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(E)-cinnamyl butyrate
(E)-cinnamyl butyrate is an ester with a medium balsamic odor, applied in flavors and fragrances, naturally found in apple fruit.
General Material Description
(E)-cinnamyl butyrate, also known as trans-cinnamyl butyrate or butanoic acid, (2E)-3-phenyl-2-propen-1-yl ester, is a synthetic ester compound with the molecular formula C13H16O2. It appears as a clear liquid featuring a medium-strength balsamic odor with soft fruity and cinnamyl nuances. This compound is mainly utilized in flavor and fragrance formulations due to its appealing aromatic profile. It naturally occurs in apple fruit and can impart olfactory impressions reminiscent of apple, balsam, and floral notes such as lily of the valley and rose. The compound is well characterized in chemical databases such as PubChem and recognized under various chemical synonyms. It can be sourced through chemical synthesis for use in industry sectors governed by safety and regulatory frameworks.
Occurrence, Applicability & Potential Uses
(E)-cinnamyl butyrate occurs naturally in apple fruit, contributing to its characteristic aroma. This ester’s odor profile encompasses apple, balsamic, floral, and fruity elements, making it suitable for enhancing flavor and fragrance products. Common applications include its use as a flavoring agent in formulations requiring notes of apple, peach, pear, or honey, and as a fragrance ingredient offering balsam, lily, or tuberose impressions. Its sensory versatility supports use in products conforming to the IFRA (Global) Code of Practice, which provides guidelines for safe usage levels in perfumery and flavoring contexts. The compound’s compliance with food and fragrance safety standards enables its application within regulated usage limits.
Physico-Chemical Properties Summary
(E)-cinnamyl butyrate is a moderately lipophilic ester with an estimated logP of 3.66, indicating preferential solubility in organic solvents such as alcohols, while showing limited water solubility (approximately 22.29 mg/L at 25 °C). It exhibits a specific gravity ranging from 1.01 to 1.015 at 25 °C and a refractive index between 1.525 and 1.53 at 20 °C. The vapor pressure is extremely low at 0.001 mmHg at 25 °C, indicating low volatility under ambient conditions. Its flash point is measured at 230 °F (~110 °C). The compound maintains chemical stability within typical formulation environments and has an acid value capped at 1 KOH/g, confirming purity consistent with Food Chemical Codex standards. These properties facilitate its incorporation into diverse flavor and fragrance matrices requiring moderate solubility and persistence.
FAQ
What is (E)-cinnamyl butyrate and what are its primary uses?
(E)-cinnamyl butyrate is an ester compound recognized for its characteristic balsamic and fruity odor notes. It is widely used in the flavor and fragrance industries to impart aromas resembling apple, balsam, and various floral nuances. Typically, it enhances the sensory profile of products such as perfumes, flavorings in food, and scented formulations. Its natural occurrence in apple fruit provides a basis for its application as a flavor additive that simulates natural fruit aromas.
Where is (E)-cinnamyl butyrate found naturally, and how is it used in formulations?
(E)-cinnamyl butyrate naturally occurs in apple fruit and likely contributes to the characteristic aroma of this food. In formulations, it is utilized as both a flavor and fragrance agent, valued for its medium intensity balsamic odor with accompanying fruity and floral notes. The compound is soluble in alcohol and poorly soluble in water, making it suitable for incorporation in various liquid and semi-solid products. Its low volatility and moderate lipophilicity support its substantivity in perfumery and flavor systems.
What regulatory standards and safety information pertain to (E)-cinnamyl butyrate?
(E)-cinnamyl butyrate is regulated under the International Fragrance Association (IFRA) Code of Practice (Global), with recommended usage levels up to 5% in fragrance concentrates and 15 ppm in finished flavor products. Safety assessments classify it as an irritant to eyes, respiratory system, and skin, necessitating appropriate handling measures. It complies with Food Chemical Codex specifications and presents no significant hazards under OSHA HCS (US) classification. Standard safety data sheets provide guidance for occupational exposure and safe use.
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: | 2915.60.0000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | (E)-cinnamyl butyrate |
| Trivial Name | trans-Cinnamyl butyrate |
| Short Description | (E)-3-phenylprop-2-en-1-yl butanoate |
| Formula | C13 H16 O2 |
| CAS Number | 78761-39-4 |
| FDA UNII | TKZ9V37P1G |
| Nikkaji Number | J35.105I |
| Beilstein Number | 3200585 |
| MDL | MFCD00027135 |
| COE Number | 279 |
| xLogP3-AA | 3.10 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| Sigma-Aldrich |
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 204.26892089844 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.404 to 8.446 |
| Refractive Index | 1.525 to 1.53 @ 20 °C |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 3.66 est |
| Solubility | |
| alcohol | Yes |
| water, 22.29 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Balsamic | |
| balsamic, fruity, cinnamyl | |
| Odor strength | medium |
| Substantivity | 152 hour(s) at 100.00 % |
| General comment | At 100.00 %. soft balsam fruity cinnamyl |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple , Crabapple , Balsam , Banana , Floral , Honey , Lily , Lily of the valley , Peach , Pear , Rose , Sweet pea , Tuberose , Valerian , Wisteria |
| Flavoring purposes | Valerian |
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 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. | |
| 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 (E)-cinnamyl butyrate usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Recommendation for (E)-cinnamyl butyrate flavor usage levels up to: | |||
| 15.0000 ppm in the finished product. | |||
Safety references
| 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 :5355254 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| [(E)-3-phenylprop-2-enyl] butanoate |
| Chemidplus:0000103617 |
| RTECS:ES8815000 for cas# 78761-39-4 |