CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE

CAS: 6290-17-1 FLAVORING AGENT OR ADJUVANT

CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE (CAS 6290-17-1) is a synthetic flavoring compound belonging to the class of fatty acid esters, used primarily for its fruity aroma in flavor formulations. It is identified by regulatory and flavoring bodies with numbers such as FEMA 4294 and has been evaluated by the Joint FAO/WHO Expert Committee on Food Additives (JECFA).

What It Is

CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE is a chemical compound defined by the CAS Registry Number 6290-17-1 and is part of the esters class of organic molecules. As a flavoring agent or adjuvant, this compound exists as a mixture of cis and trans isomers and is recognized for its use in the formulation of flavor ingredients to deliver specific sensory impressions, particularly fruity notes in food and related products. In flavor science and regulatory contexts, it may be referenced by other systematic names including ETHYL ACETOACETATE PROPYLENE GLYCOL KETAL and ethyl ester derivatives of 2,4-dimethyl-1,3-dioxolane acetic acid. The structural features of this compound reflect its classification as a substituted dioxolane ester, which contributes to its organoleptic properties.

How It Is Made

The manufacturing pathways for CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE typically involve the esterification of acetoacetic acid derivatives with ethanol under controlled conditions, leading to the formation of the ethyl ester of 2,4-dimethyl-1,3-dioxolane-2-acetic acid. Industrial production often begins with the formation of the 1,3-dioxolane ring system through reaction of appropriate ketones with glycol precursors, followed by esterification. Quality control for flavoring agents like this emphasizes achieving consistent isomeric composition and purity suitable for intended use, but proprietary details of specific commercial processes are typically held by manufacturers. Because this compound is used at very low concentrations as a flavor additive, production scale is geared toward fine chemical and flavor ingredient supply rather than bulk commodity chemical production.

Why It Is Used In Food

This compound is used in food and beverage formulations primarily for its sensory impact as a flavoring agent. As a member of the fruity ketal class of esters, CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE contributes specific fruity and sweet aroma characteristics that can enhance the overall flavor profile of a product when blended with other flavor ingredients. Flavor chemists select such agents to tailor sensory attributes of complex formulations, balancing sweetness, fruitiness, and volatility for optimal perception. Its role as an adjuvant in flavor blends enables it to support and enhance the stability and release of other volatile flavor compounds during processing and consumption.

Adi Example Calculation

Because CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE does not have a formal numeric ADI established, illustrative calculations using an ADI value are not applicable. Instead, risk assessment for flavoring agents often involves estimating typical intake from food products containing such ingredients and comparing those estimates to levels shown to be safe in toxicological studies. For example, exposure modeling may consider average consumption of flavored beverages and foods and typical usage concentrations of the flavoring compound to demonstrate that estimated intake remains far below thresholds of concern identified in safety evaluations.

Safety And Health Research

Safety evaluations for flavoring agents like this one focus on toxicological endpoints such as acute toxicity, chronic exposure, and potential for organ-specific effects at typical dietary exposure levels. The JECFA evaluation summarized that, based on available data, there is no safety concern at current intake levels encountered from food flavor use, reflecting that exposures are orders of magnitude lower than levels associated with adverse effects in standard toxicology studies. Research on esters of this type generally considers metabolism to common physiological intermediates and rapid clearance, but detailed clinical studies specific to this compound are limited in the public domain. Regulatory risk assessment frameworks integrate such data with conservative safety factors to ensure that even sensitive populations are protected under normal use scenarios. Ongoing review by expert bodies ensures that new evidence can be incorporated into safety assessments as it becomes available.

Regulatory Status Worldwide

CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE has been evaluated by international expert committees for safety in food flavoring applications. According to the Joint FAO/WHO Expert Committee on Food Additives (JECFA), it is assigned JECFA Number 1715 and was assessed in a safety evaluation meeting documented in the series TRS 947-JECFA68, with the conclusion that there is no safety concern at current levels of intake when used as a flavoring agent. This evaluation reflects a broad review of available toxicological and exposure data specific to food use contexts. In the United States, this substance is listed with a FEMA number of 4294 in flavor ingredient inventories and has been considered in the context of generally recognized as safe (GRAS) status by flavor industry expert panels, which are recognized by regulatory bodies as part of the review framework for flavoring substances. Regulatory frameworks may vary by region, and specific allowable use conditions are determined by applicable food standards authorities.

Taste And Functional Properties

CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE is appreciated in flavor science for its fruity, sweet sensory notes that resemble fresh fruit nuances when perceived at appropriate use levels. Functional properties of such esters include volatility compatible with typical food processing temperatures and a balance between hydrophobic and hydrophilic behavior that supports incorporation into a range of product matrices, from beverages to confectionery. These compounds generally exhibit moderate solubility in lipophilic phases and lower solubility in water, aligning with their use in emulsified and flavor-oil systems. Their stability under pH conditions encountered in most food systems makes them suitable for a variety of applications without rapid degradation, and the cis and trans isomeric forms may contribute subtly different olfactory impressions that experienced flavorists exploit to achieve desired sensory outcomes.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory risk assessment metric used by food safety authorities to describe the amount of a substance that can be consumed daily over a lifetime without appreciable health risk, based on available toxicological data and conservative safety factors. For CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE, JECFA’s evaluation concluded that typical exposure from food use does not raise safety concerns, and thus a formal numeric ADI was not specified in its evaluation. This outcome reflects that the estimated intake from flavoring use is well below levels associated with adverse effects in relevant studies, providing reassurance about safety under specified use conditions. The ADI concept is intended for regulatory use and is not a recommended consumption target; most flavoring agents are used at trace levels that are orders of magnitude below any threshold of toxicological concern.

Comparison With Similar Additives

This compound can be compared with other fruity ester flavoring agents such as ethyl butyrate and ethyl acetate, which also provide fruity and sweet sensory notes but differ in volatility and fruity character intensity. Ethyl butyrate is known for delivering strong pineapple-like notes and is widely used in fruit-forward formulations, whereas ethyl acetate tends toward light fruity impressions with a solvent-like edge at high concentrations. Compared with lactones such as gamma-decalactone, which contribute peach and creamy fruit notes, the dioxolane ester provides a distinctive balance of sweetness and fruity nuance with moderate volatility. Flavor formulators choose among these based on the specific sensory profile desired and the matrix in which the flavoring is incorporated.

Common Food Applications Narrative

CIS- AND TRANS-ETHYL 2,4-DIMETHYL-1,3-DIOXOLANE-2-ACETATE is encountered in food and beverage products as a flavoring ingredient that imparts fruity and sweet aromatic characteristics when used in very low concentrations. It may be included in flavor blends for carbonated soft drinks, fruit-flavored beverages, confectionery items, and desserts where a bright, fresh note enhances overall flavor balance. Within dairy-based products such as flavored yogurts or ice cream, this compound can help accentuate fruit-forward profiles when combined with natural or other synthetic flavor constituents. In baked goods and snacks, fruity ketal esters such as this one may be part of complex flavor systems designed to evoke specific fruit impressions. Its use is generally in the context of a multi-component flavor formula rather than as a stand-alone ingredient, and the concentrations used are guided by sensory evaluation and regulatory limits established by expert bodies.

Safety & Regulations

FDA

  • Notes: No specific FDA food additive regulation section verified for this compound; GRAS consideration exists via FEMA listing.

EFSA

  • Notes: EFSA specific numeric evaluations not verified from authoritative source.

JECFA

  • Notes: JECFA reported no safety concern at current intake levels; no numeric ADI specified.

Sources

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