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para-anisyl acetate
Para-anisyl acetate is a synthetic ester known for its sweet, powdery, fruity aroma used primarily in flavors and fragrances.
General Material Description
Para-anisyl acetate, also known as 4-methoxybenzyl acetate, is an aromatic ester with the molecular formula C10H12O3. It appears as a clear liquid with distinctive sweet and powdery olfactory characteristics reminiscent of vanilla, cherry, and fruity balsamic notes. This compound is commonly referenced under various synonyms such as acetic acid 4-methoxy-benzyl ester and cassie ketone. Its sensory profile contributes to its widespread use in flavor and fragrance formulations. The compound is typically synthesized for commercial use but also occurs naturally in extracts like cananga oil and cassie absolute. It is cataloged in public chemical databases such as PubChem, facilitating research and regulatory documentation.
Occurrence, Applicability & Potential Uses
Para-anisyl acetate is naturally found in several plant sources including almond flower, cananga oil from China, cassie absolute, and osmanthus flower absolute, among others. It is valued for its medium-strength powdery and sweet vanilla-like odor and fruity flavor notes, making it a key ingredient in flavor and fragrance industries. The compound enhances products by imparting balsamic, cherry, licorice, and floral attributes, which are utilized in various applications such as perfuming agents, baked goods, beverages, confectionery, and creams. Its usage and safety are governed under standards like FEMA (US) and the IFRA Code of Practice (Global), which recommend limits on concentration to ensure consumer safety and regulatory compliance.
Physico-Chemical Properties Summary
Para-anisyl acetate is a moderately lipophilic ester with an estimated logP of approximately 1.9, contributing to its solubility in alcohols, dipropylene glycol, and fixed oils while showing limited solubility in aqueous and glycol-based solvents like glycerin and propylene glycol. It has a specific gravity near 1.11 at 25 °C and a refractive index ranging between 1.551 and 1.555 at 20 °C. The compound exhibits low vapor pressure at room temperature, indicating moderate volatility, and a flash point of 212 °F (approximately 100 °C), which implies relative safety under normal formulation and storage conditions. Para-anisyl acetate demonstrates stability in various product media including creams, lotions, bath foams, and detergents, without causing discoloration. Proper storage in sealed containers protected from heat and light extends its shelf life beyond two years.
FAQ
What is para-anisyl acetate and what are its primary characteristics?
Para-anisyl acetate is an aromatic ester known chemically as 4-methoxybenzyl acetate. It possesses a clear liquid appearance and features a sweet, powdery odor with fruity and vanilla-like nuances. This compound is widely used in flavor and fragrance industries due to its appealing sensory profile, providing balsamic, cherry, and licorice notes. Its molecular formula is C10H12O3, and it is commonly identified under synonyms such as anisyl acetate and cassie ketone.
In which natural sources does para-anisyl acetate occur, and how is it used commercially?
Para-anisyl acetate naturally occurs in various botanical materials including almond flower, cananga oil, cassie absolute, and osmanthus flower absolute. Commercially, it serves as a flavoring agent and fragrance ingredient, enhancing products like baked goods, beverages, confectionery, and perfumery. Its sensory contribution includes powdery and fruity aromas that enrich formulations such as creams, lotions, and soaps. Regulatory standards like FEMA (US) and the IFRA Code of Practice (Global) guide its safe use levels in commercial applications.
What are the safety considerations and regulatory statuses for para-anisyl acetate?
Para-anisyl acetate is classified as harmful if swallowed and harmful to aquatic life, with precautionary statements advising avoidance of skin and eye contact. Oral toxicity studies report an LD50 of 2250 mg/kg in rats, and dermal toxicity is low with an LD50 of 5000 mg/kg in rabbits. Its use in flavor and fragrance products is regulated under the IFRA Code of Practice (Global) and FEMA GRAS (US). Recommended usage levels in fragrance concentrates can reach up to 8%. Safety assessments from agencies such as the European Food Safety Authority and the Research Institute for Fragrance Materials provide detailed toxicological evaluations. Proper storage and handling minimize hazards during its use.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| (4-methoxyphenyl)methyl acetate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 104-21-2 |
| Pubchem (cid): | 7695 |
| Pubchem (sid): | 134972724 |
| Pherobase: | View |
| Publications by PubMed | |
| Identification of the key odorants in Tahitian cured vanilla beans (Vanilla tahitensis) by GC-MS and an aroma extract dilution analysis. | |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB33761 |
| FooDB: | FDB011898 |
| Export Tariff Code: | 2915.39.4550 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | para-anisyl acetate |
| Trivial Name | 4-Methoxybenzyl acetate |
| Short Description | 4-methoxybenzyl acetate |
| Formula | C10 H12 O3 |
| CAS Number | 104-21-2 |
| FEMA Number | 2098 |
| ECHA Number | 203-185-8 |
| FDA UNII | 2GEC7KBO31 |
| Nikkaji Number | J31.561C |
| MDL | MFCD00048211 |
| COE Number | 209 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 873 anisyl acetate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 104-21-2 ; ANISYL ACETATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 180.20324707031 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.178 to 9.245 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 9.197 to 9.264 |
| Refractive Index | 1.551 to 1.555 @ 20 °C |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.021 mmHg @ 25 °C |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 1.887 est |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| dipropylene glycol | Yes |
| fixed oils | Yes |
| water, 782.9 mg/L @ 25 °C (est) | Yes |
| glycerin | No |
| propylene glycol | No |
| Stability | |
| bath foam | Unspecified |
| cream | Unspecified |
| detergent | Unspecified |
| hair spray | Unspecified |
| lotion | Unspecified |
| non-discoloring in most media | Unspecified |
| powder | Unspecified |
| soap | Unspecified |
Organoleptic Properties
| Odor Type: Powdery | |
| sweet, powdery, balsamic, vanilla, fruity, plum, cherry, tonka, creamy, spicy, coumarinic | |
| Odor strength | medium |
| Substantivity | 100 hour(s) at 100.00 % |
| Luebke, William tgsc, (1982) | At 100.00 %. sweet powdery balsam vanilla fruity plum cherry tonka |
| Mosciano, Gerard P&F 24, No. 2, 49, (1999) | At 5.00 %. Sweet, creamy, powdery, spicy, vanilla, cherry, coumarin, fruity |
| Flavor Type: Fruity | |
| sweet, fruity, licorice, cherry, vanilla, coumarinic | |
| Mosciano, Gerard P&F 24, No. 2, 49, (1999) | At 30.00 ppm. Sweet, fruity, licorice, cherry, vanilla, coumarin |
| General comment | Fruity floral vanilla balsam cherry licorice coumarin |
| Useful in: vanilla, fruity red, fruity yellow, fruity tropical, fruity others. | Sweet, coumarin, fruity, balsamic, floral |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Acacia , Acacia , Almond blossom , Anise , Balsam , Castoreum , Cherry , Coconut , Cream , Currant black currant , Cyclamen , Fig , Floral , Fruit , Gardenia , Hawthorn , Heliotrope , Honey , Honeysuckle , Juniper berry , Licorice , Lilac , Mimosa , Oriental , Powder , Raspberry , Vanilla , Violet |
| Flavoring purposes | Chocolate cocoa , Vermouth |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| Acute toxicity, Oral (Category 4), H302 Acute aquatic toxicity (Category 3), H402 | |
| GHS Label elements, including precautionary statements | |
| Signal word | Warning |
| Hazard statement(s) | |
| H302 - Harmful if swallowed H402 - Harmful to aquatic life | |
| Precautionary statement(s) | |
| P264 - Wash skin thouroughly after handling. P270 - Do not eat, drink or smoke when using this product. P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P330 - Rinse mouth. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Human Experience: | |
| 4 % solution: no skin irritation. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 [sex: M,F] 2250 mg/kg (Weir & Wong, 1971b) | |
| Dermal Toxicity: | |
| skin-rabbit LD50 5000 mg/kg (Weir & Wong, 1971b) | |
| 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 para-anisyl acetate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 50.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 300.00 (μg/capita/day) | ||
| 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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 12.00000 | |
| beverages(nonalcoholic): | - | 6.30000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 30.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 8.00000 | |
| fruit ices: | - | 8.00000 | |
| gelatins / puddings: | - | 11.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 15.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to Flavouring Group Evaluation 20 (FGE.20): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical group 23 View page or View pdf |
| Flavouring Group Evaluation 52 (FGE.52): Consideration of hydroxy- and alkoxy-substituted benzyl derivatives evaluated by JECFA (57th meeting) structurally related to benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters evaluated by EFSA in FGE.20 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):104-21-2 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7695 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| (4-methoxyphenyl)methyl acetate |
| Chemidplus:0000104212 |