CIS-3-HEXENYL HEXANOATE

CAS: 31501-11-8 FLAVORING AGENT OR ADJUVANT

CIS-3-HEXENYL HEXANOATE is a naturally occurring fruity green odor ester used as a flavoring agent in foods, beverages, and other consumables, recognized in regulatory flavoring evaluations.

What It Is

CIS-3-HEXENYL HEXANOATE is a specific chemical compound belonging to the family of unsaturated aliphatic esters that function as flavoring agents in food and beverage formulations. It is commonly encountered in nature in a variety of fruits and vegetables where it contributes green, fruity, and waxy aromatic notes that are sensory markers of fresh plant material. The chemical is structurally defined by a hexanoate (caproate) ester group linked to a cis-configured 3-hexenyl alcohol base, establishing its distinctive sensory properties. The CAS number 31501-11-8 identifies this substance uniquely in chemical and regulatory databases for industrial and food applications. Beyond this primary identifier, the compound is also known by multiple synonyms such as 3-Hexenyl Hexanoate and cis-3-Hexenyl Caproate, reflecting its nomenclature across databases and flavor industry references. In the context of food technology and regulatory documentation, CIS-3-HEXENYL HEXANOATE typically appears classified under functional use categories such as "Flavoring Agent" or "Adjuvant," indicating its role not as a nutritional component but as a sensory modifier to enhance aroma and taste. It is recognized by flavor expert panels such as the Flavor and Extract Manufacturers Association (FEMA) with a designated FEMA number (3403) and has been evaluated by international bodies including the Joint FAO/WHO Expert Committee on Food Additives (JECFA) under the JECFA number 165. These evaluations position the compound within an established framework for flavoring agents, guiding safe use levels and expected sensory outcomes in food products. The functional class defined in international evaluations underscores that its primary purpose is to contribute organoleptic properties rather than serve as a preservative, nutrient, or processing aid. In practical terms, the presence of CIS-3-HEXENYL HEXANOATE in food formulations aims to mirror or enhance green-fruity profiles reminiscent of fresh cut grass, green apple peel, or certain tropical fruit notes. This sensory contribution is leveraged widely in flavor blends to achieve complex aromatic profiles that consumers associate with freshness and natural fruit character. As such, it is incorporated into flavor systems for beverages, confectionery, desserts, and other categories where nuanced aroma modulation is desired.

How It Is Made

The manufacturing of CIS-3-HEXENYL HEXANOATE is based on well-understood organic esterification processes that combine cis-3-hexenol, commonly referred to as leaf alcohol, with hexanoic acid (caproic acid). This esterification reaction typically occurs under acid-catalyzed conditions, where the hydroxyl group of the alcohol and the carboxyl group of the acid undergo condensation to form the ester linkage along with the release of water. Industrially, catalysts such as strong acids or ion-exchange resins facilitate this transformation, allowing for controlled reaction kinetics and product yields. This process is analogous to classic Fischer esterification, adapted to the specific substrates used in flavor production, and may involve azeotropic removal of water to drive the equilibrium toward formation of the ester product. Purity and quality control are central to manufacturing for food flavor applications. The end product is subjected to analytical evaluation by gas chromatography and other spectroscopic methods to confirm identity, purity, and the absence of unwanted byproducts. Manufacturers aiming to supply food-grade material adhere to recognized quality specifications, which often include criteria for purity of at least ninety-five percent and limits on residual catalysts or unreacted starting materials. Compliance with flavor industry guidelines, such as those outlined by JECFA in its specifications and by FEMA for GRAS status, helps ensure that the aldehydic, estery, and unsaturated components present in the product meet sensory and safety criteria. Such specifications typically cover acceptable ranges for refractive index, density, and organoleptic profile, ensuring consistency across batches from different producers. Raw material sourcing for cis-3-hexenol and hexanoic acid influences the overall sustainability profile of CIS-3-HEXENYL HEXANOATE. While both can be derived synthetically from petrochemical feedstocks, leaf alcohol may also be obtained via biobased processes from plant volatiles and fermentation products, especially for natural flavor designations. Regardless of the source, the esterification reaction remains the core synthetic step, and post-reaction purification often involves distillation to remove low-boiling impurities and chromatographic techniques to refine the final product. In some manufacturing settings, additional treatment steps such as deodorization or blending with other approved flavor compounds may occur when producing complex flavor formulations. This production pathway ensures that the final ingredient meets the stringent sensory expectations of flavor chemists and food product developers. Unlike processes that intentionally produce multiple structural isomers, the cis configuration of the 3-hexenyl moiety is preserved to maximize the desired green, fresh profile. The cis isomer's sensory attributes are what differentiate it from trans isomers or other related esters that might offer different aromatic characteristics. Quality control includes verification of cis/trans ratios and absence of oxidized or degraded constituents that could negatively impact aroma or consumer perception. Overall, the manufacturing of CIS-3-HEXENYL HEXANOATE reflects standard practices in flavor chemistry, balancing efficient synthesis with rigorous control to meet sensory and regulatory benchmarks.

Why It Is Used In Food

CIS-3-HEXENYL HEXANOATE is used in the food industry primarily for its ability to impart and enhance green-fruity notes in complex flavor systems. Its unique organoleptic characteristics — often described as fresh, grassy, fruity with tropical undertones — make it a valuable tool for flavorists seeking to recreate or mimic natural sensory experiences. In contrast to basic sweet or sour taste modifiers, this compound contributes specific aromatic nuances that resonate with consumer expectations for freshness and complexity in products ranging from beverages to confectionery. The reasoning behind its inclusion in food formulations stems from the broader objective of creating flavors that are perceived as natural and appealing. In a competitive marketplace where sensory attributes significantly influence consumer choice, small quantities of targeted flavoring agents such as CIS-3-HEXENYL HEXANOATE help formulations achieve multi-dimensional aroma profiles. For example, in fruit-flavored beverages, the compound can provide a top-note accent that evokes freshly sliced fruit or cut grass, enhancing the overall perception of quality. It is often used in concert with other esters, aldehydes, and lactones to balance sweetness with green freshness, creating a rounded sensory signature. Formulators also value this ester for its compatibility with other flavoring substances. Its volatility and aroma threshold characteristics make it suitable for blending with both high-intensity flavor compounds and subtle background notes. As a result, it finds application not only in obvious fruit-flavored products but also in baked goods, dairy analogs, and even savory foods where a hint of green-freshness can uplift the overall flavor profile. The compound's behavior in different matrices — including solubility in lipid and alcohol phases and relative stability under mild processing conditions — contributes to its utility across diverse product categories. Moreover, its use as a flavoring agent aligns with consumer demands for sensory experiences that evoke natural food characteristics. By contributing specific aromatic cues, CIS-3-HEXENYL HEXANOATE supports the development of products that read on labels as fruit-forward, fresh, or botanical in quality. This attribute is particularly relevant in formulations aiming for ‘‘natural’’ taste profiles, even when synthetically sourced ingredients are used to achieve consistency and supply reliability. The versatility of this compound as a flavoring agent enables product developers to fine-tune aroma perception while adhering to regulatory expectations for safety and usage levels.

Adi Example Calculation

To illustrate how an Acceptable Daily Intake (ADI) might be conceptualized for a flavoring agent, consider a hypothetical example involving a numeric ADI established for a different compound. Imagine a flavoring additive with a numeric ADI of 1 mg per kilogram of body weight per day. For an individual weighing 70 kilograms, this would translate to a maximum safe intake of 70 mg per day (70 kg times 1 mg/kg). In practice, actual consumption of flavoring agents like CIS-3-HEXENYL HEXANOATE is typically orders of magnitude lower due to their potency and low usage levels in food products; flavor compounds are often used at parts-per-million or parts-per-billion levels. This illustrative calculation highlights the role ADIs play in helping regulators and product developers contextualize safety. Rather than suggesting that individuals should seek to consume flavoring agents at any specified level, ADIs serve as benchmarks derived from rigorous safety evaluations. In the case of CIS-3-HEXENYL HEXANOATE, regulatory bodies have concluded that no specific numeric ADI is necessary because anticipated exposure at typical usage rates does not raise safety concerns. Therefore, while the example above demonstrates how an ADI could be applied, it does not apply directly to CIS-3-HEXENYL HEXANOATE, which has no numeric ADI assigned but has been evaluated as having no safety concern at documented exposure levels.

Safety And Health Research

Research and regulatory safety evaluations for CIS-3-HEXENYL HEXANOATE focus on determining whether its use as a flavoring agent presents any concerns at anticipated levels of intake. Expert bodies such as JECFA undertake comprehensive reviews of available toxicological data, chemistry, and estimated exposure to assess whether a substance’s consumption is likely to pose risks to health. In the case of CIS-3-HEXENYL HEXANOATE, JECFA’s review concluded that there is no safety concern at current intake levels when the compound is used as a flavoring agent, reflecting a broad assessment of structural data, metabolism, and exposure estimates rather than reliance on high-dose toxicity studies alone. These evaluations typically consider multiple endpoints relevant to safety, including acute toxicity, chronic exposure, and potential for genotoxicity or reproductive toxicity. Flavoring esters such as CIS-3-HEXENYL HEXANOATE are metabolized through enzymatic pathways that break down ester bonds, resulting in common metabolic products such as alcohols and acids that are further processed in the body’s normal biochemical pathways. This metabolic perspective informs regulatory assessments that such substances, when used at flavor-level concentrations, do not accumulate or produce toxic effects at levels of dietary exposure typical for consumers. Additionally, evaluations by organizations such as FEMA involve expert panels reviewing both published scientific literature and proprietary safety data to support GRAS determinations. These assessments consider historical consumption patterns, structural similarity to other well-characterized esters, and the nature of sensory exposure to flavoring compounds. The consensus supporting FEMA GRAS designation for CIS-3-HEXENYL HEXANOATE further indicates that, within the context of flavor use, safety concerns have not emerged at typical application levels. Although individual academic studies may explore biological activity or sensory responses to specific aroma compounds, regulatory assessments prioritize data directly correlated with human dietary exposure. In the absence of authoritative studies indicating adverse effects attributable specifically to this compound, safety profiles rely on expert evaluation of structure and exposure rather than definitive clinical research on humans. This approach is consistent with how many flavoring agents are evaluated globally, focusing on ensuring that use levels and exposure remain within bounds that do not pose demonstrable risks.

Regulatory Status Worldwide

Worldwide, CIS-3-HEXENYL HEXANOATE has been considered within established regulatory frameworks for flavoring substances, particularly through evaluations by expert bodies that assess safety and appropriateness for use in food. One of the primary international evaluations comes from the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which has reviewed the compound under JECFA number 165. In the context of JECFA’s deliberations, the committee concluded that there is "no safety concern at current levels of intake when used as a flavouring agent," reflecting the outcome of expert toxicological and exposure assessments and indicating acceptability under typical use scenarios. This conclusion aligns with the JECFA approach to evaluating flavoring agents, which considers chemical structure, anticipated intake, and available toxicity data to determine safety margins for use. In the United States, substances intended for use as flavoring agents such as CIS-3-HEXENYL HEXANOATE may be recognized through the Flavor and Extract Manufacturers Association (FEMA) GRAS (Generally Recognized As Safe) process. FEMA assigns specific numbers to GRAS flavoring agents, and in this system, CIS-3-HEXENYL HEXANOATE is designated with FEMA number 3403. FEMA’s designation indicates that expert panels have reviewed available data on the compound and determined that its intended use as a flavoring agent is consistent with safety expectations under common conditions of use. While FEMA GRAS recognition does not automatically equate to an explicit listing in the U.S. Food and Drug Administration’s Code of Federal Regulations, such GRAS status guides industry practice and supports inclusion in flavor formulations. The U.S. FDA’s EAFUS (Everything Added to Food in the United States) database includes flavoring agents evaluated through GRAS procedures, offering a reference for substances used in food formulations. In other regions, regulatory approaches may vary. Within the European Union, flavoring substances are subject to specific regulations that govern their use in foods, requiring safety assessments and adherence to listing procedures overseen by the European Food Safety Authority (EFSA). The absence of an explicit E-number for CIS-3-HEXENYL HEXANOATE indicates that it is not covered by a numbered EU additive category, though it may be permitted as a flavoring substance consistent with EU flavoring legislation. Regulators in other countries apply comparable frameworks, balancing international evaluations such as those by JECFA with domestic assessment processes. Across these regulatory systems, the overarching consensus is that CIS-3-HEXENYL HEXANOATE can be used as a flavoring agent within defined usage levels without raising safety concerns when incorporated into food products consistent with recognized practice.

Taste And Functional Properties

CIS-3-HEXENYL HEXANOATE offers distinct sensory properties that align with its classification as a flavoring agent. Sensory descriptors frequently attributed to this compound include green, fruity, waxy, and tropical notes, which collectively evoke fresh plant material, cut grass, and ripe fruit nuances. These descriptors come from structured sensory evaluation panels and instrumental analysis of aroma-active volatiles in food matrices. The compound’s volatility contributes to its impact on the initial perception of flavor, allowing it to serve as a top-note contributor in complex flavor formulations. Its olfactory signature complements other esters and aldehydes, providing balance and depth without overpowering more dominant sweet or sour components. In terms of functional behavior, CIS-3-HEXENYL HEXANOATE is typically soluble in organic solvents such as ethanol and propylene glycol, which are common carriers in flavor blends. This solubility supports its use in liquid-based formulations like beverages and syrups, as well as in oil-based flavor components for baked goods and confectioneries. The compound exhibits limited solubility in water alone, meaning that its distribution in aqueous systems relies on co-solvents or emulsification strategies to ensure uniform flavor impact. When incorporated properly, it contributes aroma without introducing off-notes associated with solubility mismatches. The stability of CIS-3-HEXENYL HEXANOATE under typical food processing conditions is generally adequate for its intended uses. While high-heat or extreme pH conditions can alter the chemical integrity of many aroma esters, typical beverage pasteurization and baking processes allow the compound to retain its sensory contribution when included at appropriate levels. Flavor chemists often consider matrix interactions and processing effects when specifying usage rates, recognizing that heat and oxidative environments can dampen or shift aroma profiles. Understanding these functional properties helps developers optimize flavor impact while managing cost and formulation constraints. From a sensory science perspective, the threshold at which CIS-3-HEXENYL HEXANOATE contributes perceptible aroma is relatively low, meaning that small quantities can significantly affect the overall flavor profile. This characteristic makes it efficient for use in flavor systems where subtlety and nuance are priorities. It also means that careful calibration is needed to avoid overuse, which could lead to an imbalanced profile dominated by grassy or green notes at the expense of intended fruit or sweet character. Professional flavorists rely on sensory panels and analytical instrumentation to fine-tune such components within complex blends, ensuring that CIS-3-HEXENYL HEXANOATE performs its intended role effectively.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a concept used by food safety authorities to express the amount of a substance that can be consumed daily over a lifetime without appreciable health risk, based on available toxicological data and safety factors. In the context of flavoring agents like CIS-3-HEXENYL HEXANOATE, regulatory evaluations by bodies such as JECFA consider both the compound’s chemical properties and typical levels of dietary exposure. In this case, JECFA’s assessment determined that there is no safety concern at current levels of intake when used as a flavoring agent, indicating that the compound does not require a specific numeric ADI. This conclusion implies that anticipated exposure from food use is sufficiently low and that metabolism of the compound does not raise concern for accumulation or toxicity at expected intake levels. It is important to underscore that the absence of a specific numeric ADI does not mean unlimited consumption is advised. Rather, it reflects confidence that, at current and historically typical usage levels, consumption of CIS-3-HEXENYL HEXANOATE does not pose safety risks warranting establishment of a limit. Regulators apply conservative safety factors in establishing numeric ADIs for substances with identified thresholds of toxicity; for flavoring agents with no identified hazards at relevant exposure levels, expert evaluations may conclude that a formal ADI is not necessary. This approach aligns with international practice for many volatile esters and aroma compounds that, due to their biochemical profiles and low usage levels, are not expected to contribute significantly to overall dietary exposure. For consumers and product developers, the concept of ADI helps put safety assessments into context. When a numeric ADI exists, it is usually derived by identifying a no observed adverse effect level (NOAEL) from toxicology studies and applying safety factors to account for uncertainties. In the case of CIS-3-HEXENYL HEXANOATE, regulatory evaluations have not identified data necessitating such a derivation, resulting in a conclusion of no safety concern at typical usage levels. Nonetheless, ongoing monitoring and scientific review remain integral components of food safety frameworks, ensuring that new evidence can be incorporated into future assessments if needed.

Comparison With Similar Additives

CIS-3-HEXENYL HEXANOATE shares functional similarities with other ester-type flavoring agents that contribute fruity or green notes in flavor systems. For example, ethyl butyrate is another ester commonly used in food products to impart fruity characteristics reminiscent of pineapple or tropical fruits; like CIS-3-HEXENYL HEXANOATE, it is used in low concentrations due to its potent sensory impact. However, while ethyl butyrate tends toward sweeter, tropical fruit nuances, CIS-3-HEXENYL HEXANOATE offers a greener, more vegetal top note, making it suitable for applications where “fresh” character is desired. Another related compound is cis-3-hexenyl acetate, which also features a green, fresh aroma but with a slightly different ester group that shifts its sensory profile toward apple or leaf-like notes. Both cis-3-hexenyl acetate and CIS-3-HEXENYL HEXANOATE contribute to the green and fresh sensory space, yet their distinctive ester chemistries result in complementary rather than identical sensory outcomes. Formulators often combine such esters to achieve layered aroma effects, capitalizing on each compound’s unique contribution. In contrast, lactones such as gamma-decalactone provide peachy or creamy fruit tones, representing a different sensory category within the broader family of flavoring agents. While lactones like gamma-decalactone and esters like CIS-3-HEXENYL HEXANOATE may both be used in fruit-flavored applications, their functional roles within a flavor blend differ: lactones often contribute heavier, more fruity sweetness, whereas esters often provide lighter, volatile top notes that influence initial aroma perception. Understanding these distinctions helps flavorists select the right combination of compounds to achieve targeted sensory profiles in food applications.

Common Food Applications Narrative

CIS-3-HEXENYL HEXANOATE finds wide-ranging applications across various food and beverage categories where sensory appeal and nuanced flavor are essential to consumer enjoyment. One of the most common applications is in flavored beverages, including fruit drinks and carbonated soft drinks, where this compound contributes fresh, green-fruity top notes that enhance perceptions of fruit authenticity. In these contexts, it is blended with other esters and aldehydes to create complex profiles that mimic natural fruit characteristics without relying solely on sugar or sweeteners. Its inclusion supports product positioning that emphasizes flavor complexity and freshness, especially in tropical and green apple-themed flavors. In confectionery, CIS-3-HEXENYL HEXANOATE serves as a supporting flavor component in candies, gummies, and jellies. It augments sweet flavor bases with subtle aromatic layers, allowing product developers to achieve distinctive profiles that stand out on the palate. For example, in a mixed berry candy, small amounts of this ester can enhance the green or leafy facets of strawberry or raspberry notes, making the overall flavor more dynamic and true-to-fruit. The compound’s volatility and aromatic strength mean that it contributes a perceived complexity that aligns with consumer expectations for high-quality confectionery. Dairy and dairy-alternative products also benefit from the inclusion of CIS-3-HEXENYL HEXANOATE in their flavor formulations. In flavored milks, yogurts, or plant-based dairy analogs, the ester’s fruity and green nuances can elevate simple sweet or creamy notes, adding an element of freshness that distinguishes the product. For instance, in a peach-flavored yogurt drink, combining this compound with other fruit esters helps create a perception of ripe fruit complexity, enhancing the sensory experience without overwhelming the base dairy notes. Baked goods such as cakes, muffins, and pastries also utilize this compound as part of flavor systems designed to deliver memorable aromatic profiles. When incorporated into batter or filling formulations, it can contribute to the perception of fresh fruit or green top notes that complement richer, buttery, or spiced base flavors. In this setting, flavorists carefully balance CIS-3-HEXENYL HEXANOATE with other aroma components to ensure that its presence enhances rather than distracts from the overall taste experience. Beyond these categories, the compound is used in various specialty products, including desserts, gelatin-based snacks, and even savory items where a hint of green or fruity aroma can add complexity. In all applications, it functions as one component in a larger palette of flavoring agents that collectively shape the consumer’s sensory journey. Its role is not to define the entire flavor but to provide depth and sophistication, reinforcing desired notes and bridging aroma transitions between ingredients. Ultimately, CIS-3-HEXENYL HEXANOATE’s contribution to food applications lies in its ability to enrich sensory profiles, helping manufacturers achieve targeted flavor visions that resonate with diverse consumer preferences.

Safety & Regulations

FDA

  • Notes: FDA explicit CFR allowance not identified; included in FEMA GRAS listings which does not equate to a direct CFR section.

EFSA

  • Notes: EFSA specific numeric ADI not found in authoritative databases.

JECFA

  • Year: 1997
  • Adi Display: No safety concern at current levels of intake when used as a flavouring agent

Sources

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