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furfuryl butyrate
Furfuryl butyrate is a furan-derived ester with fruity aroma and flavor properties, primarily used as a flavoring agent in food products like coffee and dairy.
General Material Description
Furfuryl butyrate is an organic ester characterized by the molecular formula C9H12O3. It appears as a colorless liquid with a fruity odor described as grape-like or green and possesses gooseberry-like fruity flavor notes. Also known by synonyms such as butanoic acid 2-furanyl methyl ester and furfuryl butanoate, this compound belongs to the furan derivative chemical family. It is registered under CAS number 623-21-2 and indexed in databases like PubChem for data referencing. Synthesized chemically or extracted from natural sources, furfuryl butyrate is predominantly utilized in flavor formulation and found naturally in food items such as coffee and dairy products. Its sensory characteristics contribute notably to flavor profiles where fruity, berry, or green notes are desired.
Occurrence, Applicability & Potential Uses
Furfuryl butyrate naturally occurs in diverse food items including coffee (up to 0.8 mg/kg), dairy products, licorice, and pork, contributing to their characteristic aromas. Its application is primarily as a flavoring agent recognized under FEMA (US) and REACH (EU) regulations, where it enhances fruity and green notes in formulations. The compound is used to impart fruit-like flavors notably in bakery goods, coffee blends, dairy items, grape-flavored products, licorice confections, banana-flavored formulations, and pork-flavored foods. The presence of this ester in complex natural flavor matrices underscores its utility in mimicking or enhancing natural fruit aromas and contributing to overall flavor complexity.
Physico-Chemical Properties Summary
Furfuryl butyrate exhibits physical properties that influence its suitability in flavor applications. It is a colorless liquid with a specific gravity ranging from about 1.048 to 1.057 at temperatures between 20 to 25 °C and has a refractive index approximately between 1.457 and 1.462 at 20 °C. Its boiling point is measured near 129 to 130 °C at reduced pressure (52 mm Hg). The compound demonstrates moderate vapor pressure (0.195 mm Hg at 25 °C) indicating slight volatility relevant for aroma release in formulations. It is soluble in alcohol and estimated to have limited water solubility (~524.5 mg/L at 25 °C). The flash point is approximately 90.6 °C (195 °F), allowing safe handling under typical processing conditions. The estimated logP value of around 2.1 reflects moderate hydrophobicity affecting its partitioning behavior in complex matrices.
FAQ
What is furfuryl butyrate and what are its key characteristics?
Furfuryl butyrate is an ester derived from furfuryl alcohol and butyric acid, noted for its fruity odor and flavor resembling grape and gooseberry. It appears as a colorless liquid and has the molecular formula C9H12O3. In flavor chemistry, it is used as a flavoring agent due to its distinctive fruity sensory properties. It is registered under CAS number 623-21-2 and is known by various synonyms, including butanoic acid 2-furanyl methyl ester and furfuryl butanoate.
Where is furfuryl butyrate found naturally and how is it applied in the food industry?
Furfuryl butyrate is found naturally in food sources such as coffee, dairy products, licorice, and pork. Its concentration in coffee can be up to 0.8 mg per kilogram. In the food industry, it is primarily utilized as a flavoring agent within diverse applications, including bakery products, coffee flavoring, dairy enhancements, grape and banana flavored goods, licorice, and pork-flavored products. Its fruity character helps simulate or enhance natural fruit aromas in complex flavor compositions.
How is furfuryl butyrate regulated and are there safety considerations for its use?
Furfuryl butyrate is subject to regulatory assessments by agencies such as FEMA (United States) and REACH (European Union). Under these standards, it is approved for use as a flavoring agent with specified usage levels. Safety information classifies it as an irritant to skin and eyes, necessitating standard protective measures during handling. Data from EFSA and JECFA evaluations inform acceptable intake thresholds, and flavor manufacturers adhere to recommended usage limits to comply with food safety regulations.
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
| furan-2-ylmethyl butanoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 623-21-2 |
| Pubchem (cid): | 61167 |
| Pubchem (sid): | 135018304 |
| Publications by US Patents | |
| 3,952,024 - Furfurylthioacetone | |
| Flavoring agent | |
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): | HMDB37729 |
| FooDB: | FDB016859 |
| Export Tariff Code: | 2915.60.0000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| 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 | furfuryl butyrate |
| Trivial Name | Furfuryl butyrate |
| Short Description | furan-2-ylmethylbutanoate |
| Formula | C9 H12 O3 |
| CAS Number | 623-21-2 |
| Flavis Number | 13.13 |
| ECHA Number | 210-779-0 |
| FDA UNII | Search |
| Nikkaji Number | J47.700A |
| MDL | MFCD00082962 |
| COE Number | 638 |
| xLogP3-AA | 1.50 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 759 furfuryl butyrate |
| FDA Mainterm | 623-21-2 ; FURFURYL BUTYRATE |
| Synonyms |
|
Suppliers
| Augustus Oils | BOC Sciences |
| Ernesto Ventós | Penta International |
| Reincke & Fichtner | Sigma-Aldrich |
| Synerzine | Augustus Oils Ltd |
| Penta International Corporation | Taytonn ASCC |
| Ernesto Ventós S.A. |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.1922454834 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.731 to 8.781 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.745 to 8.795 |
| Refractive Index | 1.457 to 1.462 @ 20 °C |
| Boiling Point | 129 to 130°C @ 52 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.195 mmHg @ 25 °C |
| Vapor Density | 5.7 |
| Flash Point TCC Value | 90.56 °C TCC |
| logP (o/w) | 2.121 est |
| Solubility | |
| alcohol | Yes |
| water, 524.5 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| grape, fruity, green | |
| General comment | At 100.00 %. grape fruity green |
| Flavor Type: Fruity | |
| fruity, gooseberry | |
| General comment | Fruity gooseberry-like |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Fruit |
| Flavoring purposes | Bakery , Banana , Coffee , Dairy , Grape , Licorice , Pork |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. 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: | |||
| flavoring agents | |||
| Recommendation for furfuryl butyrate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.24 (μg/capita/day) | ||
| Threshold of Concern: | 540 (μg/person/day) | ||
| Structure Class: | II | ||
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): |
| Scientific Opinion on Flavouring Group Evaluation 13, Revision 2 (FGE.13Rev2): Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by JECFA at the 65th meeting (JECFA, 2006b) and re-evaluated at the 69th meeting (JECFA, 2009c) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13 Revision 3 (FGE.13Rev3): furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 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 :61167 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| furan-2-ylmethyl butanoate |
| Chemidplus:0000623212 |