CIS-9-OCTADECENYL ACETATE

CAS: 693-80-1 FLAVORING AGENT OR ADJUVANT

CIS-9-OCTADECENYL ACETATE (CAS 693-80-1) is a long-chain acetate ester used as a flavoring agent or adjuvant in food applications. It has been reviewed by international expert bodies for safety in its intended uses.

What It Is

CIS-9-OCTADECENYL ACETATE is an organic chemical compound classified as an ester. It is a long-chain fatty acid ester derived from oleyl alcohol and acetic acid. This compound is recognized for its role as a flavoring agent or adjuvant in food formulations. Flavoring agents are additives that contribute to or modify the taste or aroma of food products without necessarily providing nutritional value. The compound exists as a clear, colorless to pale yellow liquid with a mild fatty or fruity odor, reflecting its chemical structure and classification within fatty acid esters. Chemically, CIS-9-OCTADECENYL ACETATE belongs to the class of aliphatic esters and is identified by the CAS Registry Number 693-80-1. The structure comprises a long hydrocarbon chain with an unsaturated carbon-carbon double bond in the cis configuration and an acetate functional group attached at one end. This configuration influences both its physical properties and its functional behavior in food systems. In regulatory inventories such as flavoring substance listings and expert evaluation databases, CIS-9-OCTADECENYL ACETATE is listed with alternative names including oleyl acetate and (Z)-9-octadecenyl acetate, reflecting common nomenclature used in chemical and flavoring contexts. These synonyms help link information across scientific and regulatory databases, ensuring accurate identification of the compound in safety and formulation references.

How It Is Made

CIS-9-OCTADECENYL ACETATE is synthesized through esterification reactions between oleyl alcohol (an unsaturated fatty alcohol) and acetic acid or an acetic acid derivative under controlled conditions. Esterification is the chemical process in which an alcohol and an acid combine, usually in the presence of catalysts, to form an ester and water. In industrial contexts, alcohols and acids may be purified to achieve the desired product purity, and reaction conditions are adjusted to favor ester formation. Depending on the intended use and regulatory requirements, manufacturers may purify the resulting ester to high degrees to remove residual reactants or by-products. Typical purification methods include distillation under reduced pressure, which helps separate the desired ester product from unreacted materials and low-boiling impurities. For food-related applications, quality specifications often define acceptable levels of impurities and physical properties such as refractive index, density, and appearance. These specifications help ensure consistent performance when the additive is used in food flavoring formulations. Production of esters such as CIS-9-OCTADECENYL ACETATE often adheres to good manufacturing practices (GMP) and other quality frameworks if the product is intended for use in food or flavoring applications. While detailed proprietary methods may vary between producers, the general chemical processes rest on well-understood organic synthesis strategies for ester formation, ensuring that the final product meets relevant food industry quality and safety specifications.

Why It Is Used In Food

CIS-9-OCTADECENYL ACETATE is used in food primarily for its properties as a flavoring agent or adjuvant. Flavoring agents are added to food products to contribute specific taste or aroma characteristics or to enhance the overall sensory profile. In this role, the compound may be incorporated into flavor blends that aim to create or reinforce desired notes in a finished food or beverage. Flavor adjuvants can help modulate or stabilize flavor profiles in complex matrices. Food formulators often select specific esters like CIS-9-OCTADECENYL ACETATE for their particular sensory characteristics, solubility in lipid phases, and compatibility with other ingredients. Long-chain esters can impart subtle sensory effects that complement fruity, floral, or creamy profiles, depending on the composition of the mixture. They are also chosen for their relative stability under certain processing conditions compared to more volatile or reactive flavor compounds. Because flavoring agents are used at very low concentrations relative to the total mass of a food product, their impact on overall formulation cost and nutrient content is minimal. Instead, the focus is on achieving the target flavor profile at the lowest effective use level, consistent with good formulation practice. CIS-9-OCTADECENYL ACETATE is selected for such uses within the context of flavor chemistry and is integrated into complex formulations alongside other esters, aldehydes, and aromatic compounds to achieve balanced sensory outcomes.

Adi Example Calculation

To illustrate how an acceptable daily intake might be considered in a hypothetical scenario, imagine a flavoring compound with an established ADI of X mg/kg body weight per day (note: CIS-9-OCTADECENYL ACETATE does not currently have a numerical ADI). For an adult weighing 70 kg, the corresponding intake threshold would be calculated by multiplying the ADI by body weight. For example, an ADI of 1 mg/kg body weight per day would translate to 70 mg per day for a 70 kg adult. This hypothetical calculation helps illustrate how ADIs are used in risk assessment. In practice, actual exposure to flavoring agents such as CIS-9-OCTADECENYL ACETATE is typically orders of magnitude lower than hypothetical ADI thresholds because these compounds are used at very low levels in food formulations. Flavor formulation chemists aim to use the minimum amount needed to achieve the desired sensory effect, consistent with good manufacturing practice and safety guidance. This approach helps keep consumer exposure well within established safety frameworks.

Safety And Health Research

Safety evaluations of food flavoring agents focus on both hazard identification and exposure assessment. Regulatory and expert bodies such as JECFA review available toxicological data, including studies on genotoxicity, subchronic toxicity, reproductive toxicity, and other endpoints relevant to human health. For CIS-9-OCTADECENYL ACETATE, JECFA’s evaluation concluded that the compound does not present safety concerns at current levels of intake when used as a flavoring agent. This conclusion reflects an assessment of the compound’s toxicological profile in the context of typical human exposure through its intended use. Hazard identification examines whether the compound or its metabolites exhibit properties that could pose health risks at certain levels of exposure. Exposure assessment considers how much of the compound consumers are likely to ingest based on typical use levels in food formulations. These combined analyses help expert committees determine whether a margin of safety exists between expected human exposure and levels associated with adverse effects in experimental studies. Because flavoring agents are used at very low concentrations, exposure levels are generally far below those associated with toxicological effects in relevant studies. Nonetheless, expert evaluations consider the full body of available evidence and apply conservative assumptions to account for uncertainties. For CIS-9-OCTADECENYL ACETATE, no specific adverse health effects have been identified at exposure levels relevant to its use as a flavoring agent, based on available evaluations.

Regulatory Status Worldwide

CIS-9-OCTADECENYL ACETATE has been evaluated by international expert bodies for its safety as a flavoring agent. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) reviewed this compound in 2007 and concluded that it does not pose a safety concern at current levels of intake when used as a flavoring agent. This evaluation reflects both the available toxicological data and typical exposure scenarios consistent with its use in flavoring applications. The JECFA evaluation year of 2007 is derived from the committee’s published assessment records. In the United States, the compound appears in the FDA’s Substances Added to Food inventory (formerly EAFUS), which lists ingredients used in food based on information from FEMA and JECFA evaluations. However, inclusion in this inventory does not by itself indicate specific regulatory approval under a Title 21 CFR section, and there is no dedicated CFR listing for CIS-9-OCTADECENYL ACETATE. Therefore, its regulatory status in the U.S. is informed by expert panel evaluations and inventory listings rather than an explicit food additive regulation. In the European Union and other regions, similar flavoring compound inventories and evaluations may include this ester, typically under frameworks that assess flavoring agents based on safety data and usage levels consistent with good manufacturing practice. Where regulatory numbering systems such as E-numbers apply, CIS-9-OCTADECENYL ACETATE does not have a specific E-number assigned in current authoritative lists, indicating that formal inclusion in such systems has not been established or may not be required for its flavoring use.

Taste And Functional Properties

CIS-9-OCTADECENYL ACETATE is characterized by physical and sensory properties typical of long-chain fatty acid esters. The compound is a clear oil at ambient temperatures, with low solubility in water but good solubility in lipid phases and many organic solvents. These solubility characteristics influence how it interacts within food systems, particularly those with significant fat content or emulsified structures. From a sensory perspective, long-chain esters tend to have mild fatty or subtle fruity odor notes compared to shorter-chain esters, which are often more strongly fruity or sweet. In practical use, CIS-9-OCTADECENYL ACETATE is selected as part of a broader palette of flavor compounds that together create complex sensory impressions. Its contribution alone may be subtle, but it can play an important role when paired with other flavoring ingredients to achieve a rounded profile. Functional properties such as stability under processing conditions, heat resistance, and compatibility with other formulation constituents are important considerations for flavoring agents. Esters like CIS-9-OCTADECENYL ACETATE generally maintain their ester linkage under typical food processing conditions, though extreme temperature or pH conditions may lead to hydrolysis. Understanding these properties helps food scientists determine appropriate use levels and integration strategies for this compound in specific food applications.

Acceptable Daily Intake Explained

An acceptable daily intake (ADI) is a regulatory concept used to describe the amount of a substance that can be ingested daily over a lifetime without appreciable health risk. ADIs are typically expressed in milligrams of the substance per kilogram of body weight per day and are derived from toxicological studies using uncertainty factors to account for differences between test animals and humans, as well as variability among humans. For many flavoring agents, including CIS-9-OCTADECENYL ACETATE, expert committees such as JECFA determine that the compound does not raise safety concerns at estimated levels of human intake from its intended use. In such cases, a specific numerical ADI may not be established, and the compound is considered acceptable when used in food according to good manufacturing practice. This means that flavorists and manufacturers use the compound at levels sufficient to achieve the desired sensory effect but no higher than necessary. The concept of ADI helps provide a science-based reference frame for regulatory decisions and risk communication. It is not a recommendation for consumption but rather a threshold for safety evaluation. For compounds without a defined numerical ADI, regulatory and expert bodies often rely on qualitative evaluations and historical use data to conclude that typical exposure levels are unlikely to pose health concerns.

Comparison With Similar Additives

CIS-9-OCTADECENYL ACETATE can be compared with other flavoring esters such as ethyl octanoate and dodecyl acetate, which are also used in food flavor formulations. Ethyl octanoate, a shorter-chain ester formed from ethanol and caprylic acid, is known for its fruity odor and is commonly used in fruit-flavored products. In contrast, CIS-9-OCTADECENYL ACETATE’s longer carbon chain contributes to subtler fatty or rounded sensory impressions. Dodecyl acetate is another ester with a medium-length hydrocarbon chain and floral-rose type notes. Compared to CIS-9-OCTADECENYL ACETATE, dodecyl acetate may impart different sensory characteristics that are complementary in certain flavor blends. When formulating flavors, food scientists often select a combination of esters with varied chain lengths and structural features to achieve multidimensional sensory outcomes. Beyond sensory differences, esters vary in physical properties such as solubility and volatility, which influence their performance in specific food matrices. Shorter-chain esters tend to be more volatile and deliver noticeable aroma at low concentrations, while longer-chain esters like CIS-9-OCTADECENYL ACETATE may be less volatile and contribute more subtly to the overall profile. Understanding these differences helps flavorists design balanced formulations tailored to specific applications.

Common Food Applications Narrative

In consumer foods and beverages, flavoring agents such as CIS-9-OCTADECENYL ACETATE are used to fine-tune taste and aroma profiles, often as part of complex flavor blends. While the specific applications of this compound are determined by flavorists and food scientists, esters of this type are typically found in product categories where nuanced sensory profiles are critical. For example, in baked goods and confectionery, combining multiple esters and aromatic ingredients can create desirable sweet or creamy impressions that enhance the consumer experience. In beverages, particularly those with nuanced flavor requirements such as ready-to-drink blends, flavored waters, or alcoholic beverages, esters contribute to the overall aroma complexity. CIS-9-OCTADECENYL ACETATE’s subtle sensory characteristics may be selected as part of a broader formulation targeting specific flavor notes without overpowering other components. Ready-to-drink cocktails or flavored malt beverages might use such compounds alongside other esters and natural extracts to create layered aroma profiles. Savory products and snack seasonings also benefit from the controlled use of flavoring esters. In these contexts, flavoring agents help round out profiles that combine salty, umami, and aromatic notes. While not a primary flavor driver on its own, CIS-9-OCTADECENYL ACETATE can be part of specialized seasoning blends that deliver balanced sensory experiences to consumers seeking distinct taste sensations in savory snacks or processed foods.

Safety & Regulations

FDA

  • Notes: Inclusion in the FDA Substances Added to Food inventory reflects recognition and expert panel evaluations but does not by itself indicate formal FDA approval under a specific CFR listing.

EFSA

  • Notes: No specific EFSA E-number or ADI value was found in authoritative sources.

JECFA

  • Year: 2007
  • Notes: JECFA concluded no safety concern at current intake levels; no numerical ADI was specified.

Sources

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