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eugenyl formate
Eugenyl formate is a chemical compound used as a flavor and fragrance agent characterized by warm woody and orris-like odor notes.
General Material Description
Eugenyl formate is an organic ester compound with molecular formula C11H12O3, structurally identified as 4-(2-propenyl)-2-methoxyphenyl formate. It appears as a liquid with distinctive sensory character including warm woody and dry orris aromas, making it valuable in fragrance development. This compound is known by several synonyms such as 4-allyl-2-methoxyphenol formate and eugenol formate, reflecting its derivation from eugenol-related phenolic structures. It can be sourced via esterification processes involving eugenol and formic acid derivatives. For chemical data and structural references, eugenyl formate is indexed in public chemical databases such as PubChem CID 24835. Its presence in perfumery supports woody, mossy, and patchouli accords due to its odor profile.
Occurrence, Applicability & Potential Uses
Eugenyl formate is primarily encountered in the flavor and fragrance industry, where it is used as an odorant component in perfuming agents. Biologically, it relates structurally to eugenol, a naturally occurring phenolic compound found in clove oil and other botanical sources. The compound’s sensory influence includes woody, cedar, moss, orris, and patchouli odor notes, making it suitable for complex fragrance compositions. Regulatory frameworks such as FEMA (US) recognize eugenyl formate under FEMA number 2473 for flavoring use, and IFRA (Global) has established recommendations permitting use levels up to 5% in fragrance concentrates. Its applications extend mainly to perfumery, where it enhances the warm woody and floral nuances in fine fragrances and personal care products.
Physico-Chemical Properties Summary
Eugenyl formate is a moderately lipophilic ester with estimated log P of approximately 1.96, indicating balanced solubility characteristics favoring organic solvents such as alcohols. It has a molecular weight near 192.2 g/mol and exhibits specific gravity between 1.115 and 1.125 at 25°C, combined with a refractive index ranging from 1.524 to 1.5265 at 20°C. These parameters influence its handling and formulation characteristics in fragrance preparations. The vapor pressure is low at around 0.006 mmHg at 25°C, suggesting limited volatility under ambient conditions. The flash point measured at 235°F (about 113°C) indicates moderate flammability hazard when exposed to high temperatures. Eugenyl formate displays a minimal acid value, indicating chemical stability relevant for shelf life and compatibility. Its solubility profile includes good solubility in alcohol and low but present solubility in water, supporting its use in varied formulations.
FAQ
What is eugenyl formate and what are its primary characteristics?
Eugenyl formate is an organic ester compound derived from eugenol and formic acid, characterized by a warm woody, orris-like odor. It is an important ingredient in flavors and fragrances, noted for its distinctive sensory qualities. The compound’s molecular formula is C11H12O3, and it has several chemical synonyms including 4-allyl-2-methoxyphenol formate. It appears as a liquid and is identifiable in chemical databases for formulation and regulatory purposes.
How is eugenyl formate used and where is it commonly applied?
Eugenyl formate is primarily used as a perfuming agent in the fragrance and flavor industry due to its woody, orris, and mossy odor notes. It is applied in creating complex fragrance compositions that benefit from its warm, cedar-like aroma. This compound is recognized by standards such as FEMA (US) and IFRA (Global), which provide guidelines for its safe usage levels in products to ensure formulation consistency and consumer safety.
What are the regulatory considerations and sourcing information for eugenyl formate?
Eugenyl formate is assigned CAS number 10031-96-6 and is registered under chemical inventories including ECHA’s REACH pre-registration (EC number 233-099-6). Its use in flavor and fragrance formulations is supported by FEMA number 2473 and reviewed in FAO JECFA 1530 evaluations. IFRA (Global) standards currently allow concentrations up to 5% in fragrance concentrates. Safety assessments classify it as an irritant to eyes and skin; appropriate handling and protective measures are recommended. It is typically sourced through synthetic routes involving esterification of eugenol.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| (2-methoxy-4-prop-2-enylphenyl) formate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 10031-96-6 |
| Pubchem (cid): | 24835 |
| Pubchem (sid): | 134990481 |
| Publications by Info | |
| eugenol and related hydroxyallylbenzene derivatives | |
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): | HMDB37877 |
| FooDB: | FDB017030 |
| Export Tariff Code: | 2915.13.0000 |
| ChemSpider: | View |
General Material Information
| Preferred name | eugenyl formate |
| Trivial Name | Eugenyl formate |
| Short Description | 4-(2-propenyl)-2-methoxyphenyl formate |
| Formula | C11 H12 O3 |
| CAS Number | 10031-96-6 |
| FEMA Number | 2473 |
| Flavis Number | 9.088 |
| ECHA Number | 233-099-6 |
| FDA UNII | USW3U3L49G |
| Nikkaji Number | J69.596C |
| Beilstein Number | 3270015 |
| COE Number | 355 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1530 eugenyl formate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 10031-96-6 ; EUGENYL FORMATE |
| Synonyms |
|
Suppliers
| BOC Sciences | Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 192.21423339844 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.278 to 9.361 |
| Refractive Index | 1.524 to 1.5265 @ 20 °C |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.006 mmHg @ 25 °C |
| Flash Point TCC Value | 112.78 °C TCC |
| logP (o/w) | 1.962 est |
| Solubility | |
| alcohol | Yes |
| water, 339.9 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Orris | |
| warm, woody, orris, dry | |
| General comment | At 100.00 %. warm woody orris dry |
Potential Uses
| Applications | |
| Odor purposes | Cedar , Moss , Orris , Patchouli , Woody |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. 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. | |
| Human Experience: | |
| 12 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 3400 mg/kg Food and Chemical Toxicology. Vol. 20, Pg. 689, 1982. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 20, Pg. 689, 1982. | |
| 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 eugenyl formate usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.06 (μg/capita/day) | ||
| Threshold of Concern: | 1800 (μg/person/day) | ||
| Structure Class: | I | ||
| 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: | - | - | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 0.20000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| 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): |
| Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :24835 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| (2-methoxy-4-prop-2-enylphenyl) formate |
| Chemidplus:0010031966 |