CIS-3-HEXEN-1-YL ACETATE

CAS: 3681-71-8 FLAVORING AGENT OR ADJUVANT

CIS-3-HEXEN-1-YL ACETATE is a naturally occurring ester with a characteristic green, fruity aroma used as a flavoring agent in food and beverage products. It has been evaluated by international regulatory expert bodies for safety when used at typical flavoring levels.

What It Is

CIS-3-HEXEN-1-YL ACETATE is an organic ester compound belonging to the class of volatile aroma chemicals primarily used for its flavoring properties in a variety of food, beverage, and other consumer products. It is identified by the Chemical Abstracts Service with CAS number 3681-71-8 and is recognized under flavoring industry designations such as FEMA number 3171 and JECFA number 134. Its chemical structure consists of a hexenyl chain with an acetate ester functional group, conferring a distinctive green, fruity aroma profile reminiscent of freshly cut grass, green leaves, and fruits. This sensory quality makes it particularly valuable in applications where fresh, fruity topnotes are desired. Molecules in this class are typically volatile at room temperature, contributing to their efficacy even at low usage levels in formulations. The compound may occur naturally in foods such as certain fruits and plant-derived products and is also manufactured synthetically for consistent quality in industrial use. The presence of multiple synonymous names reflects its identification across different regulatory and industrial contexts.

How It Is Made

CIS-3-HEXEN-1-YL ACETATE is produced through a standard esterification process, where (Z)-3-hexen-1-ol (also known as leaf alcohol) reacts with an acetyl donor such as acetic acid or acetic anhydride under controlled conditions to form the acetate ester. This reaction is typically catalyzed by an acid catalyst to facilitate ester bond formation. In industrial settings, purification steps such as distillation or chromatography are applied to achieve the desired purity levels for food and flavor applications. The manufacturing process adheres to good manufacturing practice (GMP) standards applicable to food-grade flavorings and other additives. Quality control testing ensures batch consistency in terms of assay, sensory attributes, and absence of contaminants that could affect safety or performance in final products. Although specific proprietary synthesis details vary among manufacturers, the underlying chemical transformation is well established in organic chemistry and flavor ingredient production.

Why It Is Used In Food

CIS-3-HEXEN-1-YL ACETATE is used in food products primarily for its ability to impart fresh, green, and fruity aroma and flavor characteristics that enhance the sensory profile of foods and beverages. Flavor chemists often incorporate this compound into formulations to evoke fresh fruit notes such as apple, pear, or tropical fruits, or to add a crisp, green nuance that complements other flavor components. Its inclusion can balance and round out complex flavor profiles, contributing to a more lifelike sensory experience. The compound's volatility and olfactory potency mean that small amounts can have a significant impact, allowing product developers to achieve desired effects without excessive use. In beverage, confectionery, and dairy applications, CIS-3-HEXEN-1-YL ACETATE may be combined with other esters and aroma chemicals to create layered and nuanced flavor impressions that appeal to consumer preferences. Its use is aligned with broader flavor design strategies where fresh and fruity notes are sought to convey quality and naturalness.

Adi Example Calculation

This illustrative calculation demonstrates the concept of dietary exposure relative to regulatory context: if a hypothetical individual consumed foods totaling a combined 1 kilogram per day that collectively contained average concentrations of flavoring agents including CIS-3-HEXEN-1-YL ACETATE at parts-per-million levels, the absolute intake of the compound would be several orders of magnitude below thresholds evaluated in toxicological studies. Such hypothetical examples are intended to clarify how low typical dietary exposure levels compare with safety evaluation benchmarks. They are not representative of specific individual dietary habits but serve to illustrate how regulatory evaluations consider both concentration and consumption patterns.

Safety And Health Research

Safety evaluations of CIS-3-HEXEN-1-YL ACETATE by expert committees such as JECFA involve reviewing available toxicological data, including acute and subchronic studies, to assess potential hazards and margins of exposure. JECFA’s assessment concluded that at typical intake levels associated with flavor use, there is no safety concern, which aligns with its historical use in food flavorings without evidence of adverse effects at regulated use levels. Research also considers physicochemical properties, metabolic pathways, and species-specific responses to support safety assessments. Safety data sheets for technical-grade material provide hazard communication information relevant to handling and formulation, but these are focused on occupational safety rather than typical consumer exposure through diet. Overall, the weight of evidence from regulatory evaluations supports the compound’s safety profile within the context of controlled use in flavor applications.

Regulatory Status Worldwide

CIS-3-HEXEN-1-YL ACETATE has undergone evaluation by international expert bodies for safety as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated this compound and concluded that it does not present a safety concern at current levels of intake when used as a flavoring agent, a finding reflected in its JECFA record. Additionally, the compound is recognized within the Flavor and Extract Manufacturers Association (FEMA) flavor ingredient library under FEMA number 3171, indicating its use in flavor formulations within established industry guidelines. In the United States, FEMA’s assessments inform listings in the Food Additive Status List and related resources, though formal approval status under the U.S. Code of Federal Regulations is determined by FDA and other regulatory frameworks. In other jurisdictions, such as the European Union, flavoring substances are subject to specific regulatory regimes that catalog permitted flavoring agents and define conditions for use. Regulatory evaluations consider chemical identity, toxicological data, and estimated dietary exposure to support safe use in foods.

Taste And Functional Properties

CIS-3-HEXEN-1-YL ACETATE is characterized by a fresh green and fruity aroma, often reminiscent of newly cut grass or green leaves, which can translate into perceived flavor notes in foods. These sensory properties make it valuable for achieving vibrant, topnote effects in complex flavor systems. Chemically, the molecule is a moderately volatile ester that disperses readily in both aqueous and lipid phases, allowing it to contribute to aroma perception across a range of product matrices. It is generally used at low concentrations consistent with flavor industry practice to avoid overpowering the overall flavor profile. Its stability in standard food processing conditions is generally adequate, but like many esters, it may undergo hydrolysis under extreme pH or prolonged heat, which can diminish its aroma contribution if not formulated carefully. The compound’s sensory impact, combined with functional behavior in formulation, underlies its widespread use in diverse flavor applications.

Acceptable Daily Intake Explained

An Acceptable Daily Intake (ADI) is an estimate of the amount of a substance in food or drinking water that can be ingested daily over a lifetime without appreciable health risk. For flavoring agents such as CIS-3-HEXEN-1-YL ACETATE, regulatory expert committees like JECFA assess toxicological studies and dietary exposure to determine whether an ADI is needed. In the case of this compound, JECFA’s evaluation concluded there is no safety concern at current intake levels from its use in foods, which implies that a formal numeric ADI was not established. The concept of an ADI helps frame how regulators and scientists approach risk assessment, using uncertainty factors and conservative assumptions to ensure that consumer exposure through typical use remains well below levels associated with toxicity in experimental studies.

Comparison With Similar Additives

CIS-3-HEXEN-1-YL ACETATE shares functional roles with other ester-based flavoring agents such as ethyl acetate and isoamyl acetate, which also provide fruity aroma notes in foods and beverages. Compared with ethyl acetate, which tends toward more neutral fruity notes, CIS-3-HEXEN-1-YL ACETATE contributes a green, fresh character that can complement fruit-forward profiles. Isoamyl acetate, known for its banana-like aroma, overlaps in sensory space with CIS-3-HEXEN-1-YL ACETATE, but the latter’s green nuance often gives it a distinctive role in formulations seeking topnote vibrancy. Flavor chemists select among these compounds based on desired sensory outcomes, product matrix, and stability considerations.

Common Food Applications Narrative

CIS-3-HEXEN-1-YL ACETATE is used in numerous food and beverage categories to deliver fresh, fruity, and green sensory characteristics that resonate with consumer expectations for natural and appealing tastes. In beverages such as fruit-flavored drinks, sodas, or ready-to-drink teas, it contributes topnotes that suggest freshly picked fruit or leafy freshness, enhancing the overall aroma complexity. Confectionery products like candies, gummies, and breath mints benefit from its ability to accentuate sweet and fruity impressions without masking other key flavor elements. Dairy-based products, including flavored yogurts and ice creams, often incorporate this ester to boost perceived fruitiness or to balance creaminess with fresh aromatics. Bakers and snack formulators use it in fruit-filled pastries or baked goods to enhance perceived freshness, even after processing. The compound’s versatility also extends to culinary ingredients such as sauces and dressings, where a hint of green fruitiness can elevate consumer appeal. Across these applications, CIS-3-HEXEN-1-YL ACETATE is selected for its contribution to sensory quality and its compatibility with other flavor constituents, making it a widely recognized component in contemporary flavor design.

Safety & Regulations

FDA

  • Notes: Specific CFR authorization not confirmed via FDA database deep link; FEMA GRAS assessments indicate safety within flavoring use levels.

EFSA

  • Notes: No direct EFSA flavoring numeric ADI found from authoritative EFSA deep links.

JECFA

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

Sources

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