reference number is assigned, and uses are described in FEMA publications where expert panels provide usage recommendations based on safety evaluations. The lack of a precise CFR citation should not be interpreted as absence of evaluation but rather as indication that FDA’s regulatory framework for flavorings involves expert panel assessments rather than direct codification in standard CFR sections. Internationally, the European Food Safety Authority (EFSA) and other regional bodies consider flavoring substances within group evaluations, and such compounds may appear in flavor inventories and their respective evaluations. The presence of group evaluation documents indicates that the compound has been considered alongside structurally related substances with respect to safety and estimated intake, although no specific numerical Acceptable Daily Intake (ADI) has been established by EFSA for this individual compound.

Taste And Functional Properties

The sensory contribution of 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE is predominantly aromatic rather than nutritive. Compounds in this structural class of lactones typically exhibit fruity or sweet notes at very low concentrations, although detailed sensory descriptors specific to this compound are not extensively published in open literature. The functional behavior of such lactones in flavor applications often depends on their solubility in carrier systems (e.g., alcohol-water mixtures) and their volatility, which affects how they release aroma in the mouth and during ingestion. As with many lactones, slight modifications of the chemical structure—such as the position of the butyl group—can shift the sensory character perceptible to humans. Sensory chemists evaluate these properties through trained panels to determine appropriate use concentrations and to understand how the compound interacts with other flavor constituents. The stability of the compound under common food processing conditions (like heat or pH changes) will affect how it is formulated; for example, some flavoring agents may degrade or change character when exposed to high temperatures, reducing their effectiveness in baked goods versus cold-prepared products. Such functional properties are critical for flavor designers to ensure consistent consumer experiences across products.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a concept used in food safety to describe the estimated amount of a substance that can be consumed daily over a lifetime without appreciable health risk. For 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE, expert evaluation by bodies such as JECFA concluded that there was no safety concern at the levels of intake expected from its use as a flavoring agent; thus, a specific numeric ADI was not deemed necessary or established in the traditional sense. This denotes that anticipated human exposure is sufficiently low relative to levels that might raise concern in toxicology studies. In practice, assigning an ADI involves identifying a no-observed-adverse-effect level (NOAEL) in animal studies, applying safety factors to account for interspecies and intraspecies variability, and deriving an intake level considered safe for humans. When available toxicological data support a conclusion of no safety concern under typical use conditions, regulators may refrain from defining a numeric ADI, instead communicating safety through narrative conclusions such as those provided for this compound.

Comparison With Similar Additives

Flavoring agents encompass a diverse array of chemical structures tailored to deliver specific sensory attributes. In comparing 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE with other flavoring lactones—such as gamma-undecalactone or delta-decalactone—one finds shared roles in providing fruity or creamy aroma notes, albeit with distinct olfactory signatures. Each lactone derivative differs in ring size, side chain length, and functional group placement, which alters aroma perception and functional behavior in flavor matrices. Relative to simple esters like ethyl butyrate, which deliver direct fruity tones at low thresholds, lactone derivatives often contribute more nuanced or background notes that support overall flavor complexity. Such comparisons underscore the wide palette flavor chemists employ when creating flavor blends, where individual compounds complement each other to achieve a desired sensory outcome without overwhelming other components.

Common Food Applications Narrative

Common applications of flavoring agents like 2-BUTYL-5 OR 6-KETO-1,4-DIOXANE span numerous food and beverage categories where subtle aromatic enhancements are sought. While consumer products list only the flavoring system on ingredient labels rather than individual components, such compounds contribute to the sensory profiles of many everyday items. In flavored beverages, dairy products, confectionery, baked goods, and gelatin desserts, flavor chemists select and blend a suite of minor aromatic compounds—each contributing uniquely to the composite aroma profile perceived by consumers. For example, in fruit-flavored beverages, trace lactone derivatives may help reinforce natural fruit notes or provide stability to the flavor profile across varying temperatures and pH levels. Similarly, in bakery items with fruit or sweet notes, these compounds may work synergistically with other flavor ingredients to enhance consumer-perceived freshness or complexity. The ability of specialists to integrate such compounds into multi-component flavor systems allows manufacturers to achieve repeatable sensory experiences that match product positioning and consumer expectations. As with most flavoring agents, these contributions occur at concentrations that are minute relative to the overall mass of the food product, but nonetheless impactful in shaping the flavor quality.

Safety & Regulations

FDA

  • Notes: FDA evaluation framework for flavoring agents involves expert panel assessments rather than specific CFR allowances for this substance as identified.

EFSA

  • Notes: EFSA has conducted group evaluations but no specific numeric ADI or E-number was identified in available safety assessments.

JECFA

  • Year: 2005
  • Notes: JECFA concluded no safety concern at anticipated intake levels in its evaluation.
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent

Sources

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