(E,E)-2,4-DECADIEN-1-OL

CAS: 18409-21-7 FLAVORING AGENT OR ADJUVANT

(E,E)-2,4-Decadien-1-ol is a conjugated dienic alcohol used in the flavor and fragrance industry for its fatty, citrus-like aroma and is evaluated as a flavouring agent by international expert bodies.

What It Is

(E,E)-2,4-Decadien-1-ol is a specific unsaturated alcohol characterized by two double bonds at the 2 and 4 carbon positions and a terminal hydroxyl group. The IUPAC structure corresponds to a linear carbon chain with the double bonds in the E configuration, meaning the substituents across each double bond are on opposite sides of the bond axis. This structural arrangement contributes to its functional and sensory properties. The compound is identified under the Chemical Abstracts Service (CAS) Registry Number 18409-21-7 and appears in international flavouring chemical inventories under various synonyms such as 2,4-Decadien-1-ol and trans,trans-2,4-decadienol. It is typically found as a colorless oily liquid that exhibits a distinctive fatty and citrus-like aroma, making it useful in formulations seeking such sensory characteristics in flavours and fragrances. In food science and formulation, (E,E)-2,4-Decadien-1-ol is classified as a flavouring agent or adjuvant. Flavouring agents are substances that impart or modify taste and olfactory sensations in food products. Adjuvants, in this context, assist primary flavour compounds by enhancing their delivery or perception without contributing significant flavour on their own. This compound’s functional classification aligns with those roles, particularly in complex flavour systems requiring balance among fatty, fruity, or citrus notes. The designation "E,E" strictly refers to the geometrical configuration of the double bonds and is part of the analytical identification of the substance in regulatory and scientific contexts. Another important identifier associated with (E,E)-2,4-Decadien-1-ol is its FEMA (Flavor and Extract Manufacturers Association) number 3911 and JECFA (Joint FAO/WHO Expert Committee on Food Additives) number 1189. These identifiers are assigned by expert panels that review technical data and safety assessments for flavouring substances. Such listings indicate that the compound has been considered by international scientific bodies for its safety and appropriate use in food-related applications, although specific intake thresholds or approvals depend on individual national regulatory frameworks and documented evaluations. JECFA and FEMA listings are widely used by food scientists and regulatory professionals to communicate the identity and evaluation status of flavour compounds in global food systems.

How It Is Made

(E,E)-2,4-Decadien-1-ol can be produced through multiple chemistry pathways, often involving controlled reactions that introduce conjugated double bonds into a linear hydrocarbon backbone. These synthetic processes typically start with shorter hydrocarbon fragments that are elongated and desaturated through catalytic steps to achieve the precise placement and configuration of the 2,4 double bonds. Alternatively, the compound can be isolated from natural sources where it occurs as a minor volatile component, for example in certain plant extracts or fermentation-derived matrices. Extraction from such natural sources usually requires solvent extraction followed by purification steps like distillation or chromatography to concentrate the flavour compound. The production of this compound for industrial flavour use involves stringent quality control measures. Manufacturers purify the substance to food-grade specifications, removing residual solvents, isomeric impurities, and unreacted precursors. Typical analytical tools involved in quality assurance include gas chromatography coupled with mass spectrometry (GC-MS) to confirm the presence and purity of the desired E,E isomer over other possible geometric isomers. These methods also ensure that contaminants are below thresholds mandated by food safety standards or industry best practices. The purification and specification process is documented in international flavouring specification databases, which list minimum assay values, physical characteristics, and identity test parameters that define acceptable commercial quality. In many jurisdictions, producers must operate under food ingredient manufacturing practices that align with Good Manufacturing Practice (GMP). This includes controlling raw material traceability, processing conditions, and hygiene to ensure that the final product is consistent and safe for its intended use in flavour applications. Whether produced via synthesis or isolated from natural sources, the overarching goal in manufacturing (E,E)-2,4-Decadien-1-ol is to create a stable, well-characterized material with predictable sensory and functional attributes suitable for food formulation.

Why It Is Used In Food

(E,E)-2,4-Decadien-1-ol is used in food primarily as a flavouring agent or adjuvant because of its distinctive sensory impact. In flavour science, combining compounds with complementary sensory characters allows formulators to craft complex and appealing taste and aroma profiles. This compound contributes fatty, citrus-like, and waxy notes, which can enhance overall flavour perception when balanced with other constituents. Flavour agents like this are particularly useful in replicating or enhancing natural flavours where components of cooked meats, dairy, or fruit-like aromas are desired without adding substantial nutritional content. Beyond direct sensory roles, some flavouring agents function as adjuvants. This means they assist other components, helping volatile or low-threshold flavour chemicals linger in the headspace above a product or modulate the way consumers perceive combined notes. In practice, this can improve complexity, depth, or balance in flavours such as baked goods, savory snacks, beverages, or confectionery without dominating the flavour spectrum. Regulatory and industry bodies compile lists of flavouring substances that have been evaluated for safety based on chemical structure and available toxicological data. Inclusion in such inventories does not automatically imply identical regulatory status in all jurisdictions, but it supports global use with appropriate formulation and disclosures. In markets where safety and regulatory compliance are required, manufacturers consult these evaluations to determine whether a given flavouring agent is acceptable for specific product categories and usage levels. The availability of safety evaluations enhances confidence among food technologists and formulators when selecting ingredients for new or reformulated products.

Adi Example Calculation

To illustrate the concept of an acceptable daily intake (ADI) in a general way, imagine a hypothetical ADI for a flavouring compound of 10 mg/kg body weight per day as established by a regulatory body for a specific substance with an identified ADI. For a person weighing 70 kg, this hypothetical ADI would equate to an allowable intake of 700 mg per day (70 kg x 10 mg/kg/day = 700 mg/day). In practice, actual exposure from food flavouring use would be orders of magnitude lower due to the very low concentrations at which flavourings are used in products. It is essential to emphasize that this calculation is purely illustrative and not based on a verified ADI for (E,E)-2,4-Decadien-1-ol, because authoritative sources have not assigned a specific numeric ADI for this compound in the available literature. Instead, the example demonstrates how ADIs are applied in risk assessment when numerical values are determined.

Safety And Health Research

Safety assessments for flavouring agents focus on potential hazards, exposure levels, and how consumers encounter the compounds in real-world food consumption. Expert bodies like JECFA and FEMA conduct structured evaluations of chemical identity, available toxicological data, and anticipated exposure from typical use levels in foods. These evaluations aim to determine whether there are structural alerts for toxicity and whether existing data adequately characterize potential impacts on health, including aspects such as genotoxicity, acute and chronic toxicity, and other endpoints of concern. The absence of a formal ADI in some JECFA flavouring evaluations often reflects a determination that typical exposures from intended uses are very low and that structural characteristics and available data do not raise significant safety concerns at those levels. When flavouring substances lack an ADI, it often means that regulatory and expert bodies concluded that human exposure from likely use patterns is sufficiently low or that available information does not indicate a need for a numerical intake limit. Such conclusions do not imply that high doses are safe; rather, they indicate that routine use in food is unlikely to result in exposures associated with adverse effects based on current evidence. Researchers and regulators also consider available data from animal studies and structure-activity assessments to identify any potential for irritation, sensitization, or other hazards. For example, some structural analogues of unsaturated alcohols can exhibit irritant effects at high concentrations, which is relevant to occupational handling and formulation practices rather than consumer dietary exposure. Overall, safety assessments emphasize that flavouring agents are used at low levels, often measured in parts per million or lower, and that structured expert evaluation frameworks integrate multiple lines of evidence to reach balanced judgments about safety in food applications. Ongoing monitoring, new toxicological data, and advances in analytical chemistry may prompt reevaluation of flavouring substances over time, ensuring that regulatory positions remain aligned with the best available science.

Regulatory Status Worldwide

(E,E)-2,4-Decadien-1-ol has been evaluated by recognized expert organizations involved in food additive assessment. One authoritative source for specifications and identity criteria is the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which assigns a number (1189) to this flavouring substance and maintains details about its purity criteria and other specifications in its flavouring specification database. The existence of a JECFA number indicates that the compound has undergone formal review and has defined identity and quality parameters used globally for regulatory and industry reference. However, JECFA’s documentation does not always include a formal acceptable daily intake (ADI) when the available toxicological data are limited or when the flavouring evaluation concludes that an ADI is not necessary based on typical exposure levels and structural considerations. In the United States, flavouring substances evaluated by organizations like FEMA and JECFA may be included in the FDA’s Substances Added to Food inventory, which catalogs ingredients that have been reviewed for safety or regulatory status by various scientific bodies. Inclusion in this inventory indicates that the ingredient is recognized and tracked by regulatory authorities, but it does not itself constitute specific approval under a particular section of the U.S. Code of Federal Regulations. The FDA’s Code of Federal Regulations, for example section 21 CFR 172.515, outlines the conditions under which synthetic flavouring substances and adjuvants may be used in food but does not list every individual flavour compound by name, and (E,E)-2,4-Decadien-1-ol does not appear explicitly in that list. As a result, formal FDA approval status for food use via a specific CFR entry is not confirmed for this compound, and manufacturers typically rely on established flavouring inventories and expert panel evaluations to support regulatory compliance. In the European Union, flavouring substances are subject to regulation under EU food flavouring legislation, and authoritative lists such as the Union list of flavouring substances incorporate compounds evaluated by European bodies. Information about (E,E)-2,4-Decadien-1-ol’s presence or specific conditions of use within that framework requires direct consultation of the EU flavouring database and corresponding Commission Implementing Regulations. The compound’s FEMA and JECFA identifiers serve as important references for industry professionals navigating these regulatory landscapes, helping them determine applicable usage conditions and labeling requirements in international markets.

Taste And Functional Properties

(E,E)-2,4-Decadien-1-ol exhibits sensory characteristics that are broadly described as fatty and citrus-like with waxy nuances. Such sensory descriptors stem from sensory panel evaluations and instrumental analysis of aroma profiles. In flavour chemistry, "fatty" refers to a sensory impression reminiscent of lipids or cooked fats, which can complement other aromatic notes to produce rich and appealing flavours in certain foods. The citrus-like aspect adds a bright, sharp note that balances the richness, useful in flavour blends that require both depth and freshness. Functionally, flavouring agents like (E,E)-2,4-Decadien-1-ol interact with the food matrix in specific ways. They tend to be more soluble in lipophilic phases such as fats or oils and less soluble in aqueous phases. This solubility profile affects their behaviour in complex food systems. For example, in emulsified products, the partitioning between oil and water phases influences how prominently a flavour is perceived. The volatility of the compound also affects aroma release; moderately volatile compounds contribute to the headspace aroma, which is perceived by consumers during consumption. From a stability perspective, compounds with conjugated double bonds like (E,E)-2,4-Decadien-1-ol may undergo oxidation under certain conditions, especially in the presence of catalysts like light or metal ions. Formulators mitigate such degradation by controlling storage conditions, using antioxidants, or integrating the compound into encapsulation systems that protect sensitive flavour agents. Understanding these functional properties helps food scientists anticipate how the ingredient behaves over shelf life, during processing, and in combination with other recipe components.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a scientifically derived estimate of the amount of a substance that can be ingested daily over a lifetime without appreciable health risk. Regulatory bodies establish ADIs based on available toxicological studies, typically in animals, applying safety factors to account for uncertainties and to ensure protection of human health. In the context of flavouring agents, ADIs are often expressed in units of milligrams of substance per kilogram of body weight per day (mg/kg bw/day). For many flavouring substances evaluated by expert panels like JECFA, formal numeric ADIs may not be assigned when typical exposure from food use is extremely low, and when the available data and structural considerations suggest a low hazard profile at those exposure levels. Instead, expert committees may rely on other approaches—such as threshold of toxicological concern (TTC) frameworks or exposure-based decisions—to conclude that routine use is safe without specifying a formal ADI. This does not mean that consumers are encouraged to consume arbitrary amounts; rather, it reflects a conclusion that, given the compound’s intended use and expected exposure, a formal numerical intake limit is not required to ensure safety. It is important to understand that ADIs are conservative estimates designed for regulatory risk management and not direct nutritional recommendations. They provide a basis for regulators and manufacturers to assess whether typical dietary exposure exceeds levels considered protective of health. In practical terms, flavouring agents like (E,E)-2,4-Decadien-1-ol are used at very low concentrations in foods, and their contribution to overall chemical exposure is minimized by formulation practices, regulatory oversight, and Good Manufacturing Practice principles.

Comparison With Similar Additives

Flavouring agents encompass a wide range of organic compounds that contribute distinctive sensory notes. Compounds like ethyl hexanoate, hexanal, and geraniol also serve as flavouring agents with well-described sensory profiles. Ethyl hexanoate, for instance, offers fruity and pineapple-like notes and appears on regulatory flavouring lists with specific identifiers. Hexanal provides green, grassy notes that complement other aromatic components in food formulations. Comparatively, (E,E)-2,4-Decadien-1-ol’s fatty and citrus-like character differentiates it from these other agents but illustrates the diversity of roles flavouring compounds play in achieving balanced and appealing sensory outcomes. When product developers select flavouring agents, they consider attributes such as volatility, functional synergy with other components, stability in processing conditions, and alignment with desired consumer perceptions. While ethyl hexanoate may be chosen for fruity brightness and hexanal for fresh green notes, (E,E)-2,4-Decadien-1-ol may be selected to add richness and complexity in savoury or fruit-enhanced formulations. The choice among such additives depends on their complementary sensory effects, solubility profiles, and how they interact with the food matrix. Understanding the spectrum of available flavouring agents enables formulators to craft nuanced sensory experiences tailored to specific product categories and consumer preferences.

Common Food Applications Narrative

(E,E)-2,4-Decadien-1-ol finds utility across a broad range of food applications because of its ability to contribute subtle yet distinctive flavour nuances. In savoury systems, for example, it can help mimic the complex aroma of cooked meats or roasted ingredients where fatty and roasted notes are integral to consumer expectation. When integrated into seasoning blends for snack foods or meal kits, the compound can support overall flavour complexity without overwhelming other ingredients. In baked goods, flavouring agents that provide a balanced interplay of richness and brightness are valuable. (E,E)-2,4-Decadien-1-ol can contribute to the underlying aroma profile of products like cookies, crackers, and pastries, where a combination of doughy, toasted, and slightly fruity notes enhances overall sensory appeal. Beverage formulations, particularly those that aim to evoke creaminess or fruit-forward character, may also harness such compounds in carefully calibrated amounts to augment the desired flavour narrative. Confectionery and dairy-adjacent products, including ice creams, flavored milks, and dessert sauces, often incorporate fatty and fruity aromatic compounds to achieve consumer-pleasing sensory signatures. In these contexts, the compound’s interplay with sugar and fat matrices influences how flavour is released during consumption. In each application, the quantity used is typically very low and optimized for the intended sensory impact. Flavorists and product developers balance this compound with other flavour ingredients to align with product identity, regional flavour preferences, and regulatory guidelines governing flavour additive use. The choice to include (E,E)-2,4-Decadien-1-ol in a formulation is often driven by organoleptic goals: achieving a richer, more rounded taste profile that resonates with consumer expectations. Its presence in flavour libraries and expert evaluations underscores its role as one of many tools available to food scientists and flavour professionals seeking to create compelling and differentiated products in competitive food categories.

Safety & Regulations

FDA

  • Notes: FDA approval status not confirmed by a specific CFR listing; flavoring inventory presence does not imply formal FDA approval.

EFSA

  • Notes: EFSA regulatory status not confirmed due to lack of a direct EU flavoring list citation.

JECFA

  • Notes: JECFA evaluation exists with a specification number but a numeric ADI was not found on the referenced JECFA specification page.

Sources

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