9-DECEN-5-OLIDE

CAS: 74585-00-5 FLAVORING AGENT OR ADJUVANT

9-DECEN-5-OLIDE is a cyclic unsaturated lactone used as a flavoring agent or adjuvant in food formulations. It has been evaluated by international expert bodies for safety in flavoring use.

What It Is

9-DECEN-5-OLIDE is a medium-chain cyclic ester belonging to the family of lactones commonly used in the flavor and fragrance industries. Structurally, it is an unsaturated delta-lactone with a ten-carbon backbone and an internal ester linkage. The compound appears as a colorless to pale liquid with a creamy, sweet, and nutty aroma profile, characteristics that make it desirable for imparting rich flavor notes in foods. In regulatory and scientific contexts, 9-DECEN-5-OLIDE is recognized under CAS number 74585-00-5 and is described with multiple synonymous chemical names, reflecting its lactone structure and functional classification as a flavoring agent or adjuvant. Its sensory characteristics and technical designation highlight its specific contribution to flavor formulation, where it is used in low concentrations to evoke dairy-like or creamy sensory perceptions. This section provides a comprehensive overview of how 9-DECEN-5-OLIDE is defined within food science and regulatory evaluations, emphasizing its chemical identity and purpose as a flavoring additive. The classification of lactones such as 9-DECEN-5-OLIDE in food science pertains to compounds that derive from hydroxy acids through internal esterification, creating cyclic structures that contribute distinct sensory impressions. Unlike simple esters, lactones often present more complex odors and flavor impacts due to ring strain and alkene positioning, making them valuable in flavor design. The unsaturated nature of this particular lactone differentiates it from saturated analogs in both aroma and chemical behavior. Within this context, 9-DECEN-5-OLIDE's odor and taste contributions are a direct function of its molecular architecture, which influences its volatility and interaction with sensory receptors. Understanding what 9-DECEN-5-OLIDE is establishes the foundational knowledge needed for deeper discussion on its production, use in food, and regulatory evaluation.

How It Is Made

The manufacture of 9-DECEN-5-OLIDE generally involves organic synthesis approaches that build the cyclic lactone from suitable hydroxy acid precursors. Typically, a hydroxy acid with a terminal double bond undergoes intramolecular esterification, a process in which the free carboxy and hydroxyl groups react to form the lactone ring. This ring closure can be facilitated under acidic conditions or using catalysts that promote dehydration, creating a stable six-membered oxan-2-one structure. Alternatively, advanced synthetic techniques such as ring-closing metathesis, a reaction commonly used in organic chemistry to form cyclic alkenes and lactones, can be employed to achieve high yields and control over stereochemistry. These methods provide manufacturers with options to optimize production based on desired purity, yield, and cost considerations. In industrial settings, 9-DECEN-5-OLIDE is often produced to meet flavor industry specifications, where purity and consistency are crucial for reliable sensory outcomes. Suppliers working with flavor and fragrance compounds apply stringent quality control measures, including chromatographic purity checks and sensory evaluations, to ensure that products conform to expected profiles. Although the specific details of commercial manufacturing processes vary by producer, the core chemical principle remains the controlled cyclization of linear hydroxy acids into lactone ring structures. Environmental and safety considerations in manufacturing also play roles in selecting catalysts and solvents to minimize residuals and achieve desirable product safety profiles. Overall, the production of 9-DECEN-5-OLIDE reflects standard practices in flavor compound synthesis that balance technical feasibility with sensory quality and regulatory compliance.

Why It Is Used In Food

9-DECEN-5-OLIDE is used in food primarily for its flavoring properties, where it contributes creamy, sweet, and nutty notes that enhance product sensory appeal. Flavor chemists incorporate it into formulations to provide depth and complexity, especially in applications where dairy-like or rich flavor characteristics are desirable. Its utility stems from the specific lactone structure, which interacts with olfactory receptors to evoke nuanced flavors not easily replicated by simpler compounds. In practice, it is used in combination with other flavoring agents to achieve balanced and targeted sensory profiles in foods ranging from baked goods to confectionery and dairy alternatives. The reason for using lactones like 9-DECEN-5-OLIDE lies in their potent sensory impact at low concentrations, making them efficient tools in flavor design. Because human flavor perception is a complex interplay of olfactory and gustatory cues, compounds that provide multiple sensory impressions are valuable in product development. 9-DECEN-5-OLIDE's effectiveness is a function of both its molecular volatility and its specific odor qualities, which complement other flavor ingredients to enrich the overall consumer experience. In addition to sensory considerations, formulators also use such agents to offset undesirable notes or to mask off-flavors that may arise during processing or storage. The choice to include 9-DECEN-5-OLIDE in a food product reflects a deliberate design decision to achieve a particular flavor profile that resonates with consumer expectations.

Adi Example Calculation

To illustrate how acceptable daily intake concepts are used in risk assessment, consider a hypothetical scenario in which an additive had a defined ADI. Imagine a hypothetical compound with an ADI of X mg/kg body weight per day. For a person weighing 70 kilograms, the theoretical maximum safe intake would be X multiplied by 70, resulting in 70X mg per day. In regulatory practice, this calculation helps scientists compare estimated dietary exposures from multiple food sources with the ADI benchmark to evaluate whether intake remains within safe limits. Although 9-DECEN-5-OLIDE does not have a numeric ADI assigned in public expert evaluations and instead is characterized as having no safety concern at typical intake levels, the hypothetical calculation underscores how ADIs function as practical tools for exposure assessment and risk characterization.

Safety And Health Research

Scientific and regulatory evaluations of 9-DECEN-5-OLIDE focus on hazard identification, exposure assessment, and intake considerations relevant to its use as a flavoring agent. Expert committees such as JECFA review toxicological data, including studies on acute toxicity, metabolism, and any available chronic or developmental endpoints, to determine whether typical exposure levels in food raise health concerns. The JECFA conclusion that there is no safety concern at current intake levels when used as a flavoring agent reflects this holistic risk assessment, which considers both hazard data and conservative estimates of dietary exposure. While there is acknowledgment of its sensory and chemical properties in flavor formulation contexts, peer-reviewed toxicological literature specific to 9-DECEN-5-OLIDE is not widely d in public databases. Therefore, researchers and regulators rely on expert interpretation of available data and analogous compounds when assessing risk. Safety research typically encompasses standard endpoints such as genetic toxicity, subchronic studies in laboratory animals, and metabolic fate following ingestion. Regulatory assessments emphasize that the absence of observed adverse effects at levels consistent with flavoring use does not imply intrinsic safety at all possible exposure levels; rather, it indicates that typical use concentrations are consistent with safety margins based on available evidence. As with many flavoring agents, ongoing monitoring of new data and periodic reevaluation by expert bodies contribute to maintaining up-to-date safety profiles.

Regulatory Status Worldwide

The international regulatory evaluation of 9-DECEN-5-OLIDE includes review by expert bodies such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA). According to the World Health Organization’s JECFA database, this compound has been evaluated (JECFA number 1993) and was concluded not to raise safety concerns at current levels of intake when used as a flavoring agent, based on evaluations reported in the WHO Technical Report Series. This assessment indicates that, in the context of flavor use, the compound does not pose a safety concern at typical exposure levels. The specific safety evaluation is publicly documented by the WHO JECFA chemical entry for 9-DECEN-5-OLIDE. In the United States, 9-DECEN-5-OLIDE appears in the FDA’s Substances Added to Food (formerly the EAFUS) inventory, which catalogs flavoring substances as recognized by the Flavor and Extract Manufacturers Association (FEMA) panel and referenced by JECFA. Inclusion in this inventory reflects recognition of its use as a flavoring agent; however, it does not equate to an independent FDA affirmative approval or specific regulation under the Code of Federal Regulations. No explicit FDA regulation citation for this substance’s approved status has been identified in available regulatory inventories. Consequently, its regulatory status in the U.S. is linked to recognized flavor inventories and expert panel assessments rather than a standalone CFR listing. Regulatory frameworks outside the U.S. often reference JECFA evaluations and align with Codex Alimentarius standards, whereby compounds with no safety concern at intake are permitted for use within established good manufacturing practice. Overall, regulatory acceptance is tied to international expert evaluations and industry practice rather than a universally harmonized numeric authorization.

Taste And Functional Properties

9-DECEN-5-OLIDE exhibits taste and aroma characteristics typical of lactones, where cyclic ester structures impart a rich and rounded sensory perception. Organoleptic descriptions often include creamy, sweet, and nutty notes, which contribute to its utility in flavor design. These sensory attributes make it valuable for formulations requiring dairy-like or mellow flavor profiles, particularly where the base ingredients lack inherent complexity. In practical terms, the sensory impact of 9-DECEN-5-OLIDE arises from its ability to interact with olfactory receptors in ways that evoke both sweetness and creaminess, even in the absence of actual sugars or fats. Sensory scientists leverage these properties to enhance consumer appeal without altering caloric profiles. From a functional standpoint, 9-DECEN-5-OLIDE is generally stable under typical food processing conditions, including moderate heat and pH variations encountered in many culinary applications. Its solubility tends to favor organic phases, aligning with its role in flavor systems that rely on fat or ethanol carriers for effective dispersion. The compound's relatively low volatility compared to small esters or aldehydes also means it can persist through processing and storage, maintaining its sensory contribution over time. While sensory perception is subjective and influenced by matrix effects, the consistent descriptor profiles reported in flavor chemistry literature underscore 9-DECEN-5-OLIDE's reliable contribution to taste and aroma when used appropriately. These functional properties are part of why lactones remain prevalent choices in complex flavor blends.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a regulatory concept used to describe the estimate of a daily exposure to a food additive that is considered without appreciable health risk over a lifetime. It is typically derived by expert committees through analysis of toxicological data from animal studies and application of safety factors to account for uncertainty and variability across human populations. ADIs are expressed in units of milligrams per kilogram of body weight per day (mg/kg bw/day) and provide a benchmark against which estimated dietary exposure can be compared to ensure consumer safety. For flavoring agents like 9-DECEN-5-OLIDE, expert bodies such as JECFA may conclude that the compound does not raise safety concerns at current intake levels rather than assign a numeric ADI. This outcome often reflects the compound’s relatively low exposure from use in food and absence of toxicological signals at those exposures. Rather than a defined ADI value, the conclusion of no safety concern at intake encountered in food serves a similar function, indicating that exposure levels typical of intended use are expected to be within safe bounds. This narrative context helps non-expert readers understand that ADIs and related evaluations are part of a structured approach to ensuring that flavoring agents can be used safely, with acceptance tied to both hazard data and realistic exposure assessments.

Comparison With Similar Additives

Comparing 9-DECEN-5-OLIDE to other lactone flavoring agents helps illustrate similarities and differences in sensory and regulatory profiles. For example, gamma-nonalactone and gamma-decalactone are medium-chain lactones that also provide creamy, fruity notes and are used in flavor design. These compounds, like 9-DECEN-5-OLIDE, exhibit distinctive odor profiles that contribute to specific sensory impressions; however, each has a unique carbon chain length and ring substitution pattern that modulates its aroma character. From a regulatory standpoint, many such lactones have also been evaluated by expert committees, with conclusions tailored to typical exposure scenarios and safety data. While some lactones may have structured numeric ADIs assigned, others are assessed as having no safety concern at their estimated intake levels, similar to 9-DECEN-5-OLIDE. The comparison underscores that flavoring agents with structural similarities can have comparable uses and regulatory consideration frameworks, while sensory distinctions guide their application in specific food categories.

Common Food Applications Narrative

In food applications, 9-DECEN-5-OLIDE is most often encountered in products where enhanced creamy or dairy-like flavor notes are desirable. Flavor designers may use it in baked goods to add richness that mimics traditional dairy components, particularly in formulations that are low in actual fats. In confectionery items, it can provide depth and a rounded finish that complements sweet sugar bases, especially where nuances such as nutty undertones enrich the overall sensory experience. Chewing gums and breath mints occasionally incorporate lactones to create lingering creaminess that balances sharper mint or sweet flavors. In sauces and dressings, the use of such lactones can modify perception of creaminess without relying solely on high-fat ingredients, serving both sensory and marketing objectives. Beyond traditional dairy analogs, 9-DECEN-5-OLIDE may also be part of flavor systems for plant-based alternatives designed to resemble milk, cheese, or ice cream products. In these contexts, flavor chemists blend it with other lactones, esters, and aroma compounds to achieve a profile that consumers associate with familiar tastes, even when the nutritional composition differs. The selection of lactones like 9-DECEN-5-OLIDE in such applications underscores a broader trend toward using specific aroma-active compounds to craft sensory experiences that align with consumer expectations across diverse product categories. As part of a broader palette of flavor ingredients, its role is to provide nuanced and enduring sensory cues that elevate product appeal in everyday foods.

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Safety & Regulations

FDA

  • Notes: FDA inclusion in flavor inventories does not equate to formal approval and specific regulation; independent CFR regulation text was not found.

EFSA

  • Notes: EFSA-specific evaluation and numeric ADI were not identified in authoritative sources.

JECFA

  • Notes: JECFA concluded no safety concern at typical intake but did not assign numeric ADI on the d database entry.
  • Adi Display: No safety concern at current intake levels when used as a flavoring agent

Sources

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