CIS-3-HEXENYL FORMATE

CAS: 33467-73-1 FLAVORING AGENT OR ADJUVANT

CIS-3-HEXENYL FORMATE (CAS 33467-73-1) is a carboxylic ester used as a flavoring substance with green fruity and fresh odor notes in food and beverage formulations.

What It Is

CIS-3-HEXENYL FORMATE is a defined chemical substance classified as a flavoring agent or adjuvant used in the food industry for imparting specific aroma characteristics. It belongs to the class of carboxylic esters and is recognized for its green, fresh, and fruity sensory profile. Its CAS Registry Number is 33467-73-1, and it is known by multiple systematic and synonym names reflecting its chemical structure and stereochemistry. This compound is typically employed at low use levels to contribute green leafy, fruity, or vegetal top notes to flavor blends. CIS-3-HEXENYL FORMATE has been evaluated within international flavoring evaluation programs and is listed with identifiers such as FEMA Number 3353 and JECFA Number 1272, indicating its consideration in expert assessments of flavoring substances. It is distinct from simple fragrance compounds used exclusively in perfumery, as its use in food flavor systems is oriented toward complementing or modifying taste and aroma in consumable products. The chemistry of this ester involves the formate moiety attached to a cis-configured unsaturated hexenyl chain, which contributes to its volatility and sensory characteristics. While primarily recognized as a flavoring additive, the compound also finds applications in non-food sectors such as perfumery due to its appealing olfactory attributes.

How It Is Made

CIS-3-HEXENYL FORMATE is synthesized through esterification reactions between cis-3-hexenol and formic acid or formic acid derivatives under controlled conditions. Industrial processes typically involve catalysts and removal of water or byproducts to drive the reaction toward the desired ester product, with subsequent purification steps to achieve the required quality for flavor application. The general principle of ester formation is well established in organic chemistry, relying on the activation of the acid component and condensation with the alcohol moiety. Manufacturers producing this compound for flavor use often implement quality control measures that align with flavor industry standards. These measures include ensuring appropriate purity, consistent sensory attributes, and compliance with relevant specifications such as those developed by flavoring authorities. Analytical methods such as gas chromatography help confirm composition and detect impurities, ensuring that the material performed in flavor formulations meets expected performance criteria. The production of CIS-3-HEXENYL FORMATE must also account for safety data associated with handling and storage, as the parent alcohol and acid precursors can present hazards typical of volatile organic compounds. Facilities that produce or handle this ester follow standard practices for managing flammable and irritant substances, including appropriate engineering controls, personal protective equipment, and monitoring protocols to mitigate exposure risks in the chemical processing environment.

Why It Is Used In Food

CIS-3-HEXENYL FORMATE is used in food flavoring because it contributes distinctive green, fresh, and fruity aromatic notes that enhance the sensory appeal of a range of products. Flavorists leverage this compound to create or modify flavor impressions that mimic natural fruit and vegetable characteristics, such as fresh cut grass, apple, or green banana, which can make products taste more natural or vibrant. In formulation contexts, this ester can be blended with other flavoring agents to achieve balanced and complex flavor profiles. It acts as a topnote contributor in flavor systems, meaning it is one of the first odor impressions perceived when the food or beverage is consumed or smelled. Its relatively low odor threshold and volatility make it suitable for imparting impactful sensory effects at small use levels. The choice to include CIS-3-HEXENYL FORMATE in specific products stems from its performance in delivering consumer-desired flavor characteristics with minimal inclusion rates. As with other flavoring agents, its inclusion is guided by formulation objectives such as sensory complexity, naturalness perception, and synergy with other components, ensuring the final product meets consumer expectations for taste and aroma.

Adi Example Calculation

Because CIS-3-HEXENYL FORMATE does not have a numeric acceptable daily intake (ADI) assigned by authoritative expert bodies, an illustrative calculation using a numeric ADI cannot be presented here. In general terms, for substances with a defined ADI, a calculation might take the form of comparing estimated intake in milligrams per kilogram of body weight per day to the ADI value derived by regulatory authorities. For example, if a flavoring substance had a hypothetical ADI of X mg per kilogram of body weight, a person weighing 70 kilograms would have an illustrative daily intake threshold of 70 times X in milligrams. Estimated intake of the substance from all food sources would then be compared to this threshold to ensure it remained below the ADI. In the case of CIS-3-HEXENYL FORMATE, expert evaluation concluded no safety concern at anticipated intake levels, effectively obviating the need to apply numeric comparisons to an assigned ADI. This type of conclusion is typical for flavoring agents used at low levels where exposure estimates are well below thresholds associated with toxicological concern.

Safety And Health Research

Safety evaluations for CIS-3-HEXENYL FORMATE have been conducted by authoritative expert bodies, primarily focusing on its use as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) evaluated the compound and concluded that it does not raise a safety concern at dietary exposure levels typical for flavor use. This assessment involves consideration of available toxicological data relevant to its chemical class and anticipated exposure, supporting its use in food flavoring systems. As a flavoring substance, toxicological data include studies on general toxicity, metabolism, and potential adverse effects under conditions that simulate dietary exposure. These evaluations also take into account data on structurally related esters and general principles of safety assessment for flavor compounds, which often rely on conservative assumptions where specific data may be limited. The safety profile noted by expert evaluation does not imply that the compound is devoid of hazard at all doses but reflects consideration that at expected use levels in food products, consumer exposure remains well below thresholds associated with adverse outcomes. This expert opinion context supports regulatory acceptance in many regions and informs its inclusion in industry inventories and databases for flavoring substances.

Regulatory Status Worldwide

CIS-3-HEXENYL FORMATE has been evaluated by international expert committees for its use as a flavoring substance. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) assessed this compound and concluded that it presents no safety concern at levels of intake consistent with its intended use in food flavoring. This evaluation is documented in reports such as the Joint FAO/WHO Expert Committee on Food Additives evaluations series, indicating expert consideration of available toxicological data. Sources reporting this conclusion describe a safety evaluation with no specified acceptable daily intake required at typical use levels. In the United States, CIS-3-HEXENYL FORMATE appears in the FDA’s Substances Added to Food inventory, which includes flavoring substances evaluated by FEMA and JECFA, but its presence in this database does not constitute an affirmative FDA regulation or specific CFR listing. The FDA inventory inclusion reflects recognition of its use and evaluative context rather than a direct regulatory approval under specific Code of Federal Regulations sections. Within the European Union framework under Regulation (EC) No 1334/2008 on flavorings and food ingredients with flavoring properties, chemically defined flavoring substances are subject to inclusion in the Union list of permitted flavorings. While specific listing details for CIS-3-HEXENYL FORMATE in the Union list were not directly retrieved, its evaluation by JECFA and consideration in flavoring group evaluations contribute to its recognized status in food formulation practices.

Taste And Functional Properties

CIS-3-HEXENYL FORMATE is appreciated in flavor formulation for its sensory properties rather than functional effects on food chemistry. Sensory descriptions commonly attributed to this compound include green-leafy, fruity, fresh-cut grass, and subtle vegetal notes that can complement fruit and vegetable flavor profiles. These descriptors make it valuable in tailoring the aromatic dimension of food and beverage products. From a functional standpoint, its relatively low solubility in water and higher solubility in alcohol or oil phases influence how it is incorporated into different types of formulations. In aqueous systems such as beverages, its volatility and partitioning behavior must be managed so that the desired sensory impact is maintained. With this compound’s volatility, it is generally used at low levels to prevent overwhelming the overall flavor balance. While sensory characteristics are paramount, formulators also consider the stability of this ester in processing conditions. Its chemical structure can be susceptible to hydrolysis under extreme pH or temperature conditions, though typical food processing environments do not significantly degrade its sensory contribution. As with many flavor esters, proper formulation and processing controls are essential to retain its characteristic profile through production and storage.

Acceptable Daily Intake Explained

The concept of acceptable daily intake (ADI) is used by regulatory and expert bodies to indicate the amount of a substance that can be ingested daily over a lifetime without appreciable health risk. For CIS-3-HEXENYL FORMATE, expert evaluation by JECFA concluded that typical dietary intake levels from its use as a flavoring agent do not raise safety concerns, and therefore a specific numeric ADI was not assigned. This reflects that the compound’s exposure at intended use levels is considered to be within safe boundaries given available data and expert judgment. It is important to understand that an ADI is not a nutritional recommendation but a safety threshold derived from toxicological evaluations. When a numeric ADI is not deemed necessary, it usually means that exposure is expected to be low relative to levels that would cause adverse effects in animals or humans based on available studies. For flavoring substances used at low concentrations, such conclusions are common, as the margin between typical exposure and levels of toxicological concern is generally large. Consumers do not need to calculate their own intake against an ADI; rather, manufacturers and regulators use these scientific benchmarks to guide safe use levels in products. When regulatory authorities or expert committees conclude no safety concern at intended use levels, they effectively indicate that routine consumption of products containing this compound is not expected to pose a health risk.

Comparison With Similar Additives

CIS-3-HEXENYL FORMATE can be compared with other flavoring esters that contribute green and fruity sensory notes. For example, ethyl butyrate is another ester widely used in fruit flavor formulations to impart sweet and fruity character, though its sensory profile leans more toward ripe fruit notes rather than green leafy nuances. Both compounds are employed to enhance the overall flavor experience, but their contributions differ, making them complementary in multi-component flavor systems. Another comparable additive is hexyl acetate, which provides fruity and apple-like aromas commonly used in beverage and confectionery applications. Like CIS-3-HEXENYL FORMATE, hexyl acetate is selected for its volatility and sensory impact, yet its specific aroma profile is distinct, emphasizing ripe fruit over freshly cut vegetation notes. In contrast, methyl anthranilate, another fruit‑associated flavoring, contributes grape-like characteristics and illustrates how different esters are chosen based on targeted sensory effects. These comparisons highlight how flavor chemists select among structurally related esters to achieve desired aromatic outcomes. CIS-3-HEXENYL FORMATE’s unique green and fresh profile complements these other esters, enabling formulation of balanced, multi‑dimensional flavors in food and beverage products.

Common Food Applications Narrative

CIS-3-HEXENYL FORMATE finds application across a variety of food and beverage categories where green, fresh, and fruity notes are desired. In beverages such as fruit-flavored drinks and iced teas, flavorists include this ester to enhance the perception of natural fruit nuances and to provide a refreshing sensory character that aligns with consumer expectations. Its green and fruity notes can complement citrus and berry profiles, contributing to a crisp aromatic experience. In confectionery and dessert products, CIS-3-HEXENYL FORMATE may be used to support fruit flavor accents, adding complexity and freshness to selections like apple or melon candies. Similarly, in dairy desserts like frozen yogurts or sorbets, it can provide a light and refreshing aromatic lift, contributing to an overall balanced flavor profile. Beyond sweet products, it also has a role in savory applications where subtle vegetal notes can enhance the perception of freshness in formulations such as soups or sauces. In all these contexts, the usage level of CIS-3-HEXENYL FORMATE is guided by sensory targets and regulatory considerations, ensuring that the flavor contribution is consistent and desirable. Its inclusion is part of a broader palette of flavoring agents that together help manufacturers craft products with distinctive and appealing taste and aroma profiles.

Safety & Regulations

FDA

  • Notes: Inclusion in the FDA Substances Added to Food inventory does not equate to formal FDA approval under CFR and explicit approval is not verifiable from sources.

EFSA

  • Notes: EFSA authorization status on specific Union list not verifiable from sources.

JECFA

  • Notes: JECFA concluded no safety concern at intended use levels but did not assign a numeric ADI or explicit year in linked data.

Sources

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