CIS-3-HEXENYL CIS-3-HEXENOATE

CAS: 61444-38-0 FLAVORING AGENT OR ADJUVANT

CIS-3-HEXENYL CIS-3-HEXENOATE is an ester compound used in flavoring to impart green and fruity notes with regulatory evaluations indicating it is used as a flavoring agent in foods under conditions of intended use.

What It Is

CIS-3-HEXENYL CIS-3-HEXENOATE is a chemical compound classified as a flavoring agent or adjuvant used in food formulations. It is identified by the Chemical Abstract Service Registry Number (CAS) 61444-38-0 and belongs to a class of unsaturated fatty acid esters. This compound is also known by several synonyms including 3-HEXENYL CIS-3-HEXENOATE and related ester names that reflect its geometric configuration and ester linkage. It is generally characterized as a clear, colorless liquid with a distinct green and fruity odor profile that contributes to its use in flavoring applications. Its inclusion in flavor libraries and flavor databases underscores its function in contributing sensory attributes to food products where nuanced green or fruity tones are desired in the overall flavor profile. The molecular structure of CIS-3-HEXENYL CIS-3-HEXENOATE features a twelve carbon backbone with double bonds in the cis configuration, which influences its odor characteristics and volatility properties. This configuration is common in many naturally derived aroma compounds, although in commercial applications the substance is often synthesized to ensure consistency and purity. Regulatory and scientific organizations have evaluated this compound through expert committees and flavor associations which recognize its intended function in food and beverage formulation contexts. Because it is a specialized flavoring agent and not a primary nutrient, discussions around this compound focus on its sensory contribution rather than nutritional contribution.

How It Is Made

CIS-3-HEXENYL CIS-3-HEXENOATE is typically produced through classical esterification reactions between an alcohol and an acid in controlled chemical synthesis settings to achieve the desired geometric cis configuration. During the manufacturing process, raw materials such as hexenol and hexenoic acid derivatives are reacted in the presence of catalysts that facilitate the formation of the ester bond. Industrial producers of this compound employ purification techniques including distillation and chromatography to achieve high purities suitable for use in flavor and fragrance applications. These purification steps help ensure that impurities that could affect odor or taste are minimized, and that the final substance meets applicable quality specifications for organoleptic performance. The synthetic production of CIS-3-HEXENYL CIS-3-HEXENOATE reflects standard practices in flavor and aroma chemical manufacturing, where precision in reaction conditions and purification is necessary to achieve consistent functional properties. Because the sensory perception of flavor compounds can be highly sensitive to minor structural variations, producers often conduct analytical testing including gas chromatography and mass spectrometry to characterize batches. These quality control measures ensure that products used in food flavoring applications deliver the expected green, fruity notes without unintended off-flavors. Additionally, manufacturers provide technical data sheets and safety documentation that describe physical properties, stability considerations, and recommended handling procedures for formulators in the food and beverage industry.

Why It Is Used In Food

CIS-3-HEXENYL CIS-3-HEXENOATE is used in food primarily for its ability to enhance and modulate flavor profiles. Flavor formulators select this compound because it imparts distinct notes that can evoke green, fruity impressions, such as pear, melon, and tomato leaf nuances, which are difficult to achieve with more common flavoring agents alone. Its use in fruit-flavored beverages, confectionery, gelatin desserts, and other food products helps create depth and complexity in the overall sensory experience. In many cases, a compound like CIS-3-HEXENYL CIS-3-HEXENOATE is used in combination with other flavor constituents to balance sweetness, acidity, or other specific sensory attributes desired by food product developers. The inclusion of this compound in flavor blends allows food technologists to tailor sensory profiles for consumer preferences and to differentiate products in competitive markets. While its role is not nutritive, it contributes to the perception of freshness and fruitiness that can influence overall product acceptance. Because flavor perception is integral to consumer enjoyment of food and beverage products, specialized agents such as CIS-3-HEXENYL CIS-3-HEXENOATE play a valuable role in creating appealing flavor impressions that meet diverse application needs. Its presence in flavor libraries maintained by flavor associations attests to its recognized role within the flavoring ingredient portfolio.

Adi Example Calculation

To illustrate how exposure assessments are considered for flavoring agents like CIS-3-HEXENYL CIS-3-HEXENOATE, imagine a hypothetical scenario where a flavored beverage contains a trace amount of this compound at a concentration of 0.0005 grams per liter. If an adult consumes one liter of that beverage in a day, the total intake of the compound would be 0.0005 grams (0.5 milligrams). When compared to typical safety evaluation frameworks that consider intake relative to body weight and incorporate multiple orders of magnitude of safety margin, an intake of this magnitude from a single product would generally be well below levels associated with toxicological concern. It is important to emphasize that this example is illustrative and not intended as a recommendation for specific values or exposures for individual consumers. Actual exposure depends on product formulation, frequency of consumption, and the presence of the compound in other food sources. Regulatory assessments consider aggregate exposure from all relevant sources when evaluating potential risks and determining whether use levels are appropriate for consumer safety.

Safety And Health Research

Safety assessments for flavoring agents such as CIS-3-HEXENYL CIS-3-HEXENOATE focus on toxicological endpoints relevant to typical exposure from food consumption. Expert committees and flavor associations review data from studies that examine acute toxicity, subchronic exposure, and potential effects related to metabolism and organ systems. For many flavoring esters, evaluations consider metabolic pathways that break down the compound into constituents that are naturally present or metabolized efficiently by the body when consumed at levels found in food products. As documented by JECFA and FEMA evaluations, CIS-3-HEXENYL CIS-3-HEXENOATE has been reviewed with respect to typical dietary exposure and found to pose no safety concern at those exposure levels. Because regulatory evaluations draw on available toxicological data, ongoing research and monitoring of exposure data contribute to the refinement of safety conclusions. Toxicological assessments for flavoring agents also consider cumulative exposure from multiple sources and potential interactions with other flavor components in complex food matrices. Although detailed long-term human studies specific to every flavoring compound may not be available, expert reviews integrate data from structurally related compounds and approved uses to inform safety determinations. This framework allows regulatory bodies and flavor associations to make scientifically grounded decisions about the suitability of flavoring agents for their intended uses while continuing to monitor emerging data for future reevaluation.

Regulatory Status Worldwide

CIS-3-HEXENYL CIS-3-HEXENOATE has been evaluated by recognized flavor authorities and is listed in flavor ingredient inventories used globally. In the United States, it appears on the FDA Substances Added to Food (formerly EAFUS) inventory, which catalogs substances used as flavoring agents or adjuvants with specified technical effects, indicating that it has an acknowledged role in food flavoring. This listing reflects usage under intended conditions and does not represent an authorization of unrestricted use outside specified functional contexts. It is associated with a FEMA number, which is an identifier used by the Flavor and Extract Manufacturers Association to track substances that have undergone expert panel evaluation for generally recognized as safe (GRAS) status in flavor applications. In Europe and other regions, similar inventories maintained by flavor industry bodies and national regulators recognize its use in flavor formulations. Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated CIS-3-HEXENYL CIS-3-HEXENOATE as a flavoring agent and reported that at current levels of intake from flavor use there is no safety concern, though it continues to seek updated exposure data for ongoing assessment. These evaluations emphasize that the regulatory status of this compound is tied to its intended use as a flavoring agent rather than as a bulk food additive or nutrient. Manufacturers and formulators rely on these regulatory references to guide compliant usage levels and labeling practices in various jurisdictions.

Taste And Functional Properties

CIS-3-HEXENYL CIS-3-HEXENOATE has a flavor and odor profile described as green, fresh, and fruity, with nuances reminiscent of pear and melon. These sensory attributes make it particularly useful in formulations where a natural, green fruit impression is desired. From a functional perspective, this compound exhibits volatility and organoleptic potency characteristic of many aroma esters, meaning it contributes perceptible sensory effects at low concentrations when properly incorporated into flavor systems. In addition to its sensory impact, the physicochemical properties of CIS-3-HEXENYL CIS-3-HEXENOATE influence how it behaves in food matrices. It has limited solubility in water but good solubility in ethanolic or oil-based environments commonly used in flavor formulations, which allows it to integrate into complex blends. The ester linkage and unsaturated carbon chain contribute to its volatility, making it effective in aroma delivery during consumption. Because the perception of flavor occurs through both taste and aroma pathways, the presence of this compound in a blend can enhance the overall flavor experience by reinforcing green and fruity aromatic cues that consumers associate with freshness and ripe fruit.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is a regulatory concept used by food safety authorities to describe the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. For many flavoring agents, including CIS-3-HEXENYL CIS-3-HEXENOATE, specific numeric ADIs may not be assigned because evaluations conclude that exposure from normal food use does not approach levels of toxicological concern. In such cases, expert committees may state that there is no safety concern at current levels of intake rather than specifying a numeric ADI. This approach reflects the recognition that flavoring agents are typically used at very low concentrations in food products, and dietary exposure is correspondingly low. The concept of an ADI helps regulators and industry professionals contextualize safety assessments by comparing estimated intake with thresholds derived from toxicological data, often incorporating large safety factors to account for uncertainties. For consumers, understanding that a compound has been evaluated and found to have no safety concern at typical use levels provides reassurance about its inclusion in flavor formulations.

Comparison With Similar Additives

CIS-3-HEXENYL CIS-3-HEXENOATE can be compared with other flavoring esters that also contribute fruity or green notes to food products. For example, ethyl butyrate is another ester used to impart fruity aromas reminiscent of pineapple or citrus, while methyl anthranilate is used for grape-like notes. Unlike these compounds, which emphasize sweeter or tropical fruit impressions, CIS-3-HEXENYL CIS-3-HEXENOATE’s green and slightly leafy nuances offer a different sensory dimension that can enhance complexity in blends. Another related compound is cis-3-hexenol, an alcohol with a fresh-cut grass aroma used in both flavor and fragrance applications. While both compounds contribute green sensory cues, the ester linkage in CIS-3-HEXENYL CIS-3-HEXENOATE often yields a fruitier, more rounded aroma profile compared with the more intensely green note of the alcohol. Flavorists leverage these differences to tailor products for specific sensory goals, combining multiple agents to achieve a desired overall effect.

Safety & Regulations

FDA

  • Notes: Listed in FDA Substances Added to Food inventory for flavoring use but no specific CFR authorization section is provided.

EFSA

  • Notes: EFSA evaluation details for this specific compound were not available from retrieved authoritative sources.

JECFA

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

Sources

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