ALPHA-AMYLCINNAMYL ISOVALERATE

CAS: 7493-80-3 FLAVORING AGENT OR ADJUVANT

ALPHA-AMYLCINNAMYL ISOVALERATE (CAS 7493-80-3) is a synthetic ester used as a flavouring agent or adjuvant with a mild fruity and somewhat tobacco-like aroma and taste profile. It is listed among synthetic flavouring substances under US federal food additive regulations.

What It Is

ALPHA-AMYLCINNAMYL ISOVALERATE is a chemically defined flavouring agent belonging to the class of unsaturated esters used to impart or enhance aroma and taste in food and beverage formulations. Its structure is characterized by a phenyl-substituted heptyl ester of 3-methylbutanoic acid, and it is often described as having a mild fruity, tobacco, hay, and slightly spicy sensory profile based on analytical descriptors from flavouring ingredient libraries. This compound is widely d in flavour and fragrance industry references with the FEMA number 2067 and the JECFA flavouring number 678, indicating recognition by expert bodies that evaluate aroma chemicals for use in food and cosmetic applications. The compound’s role as a flavouring agent or adjuvant reflects its ability to contribute complex top notes and depth to flavour profiles in trace concentrations. As a flavouring substance, ALPHA-AMYLCINNAMYL ISOVALERATE is synthesized through established esterification chemistry involving amylcinnamyl alcohol intermediates and isovaleric acid derivatives, resulting in a molecule that mixes lipophilic and aromatic features conducive to flavour systems. Despite its usage as a food flavour, detailed regulatory authorization varies by jurisdiction, and any specific use in food and beverage must comply with local regulatory frameworks defining permissible additives and conditions of use.

How It Is Made

The production of ALPHA-AMYLCINNAMYL ISOVALERATE typically involves organic esterification reactions between a cinnamyl-derived alcohol and an appropriate branched carboxylic acid, such as isovaleric acid. Such reactions are standard in the synthesis of flavour and fragrance esters, wherein the alcohol and acid react under controlled conditions to form the ester linkage with minimal impurities. Industrial processes may include catalysts and controlled temperatures to optimize yield and purity for flavour applications. Quality and purity are central considerations in flavour ingredient manufacture. Manufacturers producing food-grade esters like ALPHA-AMYLCINNAMYL ISOVALERATE generally follow good manufacturing practices to deliver material suitable for incorporation into flavour formulations, ensuring that specifications such as minimum assay content and low levels of unwanted byproducts are met. These specifications and the identity of the molecule can be confirmed by analytical methods such as gas chromatography and mass spectrometry, which are routinely employed to verify chemical identity and purity before the compound is used in any food or fragrance context. Because this compound primarily serves flavour and aromatic purposes and is not consumed in large quantities, producers focus on delivering a product that meets sensory performance expectations without introducing contaminants beyond trace levels. While precise proprietary synthesis details may vary by supplier, the underlying chemistry revolves around well-understood esterification and purification steps that yield the characteristic flavour-active molecule.

Why It Is Used In Food

Flavouring agents such as ALPHA-AMYLCINNAMYL ISOVALERATE are utilized to introduce or enhance desirable aroma and taste attributes in a range of foods and beverages. Due to its mild and nuanced sensory properties, which can include fruity and warm top notes with subtle tobacco-like undertones, this compound is valuable in complex flavour systems where multi-layered sensory experiences are desired. In practice, such esters are added in trace amounts to provide depth and balance to flavour profiles rather than dominating the overall taste. They can be combined with other flavour ingredients to achieve specific targeted effects, such as rounding off harsher notes or contributing nuance to fruity or sweet formulations. The use of these substances is common in beverages, confectionery, baked goods, and flavour blends where a distinctive character is part of the formulation goal. Regulators and industry bodies often evaluate flavouring compounds for safety and appropriate usage contexts. Manufacturers select such agents based on their ability to perform within defined good manufacturing practice approaches, considering sensory objectives and any regulatory usage constraints. The result is an ingredient that helps food scientists and flavour formulators achieve desired sensory qualities while aligning with regulatory expectations for flavouring substances.

Adi Example Calculation

Because no numeric ADI has been explicitly established for ALPHA-AMYLCINNAMYL ISOVALERATE by authoritative bodies, an illustrative calculation is not provided here.

Safety And Health Research

Safety and health research for flavouring agents like ALPHA-AMYLCINNAMYL ISOVALERATE typically focuses on toxicological endpoints relevant to food additive evaluation, such as genotoxicity, subchronic toxicity, and potential reproductive toxicity. Expert committees examine available data to determine whether there is any indication that normal dietary exposure could pose a safety concern. In the case of this compound, expert evaluations have indicated that there is no safety concern at current levels of intake when used as a flavouring agent, based on assessments that considered the compound’s chemical structure, metabolism, and use levels. Because flavouring agents are consumed in very low concentrations, regulators typically review available toxicology data and exposure estimates rather than conducting new clinical studies for each compound. As part of these evaluations, expert panels consider available literature, structural analogs, and metabolic pathways that might inform the compound’s behaviour in biological systems. In many cases, the absence of specific toxicological data points leads experts to rely on weight-of-evidence approaches that consider chemical class and analogous compounds. Overall, safety assessments aim to ensure that when these compounds are used under intended conditions and levels, they do not pose a risk to consumers. This framework reflects regulatory practice for evaluating food flavouring substances and underscores the role of established scientific review in guiding permissible use.

Regulatory Status Worldwide

In the United States, ALPHA-AMYLCINNAMYL ISOVALERATE appears within the context of synthetic flavouring substances covered under 21 CFR 172.515, which describes the general conditions under which synthetic flavouring substances and adjuvants may be safely used in food when employed in minimum quantities required for intended effect and in accordance with good manufacturing practice. The regulation itself enumerates a list of substances that may be used, and the inclusion of this compound’s CAS and associated references indicates that it is recognized within this regulatory category. The synthetic flavouring substances regulation does not assign specific numeric usage limits beyond the general good manufacturing practice principle. In addition, the FDA’s Substances Added to Food database (formerly known as EAFUS) lists this compound with associated FEMA and JECFA identifiers, which serves as a reference for substances recognized for flavour use and GRAS evaluation contexts. While this listing itself does not confer explicit safe use levels, it indicates consideration by expert evaluation panels that assess flavouring substances for general recognition of safety. Internationally, expert evaluations such as those conducted by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) have assessed this compound and concluded that there is no safety concern at current intake levels when used as a flavouring agent, reflecting global efforts to evaluate safety based on available toxicological data and exposure estimates.

Taste And Functional Properties

The taste and functional properties of ALPHA-AMYLCINNAMYL ISOVALERATE are primarily defined by its sensory contributions at low concentrations. Flavour chemists characterize the compound as offering mild fruity notes with hints of tobacco, hay, and spice, providing complexity beyond simple sweet or fruity elements. These sensory attributes are valuable when nuanced or layered flavour profiles are targeted, such as in certain beverage or confectionery applications. Functionally, the compound’s physicochemical properties influence how it interacts with flavour matrices and solvents. Esters like this are typically more soluble in alcohol and non-polar systems than in water, which affects how they are incorporated into different products. They may exhibit high lipophilicity, a property that contributes to their preference for partitioning into lipid phases or alcohol-rich flavor bases. This behavior informs how formulators integrate the compound into aqueous systems, often requiring co-solvents or carrier materials for effective dispersion. In addition to sensory roles, the compound does not serve significant functional purposes such as preservation or texture modification. Its primary function remains to provide specific flavour notes that enhance the overall sensory experience. Because such compounds are used at very low concentrations due to their potent sensory impact and regulatory guidance, they contribute character without significantly altering other product properties.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory concept representing the estimated amount of a substance that can be consumed daily over a lifetime without appreciable health risk, based on toxicological data and uncertainty factors. While some flavouring agents have explicit ADIs assigned by expert bodies, for many flavouring esters, including ALPHA-AMYLCINNAMYL ISOVALERATE, expert evaluations have concluded that there is no safety concern at current levels of intake and therefore an explicit numeric ADI is not assigned or reported in the primary JECFA summary. This conclusion reflects the compound’s low levels of use in foods and the outcome of risk assessment processes that consider structural properties and estimated exposures. The ADI framework itself is used by regulators to contextualize exposure in relation to potential health effects; a lack of concern designation indicates confidence that normal use will not result in exposures approaching levels associated with adverse effects. It is important to note that an ADI is not a recommended intake but a safety benchmark.

Comparison With Similar Additives

ALPHA-AMYLCINNAMYL ISOVALERATE can be compared to other synthetic flavouring esters such as ALPHA-AMYLCINNAMYL ACETATE and BETA-AMYL CINNAMYL ISOVALERATE, which share similar ester functional groups but differ in chain length and aromatic substitution patterns. These structural differences influence their aroma characteristics, with some contributing brighter fruity notes and others offering deeper spicy or floral aspects. In contrast, simpler esters like ETHYL BUTYRATE are known for their pronounced fruity notes at very low concentrations, whereas more complex cinnamyl esters may contribute layered sensory profiles that combine fruity and spicy sensations. The choice among such additives depends on the specific sensory goals in a flavour formulation and regulatory contexts governing permissible use. While each compound operates within the general category of flavouring agents, their sensory contributions and physicochemical properties differ in ways that inform their application in particular product categories, with some being more suited to fruity formulations and others to warm or spicy profiles.

Common Food Applications Narrative

In product formulations, flavouring agents like ALPHA-AMYLCINNAMYL ISOVALERATE play a subtle yet impactful role in shaping the sensory profile of foods and beverages. Formulators use trace amounts of this ester to complement predominant flavour notes and add complexity to finished products. For example, when designing beverage flavour blends that mimic natural fruit or floral profiles, a small inclusion of this compound can deepen the perceived aroma and add a rounded sweetness that supports other key flavour components. In confectionery, such flavouring agents contribute top notes that help distinguish one product variant from another, enhancing consumer appeal. In baked goods or snack applications, flavour chemists may use this compound alongside other esters and aromatic ingredients to craft signature blends that appeal to targeted taste preferences, balancing sweetness with subtle complexity. Because flavouring agents operate at the intersection of chemistry and sensory perception, their use is tailored to complement other formulation components without dominating the overall taste. The result is a nuanced sensory experience that aligns with product goals, whether aiming for a bright tropical fruit character or a richer blend with layered aromatic undertones. Across these applications, the inclusion of such flavouring agents reflects industry practice that combines sensory science, regulatory compliance, and consumer-driven design. Each application considers how individual flavour chemicals interact within a matrix and contribute to the aggregate sensory profile and how regulatory frameworks inform permissible usage levels in food products.

Safety & Regulations

FDA

  • Approved: True
  • Regulation: 21 CFR 172.515

EFSA

  • Notes: Specific EFSA numeric ADIs not found in d sources

JECFA

  • Notes: JECFA assessment concluded no safety concern at current intake but did not define numeric ADI

Sources

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