CIS-3-HEXENYL BUTYRATE
CIS-3-HEXENYL BUTYRATE is an ester compound used as a flavouring agent with a green, fruity, slightly buttery sensory profile when added at typical flavouring concentrations.
What It Is
CIS-3-HEXENYL BUTYRATE is a chemical flavouring substance identified by the CAS Registry Number 16491-36-4. It belongs to a class of volatile organic esters commonly used for their pleasant aroma and flavour-enhancing properties in foods and beverages, often contributing green, fruity and slightly buttery notes. Though not assigned a specific INS/E-number in recognised flavour lists, this compound is identified in regulated flavouring inventories and by international expert committees such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA) and the Flavor and Extract Manufacturers Association (FEMA). The molecule’s structure features a cis-configured alkene linked to a butyrate ester moiety, which underpins its characteristic sensory properties.
How It Is Made
CIS-3-HEXENYL BUTYRATE is typically manufactured by esterification of cis-3-hexenol with butyric (butanoic) acid under controlled conditions. In this process, the alcohol and acid react in the presence of an acid catalyst and with the removal of water to drive the equilibrium toward ester formation. This reaction yields a colourless to pale yellow liquid that is purified to meet food-grade or flavouring specifications. The synthetic pathway mirrors processes used to produce many flavour esters that replicate or enhance aromas found naturally in fruits, herbs, and other plant materials.
Why It Is Used In Food
CIS-3-HEXENYL BUTYRATE is used in the food industry primarily as a flavouring agent or adjuvant to impart fresh, green and fruity aroma characteristics when consumed. Such esters are selected in formulations to achieve specific sensory impacts that are complementary to the inherent flavours of food products, enhancing consumer perception. Due to its volatility and sensory profile, it is suitable for incorporation into flavours for beverages, confectionery and other products where a top-note aroma effect is desired.
Adi Example Calculation
As an illustrative example of how ADI calculations are presented more generally: for a hypothetical additive with a numeric ADI of X mg per kg body weight per day, a person weighing 70 kg would have an illustrative acceptable intake of 70 times X mg per day. For CIS-3-HEXENYL BUTYRATE, a numeric ADI was not formally assigned in the most recent JECFA evaluation, and this narrative serves to explain how numeric ADIs are applied rather than to provide a specific intake figure.
Safety And Health Research
Safety evaluations of CIS-3-HEXENYL BUTYRATE have been conducted by expert bodies such as JECFA and FEMA based on available toxicological and use data. According to JECFA, this compound did not raise safety concerns at estimated current levels of intake when used as a flavouring agent. Toxicological assessments for flavouring compounds typically consider parameters such as acute toxicity, genotoxicity, and metabolic pathways, although comprehensive datasets for every compound may not be available. In general, flavouring esters are metabolised by common esterases in the body to their constituent alcohols and acids, which are further processed via normal metabolic pathways. Safety data for specific endpoints such as chronic toxicity or reproductive effects may not be available for all substances, and evaluation conclusions are based on available evidence from structural class and related compounds.
Regulatory Status Worldwide
CIS-3-HEXENYL BUTYRATE is listed in the FDA’s Substances Added to Food inventory, which compiles substances evaluated by FEMA and JECFA for flavour use but does not necessarily imply direct FDA approval under a specific CFR section. The chemical is also evaluated under JECFA flavouring evaluations, where it is recognised as a flavouring agent and associated with FEMA number 3402 and JECFA flavour number 157. JECFA’s evaluation concluded no safety concern at current levels of intake when used as a flavouring agent. In the European Union, flavouring substances must appear on the Union list of authorised flavourings; general scientific advice on groups of flavouring substances has been provided by EFSA, but specific listing and numeric allocations may not be directly published for every individual compound. Regulatory frameworks may vary by jurisdiction, and its inclusion in inventories reflects expert assessment rather than explicit numeric limits documented in primary regulations.
Taste And Functional Properties
CIS-3-HEXENYL BUTYRATE exhibits a sensory profile described as green, fresh, somewhat fruity, and slightly buttery at very low use levels typical for flavouring applications. Such volatile esters interact with olfactory receptors to deliver characteristic top-note aroma impressions that improve perceived freshness or fruitiness. Functionally, its solubility in alcohols and fixed oils and its relatively low use level make it compatible with complex flavour systems. Due to its ester linkage, it is generally stable under normal storage and formulation conditions, though like other esters it may hydrolyse under strong acidic or basic conditions.
Acceptable Daily Intake Explained
An acceptable daily intake (ADI) is an estimate of the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, expressed per unit of body weight. For many flavouring agents including CIS-3-HEXENYL BUTYRATE, expert committees like JECFA evaluate available data and may conclude that there is no safety concern at current levels of intake without assigning a numeric ADI, reflecting confidence that typical use levels are low relative to thresholds of toxicological concern. Such assessments are based on safety studies, exposure estimates, and consideration of metabolic pathways common to similar compounds. A statement of 'no safety concern at current levels of intake' should not be interpreted as establishing a numeric ADI but indicates that under normal use patterns, exposures are judged acceptable.
Comparison With Similar Additives
CIS-3-HEXENYL BUTYRATE shares functional similarities with other fruity ester flavouring agents such as ethyl butyrate and pentyl butyrate, which are also used to impart fruit-like sensory notes. While ethyl butyrate is widely known for its orange and tropical fruit nuances and pentyl butyrate for pear or apricot-like notes, CIS-3-HEXENYL BUTYRATE is distinguished by its green and fresh character. In formulation contexts, these esters are often combined to create complex flavour profiles. Regulatory evaluations for such esters similarly consider their metabolic pathways and exposure estimates, although the specific data and listing status may vary by compound and jurisdiction.
Common Food Applications Narrative
CIS-3-HEXENYL BUTYRATE is broadly used in flavour formulations designed for food and beverage products to enhance or impart green, fruity sensory characteristics. Typical applications include incorporation into beverage flavour systems (such as fruit-flavoured drinks), confectionery, baked goods, dairy desserts, and other products where a fresh or fruity note contributes to the overall sensory profile. Due to its sensory potency at low concentrations, it is often blended with other flavour compounds to achieve balanced aroma effects. In these applications, the compound contributes to the perception of freshness and complexity, supporting the overall flavour design without dominating the base flavour.
Safety & Regulations
FDA
- Notes: Included in the FDA Substances Added to Food inventory based on FEMA and JECFA evaluation but no specific CFR approval section could be verified.
EFSA
- Notes: EFSA general evaluations cover groups of flavourings, specific numeric authorisation and ADI values for this compound could not be verified in authoritative EFSA listings.
JECFA
- Notes: JECFA concluded no safety concern at current intake levels but did not assign a numeric ADI or explicit year on the database entry.
- Adi Display: No safety concern at current intake levels as flavouring agent
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