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ethyl cinnamate
Ethyl cinnamate is a naturally occurring ester with a balsamic, fruity aroma used primarily as a flavor and fragrance agent.
General Material Description
Ethyl cinnamate is an organic ester with the molecular formula C11H12O2, known chemically as ethyl 3-phenyl-2-propenoate. It appears as a clear liquid with a characteristic balsamic, sweet, and fruity aroma profile. This compound is also known by various synonyms including cinnamic acid ethyl ester and ethyl cinnamate natural. It is widely used as a flavor and fragrance ingredient due to its pleasant sensory characteristics. Ethyl cinnamate naturally occurs in botanical sources such as cinnamon bark, clove, and several fruits like peach, passion fruit, and guava. It can be sourced through extraction from natural materials or produced synthetically. For detailed chemical information, the compound is indexed on PubChem.
Occurrence, Applicability & Potential Uses
Ethyl cinnamate is found naturally in a variety of botanical sources including cinnamon bark and leaf oils, clove, cassia plants, and numerous fruits such as peach, passion fruit, guava, and wild strawberry. Its presence in these sources contributes to their characteristic aromas. In the flavor and fragrance industry, ethyl cinnamate serves as a key ingredient, imparting balsamic, fruity, sweet, powdery, and spicy notes. Its use is documented by standards such as FEMA (US), where it is identified as FEMA Number 2430 and recognized for flavor and fragrance applications. The compound is applied in perfuming agents and also functions as a fixer to enhance fragrance longevity. Additionally, ethyl cinnamate has utility as a UV absorber in cosmetic formulations, reflecting its broad applicability across sensory and functional categories.
Physico-Chemical Properties Summary
Ethyl cinnamate exhibits physicochemical properties that influence its application in formulations. It is a clear liquid with a melting point between 6 and 7.5°C and a boiling point range of 271 to 272°C at standard atmospheric pressure. At reduced pressure (24 mm Hg), it boils at approximately 158 to 159°C. The compound possesses a specific gravity near 1.045 to 1.048 at 25°C and a refractive index ranging from 1.559 to 1.561 at 20°C. Its vapor density is relatively high at 6, with a low vapor pressure of 0.00327 mmHg at 25°C, indicating low volatility under ambient conditions. Ethyl cinnamate is soluble in alcohol and fixed oils but has limited solubility in water and glycerin, restricting use in aqueous systems. It demonstrates stability without discoloration in most media. The compound has a flash point of 230°F (approximately 110°C), supporting safe handling under standard conditions if stored appropriately. Storage recommendations include keeping it in a cool, dry place, protected from heat and light. These properties make ethyl cinnamate suitable for use in diverse flavor and fragrance applications requiring moderate volatility and stability.
FAQ
What is ethyl cinnamate and what are its main characteristics?
Ethyl cinnamate is an organic ester chemically known as ethyl 3-phenyl-2-propenoate with molecular formula C11H12O2. It possesses a clear liquid form with a sweet, balsamic, fruity, and spicy aroma profile. This compound naturally occurs in various plants, including cinnamon and clove, as well as several fruits. It is primarily used as a flavor and fragrance ingredient to impart these characteristic sensory notes.
Where does ethyl cinnamate occur naturally and how is it used in industry?
Ethyl cinnamate occurs naturally in many botanical sources such as cinnamon bark and leaf oils, clove, cassia, and fruits including peach, passion fruit, guava, and wild strawberry. In industry, it is utilized mainly in flavor and fragrance formulations, contributing balsamic, sweet, fruity, and spicy notes. The compound also acts as a fragrance fixer and is employed as a UV absorber in cosmetic products, reflecting its versatility across different applications.
What regulatory standards and safety considerations apply to ethyl cinnamate?
Ethyl cinnamate is recognized by FEMA (US) as FEMA Number 2430 for flavor and fragrance use and is listed as a Generally Recognized as Safe (GRAS) substance. The IFRA Code of Practice (Global) defines recommended usage levels to ensure consumer safety. Safety data classify it as an irritant requiring proper handling to avoid skin and eye contact. Maximum usage levels in fragrance concentrates typically do not exceed 8%, with lower limits in consumer products to minimize risk. Comprehensive evaluations by authorities such as EFSA (EU) and JECFA support its safe use under regulated conditions.
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 |
| CHEMBL: | View |
| KEGG (GenomeNet): | C06359 |
| HMDB (The Human Metabolome Database): | HMDB33834 |
| FooDB: | FDB012002 |
| YMDB (Yeast Metabolome Database): | YMDB01689 |
| Export Tariff Code: | 2916.39.7900 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | ethyl cinnamate |
| Trivial Name | Ethyl cinnamate |
| Short Description | ethyl 3-phenyl-2-propenoate |
| Formula | C11 H12 O2 |
| CAS Number | 103-36-6 |
| FEMA Number | 2430 |
| ECHA Number | 203-104-6 |
| FDA UNII | C023P3M5JJ |
| Beilstein Number | 0775541 |
| MDL | MFCD00009189 |
| COE Number | 323 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 659 ethyl cinnamate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 103-36-6 ; ETHYL CINNAMATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 176.21504211426 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.695 to 8.72 |
| Refractive Index | 1.559 to 1.561 @ 20 °C |
| Melting Point | 6 to 7.5°C @ 760 mm Hg |
| Boiling Point | 271 to 272°C @ 760 mm Hg |
| Boiling Point | 158 to 159°C @ 24 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.00327 mmHg @ 25 °C |
| Vapor Density | 6 |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.99 |
| Shelf life | 24 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 |
| water, 160.6 mg/L @ 25 °C (est) | Yes |
| water | No |
| glycerin | No |
| Stability | |
| non-discoloring in most media | Unspecified |
Organoleptic Properties
| Odor Type: Balsamic | |
| sweet, balsamic, fruity, spicy, powdery, berry, plum, cinnamyl | |
| Odor strength | medium |
| Substantivity | 400 hour(s) at 100.00 % |
| Luebke, William tgsc, (1982) | At 100.00 %. sweet balsam fruity spicy powdery berry plum |
| Mosciano, Gerard P&F 23, No. 2, 43, (1998) | Sweet, balsamic, spice, cinnamic, fruity and powdery |
| Flavor Type: Balsamic | |
| balsamic, powdery, fruity, berry, spicy, sweet, green | |
| Mosciano, Gerard P&F 23, No. 2, 43, (1998) | At 20.00 ppm. Balsamic, powdery, fruity, berry, punch, spice, sweet and green |
| General comment | Sweet fruity spice powdery vanilla floral |
| Useful in: brown cocoa, brown others, fruity red, fruity yellow, fruity tropical, sweet others, alcoholics. | Cinnamon, sweet, balsamic, fruity |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Almond , Amber , Apricot , Balsam , Benzoinett , Berry , Cherry , Cherry blossom , Chypre , Cinnamon , Clary sage oil replacer , Currant , Fern , Floral , Grape , Guava , Honey , Jasmin , Lavender , Lavender flower , Narcissus , Oriental , Passion fruit , Peach , Pear , Plum , Powder , Raspberry , Rose , Spice , Strawberry , Vanilla , Woody |
| Flavoring purposes | Lavender flower , Nut |
| Other purposes | Fixer |
| Cosmetic purposes | Perfuming agents , Uv absorbers |
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) | |
| Acute toxicity, Oral (Category 4), H302 | |
| GHS Label elements, including precautionary statements | |
| Pictogram |  |
| Signal word | Warning |
| Hazard statement(s) | |
| H302 - Harmful if swallowed | |
| Precautionary statement(s) | |
| P264 - Wash skin thouroughly after handling. P270 - Do not eat, drink or smoke when using this product. P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P330 - Rinse mouth. P501 - Dispose of contents/ container to an approved waste disposal plant. | |
| Human Experience: | |
| 4 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-mouse LD50 4000 mg/kg Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974. oral-guinea pig LD50 4000 mg/kg Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974. oral-rat LD50 4000 mg/kg Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 12, Pg. 719, 1974. | |
| 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 | |||
| maximum skin levels for fine fragrances: | |||
| 0.1300 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2001) | |||
| Recommendation for ethyl cinnamate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| use level in formulae for use in cosmetics: | |||
| 0.0130 % | |||
| Dermal Systemic Exposure in Cosmetic Products: | |||
| 0.0003 mg/kg/day (IFRA, 2001) | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 89.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 70.00 (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: | - | 12.00000 | |
| beverages(nonalcoholic): | - | 4.10000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 11.00000 | 40.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 8.80000 | |
| fruit ices: | - | 8.80000 | |
| gelatins / puddings: | - | 2.40000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 9.50000 | |
| 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 55 (FGE.55): Consideration of phenyl-substituted aliphatic alcohols and related aldehydes and esters evaluated by JECFA (63rd meeting) structurally related to phenethyl alcohol, aldehyde, esters and related phenylacetic acid esters evaluated by EFSA in FGE.14 (2005) and aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives evaluated by EFSA in FGE.15 (2005) (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 |
| 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):103-36-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7649 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:1 |
| ethyl 3-phenylprop-2-enoate |
| Chemidplus:0000103366 |
| RTECS:GD9010000 for cas# 103-36-6 |