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ethyl isovalerate
Ethyl isovalerate is a naturally occurring ester known for its fruity aroma and used as a flavoring and fragrance compound in food and cosmetic applications.
General Material Description
Ethyl isovalerate is a branched-chain ester derived from isovaleric acid and ethanol, with the chemical formula C7H14O2. Recognized for its fruity, sweet aroma reminiscent of apple, pineapple, and tropical fruits, it appears as a clear, colorless liquid. The material is also known by several synonyms including ethyl 3-methylbutanoate and butanoic acid, 3-methyl-, ethyl ester. Ethyl isovalerate occurs naturally in various fruits, cheeses, and beverages, contributing to their characteristic aromas. The compound is referenced in controlled vocabulary databases such as ChEBI. It is commonly obtained by esterification of isovaleric acid with ethanol and is valued in flavor and fragrance industries for its distinct sensory profile.
Occurrence, Applicability & Potential Uses
Ethyl isovalerate naturally occurs in a range of botanical and fermented products, including apple, bilberry, blueberry, celery shoots, and various fruits such as pineapple and plum. Additionally, it is present in cheeses, ciders, cognacs, rums, and different wines. Its biologically widespread occurrence supports its acceptance as a flavor and fragrance compound. According to FEMA (US), ethyl isovalerate is a recognized flavoring agent with broad application potential, including use in dairy products, tropical and other fruits, nuts, and vegetables. It enhances fruity notes in both odor and taste profiles, making it valuable for flavoring baked goods, beverages, confectionery, and perfumery as a fragrancing agent. This ester is listed in IFRA (Global) standards with recommended use levels to ensure safe incorporation into consumer products.
Physico-Chemical Properties Summary
Ethyl isovalerate is a clear liquid with a molecular weight of approximately 130.19 g/mol. It exhibits moderate volatility with a boiling point ranging from 131 to 133°C at standard atmospheric pressure and a melting point between -99 and -98°C. The compound possesses a vapor pressure of about 7.85 mmHg at 25°C and a refractive index close to 1.397 at 20°C. Its specific gravity varies narrowly around 0.862 to 0.87 at 20–25°C. Slightly soluble in water (~2000 mg/L at 20°C), it shows good solubility in paraffin oil and propylene glycol, which affects its formulation versatility. The flash point is approximately 35°C (95°F), indicating flammability precautions during handling. The logP estimate near 2.16 suggests moderate lipophilicity, helping in balancing its distribution between aqueous and lipid phases in a product. Ethyl isovalerate’s shelf life of about 12 months is maintained under cool, dry, light-protected storage conditions in sealed containers.
FAQ
What is ethyl isovalerate and what are its main properties?
Ethyl isovalerate is an organic ester formed from isovaleric acid and ethanol, known chemically as C7H14O2. It appears as a colorless liquid with a fruity aroma that resembles apple, pineapple, and tropical fruits. It has moderate volatility with boiling points around 131–133°C and is moderately soluble in water. The compound is valued in flavor and fragrance industries due to its distinctive odor and flavor characteristics.
In which natural sources and products can ethyl isovalerate be found?
Ethyl isovalerate occurs naturally in various fruits such as apple, bilberry, blueberry, pineapple, plum, and wild strawberry. It is also detected in fermented products like cheese, cider, cognac, rum, and wine. These natural occurrences contribute to the pleasant fruity and sweet sensory profiles of these foods and beverages. Its presence is significant enough to be used as a reference for creating flavor and fragrance additives.
What are the regulatory standards and safety considerations for using ethyl isovalerate?
Ethyl isovalerate is registered with FEMA (US) and assessed for safety in flavor and fragrance applications under IFRA (Global) guidelines. It is generally recognized as safe (GRAS) when used within recommended limits, such as up to 4% in fragrance concentrates. Safety data indicate low toxicity with high oral LD50 values in animal studies and no significant irritation at low concentrations. Handling precautions include protection from ignition sources due to its flammability (flash point of 35°C) and storage in cool, dry conditions. Safety data sheets and comprehensive risk assessments are available through regulatory bodies including ECHA (EU) and FDA (US).
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
| ethyl 3-methylbutanoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 108-64-5 |
| Pubchem (cid): | 7945 |
| Pubchem (sid): | 134970678 |
| Flavornet: | 108-64-5 |
| Pherobase: | View |
| Publications by Info | |
| Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.) | |
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 |
| CHEMBL: | View |
| KEGG (GenomeNet): | C12290 |
| HMDB (The Human Metabolome Database): | HMDB30028 |
| FooDB: | FDB001326 |
| YMDB (Yeast Metabolome Database): | YMDB01334 |
| Export Tariff Code: | 2915.90.5050 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | ethyl isovalerate |
| Trivial Name | Ethyl isovalerate |
| Short Description | isovaleric acid, ethyl ester |
| Formula | C7 H14 O2 |
| CAS Number | 108-64-5 |
| Deleted CAS Number | 117442-70-3 |
| FEMA Number | 2463 |
| Flavis Number | 9.447 |
| ECHA Number | 203-602-3 |
| FDA UNII | 9ZZ5597636 |
| Nikkaji Number | J1.967D |
| Beilstein Number | 1744677 |
| MDL | MFCD00009203 |
| COE Number | 442 |
| xLogP3-AA | 1.70 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 196 ethyl isovalerate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 108-64-5 ; ETHYL ISOVALERATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 130.18698120117 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.173 to 7.206 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.181 to 7.248 |
| Refractive Index | 1.395 to 1.399 @ 20 °C |
| Melting Point | -99 to -98°C @ 760 mm Hg |
| Boiling Point | 131 to 133°C @ 760 mm Hg |
| Boiling Point | 59 to 60°C @ 50 mm Hg |
| Acid Value | 2 max KOH/g |
| Vapor Pressure | 7.853 mmHg @ 25 °C |
| Vapor Density | 4.4 |
| Flash Point TCC Value | 35 °C TCC |
| logP (o/w) | 2.158 est |
| Shelf life | 12 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| paraffin oil | Yes |
| propylene glycol | Yes |
| water, 2000 mg/L @ 20 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| fruity, sweet, apple, pineapple, tutti frutti, estery, sharp, green, orange | |
| Odor strength | high , recommend smelling in a 10.00 % solution or less |
| Substantivity | 4 hour(s) at 100.00 % |
| Luebke, William tgsc, (1987) | At 10.00 % in dipropylene glycol. fruity sweet apple pineapple tutti frutti |
| Mosciano, Gerard P&F 23, No. 2, 43, (1998) | Sweet, diffusive, estry, fruity, sharp, pineapple, apple, green and orange |
| Flavor Type: Fruity | |
| sweet, fruity, spicy, metallic, green, pineapple, apple | |
| Mosciano, Gerard P&F 23, No. 2, 43, (1998) | At 30.00 ppm. Sweet, fruity, spice, metallic and green with a pineapple and apple Iift |
| Useful in: brown nuts, fruity red, fruity yellow, fruity tropical, fruity others, alcoholics. | Sweet, fruity, green, blueberry, butter, apple |
| General comment | Fruity,sweet, wine note |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple , Apricot , Banana , Berry , Cranberry , Fruit , Grape , Honey , Hop , Melon , Peach , Pear , Pineapple , Quince , Saffron , Strawberry , Tobacco , Woodruff |
| Flavoring purposes | Cheese , Dairy , Fruit tropical fruit , Nut , Vegetable , Walnut |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 11 - Highly flammable. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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 33 - Take precautionary measures against static discharge. 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: | |
| 2 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 > 5000 mg/kg (Levenstein, 1976) oral-rabbit LD50 7030 mg/kg (Munch, 1972) oral-rabbit LD50 7031 mg/kg Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972. intraperitoneal-rat LD50 1200 mg/kg Food and Cosmetics Toxicology. Vol. 16, Pg. 743, 1978. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 16, Pg. 743, 1978. | |
| 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 ethyl isovalerate usage levels up to: | |||
| 4.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 650.00 (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: | - | 27.00000 | |
| beverages(nonalcoholic): | - | 4.90000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 80.00000 | 430.00000 | |
| condiments / relishes: | - | 1.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 7.50000 | |
| fruit ices: | - | 7.50000 | |
| gelatins / puddings: | - | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 29.00000 | |
| 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 1, Revision 1 (FGE.01Rev 1): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission View page or View pdf |
| Flavouring Group Evaluation 01 Rev2 (FGE.01 Rev2): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2 View page or View pdf |
| Scientific Opinion on the safety and efficacy of straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes (chemical group 1) when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):108-64-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7945 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3272 |
| WGK Germany:2 |
| ethyl 3-methylbutanoate |
| Chemidplus:0000108645 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:NY1504000 for cas# 108-64-5 |