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isobutyl propionate
Isobutyl propionate is a fruity ester used as a flavor and fragrance agent, naturally found in fruits, cheeses, and beverages.
General Material Description
Isobutyl propionate is an organic ester with the molecular formula C7H14O2, also known as propanoic acid, isobutyl ester. It presents as a clear, colorless liquid characterized by a fruity and sweet aroma reminiscent of banana and tutti-frutti notes. Alternative names include 2-methyl propyl propanoate and iso butyl propanoate. This compound is widely valued in the flavor and fragrance industry for its characteristic fruity scent and taste. It is naturally present in various fruits such as apples, apricots, melons, and grapes, as well as in fermented beverages and certain cheeses. Sources for isobutyl propionate often include natural extraction from these matrices or synthetic production, with data available through controlled vocabularies such as ChEBI.
Occurrence, Applicability & Potential Uses
Isobutyl propionate occurs naturally in a range of fruits including apple, apricot, melon, grape, and quince, and is also detected in fermented products like cider, rum, and wine. It appears in cheeses such as Gruyere and Parmesan, contributing to their characteristic aromas. The compound is employed as a flavor and fragrance agent, imparting fruity, sweet, and rummy notes in various formulations spanning bakery goods, beverages, and confectionery. Its use is regulated under FEMA (US) standards, where it is recognized with FEMA number 2212 and permitted within specified concentration limits to ensure safe application. In perfumery, it functions as a perfuming agent providing fresh fruity facets. The combination of its biological occurrence and sensory properties underpins its versatility in flavor and fragrance development.
Physico-Chemical Properties Summary
Isobutyl propionate is a volatile, flammable ester with a moderate vapor density of 4.1 and a logP value of approximately 2.16, indicating moderate lipophilicity. It has a melting point range from -71 to -70°C and a boiling point around 66 to 67°C measured at 60 mm Hg. Its vapor pressure at 25°C is about 6.47 mmHg, reflecting appreciable volatility at room temperature. The compound exhibits partial solubility in water, approximately 1700 mg/L at 25°C, and is soluble in alcohols, which facilitates its use in various liquid formulations. These physical and chemical attributes impact formulation parameters such as evaporation rate, solubility in different solvents, and safety considerations in handling and storage.
FAQ
What is isobutyl propionate and what are its key characteristics?
Isobutyl propionate is an organic ester formed from propanoic acid and isobutyl alcohol, with the molecular formula C7H14O2. It is noted for its fruity, sweet aroma and flavor, often described as banana-like with tutti-frutti and rummy nuances. Naturally occurring in numerous fruits and fermented products, it is used industrially as a flavor and fragrance agent due to these sensory attributes. The compound appears as a clear, colorless liquid and possesses moderate volatility and solubility characteristics.
Where does isobutyl propionate naturally occur and how is it typically used?
Isobutyl propionate is found naturally in a variety of fruits including apples, apricots, grapes, melons, and quinces, as well as in cheeses like Gruyere and Parmesan. It is also present in fermented beverages such as cider, rum, and wine. Its characteristic fruity and sweet scent makes it valuable as a flavoring agent in foods and beverages and as a perfuming ingredient in fragrances. Formulators commonly use it to impart apple, banana, and rum-like notes in products ranging from baked goods to soft drinks.
What regulations govern the use and sourcing of isobutyl propionate?
Isobutyl propionate is subject to regulatory oversight by organizations such as FEMA (US), where it holds FEMA number 2212 and is recognized as generally safe for use in flavors within defined limits. Usage levels are controlled to mitigate potential irritancy and ensure safety in consumer products. Safety data indicate flammability and skin irritation hazards, necessitating appropriate handling precautions. The compound is listed in databases like REACH (EU) and FDA registrations, reflecting scrutiny for both safety and environmental impact. Natural sourcing from fruits and fermentation is complemented by synthetic production to meet industrial demands.
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 |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | HMDB34239 |
| FooDB: | FDB012551 |
| Export Tariff Code: | 2915.39.4550 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | isobutyl propionate |
| Trivial Name | Isobutyl propionate |
| Short Description | propanoic acid, isobutyl ester |
| Formula | C7 H14 O2 |
| CAS Number | 540-42-1 |
| FEMA Number | 2212 |
| Flavis Number | 9.125 |
| ECHA Number | 208-746-0 |
| FDA UNII | 8Q382JSY9T |
| Nikkaji Number | J47.187I |
| Beilstein Number | 1745554 |
| MDL | MFCD00009307 |
| COE Number | 406 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 148 isobutyl propionate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 540-42-1 ; ISOBUTYL PROPIONATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 130.18698120117 |
| Melting Point | -71 to -70°C @ 760 mm Hg |
| Boiling Point | 66 to 67°C @ 60 mm Hg |
| Vapor Pressure | 6.47 mmHg @ 25 °C |
| Vapor Density | 4.1 |
| Flash Point TCC Value | 26.67 °C TCC |
| logP (o/w) | 2.158 est |
| Solubility | |
| alcohol | Yes |
| water, 1700 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| fruity, green, ethereal, sweet, tutti frutti, banana, rummy, pungent, bubble gum, estery, tropical | |
| General comment | At 100.00 %. fruity green ether sweet tutti frutti banana |
| Mosciano, Gerard P&F 24, No. 2, 49, (1999) | At 1.00 %. Fruity, sweet, rummy, pungent, bubblegum estry with a tropical nuance |
| Flavor Type: Fruity | |
| sweet, fruity, banana, tutti frutti, rummy | |
| Mosciano, Gerard P&F 24, No. 2, 49, (1999) | At 10.00 ppm. Sweet, fruity, banana, tutti frutti, with rummy nuances |
| General comment | Fruity, sweet: tutti-fruitti, banana, rum |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple , Apricot , Banana , Blackberry , Cherry , Ginger , Grape , Hop , Mulberry , Peach , Pear , Pineapple , Saffron , Valerian , Woodruff |
| Flavoring purposes | Caramel , Fruit punch , Valerian , Whiskey |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 10 - Flammable. R 38 - Irritating to skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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: | |
| oral-rabbit LD50 5599 mg/kg Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972. | |
| Dermal Toxicity: | |
| Not determined | |
| 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 isobutyl propionate usage levels up to: | |||
| 6.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 12.00 (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: | - | 35.00000 | |
| beverages(nonalcoholic): | - | 5.40000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 4.20000 | |
| fruit ices: | - | 4.20000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 25.00000 | |
| 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): |
| Flavouring Group Evaluation 2, Revision 1 (FGE.02) : Branched- and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (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 |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):540-42-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :10895 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2394 |
| WGK Germany:2 |
| 2-methylpropyl propanoate |
| Chemidplus:0000540421 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:UF4930000 for cas# 540-42-1 |