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isoamyl isovalerate
Isoamyl isovalerate is a naturally occurring fruity ester used as a flavor and fragrance agent, characterized by green apple and tropical fruit notes.
General Material Description
Isoamyl isovalerate is an ester compound with the molecular formula C10H20O2 and a molecular weight of approximately 172.27 g/mol. It appears as a clear liquid and is classified chemically as an isopentyl ester of isovaleric acid. This compound is considered a medium-strength fruity odorant characterized by sweet, green apple, and tropical fruit notes, making it valuable in flavor and fragrance formulations. Also referenced under synonyms such as isopentyl isovalerate and 3-methylbutyl 3-methylbutanoate, isoamyl isovalerate is naturally present in various fruits and essential oils. For detailed chemical data, see the ChEBI database entry. It is typically sourced via esterification reactions between isoamyl alcohol and isovaleric acid.
Occurrence, Applicability & Potential Uses
Isoamyl isovalerate occurs naturally in several fruits including apples, bananas, plums, and also in fermented beverages such as beer, cider, and sherry. It is present in essential oils from eucalyptus, peppermint, spearmint, and manuka. Its fruity green apple and tropical aroma profile make it useful as a flavoring agent in foods and beverages, enhancing fruitaceous notes in products like confectionery, baked goods, and beverages. It is also utilized as a perfuming agent in cosmetic formulations. Regulatory use levels are guided by standards such as FEMA (US) and IFRA (Global), with FEMA number 2085 indicating acceptance as a flavor ingredient. The compound functions primarily as a modifier to impart sweet fruity nuances in complex flavor blends.
Physico-Chemical Properties Summary
Isoamyl isovalerate is a clear, colorless liquid with a boiling range of 190 to 191 °C at 760 mm Hg. It has a refractive index ranging from 1.411 to 1.414 at 20 °C and a specific gravity between 0.851 and 0.857 at 25 °C. Its vapor pressure is approximately 0.886 mm Hg at 25 °C, indicating moderate volatility. The compound exhibits moderate lipophilicity with an estimated logP of 3.53, contributing to its solubility in alcohols, fixed oils, and paraffin oil, while being practically insoluble in pure water. It has a flash point near 67 °C (152 °F) per Tag Closed Cup method, necessitating careful storage away from ignition sources. Shelf life can extend beyond twelve months if stored in tightly sealed containers in cool, dry places protected from light and heat. These properties influence handling and formulation in flavor and fragrance applications.
FAQ
What is isoamyl isovalerate and what are its main characteristics?
Isoamyl isovalerate is an ester molecule formed from isoamyl alcohol and isovaleric acid. It is recognized for its fruity aroma profile reminiscent of green apple and tropical fruit. The compound appears as a clear liquid with a moderate vapor pressure and is widely used as a flavor and fragrance ingredient due to its sweet and fresh olfactory qualities.
Where is isoamyl isovalerate naturally found and how is it used in products?
This compound naturally occurs in various fruits such as apples, bananas, plums, and is also found in fermented beverages including beer and cider. It is present in essential oils like eucalyptus and peppermint. Isoamyl isovalerate is employed as a flavoring agent to enhance fruity notes in food and beverage products and serves as a perfuming agent in cosmetics. Usage levels are controlled to ensure desirable sensory effects while maintaining safety.
What regulatory standards and safety considerations apply to isoamyl isovalerate?
Isoamyl isovalerate is listed under FEMA (US) number 2085 and evaluated by international bodies such as IFRA (Global) for fragrance use limitations. Safety assessments indicate it can cause irritation to eyes, skin, and respiratory tract at certain exposures, requiring handling precautions including protective clothing and proper ventilation. It is combustible with a flash point near 67 °C. Usage in food and fragrance formulations follows established guidelines to ensure consumer safety.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| NCBI | Start search |
Literature & References
| 3-methylbutyl 3-methylbutanoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 659-70-1 |
| Pubchem (cid): | 12613 |
| Pubchem (sid): | 134977333 |
| Pherobase: | View |
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): | C12289 |
| HMDB (The Human Metabolome Database): | HMDB30029 |
| FooDB: | FDB001327 |
| Export Tariff Code: | 2915.60.5000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | isoamyl isovalerate |
| Trivial Name | Isoamyl isovalerate |
| Short Description | isopentyl isovalerate |
| Formula | C10 H20 O2 |
| CAS Number | 659-70-1 |
| FEMA Number | 2085 |
| Flavis Number | 9.463 |
| ECHA Number | 211-536-1 |
| FDA UNII | 16M1VA1FJY |
| Nikkaji Number | J2.103B |
| Beilstein Number | 1753884 |
| MDL | MFCD00048369 |
| COE Number | 458 |
| xLogP3-AA | 3.10 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 50 isoamyl isovalerate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 659-70-1 ; ISOAMYL ISOVALERATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 172.26780700684 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.081 to 7.131 |
| Refractive Index | 1.411 to 1.414 @ 20 °C |
| Boiling Point | 190 to 191°C @ 760 mm Hg |
| Acid Value | 2 max KOH/g |
| Vapor Pressure | 0.886 mmHg @ 25 °C |
| Vapor Density | 5.9 |
| Flash Point TCC Value | 66.67 °C TCC |
| logP (o/w) | 3.53 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 | |
| alcohol | Yes |
| fixed oils | Yes |
| paraffin oil | Yes |
| water, 44.59 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| sweet, fruity, green, ripe, apple, jammy, tropical, estery | |
| Odor strength | medium |
| Substantivity | < 3 hour(s) at 100.00 % |
| Luebke, William tgsc, (1986) | At 100.00 %. sweet fruity green ripe apple jammy tropical |
| Mosciano, Gerard P&F 24, No. 4, 27, (1999) | At 1.00 % in ethyl alcohol. Sweet fruity, green apple and estry |
| Flavor Type: Green | |
| green, fruity, apple | |
| Mosciano, Gerard P&F 24, No. 4, 27, (1999) | At 1.00 ppm. Green, fruity apple |
| Useful in: brown nuts, fruity red, fruity yellow, fruity tropical, fruity others, sweet others, alcoholics. | Sweet, fruity, green, soapy |
| General comment | Fruity, green note, ethereal |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple , Apple green apple , Apricot , Banana , Blackberry , Blueberry , Boysenberry , Bramble arctic bramble blackberry , Cherry , Cherry black cherry , Currant , Currant black currant , Date , Fruit , Fruit juicy fruit , Gooseberry , Grape , Honey , Huckleberry , Kiwi , Loganberry , Lychee , Mango , Melon , Mint , Mulberry , Papaya , Passion fruit , Peach , Pear , Pineapple , Plum , Plum mirabelle plum , Quince , Raspberry , Raspberry black raspberry , Spice , Stephanotis , Strawberry , Valerian |
| Flavoring purposes | Cloudberry bakeapple , Fruit tropical fruit , Grenadine , Jackfruit , Olive , Plum greengage plum , Tomato , Valerian , Walnut |
| Other purposes | Modifier |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. 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) | |
| Flammable liquids (Category 4), H227 Skin irritation (Category 2), H315 Eye irritation (Category 2A), H319 Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335 | |
| GHS Label elements, including precautionary statements | |
| Pictogram |  |
| Signal word | Warning |
| Hazard statement(s) | |
| H227 - Combustible liquid H315 - Causes skin irritation H319 - Causes serious eye irritation H335 - May cause respiratory irritation | |
| Precautionary statement(s) | |
| P210 - Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P261 - Avoid breathing dust/fume/gas/mist/vapours/spray. P264 - Wash skin thouroughly after handling. P271 - Use only outdoors or in a well-ventilated area. P280 - Wear protective gloves/protective clothing/eye protection/face protection. P302 + P352 - IF ON SKIN: wash with plenty of soap and water. P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P312 - Call a POISON CENTER or doctor/physician if you feel unwell. P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention. P337 + P313 - IF eye irritation persists: Get medical advice/attention. P362 - Take off contaminated clothing and wash before reuse. P370 + P378 - In case of fire: Use dry sand, dry chemical or alcohol-resistant foam for extinction. P403 + P233 - Store in a well-ventilated place. Keep container tightly closed. P403 + P235 - Store in a well-ventilated place. Keep cool. P405 - Store locked up. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Human Experience: | |
| 2 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rabbit LD50 13956 mg/kg Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 5000 mg/kg Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972. | |
| 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 isoamyl isovalerate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| 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: | - | 41.00000 | |
| beverages(nonalcoholic): | - | 8.50000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 390.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 14.00000 | |
| fruit ices: | - | 14.00000 | |
| gelatins / puddings: | 1.00000 | 61.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 33.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 10.00000 | |
| 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 Authority (EFSA) reference(s): |
| Safety of 31 flavouring compounds belonging to different chemical groups when used as feed additives 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):659-70-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :12613 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3082 |
| WGK Germany:2 |
| 3-methylbutyl 3-methylbutanoate |
| Chemidplus:0000659701 |
| RTECS:NY1508000 for cas# 659-70-1 |