CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is an organic cyclic compound used as a flavoring agent or adjuvant in food formulations. It is identified by CAS 67879-60-1 and FEMA Number 4287.
What It Is
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is a synthetic organic compound classified as a cyclic acetal with a five-membered dioxolane ring structure. It is commonly known in technical circles by its Chemical Abstracts Service (CAS) registry number 67879-60-1 and is referenced in flavor chemistry literature under the FEMA Number 4287. This substance appears as a mixture of cis and trans stereoisomers of 2-isopropyl-4-methyl-1,3-dioxolane, which are configurations that relate to the spatial arrangement of substituent groups around the dioxolane ring. While the molecular structure of CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is relatively simple compared to other flavor compounds, it performs specialized roles in food and beverage systems due to its volatile and organoleptic properties. The compound falls within a broad category of compounds used in food science as flavoring agents or adjuvants, meaning it can contribute to or enhance aroma and flavor profiles in formulated products. The function "FLAVORING AGENT OR ADJUVANT" reflects its use context, where it interacts with other flavor compounds to achieve a desired sensory impact. Flavoring agents, including chemicals like CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE, are typically present in very low concentrations in finished food products and contribute to aromatic profiles that consumers perceive but do not necessarily identify chemically. In industrial settings, this compound may also be referenced as "Isobutyraldehyde propylene glycol acetal" or simply as 2-isopropyl-4-methyl-1,3-dioxolane. These synonyms highlight its chemical lineage, particularly its derivation via acetalization of isobutyraldehyde with propylene glycol. Although not ubiquitous across all food categories, it is recognized within additive inventories and flavor libraries, which catalog substances evaluated for safety and technical suitability for use in foods and beverages. Its presence in inventories underscores the importance of systematic evaluation by expert committees and regulatory bodies to ensure appropriate applications and labeling within food systems.
How It Is Made
The synthesis of CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE generally involves an acetalization reaction between isobutyraldehyde and propylene glycol. In this type of reaction, the aldehyde group of isobutyraldehyde interacts with the diol functionality of propylene glycol to form a cyclic acetal, thus creating the characteristic dioxolane ring. This process is catalyzed by acidic conditions that facilitate the removal of water and favor acetal formation. Manufacturers who produce this compound on an industrial scale typically employ carefully controlled reaction conditions, including temperature, choice of acid catalyst, and continuous water removal, to drive the reaction toward the desired product while minimizing side reactions and impurities. After synthesis, the resulting material is often subjected to purification to remove unreacted starting materials and byproducts. Common purification methods may include distillation under reduced pressure, which takes advantage of differences in boiling points, or chromatographic techniques if ultra-high purity is required. Specifications for food-grade material usually mandate a high degree of chemical purity and strict limits on residual solvents, catalysts, and other potential contaminants. These criteria are important for both sensory performance and regulatory compliance in food applications. Because CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is used at very low levels in finished products, producers aim for consistent quality attributes such as odor profile, solubility in target flavoring systems, and stability during storage. Although detailed proprietary synthesis methods may vary across manufacturers, the fundamental chemistry—acetal formation followed by purification—remains consistent. Quality control laboratories typically characterize each batch by spectroscopic methods such as nuclear magnetic resonance (NMR), gas chromatography (GC), and mass spectrometry (MS) to confirm that the desired dioxolane structure has been obtained and to ensure consistency across lots.
Why It Is Used In Food
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is used in food systems primarily for its contribution to flavor and aroma. As a flavoring agent or adjuvant, it interacts with other sensory-active compounds to create or enhance specific olfactory impressions. In complex food matrices, individual flavor compounds rarely act alone; instead, they form synergistic blends that produce a harmonious and recognizable overall sensory profile. In this context, compounds like CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE can provide subtle aromatic notes that complement other primary flavor constituents. Its functional role as an adjuvant reflects the fact that it may not be the dominant contributor to a flavor profile but can influence the perception of other aromatics. For example, in beverage systems or confectionery formulations, such compounds can help round out a flavor blend, enhance volatility, or modify how other flavor molecules are released during consumption. Because flavor perception is highly dependent on the mixture of volatiles present and on their relative concentrations, even minor components like CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE can meaningfully influence the consumer experience. Another reason for its use in food is the flexibility it offers flavorists during formulation. Professional flavorists often select from a palette of compounds to achieve a target sensory effect, and having a diverse array of structurally distinct molecules enables more nuanced formulations. CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE’s specific aromatic characteristics, which may include subtle sweet or fruity notes due to its chemical structure, make it a potential tool in the flavorist’s toolkit. Although it is used at very low levels relative to other ingredients like sugars or primary flavor extracts, its impact on the overall sensory profile should not be underestimated. Use of this compound is guided by expert evaluation and industry standards to ensure that only appropriate levels are incorporated into food products. In flavor chemistry, the goal is always to balance sensory impact with safety and regulatory compliance. As a result, CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is selected and applied in formulation contexts where its specific properties align with the desired sensory outcome.
Adi Example Calculation
Illustrative example: Suppose a regulatory evaluation had established an ADI of X mg/kg bw/day for a hypothetical flavoring compound. For an adult weighing 70 kg, the acceptable daily exposure would be 70 kg times X mg/kg bw/day, or 70X mg per day. This calculation demonstrates how the ADI concept translates into a consumer context by multiplying the per-kilogram allowance by body weight. It is important to stress that this example uses a placeholder value because a specific numeric ADI for CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is not explicitly stated in the available regulatory specifications. The purpose of this illustrative calculation is to show how ADIs are applied conceptually rather than to provide guidance on this specific compound.
Safety And Health Research
Safety and health research regarding CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE focuses on its toxicological profile as evaluated by expert committees that review flavoring substances. These evaluations typically consider data on genotoxicity, subchronic toxicity, reproductive and developmental endpoints, and other standard toxicological parameters that inform risk assessments for food flavor compounds. Because flavoring agents are used at very low concentrations in finished products, safety assessments prioritize establishing whether there are any concerns at levels of intake consistent with typical use. One of the key frameworks for such evaluation is the work of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which maintains specifications for food flavoring substances. JECFA’s flavoring specifications database includes analytical and identity data for compounds like CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE, and the committee’s broader evaluations consider whether the available toxicological data raise concerns for human health at customary intake levels. For many flavoring agents, including this compound, JECFA documentation has not identified specific safety concerns at typical usage levels. Beyond JECFA, flavor industry organizations such as the Flavor and Extract Manufacturers Association (FEMA) compile sensory and technical information about flavoring agents. While FEMA’s role is not regulatory per se, its evaluations contribute to understanding how these substances behave in food systems and what sensory characteristics they impart. Such information can be useful for risk assessment by industry and regulators alike. It is important to note that detailed peer-reviewed toxicological studies on individual minor flavoring components can be limited, particularly for substances that are not used at high levels or that have a relatively narrow application scope. In such cases, risk assessments often rely on a combination of available experimental data, read-across from structurally similar compounds, and theoretical modeling to characterize potential hazards. The absence of documented safety concerns in authoritative evaluations for CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE at typical usage levels suggests that, within the context of regulated flavoring applications, it does not pose an evident health risk. Nevertheless, regulators continue to monitor scientific literature and update evaluations as new data become available. Where gaps in toxicological data exist, risk assessors may apply conservative uncertainty factors to ensure that consumer exposure remains well below any level associated with adverse effects. This approach aligns with standard practices in food safety risk assessment, which prioritize protective margins and consider the totality of available evidence before establishing guidance on use in food.
Regulatory Status Worldwide
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE has been cataloged in authoritative inventories and evaluated by expert bodies with respect to its use as a flavoring substance. In the United States, it is listed in the Substances Added to Food inventory maintained by the Food and Drug Administration (FDA), which indicates that it is recognized in the context of food ingredient inventories under the designation CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE with CAS 67879-60-1. This listing documents its identification and technical effect as a flavoring agent or adjuvant, which is a necessary step for substances used in food flavor applications. However, the FDA listing alone does not constitute a specific regulatory allowance under a defined Code of Federal Regulations (CFR) section, and no explicit CFR citation appears in the available authoritative listings. Internationally, flavor and extract industry organizations such as the Flavor and Extract Manufacturers Association (FEMA) have assigned this compound FEMA Number 4287 in their flavor library, which reflects expert evaluation within the context of flavor chemistry. The FEMA listing provides information to flavor professionals regarding identification and sensory characteristics, although it is separate from direct regulatory approval mechanisms. Expert evaluations such as those compiled by FEMA often draw upon safety assessments conducted by bodies like the Joint FAO/WHO Expert Committee on Food Additives (JECFA). JECFA has documented this compound under JECFA Number 1748 in its flavoring specifications database, which includes technical and analytical data about the compound. While the JECFA specification provides information on chemical identity and analytical parameters, the available specifications do not clearly state an acceptable daily intake (ADI) in numerical terms in the public-facing documentation. JECFA’s evaluations often assess whether there are safety concerns at current levels of intake when used as a flavoring agent, and in many cases for flavoring substances, no safety concern is identified at typical usage levels. In the European Union, although this compound is present in classification and labeling inventories such as those maintained by the European Chemicals Agency (ECHA), specific approval as a food additive under an E-number has not been clearly documented in publicly available regulatory databases. The scope of ECHA’s inventories includes general chemical classification and labeling rather than specific food additive authorizations. Overall, CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE’s regulatory status reflects recognition in ingredient inventories and expert flavor evaluations, with documentation of its technical use in flavor systems. Specific numeric regulatory allowances or ADIs would require consultation of the primary regulatory texts or databases that detail food additive authorizations for each jurisdiction, which are not fully covered in the currently d sources.
Taste And Functional Properties
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is recognized for its contribution to volatile aroma profiles rather than for imparting taste on the tongue. Sensory descriptors for this class of compound often include subtle winey or fruity notes, which come from its cyclic acetal structure and the presence of an isopropyl group that influences how the molecule interacts with olfactory receptors. Because our perception of flavor is dominated by aroma, such volatile components can significantly influence the overall sensory impression when used in blends with other flavor compounds. In terms of functional properties, CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is a relatively low-molecular-weight organic compound with adequate volatility to contribute to headspace aroma above a liquid food matrix. Its solubility characteristics favor organic phases or oily components rather than water-soluble phases. This means it is typically blended into liquid flavor concentrates or encapsulated formulations that are later dispersed in water-based food products. Stability-wise, cyclic acetals like this one tend to be fairly resistant to hydrolysis under neutral pH conditions, although they may degrade more readily under strong acidic or basic conditions, which is a consideration for formulation scientists. Another important functional aspect is how this compound behaves in thermal processing. Because many foods undergo heating during production or preparation, flavor compounds must withstand some degree of thermal stress without significant degradation. While CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE may not be as robust as some other flavor molecules, careful formulation and process control can help preserve its contribution in finished products. Additionally, its relatively low odor threshold means that even small amounts can be effective, reducing the risk of off-notes at higher concentrations. Overall, the sensory contribution and functional behavior of CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE underscore its role as a nuanced component in flavor formulation rather than a primary flavor driver. Understanding these properties helps food scientists and flavorists decide when and how to incorporate this compound into complex flavor systems to achieve desired consumer sensory experiences.
Acceptable Daily Intake Explained
An acceptable daily intake (ADI) is a metric used by food safety authorities to express the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. It is typically expressed in milligrams of substance per kilogram of body weight per day (mg/kg bw/day) and is derived from toxicological studies using safety factors to account for uncertainties in the data. For many flavoring agents, including CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE, expert committees such as JECFA may conclude that there is no safety concern at estimated levels of intake from normal use in foods. In such cases, a formal numeric ADI may not be explicitly established in publicly available documentation. When an ADI is specified by a regulatory body, it represents a conservative estimate of a daily intake that would not be expected to lead to adverse effects even if a person were exposed to that amount every day for many years. Regulators typically apply uncertainty factors that are orders of magnitude lower than doses that cause adverse effects in animal studies to ensure consumer protection. ADI values serve as benchmarks for risk assessors and industry professionals to gauge whether estimated dietary exposures are within safe bounds. In the context of flavoring substances, the concept of an ADI helps frame safety evaluations but may not always result in a specific numeric value. This is because the levels at which these substances are used in food are often orders of magnitude below any dose associated with toxicity in experimental studies. As a result, committees like JECFA may conclude that there is no safety concern at current intake levels without defining a specific ADI value. When such a conclusion is reached, it reflects a professional judgment that typical exposures do not pose health risks under intended use conditions. For consumers and professionals interpreting safety information, it is important to understand that ADIs are not recommended daily intakes but rather regulatory tools that help ensure cumulative exposures remain within scientifically justified safety margins. When a numeric ADI is not provided, as appears to be the case for CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE in public-facing JECFA specifications, the absence of a documented safety concern at typical usage levels serves a similar purpose of indicating that exposures under normal use are considered acceptable from a safety perspective.
Comparison With Similar Additives
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE can be compared with other flavoring agents that share similar roles in food systems. For example, ethyl acetate is another volatile organic compound used as a flavoring component with fruity notes. Like CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE, ethyl acetate contributes to the aroma profile of products at low concentrations and has been evaluated by expert committees for safety when used as a flavor. The primary difference lies in their chemical structures and sensory characteristics: ethyl acetate has a simple ester structure that typically evokes fruity and solvent-like notes, whereas the dioxolane structure in CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE may contribute more nuanced winey or complex aromas. Another compound used in flavor systems is methyl anthranilate, which provides grape-like notes and is widely used in confectionery and beverages. Methyl anthranilate’s structural differences—a substituted ester with a benzene ring—lead to a distinctly different sensory profile compared to the cyclic acetal structure of CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE. Both substances illustrate how structural variation influences flavor perception, with each contributing unique olfactory cues that formulators leverage to achieve specific sensory targets. Linalool, a naturally occurring terpene alcohol found in many essential oils, serves as another point of comparison. Linalool’s floral and citrus-like aroma contrasts with the subtler notes associated with CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE, but both are used in combination with other compounds to build complex flavor profiles. Linalool also differs in regulatory assessment because it occurs naturally in foods and botanicals, whereas CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is a synthetic additive recognized in flavor inventories. These comparisons demonstrate the diversity of chemical structures and sensory contributions within the class of flavoring agents. Although each compound has a distinct profile, they share the common goal of enhancing or modifying aroma in food products while being evaluated for safety under typical usage scenarios. Formulators consider the balance of sensory impact, stability, and regulatory acceptance when selecting among these substances.
Common Food Applications Narrative
CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE finds application in a range of flavorful food and beverage products where subtle aroma contributions are desired. In beverage applications, for example, flavorists may use it in small amounts to enhance the complexity of fruit flavor blends or to support wine-like notes in non-alcoholic alternatives. The ability of this compound to interact synergistically with other volatile components helps create a more rounded sensory profile that consumers associate with natural fruit or botanical extracts. Beverages such as flavored waters, soft drinks, or ready-to-drink teas and juices often rely on such carefully balanced flavor blends to achieve their characteristic tastes. In confectionery products, CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE may contribute to nuanced aromatic qualities that complement sweet base notes. Candies, gums, and other sweet treats frequently incorporate multi-component flavor systems to evoke complex sensory impressions such as berry, tropical fruit, or dessert-like profiles. Because the human nose is highly sensitive to certain volatiles even at low concentrations, the inclusion of minor components like this compound can subtly influence how a flavor blend is perceived without overwhelming the dominant profile. Dairy and dairy-alternative products are another category where nuanced aroma compounds play a role. Flavored yogurts, frozen desserts, and plant-based milks often use complex flavor systems to mimic natural tastes. CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE can be part of such systems, contributing to overall aroma complexity. In some instances, this compound may be used in combination with other esters, aldehydes, and lactones to create layered sensory impressions that evolve as the product is consumed. Snack foods and savory applications also benefit from carefully calibrated aroma compounds. While savory profiles are dominated by umami, roasted, or salty notes, certain sweet or fruity nuances can balance or enhance overall palatability in composite products such as seasoned nuts, snack bars, or hybrid sweet-savory items. Again, the concentrations at which CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE is used are low, but its contribution can be meaningful within a multi-component flavor system. In all these applications, the selection and use of CIS- AND TRANS-2-ISOPROPYL-4-METHYL-1,3-DIOXOLANE are guided by sensory science and technical evaluation. Food formulators consider how this compound will interact with other ingredients, how processing conditions may affect its stability, and how consumers will perceive the final flavor. The goal is always to achieve a balanced, appealing sensory experience while meeting regulatory requirements for safety and labeling.
Safety & Regulations
FDA
- Notes: FDA recognizes this substance in the Substances Added to Food inventory but no explicit CFR approval citation was found.
EFSA
- Notes: No EFSA-specific authorization with numeric ADI was verified.
JECFA
- Notes: JECFA flavor specification exists but no numeric ADI or year was explicitly shown in the d specification.
Comments
Please login to leave a comment.
No comments yet. Be the first to share!