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ortho-cresyl isobutyrate
Ortho-cresyl isobutyrate is an ester flavor and fragrance compound noted for its phenolic, berry, and floral odor characteristics.
General Material Description
Ortho-cresyl isobutyrate is an organic ester with the molecular formula C11H14O2, recognized as a member of the aromatic ester family. It appears as a colorless liquid and delivers a characteristic phenolic aroma with berry and floral nuances, lending fragrance and flavor utility. Synonyms include o-tolyl isobutyrate and 2-methylphenyl 2-methylpropanoate. The compound's sensory properties make it valuable in flavor and fragrance formulations. It is structurally indexed in chemical databases such as PubChem. Ortho-cresyl isobutyrate can be synthesized from the esterification of isobutyric acid with 2-methylphenol derivatives or obtained through chemical manufacturing routes tailored to flavor ingredients.
Occurrence, Applicability & Potential Uses
This compound is not known for natural occurrence but is widely utilized as a synthetic flavor and fragrance agent. It contributes a subtle phenolic and berry aroma profile desirable in perfumery and flavorings. The ingredient finds use in flavoring baked goods, nonalcoholic beverages, frozen dairy products, and confectionery frostings where its odor profile aligns with jasmin and narcissus floral notes. Usage levels are prudently regulated according to standards such as FEMA (US) and IFRA (Global), ensuring safe incorporation in consumer products. The controlled application aids in enhancing fruity, floral, and medicinal characteristics in complex scent and taste blends.
Physico-Chemical Properties Summary
Ortho-cresyl isobutyrate exhibits moderate volatility with a boiling point around 238 to 239°C at standard atmospheric pressure and reduced boiling points under vacuum conditions. It has a specific gravity slightly above water (1.0 to 1.007 at 25°C) and a refractive index ranging from 1.482 to 1.488 at 20°C, indicating its optical density. The estimated log P value of 2.872 suggests moderate lipophilicity, influencing its solubility and interaction in formulations. The compound is soluble in alcohols and partially soluble in water (~140 mg/L at 25°C). Its flash point at 203°F (95°C) denotes moderate flammability concerns. Vapor pressure is low at 0.039 mmHg at 25°C, reflecting limited evaporation under ambient conditions. These properties are integral for evaluating handling, stability, and compatibility in flavor and fragrance preparations.
FAQ
What is ortho-cresyl isobutyrate and what are its main applications?
Ortho-cresyl isobutyrate is an aromatic ester used primarily as a flavor and fragrance ingredient. It imparts a distinct phenolic, berry, and floral aroma, often described as reminiscent of jasmine and narcissus flowers. Its main applications include use in baked goods, nonalcoholic beverages, frozen dairy products, and confectionery frostings. These applications leverage its sensory characteristics to enhance flavor profiles and fragrance compositions in consumer products.
How is ortho-cresyl isobutyrate synthesized and what are its key physicochemical features?
The compound is typically synthesized through esterification of isobutyric acid with 2-methylphenol derivatives, yielding an aromatic ester. It is a colorless liquid with molecular formula C11H14O2. Physicochemical features include a boiling point near 238°C at atmospheric pressure, moderate solubility in alcohol and limited solubility in water, and a log P value around 2.87 indicating moderate lipophilicity. It has a moderate flash point (95°C) and low vapor pressure, which impact handling and application in formulations.
What safety and regulatory standards apply to ortho-cresyl isobutyrate in flavor and fragrance use?
Ortho-cresyl isobutyrate is recognized and evaluated by regulatory bodies such as JECFA (Joint FAO/WHO Expert Committee on Food Additives) and FEMA (Flavor and Extract Manufacturers Association, US), with assigned identifier FEMA 3753. It is listed as generally recognized as safe under specified concentration limits and subject to IFRA Code of Practice for fragrance use globally. Safety assessments indicate no classified hazards or required precautionary labels per OSHA standards, but its usage levels are regulated to ensure consumer protection. Regulatory opinions and use restrictions are published to maintain compliance in food and fragrance applications.
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 |
| HMDB (The Human Metabolome Database): | HMDB37680 |
| FooDB: | FDB016807 |
| Export Tariff Code: | 2915.60.0000 |
| ChemSpider: | View |
General Material Information
| Preferred name | ortho-cresyl isobutyrate |
| Trivial Name | 2-Methylphenyl 2-methylpropanoate |
| Short Description | o-tolyl isobutyrate |
| Formula | C11 H14 O2 |
| CAS Number | 36438-54-7 |
| FEMA Number | 3753 |
| Flavis Number | 9.48 |
| FDA UNII | X2ORQ6I00S |
| Nikkaji Number | J1.539.191J |
| MDL | MFCD00209539 |
| COE Number | 681 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 700 o-tolyl isobutyrate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 36438-54-7 ; O-TOLYL ISOBUTYRATE |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 178.23098754883 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.321 to 8.379 |
| Refractive Index | 1.482 to 1.488 @ 20 °C |
| Boiling Point | 107 to 108°C @ 8 mm Hg |
| Boiling Point | 238 to 239°C @ 760 mm Hg |
| Vapor Pressure | 0.039 mmHg @ 25 °C |
| Flash Point TCC Value | 95 °C TCC |
| logP (o/w) | 2.872 est |
| Solubility | |
| alcohol | Yes |
| water, 140.7 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Phenolic | |
| phenolic, berry, medicinal | |
| General comment | At 0.10 % in dipropylene glycol. phenolic berry medical |
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: | |
| Not determined | |
| 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 ortho-cresyl isobutyrate usage levels up to: | |||
| 0.3000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.024 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.10 (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: 14 | |||
| Click here to view publication 14 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 9.00000 | |
| beverages(nonalcoholic): | - | 8.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 8.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | 8.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| 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: | - | 8.00000 | |
| 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 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (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 |
| Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25 View page or View pdf |
| 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 :61954 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (2-methylphenyl) 2-methylpropanoate |
| Chemidplus:0036438547 |