CITRAL GLYCERYL ACETAL

CAS: 5694-82-6 FLAVORING AGENT OR ADJUVANT

CITRAL GLYCERYL ACETAL is a synthetic flavoring agent or adjuvant used in some food flavor systems.

What It Is

CITRAL GLYCERYL ACETAL is a chemical used in the flavor and fragrance industry as a flavoring agent or adjuvant. It is identified by the Chemical Abstracts Service Registry Number 5694‑82‑6 and is composed of a glycerol acetal derivative of citral, a component of citrus oils. This compound is a member of a broader class of acetal compounds that are formed by the reaction of aldehydes with alcohols, forming cyclic structures that can influence odor and flavor profiles. It is registered in flavor industry inventories such as the Flavor and Extract Manufacturers Association (FEMA) list under number 4486 and is included in the U.S. Food and Drug Administration’s Substances Added to Food inventory, indicating it is recognized as an ingredient considered for flavor use in foods. The multiple other chemical names for this compound reflect its structural descriptors and stereochemistry, and these synonyms are often used in chemical databases and regulatory inventories to ensure accurate identification across jurisdictions. As an ingredient, Citral Glyceryl Acetal functions to impart or modify flavor in food systems through its aromatic properties. Characteristics of this compound’s structure contribute to its sensory profile, which can be described in the context of flavor chemistry as providing citrus‑like nuances or modifying existing flavor notes when formulated in combination with other flavoring agents. The presence of a dioxolane ring and a substituted heptadienyl side chain distinguishes it from simple aldehydes like citral itself, which can be more reactive or volatile. From a classification standpoint, Citral Glyceryl Acetal is part of a wider group of terpenoid derivatives and acetal compounds used in food flavorings. Its designation as a "flavoring agent or adjuvant" indicates that it may be used on its own to contribute specific flavor characteristics or in conjunction with other flavoring substances to enhance or stabilize flavor impressions. Because flavoring agents are typically used at low concentrations to achieve desired sensory effects, this ingredient is incorporated into food formulations in minute quantities compliant with flavor usage practices documented by industry evaluators.

How It Is Made

The production of Citral Glyceryl Acetal involves chemical synthesis that links citral or related aldehyde precursors with glycerol under controlled conditions to form an acetal structure. In non‑proprietary terms, the process entails an acid‑catalyzed reaction between the aldehyde functional groups present in citral and the diol (two‑hydroxyl) moiety of glycerol. This reaction leads to the formation of a five‑membered cyclic acetal, specifically a dioxolane ring, which is characterized by two oxygen atoms and three carbon atoms in the ring. The cyclic structure generally enhances stability compared to simple aldehyde compounds and alters volatility and sensory characteristics in a way that is useful for flavor applications. Chemical manufacturing facilities producing Citral Glyceryl Acetal start from commercially available citral, which itself is typically obtained from natural sources such as lemon or other citrus oils or synthesized via chemical routes. Glycerol used in the synthesis is a common industrial chemical produced as a by‑product of biodiesel production or through synthetic pathways. The synthesis is generally conducted under controlled temperatures and with acid catalysts, and the reaction mixture is monitored to favor the acetal formation over potential side reactions. After reaction completion, the compound is purified using standard organic chemistry techniques such as distillation or crystallization to achieve a high purity suitable for flavor industry use. Quality control and specification are important steps in the manufacturing process. The final product’s purity, assay, and absence of undesirable reaction by‑products are verified through analytical methods like gas chromatography or mass spectrometry. These quality checks ensure that the compound meets industry specifications for use in food flavoring applications. Manufacturing processes for food‑grade flavoring ingredients also incorporate good manufacturing practices (GMP) to ensure consistency, safety, and compliance with applicable regulatory standards for chemical production and handling.

Why It Is Used In Food

CITRAL GLYCERYL ACETAL is used in food formulations primarily for its flavoring properties. Flavoring agents are added to foods to provide desirable taste and aroma characteristics or to enhance, balance, or modify existing flavors to meet consumer expectations for specific products. In the case of Citral Glyceryl Acetal, its chemical structure lends it sensory properties that can contribute to citrus‑like notes or fine‑tune complex flavor profiles in formulations where subtle aromatic modulation is desired. Flavor chemists select agents like Citral Glyceryl Acetal because of their ability to be incorporated at low concentrations and impart targeted sensory effects. For example, in beverage applications, citrus and fruity notes can be desirable to produce refreshing or well‑rounded flavor impressions. In confectionery or bakery products, specific aromatic nuances may be employed to achieve consistency across batches or to complement other flavor components. Unlike primary nutrients or texturizing agents, flavoring agents such as Citral Glyceryl Acetal play a sensory role and often do not contribute nutritional value. Their use is focused on achieving a predictable sensory outcome without adversely affecting other aspects of product performance, such as shelf life or texture. When used at appropriate levels and in compliance with industry guidelines, these compounds help manufacturers meet product quality goals and align with consumer taste preferences.

Adi Example Calculation

An Acceptable Daily Intake (ADI) is usually set by expert committees and often expressed relative to body weight. Because a specific ADI for Citral Glyceryl Acetal has not been established in publicly available regulatory documents, no numeric example calculation can be provided based on a regulatory ADI. In general terms, if an expert body were to establish an ADI for a flavoring agent at a hypothetical value of X mg/kg bw/day, the daily exposure for a person could be estimated by multiplying X by body weight. For example, with a hypothetical ADI of 1 mg/kg bw/day, a 70‑kg adult’s allowable intake would be 70 mg per day. This kind of calculation is illustrative of how ADI concepts are applied rather than reflective of an established ADI for this specific compound.

Safety And Health Research

Safety assessments for flavoring agents like CITRAL GLYCERYL ACETAL are typically conducted by expert panels and regulatory agencies that evaluate available toxicological data, exposure estimates, and structural analog information to determine whether the compound can be used safely at levels consistent with flavoring purposes. Flavoring panel evaluations and inventory listings reflect considerations of chemical structure, potential for toxicity, and exposure through food use. However, public toxicology data specific to Citral Glyceryl Acetal are limited, which is not uncommon for many specialized flavoring agents. Regulatory inventories such as the FDA’s Substances Added to Food and FEMA’s flavor library provide context for industry use, but they do not always include extensive toxicological profiles within the public domain. Research on compounds of similar structural classes focuses on endpoints such as general toxicity, metabolism, and potential irritation. Because Citral Glyceryl Acetal is used at low concentrations in flavoring applications, estimates of consumer exposure are typically low relative to doses at which systemic effects might occur in experimental systems. Experts in flavor safety consider both data derived from analogous compounds and any available experimental information when evaluating the safety of flavoring substances. These assessments often consider aspects such as mutagenicity, reproductive toxicity, and chronic exposure potential. Where data gaps exist, evaluations proceed with caution, and flavoring use levels are guided by practices that minimize unnecessary exposure. Ongoing research into flavoring agent safety may further inform regulatory reviews and industry guidelines over time.

Regulatory Status Worldwide

CITRAL GLYCERYL ACETAL is included in regulatory inventories compiled by industry and government agencies concerned with substances added to foods. In the United States, it appears in the Food and Drug Administration’s Substances Added to Food inventory (formerly known as the Everything Added to Food in the U.S. or EAFUS inventory) as an entry where it is identified with its CAS number 5694‑82‑6 and documented for its use as a flavoring agent or adjuvant. This inclusion indicates that the compound has been recognized in the context of flavor use and is listed for reference by manufacturers and regulators, but it does not, by itself, constitute an affirmative FDA approval or specific regulation in the Code of Federal Regulations. The FDA inventory entry notes the technical effect and FEMA number associated with the compound’s evaluation by flavor industry panels without specifying regulatory limits or approved uses under specific CFR sections. In the European Union, flavoring agents and related substances are subject to evaluation and approval under flavor regulation frameworks that include evaluations by agencies such as the European Food Safety Authority (EFSA). Detailed, compound‑specific EFSA evaluations and E‑number assignments are documented for a range of flavoring substances, but available public records do not indicate an E‑number specifically assigned to Citral Glyceryl Acetal at this time. Manufacturers seeking to use this compound in EU markets would typically ensure compliance with applicable flavoring regulations and demonstrate safety consistent with EU requirements. Internationally, flavoring substances are often evaluated by expert panels such as the Joint FAO/WHO Expert Committee on Food Additives (JECFA), which maintains databases and specifications for many flavoring agents. While JECFA maintains searchable flavoring specification databases that include CAS numbers and FEMA identifiers, specific summary evaluations or acceptable daily intake figures for this compound have not been identified in publicly accessible summaries to date. As a result, global regulatory status varies by jurisdiction, and compliance often depends on alignment with general flavoring use provisions and adherence to good manufacturing practices.

Taste And Functional Properties

CITRAL GLYCERYL ACETAL exhibits sensory properties characteristic of acetal derivatives of aldehydes, where the cyclic acetal structure can influence how the compound interacts with taste receptors and olfactory receptors. Sensory analysts describe related compounds in this class as contributing to citrus‑like, fruity, or floral aromatic nuances, which is why derivatives of citral and related terpenoid aldehydes are commonly used to achieve or modify such sensory impressions. The cyclic dioxolane ring of Citral Glyceryl Acetal tends to reduce the direct aldehydic harshness that is sometimes associated with free aldehydes like citral, leading to a smoother, more balanced aromatic profile when used in flavor blends. Functionally, the stability of the acetal ring contributes to reduced reactivity compared to free aldehydes. This can enhance formulation stability during processing and storage, particularly in products exposed to mild heat or pH changes. While the compound is relatively low in water solubility due to its organic structure, it can be dissolved in ethanol or other flavor solvents commonly used in beverage and food flavor systems. This allows flavorists to incorporate it effectively into aqueous products at controlled levels without significant precipitation or phase separation. Because flavor perception is influenced by the compound’s volatility, the balance between volatility and stability is critical. Citral Glyceryl Acetal’s structure provides a degree of volatility that supports aromatic delivery without rapid dissipation, enabling its sensory impact to be sustained during product consumption. However, the specific taste and aroma profiles can vary depending on the matrix into which it is incorporated, the presence of other flavor components, and the concentration used. Functional properties related to heat and pH stability also align with typical flavor formulation practices where ingredients must withstand processing conditions without significant degradation.

Acceptable Daily Intake Explained

Acceptable Daily Intake (ADI) is a concept used by regulatory and expert bodies to describe the amount of a substance that can be consumed daily over a lifetime without appreciable health risk. It is typically expressed in milligrams of substance per kilogram of body weight per day (mg/kg bw/day) and is based on toxicological data from animal studies or human observations, with safety factors applied to account for uncertainties. In the case of flavoring agents such as CITRAL GLYCERYL ACETAL, specific ADI values have not been publicly established by major regulatory bodies like the Joint FAO/WHO Expert Committee on Food Additives or EFSA because comprehensive toxicological data may not be available or have not been subjected to formal evaluation. When an ADI is established for a flavoring agent, it reflects a threshold below which intake is considered safe for the general population, including sensitive subgroups. Regulatory decisions consider typical use levels in foods, patterns of consumption across populations, and margins of safety derived from experimental data. For many flavoring agents, the absence of an explicitly published ADI does not imply a known hazard; rather, it reflects the current state of publicly accessible evaluations.

Comparison With Similar Additives

Flavoring agents and adjuvants encompass a broad range of chemically diverse compounds that contribute sensory characteristics to foods. Citral Glyceryl Acetal can be compared with other acetal derivatives and related terpenoid flavoring agents such as simple citral, citronellol derivatives, and other cyclic acetals. Citral itself is a well‑known aldehyde with strong citrus notes and is used in flavor and fragrance applications; however, citral’s free aldehyde functionality makes it more reactive and potentially less stable in certain formulations. By contrast, Citral Glyceryl Acetal’s cyclic acetal structure often exhibits improved stability and a modified sensory profile that may be smoother or less pungent. Other related compounds used as flavoring agents include acetals derived from furfural or other aldehydes, which provide different aromatic notes. These compounds share with Citral Glyceryl Acetal a balance between volatility for aroma delivery and stability to withstand processing. The choice among these agents depends on the desired sensory outcome and compatibility with product matrices. In each case, regulatory considerations and safety evaluations are important, and manufacturers select flavoring agents that meet both sensory objectives and regulatory compliance requirements in target markets.

Common Food Applications Narrative

Flavoring agents like CITRAL GLYCERYL ACETAL are incorporated into a wide variety of food and beverage products to achieve specific sensory characteristics that align with consumer expectations. In non‑alcoholic beverages, for example, citrus or fruity aromatic components are often desirable to create refreshing, balanced flavor profiles that appeal to a broad audience. Citral Glyceryl Acetal can be part of a flavor palette that enhances these impressions, particularly when other flavoring agents work synergistically to deliver complex sensory experiences. In confectionery items such as candies, gummies, or sweet sauces, nuanced aromatic agents help create distinctive taste experiences. These compounds may be blended with other flavor components to achieve a desired sweetness perception that complements the base sugar profile or to offset any potential off‑notes from other ingredients. The ability of Citral Glyceryl Acetal to contribute subtle citrus‑like notes without overwhelming the overall profile makes it a useful tool in the flavorist’s repertoire. Dairy and frozen dessert applications can also benefit from carefully selected flavoring agents. In products like ice creams or flavored yogurts, citrus or fruity undertones can add a layer of sensory appeal that enhances the perceived freshness or complexity of the product. This is particularly relevant in products that aim to evoke fruit flavors without relying solely on natural fruit inclusions. Bakery products, including cakes, breakfast goods, and pastries, sometimes incorporate flavoring agents to achieve consistent sensory profiles across batches. Here, Citral Glyceryl Acetal may be used in conjunction with other flavoring ingredients to balance sweetness, complement spices, or create signature aromatic notes that define a specific product. The versatile use of flavoring agents in these applications demonstrates how technical flavor components support both product differentiation and consistent consumer experience.

Safety & Regulations

FDA

  • Notes: Inclusion in the FDA Substances Added to Food inventory does not by itself establish FDA approval; specific CFR citation not found in public sources.

EFSA

  • Notes: No specific EFSA evaluation or E number assignment identified in available records.

JECFA

  • Notes: No specific JECFA ADI or evaluation summary publicly identified for this substance.

Sources

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