(+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE

CAS: 904929-41-5 FLAVORING AGENT OR ADJUVANT

**(+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE** is an organic flavouring compound used as a flavouring agent or adjuvant in food applications. It exists as a mixture of cis and trans isomers and is recognized by JECFA under number 1908 with no safety concern at current levels of intake when used as a flavouring agent. It may be used to impart specific flavour characteristics in food formulations.

What It Is

The compound (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE is a synthetic flavouring substance identified by the CAS number 904929-41-5 and classified technically as a flavouring agent or adjuvant. It is comprised of two geometric isomers, cis and trans, which contribute to its sensory properties. In the context of food science, flavouring agents are compounds that contribute characteristic tastes or aromas to foods and beverages. This compound falls within that category due to its use in flavour formulations. The substance is not assigned an official INS or E-number in widely recognized additive lists available through authoritative regulators. It has also been referenced by alternative names reflecting its chemical structure. The presence of both isomers implies that the compound’s sensory profile can involve complex interactions with other flavour components in formulations. From a chemical standpoint, the structural motif of a cyclopropane ring connected to an aldehyde group and a branched alkyl side chain contributes to the compound’s volatility and potential aroma characteristics. Aldehydes in general are known for their strong sensory impact, often described with notes ranging from citrus to fruity depending on the specific substitution patterns. The compound’s functional description as a flavouring agent or adjuvant underlines its role as a sensory-enhancing ingredient rather than a nutritive component. Given its role, this flavouring agent is typically deployed in very small quantities relative to the bulk of the food or beverage matrices in which it is used. Its inclusion in regulatory evaluations and flavour databases reflects its use within the flavour industry and food science research. As with all flavouring agents, understanding the compound’s chemical identity, isomer distribution, and sensory profile is essential for formulating products that meet consumer and regulatory expectations.

How It Is Made

The manufacturing of synthetic flavouring agents such as (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE involves controlled chemical synthesis rather than extraction from natural sources. In broad terms, organochemical synthesis of aldehydes with specific structural motifs typically begins with precursor molecules containing reactive functional groups that allow for controlled ring formation and side chain elaboration. For example, a precursor alkene with the desired carbon skeleton might undergo a series of reactions such as cyclopropanation, which introduces the cyclopropane ring, followed by functional group transformations to install the aldehyde moiety. These steps are conducted under conditions that favour the formation of both cis and trans stereoisomers when applicable, as in the case of this compound. The production process in industrial settings prioritizes high purity and reproducibility, ensuring that the resultant flavouring agent meets technical specifications such as isomer ratio, concentration, and absence of undesirable by-products. Manufacturers often follow standardized quality control procedures including chromatographic analysis to verify the composition and ensure consistency batch to batch. The synthesis route can be adapted to optimize yield and reduce the formation of impurities. After synthesis, purification steps such as distillation or crystallization may be employed to refine the compound. In many cases, the final product is a mixture of isomers that is evaluated for sensory quality and stability under expected storage and use conditions. Formulators and regulatory bodies often require documentation of the manufacturing process, quality checks, and certificates of analysis to support the safe and intended use of the compound in food applications. Industry practices also consider environmental and safety aspects of manufacturing, including proper handling of reagents, containment of volatile organic compounds, and adherence to good manufacturing practices (GMP). Ultimately, while the exact proprietary synthesis methods can vary among producers, the overall process emphasizes precision, safety, and compliance with regulatory standards that govern supply of flavouring ingredients for the food industry.

Why It Is Used In Food

In food and beverage formulation, flavouring agents such as (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE are used to introduce or enhance specific sensory notes that may be absent or weak in the base ingredients. The compound’s chemical structure, which includes a cyclopropane core linked to a branched alkyl chain and an aldehyde functional group, can contribute distinctive aroma characteristics. Aldehydes, in general, are known for their impactful sensory properties at very low concentrations, making them valuable tools in creating desirable flavour profiles. This flavouring agent may be chosen for its ability to impart fruity or citrus-like nuances in complex flavour systems. In practice, it is used at trace levels consistent with good manufacturing practices, ensuring that the final product achieves the intended sensory quality without overwhelming other flavour components. Flavour chemists consider such compounds based on factors including compatibility with other ingredients, volatility and stability under processing conditions, and regulatory acceptability in the target market. The use of synthetic flavouring agents is particularly common in applications where natural extraction is impractical or unreliable in delivering consistent sensory results. For instance, when a natural flavour is rare, expensive, or subject to agricultural variability, synthetic analogues that mimic key sensory attributes can provide a stable alternative. Additionally, synthetic agents can be engineered to exhibit specific sensory characteristics that complement or enhance other flavour constituents. The decision to use a particular flavouring compound is ultimately guided by sensory evaluation panels, application testing in relevant food matrices, and compliance with safety and regulatory frameworks. By carefully integrating compounds like this one into formulations, product developers aim to create appealing taste and aroma experiences for consumers while maintaining control over quality and consistency across production runs.

Adi Example Calculation

The following is an illustrative explanation of how an Acceptable Daily Intake (ADI) calculation works in general and is not a personal recommendation. ADIs are typically expressed relative to body weight (for example, milligrams per kilogram of body weight per day). If a compound had an established ADI of a hypothetical value, say X mg/kg body weight per day, the calculation would proceed by multiplying that value by a person’s body weight to estimate an intake threshold. For example, for a hypothetical compound with an ADI of X mg/kg body weight per day, an adult weighing 70 kg would have an estimated threshold intake of 70 times X milligrams per day. If actual dietary exposure based on typical usage and consumption patterns were significantly below that threshold, regulators would consider the safety margin acceptable. However, for (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE, no numeric ADI has been established because the Joint FAO/WHO Expert Committee on Food Additives concluded there was no safety concern at typical intake levels. Consequently, constructing a numeric example for this specific compound based on an ADI is not applicable. Instead, understanding how ADIs function in risk assessment can help frame how regulatory decisions about safety are made.

Safety And Health Research

Safety assessments for flavouring agents like (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE focus on evaluating potential toxicological effects relative to expected exposure levels from food use. International expert bodies such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA) review available data including chemical structure, metabolic pathways, and intake estimates to determine whether a substance poses a concern at typical usage levels. For this compound, the JECFA evaluation concluded that there is no safety concern at current levels of intake when utilised as a flavouring agent. This type of conclusion is reached after examining genotoxicity, subchronic toxicity, and other relevant endpoints reported in scientific studies considered during the evaluation. It is important to emphasise that safety assessments consider the compound’s expected usage, which for flavouring agents is typically very low compared to bulk ingredients in food products. Flavouring substances are often present at trace levels that produce sensory impact without constituting a significant dietary exposure. As such, the margin of exposure between typical intake and levels associated with adverse effects in experimental models is a key factor in establishing a conclusion of no safety concern. Toxicological data for many flavouring agents are generated through a combination of in vitro and in vivo studies, which may include evaluations of acute toxicity, repeated dose toxicity, and genotoxic potential. Where available, these data are considered alongside human exposure estimates derived from usage patterns in relevant food categories. The flavour industry and regulators also consider structure-activity relationships, which help predict biological behaviour based on chemical similarity to other compounds with established safety profiles. It should be noted that safety research is ongoing and assessments are revisited as new data become available. Regulatory agencies and expert committees periodically review evaluations to ensure that conclusions remain consistent with the latest scientific evidence. For compounds with limited data, conservative approaches are applied in risk assessment to protect public health. Overall, the safety profile of this compound as determined by international evaluations reflects an understanding that exposure via food use at typical levels is unlikely to pose a risk, provided good manufacturing and usage practices are observed.

Regulatory Status Worldwide

The regulatory status of flavouring agents such as (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE varies across jurisdictions and depends on evaluations by competent authorities. One key international evaluation is provided by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which assesses flavouring substances to determine whether there is a safety concern at current intake levels. According to the JECFA database, this compound is identified under the JECFA number 1908 and classified within the functional class of flavouring agents. The available evaluation indicates that there is no safety concern at current levels of intake when used as a flavouring agent. This conclusion arises from a review of available toxicological and intake data assembled during the relevant JECFA session. In the United States, flavouring agents are generally subject to regulation by the Food and Drug Administration (FDA). Synthetic flavouring substances may be permitted for use provided they meet safety criteria and are consistent with good manufacturing practices. While some flavouring agents are explicitly listed in FDA regulations, others may be evaluated through the FEMA GRAS (Flavor and Extract Manufacturers Association Generally Recognized as Safe) process. Industry references associate this compound with FEMA GRAS Reference number 4393, indicating that it has been evaluated for safety among flavour professionals. However, it is important to note that FEMA GRAS status does not equate to an explicit FDA approval listing within the Code of Federal Regulations. Therefore, the FDA approval status for this specific compound remains uncertain, and manufacturers should consult regulatory guidance when using it in food products. In the European Union, flavouring substances are regulated under the EU Regulation on flavourings, which requires evaluation of safety and use levels. While specific E-number assignments are common for many additives, flavouring agents often fall under general flavouring regulations without individual E-number identification. As a result, the EU status for this compound would depend on inclusion in flavouring inventories and compliance with conditions set forth in relevant regulations. Overall, while international expert bodies such as JECFA have conducted evaluations with no safety concern at typical intake levels, individual regulatory regimes may handle flavouring agents differently. Compliance with regional and national requirements, including usage conditions and labelling, is essential for any product incorporating such compounds.

Taste And Functional Properties

The sensory and functional properties of (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE are determined by its molecular structure and physicochemical characteristics. As a flavouring agent, one of its primary attributes is the ability to contribute distinct aroma notes. Aldehydes are well known in food chemistry for their pronounced olfactory impact; even at low concentrations they can impart noticeable sensory qualities. For this compound, industry data indicate that it may exhibit fruity and citrus-like aroma characteristics that can enrich flavour profiles when used in combination with other agents. From a functional perspective, this compound is relatively volatile due to its low molecular weight and the presence of a reactive aldehyde group. Volatility is an important attribute for flavour compounds because it influences how the aroma is released during consumption. Compounds with moderate to high volatility can contribute significantly to the immediate olfactory perception as food is heated or in the mouth during eating. In terms of solubility, flavouring aldehydes are often more soluble in organic phases than in water. This characteristic informs how formulators incorporate them into products. For example, when used in oil-based or alcoholic matrices, the compound may dissolve more readily, whereas in aqueous systems it may require emulsification or other formulation techniques to achieve uniform distribution. The functional stability of flavouring agents also depends on processing conditions. Heat, pH, and interaction with other ingredients can influence the integrity of aldehyde compounds. For instance, exposure to high temperatures during baking or cooking may lead to degradation or transformation of some aldehyde structures. Therefore, formulators evaluate functional properties in model systems to ensure that the sensory attributes are retained under expected processing and storage conditions. Overall, the combination of a characteristic sensory profile and predictable functional behaviour in formulations makes this compound a useful option for enhancing flavour complexity in a range of food and beverage products when applied according to good flavouring practices.

Acceptable Daily Intake Explained

The concept of an Acceptable Daily Intake (ADI) is used in food safety to describe the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. For many food additives, including flavouring agents, ADIs are established based on toxicological data and safety factors that account for uncertainties between animal studies and human exposure. In the case of (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) did not assign a numeric ADI. Instead, the evaluation concluded that there is no safety concern at current levels of intake for its use as a flavouring agent. When a regulatory authority determines that typical dietary exposure is below levels associated with toxic effects, it may communicate that there is no safety concern rather than establishing a specific numeric ADI. It is critical to understand that the absence of an explicit ADI does not imply that unlimited consumption is safe. Rather, it indicates that based on the data reviewed, the expected exposure from use in foods at technologically necessary levels does not raise health concerns under intended conditions of use. ADI values, when established, serve as reference points for risk management and regulatory decisions, providing a margin of safety between human exposure and levels without observed adverse effects in studies. In the context of flavouring agents, where usage levels tend to be very low, regulators may conclude that intake is sufficiently limited to not warrant a defined ADI. For consumers and manufacturers alike, the important takeaway is that safety evaluations consider typical use patterns and available toxicology evidence to ensure that the compound’s presence in food products does not compromise health when used appropriately. Regulatory bodies continue to monitor scientific developments and may update assessments if new data suggest a need for revision of safety conclusions.

Comparison With Similar Additives

Flavouring agents cover a diverse range of chemical classes, including aldehydes, ketones, esters, and terpenoids. Comparing (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE with structurally related aldehydic flavour compounds can help illustrate differences and similarities in sensory and usage characteristics. For example, compounds such as trans-2-hexenal and other unsaturated aldehydes are known for their green, leafy or fruity notes and are used in specific food flavouring contexts. Each aldehyde’s sensory contribution depends on its molecular structure, including chain length, degree of unsaturation, and functional group placement. Similarly, other cyclopropane-containing flavour compounds may exhibit unique aroma profiles that complement base flavours in complex formulations. Functional considerations such as volatility, solubility, and stability under processing conditions vary from one flavouring agent to another. While some aldehydes may be more volatile and suitable for aroma enhancement in beverages, others with higher molecular weight and lower volatility may be better suited for applications where retention during processing is necessary. Regulatory evaluations also differ among flavouring agents. Some well-studied compounds have numeric ADIs established by expert committees, while others are concluded to have no safety concern at typical intake levels without assigning a numerical ADI. This reflects differences in the available toxicological data and intake estimates, as well as the compound’s frequency and levels of use in food products. Ultimately, formulation scientists consider a suite of flavouring agents, selecting those that achieve the desired sensory profile while meeting regulatory and safety criteria. Understanding each additive’s sensory and regulatory profile aids in creating balanced and compliant food products.

Common Food Applications Narrative

Flavouring agents are integral to the sensory experience of many food and beverage products, and (+/-)-CIS- AND TRANS-2-METHYL-2-(4-METHYL-3-PENTENYL)CYCLOPROPANECARBALDEHYDE is one such compound that may be encountered in industry formulations. These agents are typically selected to deliver specific aroma nuances that complement or enhance the base ingredient profile. In broad terms, this compound could be used in products where fruity or citrus-like flavour notes are desired. Examples include beverage concentrates, confectionery systems, dairy-based desserts, and certain savoury applications where brightness or complexity is sought. In beverage processing, flavouring agents are often combined with sweeteners and acidulants to create balanced profiles in soft drinks, juice blends, and ready-to-drink teas. Aldehyde-based flavour compounds can help impart top-note aroma components that consumers perceive upon opening a package or taking a first sip. In confectionery, they can contribute to the richness and character of fruit-flavoured candies, gummies, and chews, again at levels that support the overall sensory goal without dominating the formulation. Dairy and dessert products such as yogurts, ice creams, and custards may also incorporate flavouring agents to achieve consistent flavour character, especially when the natural ingredient variability is undesirable or insufficient. Functional foods and fortified products may use specialised flavouring agents to mask off-notes from added nutrients while providing a pleasant and familiar aroma. Across these applications, the role of a flavouring agent is highly targeted: to enhance consumer appeal by contributing desirable sensory attributes that align with the product concept. Formulators typically work iteratively, combining analytical data with sensory evaluation to determine appropriate usage levels. Given the regulatory context for flavour use, these agents are applied in accordance with principles of good manufacturing practice, ensuring that sensory benefits are achieved without exceeding recommended or permissible levels.

Safety & Regulations

FDA

  • Notes: Specific FDA approval listing in CFR could not be verified for this compound.

EFSA

  • Notes: EFSA evaluation status could not be verified with authoritative deep link.

JECFA

  • Notes: JECFA concluded no safety concern at typical intakes; numeric ADI not assigned.
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent

Sources

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