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isopropyl anthranilate
Isopropyl anthranilate is a floral-scented ester used primarily in flavor and fragrance applications.
General Material Description
Isopropyl anthranilate is a synthetic organic ester derived from anthranilic acid, possessing a molecular formula of C10H13NO2. This colorless liquid is characterized by a floral odor reminiscent of neroli, hawthorn, and honey notes. It is known under various synonyms including 2-aminobenzoic acid 1-methyl ethyl ester and propan-2-yl 2-aminobenzoate. The substance is linked in chemical databases such as PubChem (CID 87499) and is primarily manufactured for use in flavor and fragrance formulations. Its production involves esterification of anthranilic acid with isopropanol or similar intermediates. The compound's floral profile makes it valuable in recreating delicate and fresh scent notes.
Occurrence, Applicability & Potential Uses
Isopropyl anthranilate does not occur naturally but is synthesized for its distinctive floral fragrance. It is commonly employed in flavor and fragrance agents to impart scents reminiscent of hawthorn, jasmine, mandarin, and neroli. The compound is utilized in perfumery, cosmetic products, and flavor blends where its aromatic profile enhances product character. Its usage aligns with standards such as IFRA (Global), which recommends safe incorporation levels, specifically permitting up to 4.0% concentration in fragrance concentrates. This guidance helps ensure compliance with safety requirements in consumer products.
Physico-Chemical Properties Summary
Isopropyl anthranilate is a colorless liquid with a boiling range between 274 and 275°C at standard atmospheric pressure, indicating moderate volatility suited for fragrance applications. It exhibits a low vapor pressure of approximately 0.006 mmHg at 25°C, contributing to its stability in formulations. The compound is soluble in alcohol and has limited water solubility estimated at around 108.3 mg/L at 25°C, influencing its use in various solvent systems. Its estimated log P value of 3.042 suggests moderate lipophilicity, which affects its diffusion and persistence on skin or materials. The flash point near 134°C (converted from 273°F) indicates a relatively low flammability hazard under typical handling conditions.
FAQ
What is isopropyl anthranilate used for in fragrances and flavors?
Isopropyl anthranilate serves as a floral fragrance agent contributing distinct notes reminiscent of neroli, hawthorn, jasmine, and mandarin. It is used broadly in perfume compositions and flavor formulations to impart fresh, sweet floral characteristics. Its aromatic profile enhances the complexity and appeal of many fragrance blends.
Where does isopropyl anthranilate occur naturally, and how is it produced industrially?
Isopropyl anthranilate is not naturally occurring and is produced synthetically through the esterification of anthranilic acid with isopropanol or related alcohols. This industrial process yields a compound with consistent purity, suitable for use in flavor and fragrance applications. Its chemical synthesis permits controlled quality and supply for commercial purposes.
What safety and regulatory standards apply to isopropyl anthranilate?
Isopropyl anthranilate is subject to safety assessments by organizations such as IFRA (Global), which sets usage limits to ensure consumer safety; currently, it is recommended at maximum 4.0% concentration in fragrance concentrates. The compound has no recognized GHS hazard classifications under OSHA HCS. Its physical and toxicological profiles are documented in public chemical registries including ECHA and FDA databases, supporting its regulatory compliance in flavor and fragrance markets.
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 |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2922.49.3800 |
| ChemSpider: | View |
General Material Information
| Preferred name | isopropyl anthranilate |
| Trivial Name | Isopropyl anthranilate |
| Short Description | benzoic acid, 2-amino-, 1-methylethyl ester |
| Formula | C10 H13 N O2 |
| CAS Number | 18189-02-1 |
| ECHA Number | 242-074-9 |
| FDA UNII | Search |
| Nikkaji Number | J110.730E |
| MDL | MFCD00060604 |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 179.21900939941 |
| Boiling Point | 274 to 275°C @ 760 mm Hg |
| Vapor Pressure | 0.006 mmHg @ 25 °C |
| Flash Point TCC Value | 133.89 °C TCC |
| logP (o/w) | 3.042 est |
| Solubility | |
| alcohol | Yes |
| water, 108.3 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Floral | |
| neroli, hawthorn, honey, floral | |
| General comment | At 100.00 %. neroli hawthorn honey floral |
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 isopropyl anthranilate usage levels up to: | |||
| 4.0000 % in the fragrance concentrate. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):18189-02-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :87499 |
| National Institute of Allergy and Infectious Diseases:Data |
| propan-2-yl 2-aminobenzoate |
| Chemidplus:0018189021 |