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3-phenyl propyl isobutyrate
3-phenyl propyl isobutyrate is a fragrant ester with a fruity odor profile used primarily in flavors and fragrances, naturally occurring in chamomile.
General Material Description
3-phenyl propyl isobutyrate is an ester compound with the molecular formula C13H18O2, known for its medium-strength fruity odor and flavor characteristics. It appears as a clear, colorless liquid and has multiple synonyms including hydrocinnamyl isobutyrate and iso butyric acid 3-phenyl propyl ester. The compound contributes sweet, fruity, and slightly floral notes reminiscent of blackberry, plum, and tropical fruits. It naturally occurs in chamomile and is also synthesized for use in flavor and fragrance industries. Structural and chemical information can be referenced via PubChem (CID 7662). This compound is derived typically through esterification reactions involving isobutyric acid and 3-phenylpropanol. It is valued for imparting fruity and balsamic nuances in various products.
Occurrence, Applicability & Potential Uses
3-phenyl propyl isobutyrate occurs naturally in chamomile plants, contributing to their characteristic aroma. It finds application primarily as a flavor and fragrance agent, utilized to enhance fruity and balsamic notes in perfumery and flavor formulations. Its odor profile includes elements described as apricot, plum, osmanthus, and tropical fruit, with scent nuances that can improve products such as baked goods, beverages, and confectionery. Cosmetic applications focus on its use as a perfuming ingredient to provide medium-intensity fruity and floral highlights. Usage recommendations comply with IFRA (Global) standards, which govern safe concentration levels in fragrance concentrates to ensure consumer safety.
Physico-Chemical Properties Summary
This ester exhibits moderate volatility with a vapor pressure around 0.002 mmHg at 25 °C, indicating a relatively low evaporation rate suitable for sustained fragrance release. It has an estimated logP value of 3.71, suggesting moderate lipophilicity that affects its solubility and compatibility with various formulation bases. The specific gravity ranges between 0.98 and 0.983 at 20 °C, and its refractive index varies from 1.485 to 1.487 at the same temperature, consistent with typical ester characteristics. It is soluble in alcohol and has limited water solubility estimated at approximately 16.47 mg/L at 25 °C. The flash point is measured at 110 °C (230 °F), indicating moderate flammability risks under elevated temperature conditions. These properties influence formulation strategies, ensuring stability and desirable sensory profiles in both flavor and fragrance applications.
FAQ
What is 3-phenyl propyl isobutyrate and where is it found?
3-phenyl propyl isobutyrate is a chemical ester known for its fruity and balsamic odor and flavor profile. It occurs naturally in chamomile and is widely used as a flavor and fragrance compound. Its pleasant fruity aroma includes notes similar to plum, apricot, and osmanthus, making it desirable in perfumery and food flavoring to impart sweet and tropical nuances.
How is 3-phenyl propyl isobutyrate used in products and what are its typical properties?
This compound is primarily applied as a flavor and fragrance ingredient, enhancing products with medium-intensity fruity notes. It is soluble in alcohol but has limited solubility in water, which affects how it blends in various formulations. With moderate volatility and a flash point around 110 °C, it provides lasting scent impact while maintaining safe handling characteristics. Its lipophilic nature allows it to integrate well into oil-based fragrance and flavor systems.
What regulations govern the use of 3-phenyl propyl isobutyrate and how is it sourced?
The use of 3-phenyl propyl isobutyrate follows guidelines established by IFRA (International Fragrance Association) globally, which sets maximum usage levels in fragrance concentrates to ensure safety. Additionally, it is recognized by FEMA (Flavor and Extract Manufacturers Association) with the number 2893, confirming its acceptability in flavor applications. The compound is obtained either through extraction from natural sources such as chamomile or synthesized chemically for commercial uses.
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 |
| KEGG (GenomeNet): | C02008 |
| HMDB (The Human Metabolome Database): | HMDB34472 |
| FooDB: | FDB012882 |
| Export Tariff Code: | 2915.90.2000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 3-phenyl propyl isobutyrate |
| Trivial Name | 3-Phenylpropyl isobutyrate |
| Short Description | 3-phenylpropyl isobutyrate |
| Formula | C13 H18 O2 |
| CAS Number | 103-58-2 |
| FEMA Number | 2893 |
| Flavis Number | 9.428 |
| ECHA Number | 203-125-0 |
| FDA UNII | Y9O48YFN18 |
| Nikkaji Number | J36.972A |
| Beilstein Number | 2454387 |
| MDL | MFCD00082227 |
| COE Number | 303 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 640 3-phenylpropyl isobutyrate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 103-58-2 ; 3-PHENYLPROPYL ISOBUTYRATE |
| Synonyms |
|
Suppliers
| Alfrebro | Berjé |
| BOC Sciences | Inoue Perfumery |
| Parchem | Penta International |
| Sigma-Aldrich | TCI AMERICA |
| WholeChem | Alfrebro LLC/ Archer Daniels Midland Company |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 206.28486633301 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.164 to 8.189 |
| Refractive Index | 1.485 to 1.487 @ 20 °C |
| Vapor Pressure | 0.002 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 3.71 est |
| Solubility | |
| alcohol | Yes |
| water, 16.47 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| fruity, tropical, apricot, plum, balsamic, jammy, honey, bready, osmanthus, fruit dried fruit, sweet, juicy fruit, fermented, sugar | |
| Odor strength | medium |
| Substantivity | 189 hour(s) at 100.00 % |
| Luebke, William tgsc, (2021) | At 100.00 %. fruity tropical apricot plum balsamic jammy honey bready osmanthus dried fruit |
| Mosciano, Gerard, (2009) | At 1.00 %. sweet rich fruity, juicy fruit, honey, tropical fruity with fermented sugar, and jammy osmanthus like nuances |
| Flavor Type: Fruity | |
| fruity, fruit ripe fruit, plastic, juicy, blackberry, fruit dried fruit, fig, tropical, orris, sweet, ripe, blueberry, grape, fermented | |
| Luebke, William tgsc, (2021) | Fruity ripe fruit plastic juicy blackberry dried fruit fig tropical orris |
| Mosciano, Gerard, (2009) | At 10.00 ppm. sweet rich fruity, ripe juicy notes reminiscent of blackberry, blueberry, fig and grape, slightly fermented miso like nuances |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Balsam , Currant black currant , Fruit , Hovenia , Narcissus , Peach , Wisteria |
| Cosmetic purposes | Perfuming agents |
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. | |
| Human Experience: | |
| 8 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 > 5000 mg/kg One group of 10 animals received 5000 mg/kg, mortality 1/10, only summary available. (Levenstein, 1975f) | |
| 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 3-phenyl propyl isobutyrate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 3.70 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 16.00 (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: | - | 5.80000 | |
| beverages(nonalcoholic): | - | 1.30000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 3.00000 | |
| fruit ices: | - | 3.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 5.00000 | |
| 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): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 15, Revision 1 (FGE.15Rev1) - Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 68 (FGE.68): Consideration of cinnamyl alcohol and related flavouring agents evaluated by JECFA (55th meeting) evaluated by EFSA in FGE.15Rev1 (2008) View page or View pdf |
| Safety and efficacy of aryl-substituted primary alcohol, aldehyde, acid, ester and acetal derivatives belonging to chemical group 22 when used as flavourings for all animal species View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):103-58-2 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7662 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 3-phenylpropyl 2-methylpropanoate |
| Chemidplus:0000103582 |
| RTECS:NQ5440000 for cas# 103-58-2 |