2-TRANS-4-TRANS-7-CIS-DECATRIENAL

CAS: 66642-86-2 FLAVORING AGENT OR ADJUVANT

2-TRANS-4-TRANS-7-CIS-DECATRIENAL is a chemical compound with CAS 66642-86-2 used as a flavoring agent or adjuvant, often described with a green citrus odor profile and is evaluated by international expert panels for its use in food.

What It Is

2-TRANS-4-TRANS-7-CIS-DECATRIENAL is an organic aldehyde compound used in the flavor and fragrance industry as a flavoring agent or adjuvant due to its distinctive odor characteristics and functional properties. It is identified by the CAS number 66642-86-2 and is known under various synonyms including 2,4,7‑decatrienal, trans,trans,cis‑2,4,7‑decatrienal, and (2E,4E,7Z)‑2‑trans,4‑trans,7‑cis‑decatrienal, reflecting different nomenclature conventions for its geometric isomers. Compounds of this class belong to medium‑chain aldehydes, organic molecules composed of a ten‑carbon backbone with multiple carbon‑carbon double bonds and a terminal aldehyde group. These structural features impart characteristic sensory properties important for flavor applications. In the context of food science and formulation, flavoring agents like this are incorporated in minute quantities to modify or enhance the sensory profile of food products, especially where green, citrus, or fresh notes are desirable. Aldehyde functional groups are common in flavor chemistry because they interact strongly with human olfactory receptors, enabling perception of specific aromatic qualities at low concentrations. The designation “flavoring agent or adjuvant” describes its role in modifying taste or aroma without contributing nutritive value. Its categorization as a flavoring agent indicates that its primary purpose in formulations is sensory rather than nutritional or preservative. In summary, this compound is a technical ingredient used to impart particular flavor characteristics, recognized by various industrial nomenclatures and evaluated by regulatory and expert bodies for safe use in food systems.

How It Is Made

The manufacturing of 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL typically involves synthetic organic chemistry techniques tailored to produce unsaturated aldehydes with specific geometric configurations. Although detailed proprietary routes are often developed by individual chemical suppliers, general preparation methods for similar aliphatic aldehydes include selective oxidation of corresponding alcohol precursors or controlled assembly of carbon units using aldehyde building blocks followed by controlled double‑bond formation. The presence of multiple double bonds in specific trans and cis configurations suggests that the synthetic strategy involves careful control of stereochemistry to ensure the desired isomer predominates, as geometric isomerism can significantly influence odor and flavor characteristics. In commercial settings, manufacturers may employ catalytic processes or use protecting groups to prevent unwanted reactions during synthesis, ensuring that the chain length and unsaturation pattern remain intact. After synthesis, the crude product is typically purified via distillation or chromatographic separation to achieve high purity suitable for flavor application. The final material is subject to quality control measures that assess chemical identity, purity, and absence of undesirable by‑products, consistent with industry standards for flavor ingredients. Although exact production techniques vary by supplier and are often proprietary, general principles of organic synthesis and purification apply, emphasizing stereochemical control and product consistency.

Why It Is Used In Food

In food formulation, 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL is employed because of its ability to contribute specific sensory notes that can enhance or complement the overall flavor profile of products. Flavoring agents like this are used to add depth, balance, and complexity to aroma and taste, particularly where green, citrus, or fresh notes are desired. The compound’s structure allows it to interact with olfactory receptors in ways that evoke sensory perceptions associated with natural citrus or green aromatics, making it valuable for products that aim for a fresh or fruity character. Food scientists incorporate this compound in formulations where subtle sensory modulation is needed. It functions as part of a flavor blend rather than a standalone ingredient, contributing to the overall harmony of flavors in complex formulations. Its use is not intended to provide nutritional benefit but to influence sensory perception, improving consumer acceptability when a green or citrus nuance is desirable. For example, it may be blended with other flavor ingredients to enrich the sensory experience of confectionery, beverages, or savory seasonings. The careful use of such flavoring agents supports product differentiation and helps manufacturers tailor sensory profiles to specific market preferences.

Adi Example Calculation

The following example is illustrative and not indicative of an actual health recommendation. Suppose a hypothetical flavoring agent had a notional acceptable daily intake of X mg per kilogram of body weight per day (this compound’s actual ADI is not numerically defined). For a person weighing 70 kilograms, the hypothetical maximum safe intake would be X times 70, or 70X mg per day. If a food product contained 0.001 mg of the compound per serving and a person consumed 10 servings in a day, the total intake would be 0.01 mg, which, if compared to the hypothetical 70X mg threshold, would be orders of magnitude lower. This example illustrates how tiny amounts of flavoring compounds relative to body weight and hypothetical safety thresholds can indicate a large margin of safety, which is often part of why expert bodies conclude there is no safety concern at current use levels. It is critical to understand that actual intake values and regulatory determinations are based on detailed assessments by expert panels reviewing toxicology and exposure data, not simple illustrative arithmetic.

Safety And Health Research

Safety evaluations of 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL focus on toxicological data relevant to its use as a flavoring agent. Regulatory and expert bodies such as JECFA assess the chemical’s genotoxicity, subchronic toxicity, and potential for adverse effects at estimated levels of dietary exposure. Based on the JECFA evaluation, this compound was not found to raise safety concerns at current levels of intake when used as a flavouring agent, reflecting a risk assessment process that considers typical exposure scenarios and available toxicology data. This type of evaluation examines studies on relevant endpoints including acute toxicity, potential carcinogenicity signals, and other endpoints informed by standard toxicology protocols, though specific details of individual studies are part of expert monographs rather than summarized numerically in regulatory inventories. The absence of specific numeric findings such as an established acceptable daily intake (ADI) reflects the nature of flavor compound evaluations, which often conclude that typical use levels are sufficiently low to avoid concern without defining a strict numerical threshold. Because direct human health studies at relevant exposure levels are limited for many minor flavoring agents, assessments rely on available animal data and expert interpretation of the margin of exposure between no observed adverse effect levels and estimated human intake. This careful, evidence‑based approach supports regulatory positions that permit use under defined conditions without overstating human health effects beyond what is established by scientific bodies.

Regulatory Status Worldwide

The regulatory status of 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL reflects evaluations by international expert bodies and inclusion in food additive inventories where flavoring agents are catalogued. According to the Joint FAO/WHO Expert Committee on Food Additives (JECFA), this compound (listed under JECFA number 1786) has been evaluated and is noted as having no safety concern at current levels of intake when used as a flavouring agent, according to JECFA’s monograph and evaluation reports. This indicates that, based on available data, typical dietary exposure to this compound in flavor use does not raise safety concerns under intended conditions of use, though specific numeric acceptable daily intake values were not assigned. EFSA and EU regulations do not currently list a specific E‑number for this compound, and formal approval status can vary across jurisdictions, with regulatory frameworks focusing on flavoring inventories and expert panel assessments rather than a single harmonized numeric designation. In the United States, it appears in flavor ingredient listings such as the Substances Added to Food (formerly EAFUS) database, indicating recognition of its use as a flavoring agent; however, a specific CFR citation authorizing its direct use as a food additive may not be explicitly defined in Title 21 of the Code of Federal Regulations. These different references reflect the varied regulatory approaches taken by authorities to catalog and assess flavoring agents, balancing scientific evaluation with practical use in food systems.

Taste And Functional Properties

2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL is characterized by sensory attributes often described as green and citrus‑like, reflecting its influence on olfactory perception when used in minute concentrations. Compounds with conjugated double bonds and an aldehyde group are known to exhibit potent sensory effects, even at low levels, because they bind effectively to specific olfactory receptors. The presence of this compound in a flavor blend can introduce or amplify fresh, citrusy notes, which are desirable in many food applications seeking to evoke fruitiness or natural aromatics. Functionally, flavoring agents do not typically provide physical stabilization or preservation like some other food additives; rather, their primary functional property lies in sensory modulation. Its solubility profile tends toward limited water solubility due to the non‑polar carbon chain, making it generally soluble in alcohols or lipophilic media. In formulation practice, it is often pre‑diluted in suitable carriers to ensure even distribution and controlled perception in the final product. Stability of this compound can vary with processing conditions, and it may degrade or transform under high heat or extended storage, necessitating careful formulation strategies to preserve the intended sensory effect.

Acceptable Daily Intake Explained

In regulatory toxicology, an acceptable daily intake (ADI) is a health‑based metric that estimates the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. ADIs are typically derived from animal studies by identifying a no observed adverse effect level (NOAEL) and applying safety factors to account for uncertainties in translating animal data to humans. In the context of flavoring agents such as 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL, some expert evaluations, such as those by JECFA, conclude that there is no safety concern at the current levels of intake associated with intended use, indicating that typical dietary exposure is far below levels that raise concern in toxicological studies. However, a formal numeric ADI was not set in that evaluation, meaning that while current use patterns are considered safe, an explicit milligram‑per‑kilogram body weight figure was not established. For lay readers, it is important to understand that the absence of a numeric ADI does not imply unrestricted consumption; rather, it reflects a scientific judgment that exposure from normal use as a flavoring agent is minimal and does not require a defined safety threshold. Flavoring agents are typically present in very small quantities, and expert panels assess both the estimated intake and toxicological data to determine whether a specific ADI is necessary. In this case, the conclusion of no safety concern suggests that intake levels under intended use are well within margins considered acceptable by regulatory experts.

Comparison With Similar Additives

Comparing 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL with other flavoring agents helps contextualize its role in food formulation. For example, citral is another aldehyde used to impart citrus notes and is widely used in flavor systems due to its strong lemon‑like aroma; both compounds contribute citrus nuances, but their specific odor profiles and intensity differ, leading formulators to select one or combinations depending on desired sensory outcomes. Hexanal is a green note compound often used to provide fresh, grassy nuances; like 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL, it interacts with olfactory receptors to evoke specific sensory cues, though hexanal’s odor profile tends more toward freshly cut grass than citrus. Another class to consider is ethyl butyrate, a fruity ester used for tropical and pineapple notes; esters and aldehydes differ in their sensory contribution, with esters typically providing sweet fruit impressions and aldehydes contributing sharper green or citrus characteristics. While all these compounds serve in the palette of flavor ingredients, differences in chemical structure result in varied sensory effects and functional considerations. Formulators often balance such compounds to achieve complex flavor profiles where complementary properties enhance overall perception. Understanding these differences underscores the specialized roles that volatile flavor compounds play in creating desirable sensory experiences in food products.

Common Food Applications Narrative

In culinary and industrial food applications, flavoring agents like 2‑TRANS‑4‑TRANS‑7‑CIS‑DECATRIENAL play nuanced roles in shaping the sensory landscape of products. While used at very low concentrations, its green and citrus attributes make it suitable for inclusion in flavor systems where a fresh or zesty character is desirable. Common food categories where such flavoring agents are applied include confectionery, beverages such as soft drinks and flavored waters, dairy‑based desserts, and savory seasonings where a hint of citrus or green note enhances the overall profile. Flavor professionals often work with a palette of volatile compounds like this one to achieve targeted sensory outcomes. In beverage applications, it can contribute to crisp, refreshing notes that complement fruit‑derived flavors. In confectionery, it assists in reinforcing fruit nuances, particularly in products that aim to replicate or enhance natural fruit profiles. Even in savory products, a subtle green or fresh citrus undertone can provide balance and complexity when blended judiciously with other aromatic ingredients. Across these applications, the emphasis is on harmony; the compound is rarely used in isolation but rather as part of a carefully calibrated flavor mix designed to meet specific product objectives. Its utility reflects the broader practice in food formulation of leveraging minor volatile compounds to achieve desired sensory impacts while complying with regulatory and safety considerations.

Safety & Regulations

FDA

  • Notes: FDA direct food additive regulation status not explicitly defined in CFR; listed in flavor ingredient inventories like EAFUS without specific numeric citation.

EFSA

  • Notes: EFSA specific numerical ADI or E-number not found in consulted sources.

JECFA

  • Year: 2007
  • Notes: JECFA concluded there is no safety concern at current intake levels without assigning a numeric ADI.
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent (numeric ADI not defined)

Sources

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