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2-pentenoic acid
2-pentenoic acid is a fatty acid flavor compound with a pungent cheesy odor found naturally in banana, beef, and chicken fat.
General Material Description
2-pentenoic acid is a monounsaturated fatty acid characterized by the molecular formula C5H8O2. It appears as a clear liquid with a distinctive pungent, cheesy odor often described as fatty. Also referred to as pent-2-enoic acid and pent-2-en-1-oic acid, this compound is recognized under several synonyms including 3-Ethylacrylic acid and NSC 26713. It is registered as FEMA 4193 in the flavor industry and is included in the PubChem database as a well-documented chemical entity. Naturally occurring in foods such as banana fruit, beef, and chicken fat, 2-pentenoic acid is generally derived by extraction or synthesis for its use as a flavoring agent. The compound contributes characteristic notes in flavor profiles and is subject to standardized use levels.
Occurrence, Applicability & Potential Uses
2-pentenoic acid is naturally found in several biological sources including banana fruit, beef, and chicken fat. It contributes to the characteristic flavors associated with these foods. Due to its pungent and cheesy odor profile, it is utilized as a flavoring agent in food formulations. It is approved under FEMA (US) standards for use in various food categories, with specified usage limits to maintain safety and sensory quality. Typical applications include baked goods, dairy products, cheeses, and meat products where precise flavor enhancement is required. Its distinctive sensory attributes make it valuable for imparting fatty and savory nuances in complex flavor blends.
Physico-Chemical Properties Summary
The physico-chemical properties of 2-pentenoic acid influence its behavior in flavor formulations. It has a molecular weight of approximately 100.12 g/mol and a moderate estimated log P value near 1.17, indicating balanced lipophilicity. The compound boils between 201 and 203°C at atmospheric pressure, reflecting moderate volatility. Its vapor pressure at 25°C is low at 0.107 mmHg, contributing to controlled aroma release. It is soluble in alcohol and moderately soluble in water at 6.29×104 mg/L under room temperature conditions, though some notes report limited water solubility. The flash point is 153°F (around 67°C). These properties enable its incorporation in diverse matrices, affecting stability and sensory impact under typical processing and storage conditions.
FAQ
What is 2-pentenoic acid and what are its characteristics?
2-pentenoic acid is a naturally occurring unsaturated fatty acid with the molecular formula C5H8O2. It exhibits a characteristic pungent, cheesy, and fatty odor, which is utilized in flavor applications. Also known as pent-2-enoic acid or 3-Ethylacrylic acid, it appears as a clear liquid under standard conditions. The compound is identified in various foods such as banana, beef, and chicken fat where it contributes to their aroma profiles. Registered under FEMA number 4193, its chemical structure features a double bond contributing to its sensory properties.
Where does 2-pentenoic acid occur naturally and how is it applied industrially?
This acid naturally occurs in foods including banana fruit, beef, and chicken fat, playing a role in their distinct flavors. Industrially, 2-pentenoic acid is applied as a flavoring agent to impart fatty and cheesy notes in food products. According to FEMA (US) standards, its allowable use is controlled across numerous food categories such as baked goods, cheeses, dairy, and meat products to ensure sensory consistency and safety. Its chemical and sensory properties make it useful for enhancing flavor complexity in diverse formulations.
What safety standards and regulations apply to 2-pentenoic acid in food use?
2-pentenoic acid is classified as generally recognized as safe (GRAS) for use as a flavoring agent under FEMA (US) specifications. Usage levels are regulated for various food types to prevent excessive exposure. Toxicological data indicate relatively low toxicity by oral and dermal routes in animal studies, without classifications for acute hazards under OSHA hazard communication standards. No specific inhalation toxicity has been determined. Regulatory frameworks require adherence to recommended concentration limits to maintain safety and compliance in food products.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| 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): | HMDB32459 |
| FooDB: | FDB010036 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-pentenoic acid |
| Trivial Name | 2-Pentenoic acid |
| Short Description | pent-2-enoic acid |
| Formula | C5 H8 O2 |
| CAS Number | 626-98-2 |
| FEMA Number | 4193 |
| ECHA Number | 210-975-6 |
| FDA UNII | Search |
| xLogP3-AA | 1.00 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 626-98-2 ; 2-PENTENOIC ACID |
| Synonyms |
|
Suppliers
| Axsyn | BOC Sciences |
| LBB Specialties | Parchem |
| Synerzine |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 100.11715698242 |
| Boiling Point | 201 to 203°C @ 760 mm Hg |
| Vapor Pressure | 0.107 mmHg @ 25 °C |
| Flash Point TCC Value | 67.22 °C TCC |
| logP (o/w) | 1.167 est |
| Solubility | |
| alcohol | Yes |
| water, 6.29E+04 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Cheesy | |
| pungent, fatty | |
| General comment | At 100.00 %. pungent fatty |
Occurrences
| (data available) |
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: | |
| intraperitoneal-mouse LD50 1580 mg/kg Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. | |
| Dermal Toxicity: | |
| subcutaneous-mouse LD50 1580 mg/kg Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2-pentenoic acid usage levels up to: | |||
| not for fragrance use. | |||
| 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: 22 | |||
| Click here to view publication 22 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 10.00000 | 50.00000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | 5.00000 | 25.00000 | |
| cheese: | 3.00000 | 15.00000 | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 10.00000 | 50.00000 | |
| egg products: | - | - | |
| fats / oils: | 2.00000 | 10.00000 | |
| fish products: | 2.00000 | 10.00000 | |
| frozen dairy: | 3.00000 | 15.00000 | |
| fruit ices: | 3.00000 | 15.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 15.00000 | 75.00000 | |
| hard candy: | 10.00000 | 50.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 2.00000 | 10.00000 | |
| milk products: | 3.00000 | 15.00000 | |
| nut products: | - | - | |
| other grains: | 5.00000 | 25.00000 | |
| poultry: | 2.00000 | 10.00000 | |
| processed fruits: | 2.00000 | 10.00000 | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 5.00000 | 25.00000 | |
| snack foods: | - | - | |
| soft candy: | 10.00000 | 50.00000 | |
| soups: | 5.00000 | 25.00000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | 5.00000 | 25.00000 | |
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 :12299 |
| National Institute of Allergy and Infectious Diseases:Data |
| pent-2-enoic acid |
| Chemidplus:0000626982 |