CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE

CAS: 29725-66-4 FLAVORING AGENT OR ADJUVANT

CIS- and TRANS-L-Mercapto-p-menthan-3-one is an organic flavoring compound with a citrus or mint-like scent used in the flavor industry and evaluated internationally for safety by expert committees.

What It Is

CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE is a synthetic organic compound with the chemical formula C10H18OS used as a flavoring agent or adjuvant to impart or enhance specific sensory notes in food products. It exists as both cis and trans stereochemical forms and is identified by the Chemical Abstracts Service registry number 29725-66-4. Characterized by a minty citrus odor, it is recognized in flavor industry registries with a FEMA number (4300) and a JECFA number (1673) as a flavoring agent component. This compound’s structure incorporates a mercapto (thiol) functional group attached to a substituted menthanone backbone, giving it odor-active properties that are useful in formulating complex flavor profiles. Flavoring agents such as this are typically used at very low concentrations to contribute to perception of freshness or citrus-mint nuances in finished products. It is important to distinguish this specific compound from other organosulfur substances that may have distinct applications; here its primary role is sensory rather than nutritive or preservative. Despite being synthetic, the sensory effects parallel those of certain natural volatile thiols that contribute to aromas in fruits and herbs. The chemical name reflects its stereochemistry and functional groups, with cis and trans designations referring to different spatial arrangements of atoms within the molecule.

How It Is Made

The production of CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE involves well-established chemical synthesis techniques common to flavor and fragrance intermediates. In general, chemists start with appropriate precursors that contain the cyclohexanone core and introduce the mercapto (thiol) group via substitution reactions under controlled conditions. Though the precise industrial methods are proprietary to manufacturers, the key steps include formation of the p-menthanone skeleton followed by functionalization at the desired carbon position to yield the mercapto derivative. Purification strategies typically involve distillation or chromatography to separate the target compound from unreacted starting materials and byproducts. Quality control in manufacturing is critical to ensure consistency of sensory properties and compliance with specifications set by evaluating bodies. The final product is typically a colorless to pale liquid with the characteristic citrus-mint aroma, and manufacturing facilities adhere to good manufacturing practices and safety protocols to handle thiol-containing compounds. Because mercapto derivatives can have strong odors even at trace levels, synthesis and formulation steps are designed to minimize odor contamination and ensure consistent quality in flavor applications.

Why It Is Used In Food

This compound is used in food primarily because of its ability to influence flavor perception at low concentrations. Flavor chemists exploit its sensory characteristics—often described as fresh, citrusy, or minty—to complement or enhance other flavor components in complex formulations. In multi-ingredient flavor systems, such agents help round out the profile, adding depth or accentuating specific notes desired in the finished product. They are especially valuable in products where bright, refreshing sensory qualities are sought, such as confections, chewing gums, mints, oral care formulations, and certain beverage categories. The choice to use such a compound is driven by formulation needs: achieving a balance between sweetness, acidity, and aromatic intensity. Its compatibility with common food matrices, solvent systems, and other flavor ingredients makes it a versatile tool for flavor designers. Because it acts as an adjuvant, its impact is not on nutritional value but on the consumer’s sensory experience. Regulatory evaluations have focused on ensuring that its use as a flavoring agent at typical levels does not raise safety concerns, supporting its continued use within industry-defined limits.

Adi Example Calculation

Because CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE has been evaluated with a conclusion of no safety concern at typical levels of intake rather than a numeric acceptable daily intake, example calculations in numeric terms are not directly applicable. In a hypothetical scenario where an ADI were available, one would multiply a body weight (for example, 70 kilograms) by the ADI value to estimate a daily limit of intake, and then compare estimated intake from foods to that limit. In this context, the absence of an explicit numeric ADI reflects that expert evaluation did not identify risk at the low exposure levels expected from flavor use. (世界卫生组织应用程序

Safety And Health Research

Toxicological evaluation of flavoring agents like CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE typically examines endpoints such as general toxicity, organ effects, and potential for adverse reactions at realistic intake levels. Regulatory reviews performed by bodies such as JECFA focus on available data from animal studies and exposure assessments to determine whether there are safety concerns at levels consistent with intended use. For this compound, JECFA’s assessment indicated no safety concern at current levels of intake when used as a flavoring agent, reflecting that exposure from foods is low and not associated with adverse effects in reviewed studies. (世界卫生组织应用程序) Research in flavor chemistry also considers how such compounds behave in food matrices and during digestion, though specific human clinical studies on this particular ingredient are limited. The absence of explicit safety concerns in authoritative reviews should not be interpreted as absence of risk at high exposures; rather, evaluations consider typical use and consumption patterns. Industry practice involves ongoing monitoring of scientific literature and regulatory updates to ensure that flavoring agents remain safe in light of new data.

Regulatory Status Worldwide

International evaluation by expert committees has considered the safety of CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE when used as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) assigned this compound the evaluation number 1673 and, in assessments around 2007, concluded that its use as a flavoring does not raise safety concerns at typical levels of intake in foods. This determination reflects review of toxicological data and intake estimates relevant to its use as a flavor ingredient. The compound is listed in the JECFA Flavouring Agents database with an explicit statement about safety at current use levels, supporting industry confidence in its inclusion in flavor formulations. (世界卫生组织应用程序) In the United States, flavor ingredients such as this are included in the Substances Added to Food inventory maintained by the Food and Drug Administration (FDA). Listings provide reference information including FEMA numbers and JECFA flavor numbers; however, specific codified allowances under the Code of Federal Regulations for this compound as a food additive are not explicitly stated in CFR parts for colorants or preservatives. Presence in the FDA inventory indicates recognition of use and evaluation context. Expert panels such as the Flavor and Extract Manufacturers Association (FEMA) have also assigned a FEMA GRAS number (4300) to this compound, reflecting that it has been evaluated by industry experts for use as a flavoring agent. (世界卫生组织应用程序

Taste And Functional Properties

CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE exhibits distinct sensory qualities that can be perceived as citrus-like, minty, or fresh depending on the context and concentration. Such compounds are typically potent odorants, meaning that very small amounts can significantly influence overall flavor perception. Organosulfur compounds are well known in flavor science for their sometimes powerful odor characteristics, and when judiciously formulated, they contribute complexity without overwhelming other notes. In terms of functional behavior, this compound is generally more soluble in organic solvents such as ethanol than in water, reflecting its chemical character. It integrates well into flavor systems that use alcohol-based carriers or encapsulation technologies. Its stability under typical food processing conditions—such as mixing and packaging—is sufficient for many applications, though formulators consider volatility and interactions with other ingredients when designing final products. Sensory panels and analytical chemistry tools are often used to measure its contribution within complex mixtures and ensure consistency from batch to batch.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory concept used to express 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 many flavoring agents, including CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE, international expert bodies such as JECFA may conclude that no safety concern exists at current levels of intake rather than assign a numeric ADI. In such cases, the compound is considered safe when used as intended and at levels typical in food products. This reflects that expected exposure from normal consumption is far below any level associated with adverse effects in studies reviewed by experts. (世界卫生组织应用程序) It is important to understand that ADIs are not recommended consumption targets; they are reference points for safety assessments and regulatory decisions. A conclusion of no safety concern indicates that dietary exposure from flavor use is within a range that does not warrant a specific ADI based on available data and exposure estimates.

Comparison With Similar Additives

Flavoring agents span a wide range of chemical classes, including esters, aldehydes, ketones, and thiols. CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE can be compared with other sulfur-containing flavor compounds such as 4-mercapto-4-methyl-2-pentanone or 3-mercapto-3-methylbutan-1-ol, which also contribute potent sensory notes in specific applications; however, each has unique odor profiles and regulatory status. The mercapto group in these compounds often imparts strong odor characteristics that are harnessed at low concentrations to add complexity or accentuate fruity, herbal, or fresh notes. (世界卫生组织应用程序)(维基百科) Other non-sulfur flavoring agents, such as esters used for fruity notes, differ chemically and in sensory impact but share the common role of shaping the overall flavor experience in foods. The selection of one compound over another depends on the desired sensory outcome, formulation constraints, and regulatory considerations specific to the application.

Common Food Applications Narrative

In practical use, CIS- AND TRANS-L-MERCAPTO-P-MENTHAN-3-ONE finds application in a range of food and beverage categories where refreshing, minty, or citrus-like sensory impressions are desired. Flavorists often use it as one component among many to craft signature profiles in products such as chewing gums, mints, gel-based confections, and oral care products that benefit from a clean, fresh aroma. It may also be included in certain beverage flavors formulated to evoke citrus or herbal nuances, where it acts alongside other aromatic compounds to create a layered sensory experience. Beyond confectionery and oral care, flavor chemists can integrate this compound into savory seasoning blends or specialty culinary flavorings to achieve subtle aromatic effects that enhance the perception of freshness. Its role is almost always supportive—balancing and amplifying desirable sensory qualities without dominating the overall flavor profile. As with all flavoring agents, careful formulation, sensory evaluation, and adherence to regulatory guidelines are key to ensuring that the intended flavor impact is achieved consistently in finished products.

Safety & Regulations

FDA

  • Notes: Listing in FDA Substances Added to Food reflects recognition of use, but no specific CFR section explicitly authorizes additive status.

EFSA

  • Notes: EFSA E-number and numeric ADI not identified in available sources.

JECFA

  • Notes: JECFA concluded no safety concern at current intake levels rather than establish a numeric ADI.

Sources

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