5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE

CAS: 164524-93-0 FLAVORING AGENT OR ADJUVANT

5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE is a synthetic heterocyclic organic compound used as a flavoring agent with a nutty, roasted aroma profile in food formulations, identified by CAS 164524-93-0.

What It Is

5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE is a heterocyclic organic compound featuring a six-membered ring with nitrogen and sulfur atoms and an acetyl functional group. It has the Chemical Abstracts Service registry number 164524-93-0 and is recognized in flavor databases under FEMA number 4296 and JECFA number 1766, indicating its categorization as a flavoring agent. The molecule is known under several synonyms such as ethanone, 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)- and 1-(3,4-dihydro-2H-1,4-thiazin-5-yl)ethanone, reflecting its structural characteristics. Its flavor profile is described as nutty, cooked, and roasted, which makes it useful in enhancing savory and roasted aroma notes in food products. Its inclusion in regulatory molecular databases underscores its use as a specific flavoring substance rather than a general food additive. Flavor compounds of this class belong to the broader chemical category of 1,4-thiazines, which are organoheterocyclic compounds containing both sulfur and nitrogen in the ring. This structural class imparts distinctive organoleptic properties and chemical stability characteristics valued in flavor chemistry. The nature of the thiazine ring and acetyl group influences both the sensory perception and the way the molecule interacts with other flavor components in formulations. Given its recognized presence in authoritative flavor inventories, chemists and formulation specialists refer to it when seeking nutty and roasted notes in complex flavor systems. In regulatory and safety contexts, flavoring agents like 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE are evaluated for their safety at use levels in food; however, they are not primary nutrients, preservatives, or stabilizers. Instead, they fulfill a sensory function and are subject to evaluation by expert panels for use in specific food categories rather than broad-spectrum food additive approvals.

How It Is Made

The production of 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE generally involves synthetic organic chemistry methodologies rather than extraction from natural sources. Flavor chemists create this compound using precursors that form the thiazine ring and append the acetyl moiety, with common routes involving condensation and cyclization steps that construct the heterocyclic framework. This type of synthesis typically starts from substituted amines or thioamines and alpha-diketones under controlled reaction conditions to ensure the desired ring closure occurs with minimal byproducts. The synthetic route is chosen to yield sufficient quantities of the compound with appropriate purity for flavor use. Upon synthesis, the compound is purified using techniques such as distillation, crystallization, or chromatography to remove residual reactants and impurities. Purity specifications for flavor compounds are critical because trace impurities can significantly alter sensory characteristics or raise safety concerns. While individual manufacturers may have proprietary approaches for optimizing yields and sensory quality, the general process emphasizes closed systems and controlled conditions to produce batches consistent with food-grade material requirements. In industrial settings, strict quality control procedures accompany the production of flavor molecules like 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE. Analytical methods such as gas chromatography and mass spectrometry are used to confirm identity, evaluate purity, and ensure absence of undesirable contaminants. These steps help align the final product with regulatory expectations for flavoring substances used in food applications, even though detailed manufacturing conditions are often proprietary.

Why It Is Used In Food

5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE is used in food because of its ability to impart distinct nutty, roasted, and cooked aroma notes that are challenging to replicate using natural ingredients alone. These sensory attributes are particularly valuable in formulations where roasted, savory, or toasted character enhances consumer perception and overall flavor complexity. The compound offers formulation flexibility and potency at low concentrations, enabling flavorists to achieve desired profiles without negatively affecting the base product. In flavor design, such heterocyclic compounds are often selected when specific aroma notes—such as those reminiscent of nuts, roasted meats, or popcorn—are sought. They complement other flavor components and can act synergistically to enrich the overall sensory profile. Their use is typically in minute amounts because of their strong sensory impact, which aligns with the goal of enhancing flavor without adding bulk or interfering with primary taste attributes. Flavoring agents like 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE are also used because they maintain sensory integrity through certain processing conditions. While intense heat or extreme pH can degrade some flavor compounds, heterocyclic compounds often retain their organoleptic properties better, making them suitable for applications such as baked goods, roasted snacks, and heat-processed products where stable flavor perception is desired.

Adi Example Calculation

Because no numeric acceptable daily intake (ADI) is explicitly established by authoritative bodies for 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE, an illustrative calculation using an ADI is not provided here. The JECFA evaluation indicates there is no safety concern at typical levels of intake when used as a flavoring agent, which suggests that estimated exposure from food use remains comfortably below levels of toxicological concern. In contexts where ADIs are available for other substances, a hypothetical example would multiply the numeric ADI by body weight to estimate allowable daily intake. In the absence of a numeric ADI for this compound, focusing on regulatory conclusions about safety at current intake levels aligns with authoritative assessments.

Safety And Health Research

Regulatory bodies and expert committees evaluate flavoring agents like 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE primarily on the basis of safety at typical levels of intake rather than pharmacological or nutritional effects. JECFA’s evaluation concluded that there is no safety concern at estimated levels of intake when used as a flavoring agent, indicating that available toxicological data did not indicate adverse effects under normal conditions of use. This type of assessment generally considers parameters such as acute toxicity, genotoxicity, and chronic exposure in the context of typical flavor usage patterns rather than high-dose exposures. Because flavor compounds are used at trace levels, consumer exposure is limited, and safety research focuses on whether such low-level intake could pose any risk. In JECFA evaluations, expert panels review available data from animal studies and structure-based assessments to determine whether a safety concern is present. In the case of this compound, the committee noted no concerns at current intake levels. Other organizations, such as FEMA, conduct independent expert panel assessments to support GRAS conclusions for flavor use. It is important to note that comprehensive toxicological data for every flavor compound may not be as extensive as for widely used food additives; nevertheless, inclusion in authoritative flavor inventories and evaluations reflects consideration of available safety evidence. Ongoing research in flavor chemistry continues to refine assessments of sensory ingredients and their exposure profiles.

Regulatory Status Worldwide

5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE appears in the flavor inventories maintained by organizations such as FEMA, where it is listed under FEMA number 4296, indicating recognition for use as a flavor ingredient. It also corresponds to JECFA number 1766, and JECFA’s evaluations have indicated that there is "no safety concern at current levels of intake when used as a flavouring agent," according to the JECFA evaluation database. This reflects a safety assessment by the Joint FAO/WHO Expert Committee on Food Additives that considered typical intake levels in food usage patterns; however, it does not constitute a broad food additive approval outside of flavor use contexts. Sources confirm its inclusion and evaluation by WHO/JECFA. In the United States, flavoring substances are typically managed under FEMA GRAS assessments rather than direct numeric regulatory approvals in the Code of Federal Regulations. The Flavor and Extract Manufacturers Association expert panel evaluates such compounds for general recognition of safety at specified use levels, providing a basis for their use in food flavor formulations. Presence in such inventories suggests that industry professionals consider it suitable within defined sensory and use parameters rather than as a preservative, nutrient, or structural food additive. In other jurisdictions, similar flavor inventory systems guide permitted uses; however, specific numeric regulatory designations (such as E-numbers in the European Union) were not confirmed for this compound based on the available authoritative sources. Therefore, its status may vary by region and should align with local flavoring substance regulations and inventory listings.

Taste And Functional Properties

The sensory profile of 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE is characterized by nutty, roasted, and cooked aroma notes that are detected at low concentrations, making it suitable as a flavoring molecule that enhances complexity. At typical use levels, it contributes desirable sensory attributes somewhat akin to roasted nuts or popcorn, which are appealing in a variety of culinary contexts. The sulfur and nitrogen heteroatoms in its structure influence both odor perception and interaction with other flavor compounds, contributing to its overall character. Functionally, the compound exhibits moderate volatility and stability, which means it can contribute aroma both in the headspace of food products and within the bulk of flavored matrices. Its chemical structure suggests modest solubility in organic solvents and limited water solubility, which affects how it is incorporated into different formulations. Such solubility behavior guides how flavorists balance its use with other components to achieve uniform distribution in complex food systems. The compound’s stability under typical food processing conditions—such as moderate heat and pH—also supports its functional utility. While extreme conditions can alter flavor chemistry, 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE has been observed to withstand conventional processes without significant loss of sensory characteristics. This functional robustness adds to its appeal in flavor formulation.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a safety concept used by regulatory bodies to express the amount of a substance that can be ingested daily over a lifetime without appreciable risk. For compounds like 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE, regulatory evaluations by expert committees such as JECFA do not always establish a numeric ADI because typical intake levels are far below thresholds of concern. In such cases, the conclusion that there is no safety concern at current intake levels serves a similar role in informing risk assessment without a defined numeric ADI. The ADI concept incorporates large safety factors to account for uncertainties in extrapolating from animal studies to humans and variability within human populations. For flavoring agents used at very low concentrations, estimated human exposure often falls well below levels associated with adverse findings in toxicological studies, leading to conclusions of safety without specific numeric ADI values. This approach underscores the focus on actual exposure risks in food use rather than setting a prescriptive intake limit. In lay terms, the absence of a defined numeric ADI for this compound reflects that authoritative evaluations have not identified patterns of intake in food that would raise safety concerns based on existing data. This does not imply unrestricted use; rather, it emphasizes regulatory assessments aligned with realistic consumption patterns in food applications.

Comparison With Similar Additives

Flavoring agents that impart roasted, nutty, or savory notes often encompass a range of heterocyclic compounds with similar sensory roles. Examples include 2-acetyl-1-pyrroline and 6-acetyl-2,3,4,5-tetrahydropyridine, which also contribute roasted and bread-like aroma notes in formulations. While these compounds share sensory characteristics, their chemical structures differ; 2-acetyl-1-pyrroline contains an oxygen and nitrogen heterocycle, whereas 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE incorporates sulfur and nitrogen, leading to distinct nuances in sensory perception and volatility profiles. These structural differences influence how each interacts with other flavor components and how they are perceived by consumers. Other flavor molecules like acetylpyrazines provide nutty and toasted notes as well, but their aromatic ring systems contrast with the thiazine framework of 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE. Such differences affect their functional properties, including volatility and stability under processing conditions. Formulators select among these compounds based on the specific aroma profile desired and the product matrix, balancing factors such as volatility, solubility, and interaction with other flavors. Although all serve as flavoring agents, their distinct chemical identities result in differential sensory impacts and regulatory considerations.

Common Food Applications Narrative

In commercial food applications, 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE is prized for introducing roasted and nutty aroma nuances that resonate with consumers’ expectations of rich sensory experiences. Its nutty character finds application in baked goods such as artisan breads, crackers, and savory pastries where a warm, roasted sensory dimension is desirable. In snack products, its aroma complements ingredients like nuts or toasted grains, enhancing the perception of depth and flavor complexity. Beyond baked goods, this flavoring agent is relevant in beverage applications where subtle roasted notes can augment coffee substitutes, malted drinks, and certain flavored teas. Beverage formulators use trace levels of such compounds to fine-tune sensory profiles, especially where bitterness or acidity might otherwise dominate. Similarly, in dairy products like flavored yogurts or ice creams, small amounts of nutty aroma components can elevate overall sensory balance without overpowering the primary flavor base. In confectionery and savory sauces, the roasted character offered by this compound plays a supportive role, harmonizing with ingredients such as nuts, cocoa, or umami-rich spices. Flavorists consider it as a tool for accentuating signature notes in complex flavor systems. Although used in minute amounts due to its potency, its consistent sensory impact makes it a component of choice in tailored flavor blends that demand roasted, toasted, or nutty accents.

Safety & Regulations

FDA

  • Notes: FDA does not list a specific CFR approval for this compound; use is generally addressed through FEMA GRAS mechanisms. FDA status not explicitly confirmed on a regulation page.

EFSA

  • Notes: No EFSA numeric ADI or E-number found in available authoritative sources.

JECFA

  • Year: 2007
  • Notes: JECFA concluded no safety concern at current intake levels but did not establish a numeric ADI.

Sources

Comments

No comments yet. Be the first to share!