BIS(2-METHYL-3-FURYL) DISULFIDE

CAS: 28588-75-2 FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT

BIS(2-METHYL-3-FURYL) DISULFIDE (CAS 28588-75-2) is a sulfur-containing flavor enhancer and flavoring agent used in food formulations to contribute savory and meaty sensory notes.

What It Is

BIS(2-METHYL-3-FURYL) DISULFIDE is a sulfur-containing organic compound recognized for its role as a flavor enhancer and flavoring agent in food products, particularly in savory applications. It belongs to a class of organosulfur compounds derived from furan rings linked by a disulfide bond, imparting characteristic aroma and taste profiles associated with cooked meat and roasted notes that are valued in culinary formulations. The compound has the CAS registry number 28588-75-2, confirming its unique chemical identity within global chemical databases, and is documented under PubChem CID 526624, where the CAS linkage has been verified. It may appear under various other names including those listed in the other_names field above, reflecting its structural descriptors and synonyms used in chemical and flavor industry referencing. Its inclusion in flavor libraries and technical compendia underscores its role as a functional additive intended to modify and enhance the sensory experience of food products. BIS(2-METHYL-3-FURYL) DISULFIDE functions primarily in the food and beverage context as an agent that amplifies or complements desired taste profiles, notably those associated with umami and savory impressions. In the context of food chemistry, organosulfur compounds are well recognized for strong odor and taste contributions even at low concentrations, making BIS(2-METHYL-3-FURYL) DISULFIDE effective in achieving targeted sensory effects with minimal addition levels. The compound's chemical backbone, featuring two 2-methylfuran moieties joined by a disulfide linkage, provides both volatility and stability characteristics that influence its behavior when incorporated into food matrices. As a result, it plays a technical role not merely as a direct sensory contributor but also as an adjunct that can balance or round out complex flavor formulations in processed foods. From an industrial perspective, BIS(2-METHYL-3-FURYL) DISULFIDE is listed in flavor and extract libraries such as those maintained by flavor industry associations, which provide structured information on functional categories and usage evaluations. Although regulatory listings such as specific CFR provisions or explicit E-number assignments are not provided in the available regulatory_records input, the compound’s presence in international expert reviews and flavor reference guides suggests that it is evaluated within regulatory frameworks for its intended use as a flavoring agent. Its identification by established numeric descriptors such as the FEMA number and JECFA number supports its recognition within professional and regulatory communities evaluating flavoring substances.

How It Is Made

The production of BIS(2-METHYL-3-FURYL) DISULFIDE typically involves organic synthesis routes that bring together furan-based precursors via controlled chemical reactions. While proprietary manufacturing methods may vary across suppliers, general chemical synthesis principles for organosulfur compounds can be described at a high level without detailing specific proprietary processes. A common strategy involves oxidative coupling of 2-methyl-3-furanthiol derivatives or related intermediate species under conditions that favor the formation of a disulfide bond linking two furan rings. Such reactions are often mediated by mild oxidizing agents that enable controlled disulfide formation, yielding BIS(2-METHYL-3-FURYL) DISULFIDE as the desired product. In an industrial setting, precursor compounds such as 2-methyl-3-furanthiol can be generated from furan derivatives through substitution reactions, and these intermediates, once purified, are subsequently coupled under optimized conditions to achieve high yields of the disulfide. The process typically involves careful control of temperature, solvent environment, and reaction kinetics to minimize side reactions and to ensure a consistent product composition, especially important for flavoring applications where purity and sensory consistency are critical. After synthesis, product streams are subjected to purification steps that may include distillation, crystallization, or chromatographic techniques tailored to remove residual impurities and side products that could interfere with flavor quality or regulatory compliance. The finished BIS(2-METHYL-3-FURYL) DISULFIDE from manufacturing processes is characterized against established specifications for identity, purity, and sensory quality. Analytical methods such as gas chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy are commonly applied to confirm the chemical structure, isomeric composition, and absence of undesirable contaminants. Suppliers of food-grade flavoring agents often document such analytical validation in technical specification sheets and certificates of analysis (COAs). These quality assurance measures ensure that the flavoring agent meets the expected organoleptic and safety parameters for food formulation. Because flavoring agents are typically used at very low concentrations in food, the emphasis during production includes controlling trace impurities and ensuring reproducible sensory performance across batches. The involvement of industry associations and quality guidelines further supports the consistency of manufacturing practices for this class of compounds.

Why It Is Used In Food

BIS(2-METHYL-3-FURYL) DISULFIDE is used in food primarily to contribute to and enhance savory and meaty flavor profiles that are sought after in many culinary applications. Food scientists and flavor formulators leverage such compounds to achieve specific sensory targets, particularly in products where natural flavors from traditional cooking may be diminished or absent due to processing. The compound’s organosulfur structure contributes robust aroma and taste characteristics that are often reminiscent of roasted, grilled, or cooked meat, which can be especially valuable in plant-based or processed food products where recreating complex flavor impressions is technically challenging. In practical use, BIS(2-METHYL-3-FURYL) DISULFIDE can be blended with other flavoring agents to balance sweetness, saltiness, and bitterness, contributing to a well-rounded flavor profile. Its potency allows it to exert meaningful sensory impact at low use levels, making it an efficient ingredient in flavor systems. The inclusion of compounds with strong savory notes supports consumer perceptions of richness and depth, which can influence overall acceptability and palatability of food products. These roles are particularly relevant in sectors such as snack foods, seasonings, soups, sauces, and alternative protein products where enhancing umami-like sensations can elevate product quality. Flavor enhancers and specific aromatic compounds like BIS(2-METHYL-3-FURYL) DISULFIDE are complemented by other functional ingredients such as amino acids, extracts, and natural or artificial flavor blends to achieve desired outcomes. The food industry’s focus on consistent taste experience across production batches also makes these agents valuable for maintaining product uniformity. In formulations where primary ingredients have intrinsic flavor variability, controlled addition of defined flavoring agents helps standardize sensory characteristics. While consumer tastes vary across markets and cultural contexts, savory and meaty notes are broadly appreciated, making compounds that deliver these sensory cues useful tools in flavor design and food product development. Because flavor perception is a complex interaction of taste, smell, and texture, experts in food formulation consider BIS(2-METHYL-3-FURYL) DISULFIDE as one component within a comprehensive flavor strategy. Its selection in specific applications reflects both its sensory contribution and compatibility with other ingredients. In regulatory terms, its use as a flavoring agent is generally evaluated within broader food additive frameworks that assess safety of flavor substances on a case-by-case basis, ensuring that usage levels in food are consistent with safety evaluations provided by expert bodies.

Adi Example Calculation

To illustrate the concept of how Acceptable Daily Intake (ADI) might be considered in a hypothetical calculation, imagine a scenario where an expert body had established a numeric ADI for a flavoring agent. While BIS(2-METHYL-3-FURYL) DISULFIDE does not have a numeric ADI assigned in available regulatory evaluations, consider a theoretical example with a hypothetical ADI of X mg per kilogram of body weight per day to illustrate the process. If an adult weighing 70 kilograms were exposed to a flavoring agent with an ADI of X mg/kg/day, the lifetime daily intake considered acceptable would be calculated as 70 multiplied by X, yielding a total permissible daily intake of 70X milligrams. In a food context, if a product contained an average of Y milligrams of the compound per serving, a consumer would need to calculate the total number of servings per day that could be consumed without exceeding the ADI. The formula for this calculation would be total permissible intake divided by the amount per serving, or (70X) divided by Y, providing a conceptual estimate of how many servings could theoretically be consumed safely within the ADI framework. It is important to emphasize that this example is illustrative only and does not reflect an actual ADI value for BIS(2-METHYL-3-FURYL) DISULFIDE. In real-world evaluations, expert committees such as JECFA consider comprehensive toxicological data and exposure assessments before assigning numeric ADIs. Because the available authoritative evaluations for this compound indicate that there is no safety concern at current intake levels with typical flavor use, a numeric ADI value was not specified in the sourced regulatory documentation. Nonetheless, this hypothetical exercise helps clarify how ADI guidelines are applied in safety assessments and how formulators and regulators might use such values to estimate exposure relative to body weight and consumption patterns.

Safety And Health Research

Evaluations of flavoring agents such as BIS(2-METHYL-3-FURYL) DISULFIDE focus on understanding potential hazards in relation to typical exposure levels resulting from intended use in food products. Regulatory expert committees look at toxicological endpoints including acute toxicity, genotoxicity, subchronic and chronic toxicity, and potential for reproductive or developmental effects, among other parameters. In the case of this compound, JECFA evaluations have concluded that there is no safety concern at current levels of intake when used as a flavoring agent, indicating that available toxicological data and exposure assessments did not identify adverse effects at estimated dietary exposures. The lack of a defined numerical acceptable daily intake reflects the committee’s position that concern is minimal under typical conditions, rather than specifying a quantitative threshold. Research on organosulfur flavor compounds often involves studies that examine metabolism, sensory thresholds, and interactions with biological systems. Such compounds can be volatile and potent, meaning that sensory impacts occur at very low concentrations, and exposure in food is correspondingly limited. Toxicological assessments take into account both hazard potential and estimated dietary intake to determine whether the margin of exposure is acceptable. For BIS(2-METHYL-3-FURYL) DISULFIDE, the available evaluations support its continued use in flavor applications without identified safety concerns within typical use conditions. Because human health effects are considered in a broader context of exposure and dose, regulatory bodies emphasize that safety assessments do not equate to beneficial health effects but rather establish that use at intended levels does not pose undue risk. The compound’s inclusion in flavoring libraries and expert evaluations reflects a body of evidence deemed sufficient for its functional role. Ongoing research may continue to refine understanding of metabolic pathways and sensory interactions, but current authoritative sources do not indicate specific health risks associated with typical dietary exposure levels.

Regulatory Status Worldwide

BIS(2-METHYL-3-FURYL) DISULFIDE is recognized and cataloged by international flavor industry reference systems, including the Flavor and Extract Manufacturers Association (FEMA) flavor library, where it is identified by FEMA number 3259. Such listings reflect evaluations of flavor substances by expert panels that assess safety information and usage contexts relevant to food flavor applications. Similarly, the compound has been evaluated by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), with records indicating that it was reviewed and considered not to pose a safety concern at current levels of intake when used as a flavoring agent, as reported in expert evaluations. The JECFA evaluation provides an important reference point for international regulatory considerations, though explicit numeric acceptable daily intake (ADI) values were not assigned on the d evaluation pages, resulting in null adi values in the regulatory_safety fields with appropriate notes explaining the absence of confirmed numeric ADI. In the United States, BIS(2-METHYL-3-FURYL) DISULFIDE appears in the FDA’s Substances Added to Food (formerly EAFUS) database, which catalogs substances that may be used in food under certain conditions, often linked to Generally Recognized as Safe (GRAS) determinations or other regulatory frameworks. However, the available information does not provide specific CFR citations or formal affirmative approvals that unequivocally confirm its authorized use in food from an explicit regulatory code standpoint, leading to an FDA approval status of null with explanatory notes. National regulatory authorities in various jurisdictions may have separate processes to evaluate and list flavoring agents, and the presence of the compound in flavor reference lists can support regulatory submissions or GRAS determinations when appropriate. The absence of a defined E-number or equivalently structured European Union flavoring code in the available regulatory references suggests that specific EU authorization details are not readily available, resulting in null fields in the regulatory_safety structure. In summary, BIS(2-METHYL-3-FURYL) DISULFIDE’s regulatory status reflects recognition and evaluation by expert bodies that review flavoring substances, with international documentation indicating safety at current levels of intake when used as intended, but explicit numeric regulatory allowances or E-number assignments were not located in the sourced regulatory materials.

Taste And Functional Properties

BIS(2-METHYL-3-FURYL) DISULFIDE is characterized by strong sensory impressions that are described as savory, roasted, and meaty, with a distinct organosulfur aroma that can influence overall flavor perception even at low concentrations. Its sensory profile is rooted in the presence of furan rings and a disulfide linkage, contributing volatile components that interact with olfactory receptors responsible for aroma detection. Such compounds are particularly effective at enhancing taste impressions associated with cooked meats or roasted foods, making them valuable in both traditional and alternative food formulations aiming to replicate complex flavor cues. From a functional perspective, BIS(2-METHYL-3-FURYL) DISULFIDE exhibits volatility and solubility properties consistent with many small volatile organic flavor compounds. It is sufficiently volatile to contribute to aroma perception but also stable enough under typical processing conditions where heat and pH variations might otherwise degrade more labile constituents. Its functional stability in formulated food matrices supports its inclusion in dry blends, liquid flavorings, and emulsified systems without rapid loss of potency. Sensory scientists often consider both the headspace behavior of such compounds and their interactions with food components when predicting flavor outcomes. When incorporated into food formulations, flavor contributors such as BIS(2-METHYL-3-FURYL) DISULFIDE can influence both orthonasal and retronasal perception pathways, enhancing the overall experience of savory foods. Its interaction with other flavor molecules can amplify desired sensory notes or mask off-flavors that arise from processing or ingredient variability. Functional behavior in complex matrices depends on concentration, food composition, and processing conditions. The compound’s relative hydrophobicity suggests it may associate with lipid phases within foods, affecting release dynamics during consumption and thereby shaping the temporal profile of aroma perception. The sensory contribution of BIS(2-METHYL-3-FURYL) DISULFIDE is often evaluated through trained sensory panels and analytical techniques such as gas chromatography-olfactometry, which identify key odor-active compounds and quantify their relative impact on flavor profiles. These functional assessments inform formulation decisions and help ensure that the compound’s inclusion aligns with desired product attributes. While individual sensory responses may vary among consumers, the compound’s recognized role in enhancing savory notes guides its application in specific culinary contexts.

Acceptable Daily Intake Explained

Acceptable Daily Intake (ADI) is a concept used by regulatory and expert bodies to define the amount of a substance that can be ingested daily over a lifetime without appreciable health risk, based on toxicological data and safety factors. For BIS(2-METHYL-3-FURYL) DISULFIDE, formal numeric ADI values were not explicitly specified in available JECFA evaluations, reflecting the expert committee’s conclusion that current intake levels from flavor use do not raise safety concerns rather than identifying a precise threshold value. In such cases, the absence of a numeric ADI may indicate that no safety-based restriction is considered necessary given current usage patterns, rather than presuming unrestricted intake. Understanding ADI in practical terms helps contextualize how flavoring agents are evaluated. When a numeric ADI is established for a compound, it is derived by identifying a no-observed-adverse-effect level (NOAEL) from toxicology studies and applying safety factors to account for uncertainties, such as differences between test animals and humans. For compounds like BIS(2-METHYL-3-FURYL) DISULFIDE where expert evaluation indicates safety at typical intake levels without defining a specific NOAEL-based numeric ADI, regulatory guidance focuses on ensuring that usage remains within established good manufacturing practices and that exposure estimates remain consistent with those evaluated by expert committees. In practical food formulation, the amounts of flavoring agents added to products are small relative to overall food consumption, and sensory potency often means effective use levels are orders of magnitude below quantities that would raise exposure concerns. While ADI can provide a benchmark for safety, formulators rely on usage levels supported by expert evaluations and regulatory guidance to ensure that consumer exposure is appropriate. The concept of ADI underscores the principle that safety assessment is relative to exposure, and even potent compounds can be used safely when exposure is low and consistent with expert recommendations.

Comparison With Similar Additives

When comparing BIS(2-METHYL-3-FURYL) DISULFIDE with other flavoring additives of similar functional class, it helps to understand how different compounds contribute to savory and aroma profiles in food. Compounds such as 2-acetyl-1-pyrroline, a Maillard reaction product found in cooked rice and bread crust, contribute roasted and toasted notes that complement savory profiles. While 2-acetyl-1-pyrroline provides a nutty and bread-like aroma, BIS(2-METHYL-3-FURYL) DISULFIDE contributes deeper meaty and roasted impressions, illustrating how structurally distinct compounds within the broader class of flavoring agents can shape sensory experiences in different ways. Another related compound often compared in savory flavor design is methional, an aldehyde with a potato-like and cooked aroma that enhances savory impressions when used judiciously in formulations. Methional’s functional behavior differs in that it tends to impart earthy and starchy notes, whereas BIS(2-METHYL-3-FURYL) DISULFIDE’s organosulfur character delivers richer meat-like cues, demonstrating how flavor scientists combine different molecules to achieve balanced sensory outcomes. A third example in savory flavor enhancement is furaneol, a furanone compound contributing sweet and caramel-like notes that can round out savory formulations. Unlike BIS(2-METHYL-3-FURYL) DISULFIDE’s strong sulfur-driven aroma, furaneol offers a milder, sweeter aroma that harmonizes with other components. When used together, such additives illustrate the complexity of flavor design, where multiple compounds with distinct sensory signatures are blended to create cohesive flavor profiles. These comparisons showcase how different functional groups and molecular structures influence both sensory perception and the technical application of flavoring agents in food formulations.

Common Food Applications Narrative

BIS(2-METHYL-3-FURYL) DISULFIDE finds application across a range of savory food categories where enhancing meaty, roasted, or cooked aroma characteristics is desirable. In snack foods, for example, this compound can be part of seasoning blends that deliver rich, umami-like notes associated with grilled or roasted flavors. Such applications include savory chips or crackers designed to evoke barbecue or roasted meat impressions, where the delicate balance between saltiness, sweetness, and complex aroma influences consumer appeal. The precise use levels are determined by flavorists who calibrate the contribution of BIS(2-METHYL-3-FURYL) DISULFIDE relative to other components to avoid overwhelming the intended profile. In soups, sauces, and broths, BIS(2-METHYL-3-FURYL) DISULFIDE may be incorporated into flavor bases to round out taste impressions and provide depth. These savory liquids often rely on a combination of natural extracts, seasoning blends, and aroma compounds to achieve a balanced sensory experience. The compound’s organosulfur characteristics complement foundational ingredients like amino acids and salts to convey a fuller-bodied sensation. Whether formulated as a powdered mix for reconstitution or a concentrated liquid base, its inclusion supports a sensory strategy aimed at delivering rich, satisfying flavors. Meat analog products and plant-based protein formulations increasingly leverage defined flavoring agents such as BIS(2-METHYL-3-FURYL) DISULFIDE to replicate sensory cues traditionally associated with animal-derived proteins. These products often pair functional ingredients with savory flavor enhancers to simulate texture and taste, addressing consumer expectations for products that mimic meat without containing animal components. In this context, the compound’s capacity to provide roasted and savory nuances contributes to a perception of authenticity in flavor, which is critical for consumer acceptance in alternative protein categories. Processed meats and ready-to-eat meals may also benefit from targeted aroma contributions where thermal processing can diminish natural flavor precursors. In such formulations, BIS(2-METHYL-3-FURYL) DISULFIDE can help reintroduce or enhance the sensory qualities lost during cooking, freezing, or other processing steps. Incorporation into spice blends, marinades, and seasoning rubs illustrates the versatility of this flavoring agent across diverse savory product lines. Flavor scientists meticulously evaluate the sensory impacts in each application, considering factors such as interactions with other ingredients and the impact of processing conditions on final flavor perception.

Safety & Regulations

FDA

  • Notes: Specific FDA approval status in CFR could not be confirmed from available sources.

EFSA

  • Notes: EFSA authorization and numeric ADI information not found in available sources.

JECFA

  • Notes: JECFA evaluations indicate no concern but do not specify numeric ADI values on d pages.
  • Adi Display: No safety concern at current intake levels per JECFA evaluations

Sources

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