DEHYDRONOOTKATONE

CAS: 5090-63-1 FLAVORING AGENT OR ADJUVANT

DEHYDRONOOTKATONE is an organic compound used as a flavoring agent with a citrus or grapefruit profile. It has been evaluated by international expert bodies and appears on flavoring inventories.

What It Is

DEHYDRONOOTKATONE is a naturally occurring organic compound classified among flavoring agents or adjuvants. Chemically it is an alicyclic carbonyl compound with the CAS Registry Number 5090-63-1 and is one of a group of terpene-derived molecules that impart citrus, grapefruit, and fruity sensory characteristics in formulations. This compound appears in regulatory inventories and flavoring databases as being used for its organoleptic properties, particularly in applications where a citrus-like note is desired. DEHYDRONOOTKATONE is recognized by flavor industry panels and international bodies such as the Flavor and Extract Manufacturers Association (FEMA) with a FEMA number assignment and by JECFA with a flavour number in their specifications database. When described in literature, it is often accompanied by synonyms that reflect its complex chemical nomenclature, such as 8,9-didehydronootkatone and various naphthalenone structural descriptors, which reflect the ringed carbon structure and terpenoid origin of the compound. At standard conditions, DEHYDRONOOTKATONE typically exists as a pale yellow to brownish liquid with a distinctive aroma that has been characterized as citrusy and grapefruit-like. These sensory descriptors are consistent with its use as a flavoring agent or adjuvant in certain food and beverage formulations that seek to enhance or complement fruit-forward flavor profiles. The classification as a flavoring agent or adjuvant indicates that its primary role is to contribute to the desirable sensory characteristics of foods or beverages rather than to provide nutritional or preservative functions. Because of its specific sensory attributes, it is typically deployed in small quantities where potent aroma and flavor impact is required. The presence of DEHYDRONOOTKATONE in flavoring inventories and evaluations by expert committees underscores its relevance to food science and sensory studies. It should be noted that while industry catalogs often list its physical and chemical properties, its regulatory status in specific jurisdictions is informed by international assessments such as those performed by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which has considered its safety at current levels of intake. These evaluations provide a framework for understanding how this compound is viewed in regulatory and safety contexts worldwide, contributing to its acceptance in specific flavoring applications.

How It Is Made

The production of DEHYDRONOOTKATONE typically involves either extraction from natural sources or synthesis through chemical pathways tailored to yield its specific molecular structure. Natural extraction methods focus on isolating the compound from botanicals or plant materials where related terpenoid compounds are prevalent, such as certain heartwood and other aromatic plant parts. Traditional processes begin with maceration or solvent extraction of plant materials, followed by distillation and purification steps to concentrate the compound of interest. Fractional distillation and chromatographic separation techniques are often applied to isolate DEHYDRONOOTKATONE from a mixture of related terpenes and other aromatic constituents. In addition to natural extraction, synthetic chemistry approaches can be employed to produce DEHYDRONOOTKATONE in a more controlled and scalable manner. Synthetic pathways may begin with precursor compounds such as nootkatone derivatives or bicyclic ketones, which undergo controlled dehydrogenation reactions to introduce the double bonds characteristic of the dehydro form. Catalytic dehydrogenation and selective oxidation procedures are common techniques in organic synthesis for constructing complex cyclic ketones. These synthetic approaches allow producers to achieve consistent purity and yield for applications where natural variability may not be acceptable. Regardless of the source, production methods for DEHYDRONOOTKATONE are designed to meet flavor industry specifications for purity, sensory quality, and consistency. International flavoring panels and industry consensus groups provide guidance on acceptable purity thresholds and analytical methods for identification, which ensure that the compound being used in food formulations is of suitable quality. This involves rigorous analytical testing, including gas chromatography and mass spectrometry, to confirm identity and the absence of undesirable contaminants. The manufacturing context also includes adherence to safety guidelines for handling volatile organic compounds, as many flavoring agents, including DEHYDRONOOTKATONE, can be flammable or pose inhalation risks if not properly controlled. Through these processes, flavor houses and ingredient manufacturers can supply DEHYDRONOOTKATONE for use in a variety of formulations where its characteristic citrus notes are desired.

Why It Is Used In Food

DEHYDRONOOTKATONE is used in food and beverage formulations primarily for its distinct citrus and grapefruit-like sensory attributes, which can enhance or round out flavor profiles in a wide range of products. Flavor chemists often seek compounds with specific aromatic signatures to achieve desired sensory impacts in complex food systems, and DEHYDRONOOTKATONE, with its potent and recognizable citrus notes, serves this role effectively. When combined with other flavoring agents, it can provide depth, brightness, and a fruit-forward dimension that complements sweet, bitter, or tangy components in formulations. The use of DEHYDRONOOTKATONE is typically in very small quantities because of its potency; this means that it functions effectively as an adjuvant or modifier of flavor rather than as a main ingredient. Its high sensory impact means that only trace amounts are needed to influence the overall flavor perception of a product. This characteristic is valuable in the food industry, where precise control of flavor intensity is essential for product consistency and consumer acceptance. The ability to achieve a citrus or grapefruit-like note without adding significant quantities of other ingredients also supports formulation efficiency. In addition to direct sensory effects, compounds such as DEHYDRONOOTKATONE may be used to balance flavor profiles, mask off-notes from other ingredients, or reinforce a particular flavor theme in a product. Because modern consumers often seek nuanced and layered flavor experiences, manufacturers may include flavoring agents like DEHYDRONOOTKATONE as part of a broader palette of sensory tools to meet market expectations. Its use is informed by sensory science research and industry expertise that evaluates how specific molecules interact with taste receptors and olfactory pathways, thereby shaping the perceived flavor of foods and beverages across various categories.

Adi Example Calculation

An illustrative example of how acceptable daily intake considerations might be understood (although no numeric ADI is assigned for DEHYDRONOOTKATONE) can be framed in terms of a hypothetical substance with a defined ADI. For example, if a compound had an ADI of X mg per kg body weight, a person weighing 60 kilograms would have a theoretical maximum daily intake of 60 × X mg per day. This calculation helps regulators and formulators understand how exposure scales with body size. In the case of DEHYDRONOOTKATONE, because regulatory evaluations have concluded there is no safety concern at current levels of intake and no numeric ADI is established, an ADI example calculation is not applicable. Instead, the narrative evaluation by expert committees serves as the reference for understanding how typical exposure compares to levels of concern. Consumers should interpret narrative safety conclusions as an indication that flavoring agents are used at levels well below thresholds of toxicological concern. Typical food formulations involve trace amounts of potent flavoring substances, meaning that even frequent consumption of products containing such agents contributes minimally to overall dietary exposure. The focus on narrative safety conclusions rather than numeric thresholds underscores the importance of context in safety assessments, where both exposure and hazard data inform regulatory judgments about whether use levels are acceptable.

Safety And Health Research

Regulatory evaluations of DEHYDRONOOTKATONE focus on its technical function as a flavoring agent and the safety of its use at levels typical in food applications. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) has reviewed this compound and determined that there is no safety concern at current levels of intake when used as a flavouring agent, which reflects an assessment of available toxicological and exposure data relevant to typical human consumption. This conclusion suggests that under normal conditions of use in flavoring applications, DEHYDRONOOTKATONE does not pose identified risks that would warrant specific restrictions, and this finding provides a basis for industry practice in formulating products within established sensory and safety norms. It is important to note that flavoring agents like DEHYDRONOOTKATONE are evaluated for general safety and potential effects using standard toxicological endpoints including acute toxicity, subchronic studies, and evaluations of metabolic handling. These assessments consider the expected exposure levels from intended uses and the compound’s biochemical behavior, informing expert judgments about risk. While JECFA’s evaluation indicates no safety concern at current intake levels, specific numeric values such as an acceptable daily intake (ADI) may not be assigned when exposure estimates are low and data do not indicate the need for a quantified threshold. As a result, narrative conclusions are often used to guide safe use rather than precise numeric limits. In addition to international expert assessments, flavor industry groups such as the Flavor and Extract Manufacturers Association (FEMA) compile sensory and safety data and assign FEMA numbers to flavoring substances, which include context on usage levels and sensory attributes. Such industry evaluations supplement regulatory perspectives by providing detailed usage information and supporting safe application in food formulation. Together, these assessments inform product developers about how DEHYDRONOOTKATONE can be used responsibly in consumer products while adhering to safety standards that prioritize minimal risk at intended exposure levels.

Regulatory Status Worldwide

DEHYDRONOOTKATONE is listed in the United States Food and Drug Administration’s Substances Added to Food inventory, formerly known as the Everything Added to Food in the U.S. (EAFUS) inventory, indicating that it is recognized as a flavoring agent or technical ingredient used in foods based on evaluations by flavor industry bodies and international expert committees rather than through a specific CFR regulation. This listing provides information about its use and classification but does not constitute a specific FDA affirmative approval under a Code of Federal Regulations section, and as such, regulatory approval status is set to null in the FDA context with a note explaining that FDA has not provided a dedicated CFR listing for this compound. In Europe, DEHYDRONOOTKATONE may appear in flavor inventories, but a specific E-number designation has not been established in the available authoritative documentation, resulting in null values for formal EU additive numbers in the EFSA context. Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated DEHYDRONOOTKATONE and concluded that at current levels of intake when used as a flavouring agent there is no safety concern, reinforcing its acceptability for use within the scope of flavor applications. This evaluation by JECFA provides a scientific basis for its use in foods from a safety perspective, though it does not assign a numeric acceptable daily intake value in the traditional sense because the conclusion is framed in terms of safety at current intake levels rather than a quantified ADI. As such, the jecfa.adi_mg_per_kg field remains null with a note reflecting this context. Regulatory frameworks for flavoring agents often rely on such expert committee evaluations in the absence of specific statutory listings, and manufacturers incorporate additive specifications and usage guidelines informed by these evaluations to ensure compliance with local food regulations.

Taste And Functional Properties

DEHYDRONOOTKATONE is recognized for its sensory profile that is commonly described as citrusy, fruity, and reminiscent of grapefruit. This sensory signature makes it a valuable tool in flavor development, particularly in beverages, confections, and other food systems where citrus notes are desirable. Sensory descriptors compiled by flavor research inform its application, indicating that its aroma and taste contributions are most pronounced when integrated with other complementary aromatic compounds. The compound’s functional properties go beyond mere odor contribution; it can influence the overall flavor balance by enhancing fruity top notes while blending with other components to create a more rounded flavor profile. From a functional perspective, DEHYDRONOOTKATONE exhibits physicochemical behaviors characteristic of small, moderately lipophilic ketones. Its solubility profile, as inferred from analytical data, suggests greater affinity for organic phases than for aqueous systems, meaning it disperses more readily in fats, oils, and non-polar solvents than in water. This behavior influences how it is formulated into food systems; it may require appropriate carriers or emulsification strategies to achieve uniform distribution in products with significant water content. Stability under processing conditions such as moderate heat and pH variations is also a consideration for formulators, as these factors can affect both sensory impact and molecular integrity over the shelf life of a product. The compound’s moderate volatility is part of what gives it a strong aromatic presence, as volatiles are readily released into the headspace of a food or beverage, contributing to aroma perception before taste. Understanding these functional properties allows food scientists to anticipate how DEHYDRONOOTKATONE will behave during manufacturing, storage, and consumption, and to design formulations that optimize its contribution while maintaining product quality. Its sensory and functional attributes, combined with considerations of solubility and stability, inform formulation decisions across a range of food categories where citrus-like notes are a key part of the consumer experience.

Acceptable Daily Intake Explained

The concept of an acceptable daily intake (ADI) is used by international expert bodies to describe the amount of a substance that can be consumed daily over a lifetime without appreciable risk. For DEHYDRONOOTKATONE, a specific numeric ADI is not established because the Joint FAO/WHO Expert Committee on Food Additives (JECFA) concluded that there is no safety concern at current levels of intake when used as a flavouring agent. This type of conclusion reflects an evaluation where typical exposure estimates are sufficiently low and toxicological data do not indicate the need for a defined quantitative ADI. In practice, this means that, based on available evidence and typical use levels in flavoring applications, DEHYDRONOOTKATONE is not expected to pose safety concerns within ordinary consumption patterns. It is important to understand that an ADI is not a recommended intake level; rather, it is a risk management tool that helps regulators and industry determine whether use levels are consistent with safety expectations. When a numerical ADI is not assigned, expert committees often use narrative statements like "no safety concern at current intake levels" to communicate that the substance, as used, does not present identified risks based on the data reviewed. This narrative provides flexibility for manufacturers to use the compound within standard flavoring practice while ensuring that safety considerations inform formulation decisions. Consumers typically encounter flavoring agents like DEHYDRONOOTKATONE in very low concentrations, and the overall exposure from a varied diet is generally below levels that would raise concerns according to expert evaluations. The narrative conclusion from JECFA emphasizes that typical intake patterns do not present a safety issue, underscoring the role of careful scientific assessment in supporting the safe use of flavoring agents in food products.

Comparison With Similar Additives

DEHYDRONOOTKATONE is one of several citrus or fruit‑derived ketone flavoring agents used in food and beverage applications. Similar compounds include nootkatone, which also provides grapefruit and citrus notes, and other terpene‑derived ketones that contribute distinct aroma characteristics. When comparing DEHYDRONOOTKATONE with related additives such as nootkatone, formulators consider factors like sensory strength, volatility, and solubility, which influence how each compound interacts with a particular product matrix. For example, while both compounds may impart citrus notes, differences in molecular structure can lead to variations in perceived intensity and stability under processing conditions. Another class of compounds used for similar sensory objectives includes esters such as ethyl butyrate or methyl anthranilate, which provide fruity and sweet aromatic profiles. These esters differ from ketones like DEHYDRONOOTKATONE in both sensory quality and physicochemical behavior, often exhibiting different thresholds of detection and solubility characteristics. Comparing these additives highlights how flavor chemists select specific molecules based on the target sensory profile and functional requirements of a formulation, balancing factors like aroma intensity, compatibility with other ingredients, and stability. Understanding the similarities and differences among flavoring agents enables formulators to tailor sensory outcomes effectively. While DEHYDRONOOTKATONE is particularly valued for its grapefruit‑like character, other molecules may be chosen to achieve complementary or contrasting effects, resulting in complex and appealing flavor profiles. The diversity of flavoring agents reflects the nuanced approaches used in modern food science to meet consumer expectations for variety and depth in taste and aroma.

Common Food Applications Narrative

DEHYDRONOOTKATONE finds application in food and beverage products where citrus-like flavor enhancement is desirable. In beverage formulations such as soft drinks, fruit juices, flavored waters, and energy drinks, the compound can provide a pronounced citrus or grapefruit note that complements natural and artificial sweeteners alike. Its inclusion in these products can help achieve a flavor profile that meets consumer expectations for brightness and freshness, particularly in citrus-forward varieties. Beverage formulators often rely on a suite of aroma compounds, including those like DEHYDRONOOTKATONE, to deliver a balanced sensory experience that is both recognizable and appealing. In confectionery, small amounts of DEHYDRONOOTKATONE may be used in hard candies, gummies, and other sweets where a citrus note is part of the flavor profile. Its potent sensory impact allows it to contribute effectively even in the presence of sugar and other dominant taste components. Similarly, in dairy-based desserts, such as fruit-flavored yogurts and ice creams, it can enhance the perception of fruitiness without overwhelming the base ingredients. In these applications, flavor consultants and developers carefully calibrate the use level to ensure that the compound’s contribution aligns with the intended sensory character of the product. The compound is also used in savory applications where a touch of citrus can elevate the overall flavor complexity. For example, it might be part of seasoning blends for snack foods, sauces, and salad dressings that benefit from a hint of fruitiness or brightness. In each of these contexts, DEHYDRONOOTKATONE is used judiciously as a component of a broader flavor strategy, where its specific sensory qualities contribute to a holistic taste experience that aligns with consumer preferences for nuanced and dynamic flavor profiles.

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Safety & Regulations

FDA

  • Notes: FDA has not provided a specific CFR regulation listing for DEHYDRONOOTKATONE; inclusion in the Substances Added to Food inventory does not itself indicate an affirmative approval.

EFSA

  • Notes: No specific EFSA E-number or numeric ADI could be verified from available authoritative sources.

JECFA

  • Notes: JECFA concluded no safety concern at current levels but did not assign a numeric ADI value or specify the year on the available database entry.
  • Adi Display: No safety concern at current intake levels when used as a flavouring agent

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