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methyl furfuracrylate
Methyl furfuracrylate is an ester known for its fruity and clove-like odor, commonly used as a flavoring agent with raisin and spice notes.
General Material Description
Methyl furfuracrylate is an organic ester with the molecular formula C8H8O3, identified chemically as 2-propenoic acid, 3-(2-furanyl)-, methyl ester. It appears as a clear liquid and exhibits a distinct fruity odor often described as cherry combined with clove-like cinnamate notes. This compound is related to various synonyms including methyl 3-(2-furanyl)-2-propenoate, acrylic acid methyl ester derivatives, and methyl 2-furanacrylate. Its chemical structure features a furan ring connected to an acrylate moiety. Methyl furfuracrylate is primarily sourced via esterification reactions involving acrylic acid derivatives and furanyl alcohols. The compound is referenced in databases such as PubChem for further chemical data. It plays a role in flavor chemistry due to its recognized aromatic qualities.
Occurrence, Applicability & Potential Uses
Methyl furfuracrylate naturally occurs as a constituent in certain plant-derived flavor profiles but is mainly synthetically produced for industrial use. It functions chiefly as a flavoring agent, imparting fruity, spicy, raisin, and clove-like sensory notes in food and beverage formulations. Its presence in flavor blends emphasizes its utility in enhancing aromatic complexity. Regulatory evaluation under the Flavor and Extract Manufacturers Association (FEMA) (US) confirms its accepted use as a flavoring substance. Although widely used for flavor development, it is not intended for fragrance applications. The compound's sensory profile supports its application in culinary flavorants and potentially in fine chemical synthesis requiring aromatic esters.
Physico-Chemical Properties Summary
Methyl furfuracrylate exhibits physical and chemical properties that support its functionality in flavor formulations. It is a liquid with a boiling range of 216 to 218°C at atmospheric pressure, indicating moderate volatility. Its vapor pressure at 25°C is measured at 0.131 mmHg, reflecting low volatility suitable for stable aroma release. The compound has a calculated logP value near 2.16, suggesting moderate lipophilicity which can influence solubility and interaction within complex flavor matrices. It is soluble in alcohol and has an estimated water solubility of approximately 2489 mg/L at 25°C, though it is generally considered poorly soluble in pure water. The flash point is reported as 185°F (about 85°C), signifying moderate flammability precautions. These properties influence formulation decisions, handling, and application dosage.
FAQ
What is methyl furfuracrylate and what are its main characteristics?
Methyl furfuracrylate is an organic ester known chemically as 2-propenoic acid, 3-(2-furanyl)-, methyl ester with the formula C8H8O3. It is characterized by a fruity aroma with notable clove and cherry-like notes, commonly used as a flavoring agent. It appears as a clear liquid and is recognized for imparting raisin and spice sensory attributes. The compound is a synthetic derivative typically formed by esterification involving furan-containing precursors.
How is methyl furfuracrylate typically used and where is it applied?
This compound finds application primarily in the flavor industry where it functions as a flavoring agent to convey fruity, spicy, and clove-like aromas. Its use is mainly in food and beverage flavor formulations to achieve desirable aromatic profiles such as raisin and clove notes. It is not used as a fragrance ingredient in perfumery due to regulatory guidance. Methyl furfuracrylate is appreciated for its stability and compatibility with alcohol-based solvents. The Flavor and Extract Manufacturers Association (FEMA) (US) provides standards that support its use within specified limits.
What regulatory and safety considerations are associated with methyl furfuracrylate?
Methyl furfuracrylate has no classified hazards under the Globally Harmonized System (GHS) according to OSHA regulations in the US and lacks specified precautionary or hazard statements. It is recommended solely for use as a flavoring agent and not for fragrance applications. Toxicological data such as oral, dermal, and inhalation toxicity have not been fully determined. Safety assessments from authoritative sources including the EPA and FDA acknowledge its use within regulated limits. Comprehensive chemical safety summaries and toxicology citations are available via databases such as the EPA ACToR and PubChem. Users should follow standard safety practices when handling this compound.
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 |
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): | HMDB32399 |
| FooDB: | FDB009832 |
| Export Tariff Code: | 2916.12.6000 |
| ChemSpider: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
General Material Information
| Preferred name | methyl furfuracrylate |
| Trivial Name | Methyl 3-(2-furanyl)-2-propenoate |
| Short Description | 2-propenoic acid, 3-(2-furanyl)-, methyl ester |
| Formula | C8 H8 O3 |
| CAS Number | 623-18-7 |
| FDA UNII | Search |
| Nikkaji Number | J79E |
| COE Number | 2267 |
| NMR Predictor | External link |
| FDA Mainterm | 623-18-7 ; METHYL FURFURACRYLATE |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 152.14935302734 |
| Boiling Point | 216 to 218°C @ 760 mm Hg |
| Vapor Pressure | 0.131 mmHg @ 25 °C |
| Flash Point TCC Value | 85 °C TCC |
| logP (o/w) | 2.157 est |
| Solubility | |
| alcohol | Yes |
| water, 2489 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| cherry, clove, cinnamyl | |
| General comment | At 10.00 % in dipropylene glycol. cherry clove cinnamate |
Safety Information
Safety information
| 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: | |||
| flavoring agents | |||
| Recommendation for methyl furfuracrylate usage levels up to: | |||
| not for fragrance use. | |||
Safety references
| 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 :5355414 |
| National Institute of Allergy and Infectious Diseases:Data |
| methyl (E)-3-(furan-2-yl)prop-2-enoate |
| Chemidplus:0000623187 |