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methyl ionyl acetate
Methyl ionyl acetate is a synthetic aromatic compound used in flavors and fragrances, characterized by woody and floral sensory notes and a molecular formula of C16H26O2.
General Material Description
Methyl ionyl acetate, known systematically as 1,2-dimethyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propen-1-yl acetate, is a synthetic organic ester with molecular formula C16H26O2. It appears as a colorless liquid with characteristic woody and floral odor notes often described as powdery violet and subtle fruity nuances. Synonyms include alpha-isomethylionyl acetate and methyl-a-ionyl acetate. This compound is principally manufactured via chemical synthesis involving ionyl intermediates. It serves as a key fragrant molecule in perfumery and flavor industries. A detailed chemical profile is accessible through PubChem. The compound’s sensory complexity supports its role as both a flavoring and fragrance agent.
Occurrence, Applicability & Potential Uses
Methyl ionyl acetate does not occur naturally but is widely employed in the flavor and fragrance sectors for its woody, floral, and fruity olfactory qualities. It contributes subtle blackberry, cherry, raspberry, and strawberry undertones, alongside vetiver and woody accents, enhancing various consumer products. Its applications range from baked goods and beverages to confectionery and fine fragrances. Regulatory frameworks include FEMA (US), where it is registered under number 3845, and IFRA (Global), which provides usage guidelines. The compound’s versatile aroma profile allows for creative formulation in both flavoring and perfumery contexts.
Physico-Chemical Properties Summary
Methyl ionyl acetate exhibits moderate volatility, with a vapor pressure of 0.001 mmHg at 25 °C, indicating low evaporation under ambient conditions. The specific gravity ranges between 0.93 and 0.94 at 25 °C. It has a refractive index between 1.47 and 1.48 at 20 °C, consistent with its liquid state. The compound is soluble in alcohol and slightly soluble in water, estimated at 0.1544 mg/L at 25 °C, which aids its incorporation into diverse formulations. Its flash point is approximately 210 °F (99 °C), reflecting reasonable safety parameters for handling and storage. The octanol-water partition coefficient (logP) is estimated at 5.824, indicating significant lipophilicity that influences its fragrance release and persistence behaviors.
FAQ
What is methyl ionyl acetate?
Methyl ionyl acetate is a synthetic ester used primarily as a flavor and fragrance ingredient. It possesses a complex aroma combining woody, floral, and subtle fruity notes, making it valued in perfumery and flavorings. The compound’s molecular formula is C16H26O2, and it is chemically related to ionones. It is not found naturally but is manufactured through organic synthesis. Methyl ionyl acetate is known under various synonyms, including alpha-isomethylionyl acetate.
How is methyl ionyl acetate used and what are its main applications?
This compound finds use as a flavoring agent contributing woody, floral, and berry-like characteristics to products such as baked goods, beverages, confectionery, and fragrances. It enhances sensory profiles with notes reminiscent of blackberry, cherry, and vetiver. Regulatory bodies like FEMA (US) have assigned number 3845 to it, documenting its permitted use levels. IFRA (Global) also offers guidelines on concentration limits in perfumery. Methyl ionyl acetate’s solubility in alcohol and moderate volatility make it suitable for various formulation technologies.
What safety and regulatory considerations apply to methyl ionyl acetate?
Methyl ionyl acetate is classified as an irritant under European regulation, prompting precautions to avoid eye, skin, and respiratory exposure. Safety assessments by IFRA recommend maximum usage levels up to 8% in fragrance concentrates. The FEMA Expert Panel considers it generally recognized as safe (GRAS) for flavor applications within specified concentration ranges. Toxicological data remain limited for oral, dermal, and inhalation exposure, but no severe hazard classifications have been assigned under OSHA standards. Manufacturers and formulators should consult relevant regulatory documents for compliance.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| NCBI | Start search |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| HMDB (The Human Metabolome Database): | HMDB37631 |
| FooDB: | FDB016747 |
| Export Tariff Code: | 2915.39.9500 |
| ChemSpider: | View |
General Material Information
| Preferred name | methyl ionyl acetate |
| Trivial Name | 1,2-Dimethyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propen-1-yl acetate |
| Short Description | alpha-isomethylionyl acetate |
| Formula | C16 H26 O2 |
| CAS Number | 68555-61-3 |
| FEMA Number | 3845 |
| ECHA Number | 271-437-4 |
| FDA UNII | 65HMI3WU1Q |
| Nikkaji Number | J309.198H |
| xLogP3-AA | 4.20 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1410 alpha-isomethylionyl acetate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 68555-61-3 ; ALPHA-ISOMETHYLIONYL ACETATE |
| Synonyms |
|
Suppliers
| BOC Sciences | Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 250.38162231445 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.739 to 7.822 |
| Refractive Index | 1.47 to 1.48 @ 20 °C |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Vapor Density | 1 |
| Flash Point TCC Value | 98.89 °C TCC |
| logP (o/w) | 5.824 est |
| Solubility | |
| alcohol | Yes |
| water, 0.1544 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Floral | |
| powdery, violet, woody, vetiver, fruity, floral | |
| General comment | At 10.00 % in dipropylene glycol. powdery violet woody vetiver fruity floral |
| Mosciano, Gerard P&F 25, No. 1, 49, (2000) | At 1.00 % in ethyl alcohol. Powdery, perfumey, woody with fruity and floral nuances. It has an interesting floral character on dry down |
| Flavor Type: Woody | |
| woody, powdery, floral, violet, berry, cherry, licorice, candy | |
| Mosciano, Gerard P&F 25, No. 1, 49, (2000) | At 1.00 - 20.00 ppm. Woody, powdery, floral with ionone and berry nuances. It has a lingering cherry-red licorice-candy aftertaste |
| Used for powdery, perfumery notes and for woody notes in flavors. | Woody powdery |
Potential Uses
| Applications | |
| Odor purposes | Blackberry , Blueberry , Cherry , Floral , Raspberry , Strawberry , Vetiver , Woody |
| Flavoring purposes | Licorice red licorice , Tomato |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for methyl ionyl acetate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 18 | |||
| Click here to view publication 18 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.15000 | 3.00000 | |
| beverages(nonalcoholic): | 0.05000 | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 0.50000 | 5.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 0.10000 | 2.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 0.10000 | 2.00000 | |
| fruit ices: | 0.07000 | 1.50000 | |
| gelatins / puddings: | 0.20000 | 2.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 0.25000 | 4.00000 | |
| imitation dairy: | 0.10000 | 2.00000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | 0.10000 | 2.00000 | |
| meat products: | - | - | |
| milk products: | 0.10000 | 2.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | 0.12000 | 2.50000 | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):68555-61-3 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6437467 |
| National Institute of Allergy and Infectious Diseases:Data |
| [(E)-3-methyl-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-yl] acetate |
| Chemidplus:0068555613 |