TRANS-ALPHA-DAMASCONE

CAS: 24720-09-0 FLAVORING AGENT OR ADJUVANT

TRANS-ALPHA-DAMASCONE is a synthetic flavouring agent used to add or modify aroma notes in foods and beverages. It is a floral and fruity ketone commonly used in flavour formulations.

What It Is

TRANS-ALPHA-DAMASCONE is a synthetic flavouring agent classified chemically as an alicyclic ketone with the CAS number 24720-09-0. It is part of a class of compounds used to impart or enhance aroma and flavour in foods and beverages. The structure of this compound consists of a trimethylcyclohexenyl moiety attached to an unsaturated butenone group, giving it a distinct profile of floral and fruity sensory characteristics. Other synonyms for this compound include alpha-damascone and various systematic chemical names reflecting its precise molecular composition. In flavour chemistry, it is recognized for contributing complex aroma notes that can resemble floral, rose, apple, black currant, and fruity impressions in finished formulations. The compound is evaluated for food use in many jurisdictions and may be included in inventories of flavouring substances by expert panels. Flavouring agents like TRANS-ALPHA-DAMASCONE are typically used at low concentrations because of their potent sensory effects. As a technical function, it acts to modify and enhance specific flavour profiles in food products, often as part of a broader flavour blend. Its inclusion in flavour libraries reflects its established utility among flavourists and formulators for achieving desired sensory profiles in diverse edible products. Consumers would encounter this additive indirectly as a component within complex flavour systems rather than as an isolated ingredient. The sensory contributions of this agent are contextual and depend on the overall formulation, matrix interactions, and processing conditions used in the food product. In regulatory and technical contexts, the identification of this compound is standardized by its CAS number and by entries in flavouring agent databases. These identifiers help ensure consistent use and evaluation across scientific, regulatory, and industrial domains.

How It Is Made

The manufacturing of TRANS-ALPHA-DAMASCONE involves organic synthesis pathways typical for alicyclic ketone flavouring compounds. While proprietary processes can vary among manufacturers, the general chemical synthesis starts with building the cyclohexenyl framework and then introducing the unsaturated ketone functional group through well-established reactions such as aldol condensations or enone-forming steps. These reactions are chosen to achieve the desired stereochemistry and purity required for flavour use. Industrially, producers aim to achieve high chemical purity and control by-products that could affect sensory properties or safety. After synthesis, the compound is purified using techniques such as distillation and chromatography to meet flavour industry specifications. Quality control is critical to verify identity, purity, and organoleptic properties of the product before it is released for application. Documentation from flavour industry associations indicates that TRANS-ALPHA-DAMASCONE is catalogued with a FEMA number that corresponds to its evaluation by expert panels. These panels assess technical specifications, including identity, physical properties, and safety considerations relevant to its use as a flavouring substance. Manufacturing locations and processes may be subject to regulatory oversight in different jurisdictions, and quality systems often follow good manufacturing practices appropriate for food-grade ingredients. Producers typically perform rigorous analytical characterization to confirm chemical composition and sensory quality. Although the specific manufacturing details are proprietary, the overarching approach reflects standard practices in fine chemical synthesis for food flavouring agents.

Why It Is Used In Food

TRANS-ALPHA-DAMASCONE is used in food primarily for its ability to impart complex and desirable aroma characteristics. As a flavouring agent, it contributes floral, fruity, and rosy sensory notes that are difficult to achieve with simple natural extracts or other single compounds. Its inclusion in flavour formulations can enhance or round out the overall profile of a product, delivering sensory nuances valued in beverages, confections, and other processed foods. Flavor chemists often select compounds like TRANS-ALPHA-DAMASCONE based on the target sensory profile of the food product. Because it has a potent aroma, only small quantities are needed to achieve noticeable effects, making it efficient in flavour applications. It may be combined with other flavouring agents to achieve balance and complexity, particularly when aiming to replicate natural flavours or to create novel sensory experiences. For example, it may be used to enhance berry, floral, or fruit impressions without dominating the formulation. From a formulation perspective, such flavouring agents help producers achieve consistent taste and aroma across production batches. They also assist in masking undesirable notes from processing or other ingredients, supporting product quality and consumer appeal. The functional use of flavouring agents like TRANS-ALPHA-DAMASCONE is aligned with industry practices that rely on expert evaluation and sensory science to tailor food flavours to specific consumer preferences.

Adi Example Calculation

To illustrate how an ADI-based calculation might work if an ADI were available, consider a hypothetical scenario in which a flavouring compound has an established ADI of X milligrams per kilogram of body weight per day. For a person weighing Y kilograms, the daily intake below which no appreciable health risk is expected would be X multiplied by Y. For instance, if the ADI were 1 mg per kg body weight and the adult weighed 70 kg, the acceptable daily intake would be 70 mg per day. This calculation does not reflect an actual regulatory value for this compound, since an ADI has not been allocated by JECFA. Such hypothetical exercises are useful for understanding how ADIs are applied in risk assessment.

Safety And Health Research

Safety assessments of flavouring agents typically involve evaluation of toxicological data, including genotoxicity, subchronic toxicity, reproductive and developmental toxicity, and potential for adverse effects at realistic consumption levels. Expert panels like JECFA review available data and determine whether a health-based guidance value can be established. For TRANS-ALPHA-DAMASCONE, the Joint FAO/WHO Expert Committee on Food Additives did not allocate a numerical acceptable daily intake due to insufficient information at the time of evaluation. This suggests that while the compound has been evaluated, the data were not adequate to define a conventional ADI value. Regulatory bodies may also consider aggregate exposure from multiple sources, structural analogues, and metabolism when assessing safety. Because many flavouring compounds share common metabolic pathways, data from related substances may inform evaluations, but formal assessments focus on the compound in question. The absence of a formal ADI does not inherently imply a safety concern at practical use levels, but rather highlights a data gap that regulators recognize in formal terms. Further research and data submissions could support future evaluations and refinement of safety descriptors.

Regulatory Status Worldwide

International expert panels have evaluated TRANS-ALPHA-DAMASCONE as a flavouring substance. According to the JECFA database, the compound has been reviewed by the Joint FAO/WHO Expert Committee on Food Additives, which assigns it a JECFA number and evaluates toxicological and exposure data. The JECFA entry indicates that an ADI was not allocated due to incomplete information, meaning that the committee did not establish a specific numerical acceptable daily intake at the time of assessment. This does not imply it is prohibited, but rather that additional data would be needed to define a formal ADI in that context (JECFA notes additional information was required). In the United States, flavouring substances evaluated by FEMA and JECFA may appear in the FDA Substances Added to Food inventory, but inclusion in that inventory does not equate to formal FDA approval under 21 CFR parts. The FDA inventory lists such substances as part of the flavouring landscape, and it is noted that presence in the inventory itself does not confirm regulatory approval by FDA. (cfsanappsexternal.fda.gov) European regulatory bodies evaluate flavouring agents under EU frameworks that govern food additive usage and safety assessments. However, specific listings, usage conditions, or numerical E-numbers for this compound are not readily identifiable in the available public regulatory records.

Taste And Functional Properties

TRANS-ALPHA-DAMASCONE is characterized by a complex sensory profile that combines floral and fruity notes with nuances reminiscent of rose, apple, and berry-like impressions. The compound’s organoleptic properties make it a valuable ingredient in flavour formulations where such sensory qualities are desired. Its potency means that even at low concentrations, it can significantly influence the aroma and perceived flavour of a food or beverage system. In terms of functional behaviour, flavouring agents such as TRANS-ALPHA-DAMASCONE must be compatible with the base food matrix and processing conditions. These compounds are generally stable under typical formulation and processing conditions used in foods and beverages, but like many flavouring molecules, they can be sensitive to extreme heat, pH, or oxidative environments depending on the matrix. Solubility characteristics influence how the compound disperses in a given food system, and it is typically incorporated in a flavour blend or carrier solution to facilitate uniform distribution. Its interactions with other flavour components and food ingredients can modulate both perception and stability. Overall, the sensory and functional properties of this compound make it a preferred choice for formulating nuanced floral and fruity notes. Its performance is evaluated within the context of the full flavour profile, and experienced flavourists adjust usage levels to achieve the desired sensory outcome without overpowering other components of the product.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a health-based estimate of the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, expressed relative to body weight. ADIs are typically derived by regulators through detailed evaluation of toxicological studies, identification of a no-observed-adverse-effect level, and application of safety factors to account for uncertainty. For some flavouring agents, a numerical ADI may not be assigned if the available data are inadequate. In the case of TRANS-ALPHA-DAMASCONE, the JECFA database entry indicates that an ADI was not allocated at its last evaluation, reflecting a need for additional data rather than establishing a specific health guideline. ADI values provide a context for understanding regulatory assessments, but they are distinct from recommended intake levels. They are used by risk assessors and food safety authorities to gauge whether estimated consumption levels of flavouring substances in foods are likely to be of concern. Lack of an ADI allocation means that regulators have not defined this estimate based on the current evidence. This absence highlights the importance of continued research and evaluation as part of ongoing safety assessment programs.

Comparison With Similar Additives

Compounds with functional similarities to TRANS-ALPHA-DAMASCONE include other alicyclic ketone flavouring agents like beta-damascone, ionones, and certain substituted cyclohexenones. These substances also contribute distinct fruity, floral, or woody notes and are selected based on their sensory profiles. For example, ionones may provide violet-like notes that differ from the rosy-fruity character of damascones. Usage levels and sensory impact vary among these flavouring agents, and flavourists choose them based on desired aroma nuance. From a regulatory standpoint, many flavouring agents are subject to similar evaluation processes by expert panels for safety and specifications. Some, like certain ionones, may have clearer allocations of acceptable daily intake values based on robust toxicological data, whereas others, such as TRANS-ALPHA-DAMASCONE, currently lack formal numeric ADIs due to data gaps. Understanding these differences helps formulators and regulators contextualize the technical and safety profiles of related compounds used in flavour formulations.

Common Food Applications Narrative

Flavouring agents with complex sensory profiles, such as TRANS-ALPHA-DAMASCONE, are employed in various food categories where the perception of floral and fruity notes is important. In beverage applications, these compounds may be part of flavour systems that evoke the character of berries, fruits, or floral essences, contributing to the overall consumer experience. In confectionery and bakery products, they help achieve nuanced aromatic profiles that enhance sweetness and fruit impressions without adding sugars or colours. Processed snacks, dessert toppings, and dairy-based products also benefit from the inclusion of specialised flavouring substances when specific sensory qualities are sought. For example, a floral-fruity character may be desirable in yogurt formulations or fruit-flavoured desserts, where balancing aroma intensity with the base food matrix is critical. Similarly, ready-to-drink beverages and powdered drink mixes rely on carefully crafted flavour blends that can include such agents to deliver consistent and appealing sensory profiles. These technical uses do not necessarily indicate high inclusion levels of the compound itself, but rather its strategic role in flavour design. Because consumers often associate specific aroma cues with product quality and identity, ingredients that help achieve those cues are valuable tools for flavour developers. Ultimately, the use of TRANS-ALPHA-DAMASCONE in food applications reflects broader industry practices for meeting sensory targets in competitive marketplaces.

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Safety & Regulations

FDA

  • Notes: Inclusion in FDA food substance inventories does not confirm formal FDA food additive approval; regulatory approval status is not clearly defined based on available evidence.

EFSA

  • Notes: No specific EFSA evaluation or E-number/ADI was found in available public records.

JECFA

  • Notes: JECFA evaluated this flavouring agent but did not allocate a numeric ADI due to insufficient data; specific year not explicitly shown on entry.

Sources

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