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ethyl hydrocinnamate
Ethyl hydrocinnamate is a floral ester with honey and fruity notes, widely used as a flavor and fragrance agent.
General Material Description
Ethyl hydrocinnamate, also known by its trivial name ethyl 3-phenylpropanoate, is a synthetic organic ester with the molecular formula C11H14O2. It appears as a clear liquid and features a characteristic floral aroma with notes reminiscent of honey, hyacinth, and fruity rum accords. This compound is referenced under various synonyms, including hydrocinnamic acid ethyl ester and ethyl dihydrocinnamate. Its chemical structure comprises an ethyl ester of 3-phenylpropanoic acid, linking an aromatic ring and a propionate moiety. Ethyl hydrocinnamate is typically sourced synthetically but can be identified as a minor constituent in essential oils such as labdanum and cistus oil. For comprehensive molecular information, see the PubChem entry.
Occurrence, Applicability & Potential Uses
Ethyl hydrocinnamate occurs naturally at low levels in certain essential oils including cistus and vassoura oils, as well as in fermented beverages like rum, contributing to their complex aroma profiles. Its primary utility lies in the flavor and fragrance industry, where it enhances floral, honey-like, and fruity notes in various consumer products. The agent is employed to evoke scents reminiscent of lilac, lily of the valley, linden flower, and sweet pea, among others. Regulatory frameworks such as FEMA (US) recognize ethyl hydrocinnamate under FEMA number 2455, allowing its use as a flavoring substance within defined concentration limits. Compliance with IFRA (Global) guidelines ensures safe usage in perfumery formulations.
Physico-Chemical Properties Summary
Ethyl hydrocinnamate exhibits moderate volatility with a boiling point range of 247 to 249 °C at standard atmospheric pressure (760 mm Hg). Its measured vapor pressure at 25 °C is low, approximately 0.028 mmHg, indicating limited evaporation under ambient conditions. The compound is a liquid at room temperature, possessing a specific gravity between 1.015 and 1.017 and a refractive index ranging from 1.493 to 1.495 at 20 °C. A log P value of 2.73 suggests significant lipophilicity, favoring solubility in organic solvents including alcohols. Flash point measurement indicates thermal stability up to 107 °C (226 °F) before ignition risk increases. These physicochemical characteristics influence its behavior in fragrance blends and flavor matrices, facilitating formulation with both hydrophobic and slightly polar components.
FAQ
What is ethyl hydrocinnamate and what are its primary characteristics?
Ethyl hydrocinnamate is an organic ester chemically known as ethyl 3-phenylpropanoate. It is a clear liquid recognized for its floral scent combining honey, hyacinth, and fruity rum nuances. The compound is widely utilized in flavor and fragrance industries due to its pleasant aroma profile. Structurally, it consists of an ethyl ester group attached to a 3-phenylpropanoic acid backbone, contributing to its characteristic sensory attributes.
Where is ethyl hydrocinnamate found naturally and how is it used in industry?
Natural occurrence of ethyl hydrocinnamate is noted in small concentrations within essential oils such as cistus and vassoura, as well as in rum. Industrially, it is synthesized and primarily used as a flavor and fragrance agent to impart floral and fruity notes to consumer products. Its applications span perfumes, cosmetics, and food flavorings, where it enhances scents associated with flowers like lilac and lily of the valley, and sweet pea.
What regulatory standards govern the use and safety of ethyl hydrocinnamate?
Ethyl hydrocinnamate is recognized by FEMA (US) under number 2455 as a flavoring substance with established usage limits. It is subject to safety assessments by organizations such as IFRA, which provide guidelines to ensure safe levels in fragrance formulations globally. Toxicity data indicate no classified hazards under OSHA or GHS standards, but standard precautions include avoiding contact with skin and eyes. Its use conforms to regulatory frameworks that monitor flavor and fragrance ingredient safety.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| PubMeb | Start search |
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Literature & References
| ethyl 3-phenylpropanoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 2021-28-5 |
| Pubchem (cid): | 16237 |
| Pubchem (sid): | 134981877 |
| Flavornet: | 2021-28-5 |
| Pherobase: | View |
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 |
| HMDB (The Human Metabolome Database): | HMDB40411 |
| FooDB: | FDB020143 |
| YMDB (Yeast Metabolome Database): | YMDB01690 |
| Export Tariff Code: | 2916.39.7900 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | ethyl hydrocinnamate |
| Trivial Name | Ethyl 3-phenylpropanoate |
| Short Description | ethyl 3-phenylpropionate |
| Formula | C11 H14 O2 |
| CAS Number | 2021-28-5 |
| FEMA Number | 2455 |
| Flavis Number | 9.747 |
| ECHA Number | 217-966-6 |
| FDA UNII | 58E9Z9V64D |
| Nikkaji Number | J136.534G |
| Beilstein Number | 1910432 |
| MDL | MFCD00009206 |
| COE Number | 429 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 644 ethyl 3-phenylpropionate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 2021-28-5 ; ETHYL 3-PHENYLPROPIONATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 178.23098754883 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.456 to 8.472 |
| Refractive Index | 1.493 to 1.495 @ 20 °C |
| Boiling Point | 247 to 249°C @ 760 mm Hg |
| Vapor Pressure | 0.028 mmHg @ 25 °C |
| Flash Point TCC Value | 107.78 °C TCC |
| logP (o/w) | 2.73 |
| Solubility | |
| alcohol | Yes |
| water, 220 mg/L @ 25 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Floral | |
| hyacinth, rose, honey, fruity, rummy | |
| Luebke, William tgsc, (1988) | At 100.00 %. hyacinth rose honey fruity rum |
| General comment | Labdanum, Honney Fruity rum |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Honey , Hyacinth , Lilac , Lily of the valley , Linden flower , Lotus , Oriental , Reseda , Sweet pea |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| None - None found. | |
| S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. | |
| 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 ethyl hydrocinnamate usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.20 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.07 (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: | 0.50000 | 3.00000 | |
| beverages(nonalcoholic): | - | 1.80000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 1.00000 | |
| fruit ices: | - | 1.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 2.50000 | |
| 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 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 |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):2021-28-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :16237 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| ethyl 3-phenylpropanoate |
| Chemidplus:0002021285 |
| EPA/NOAA CAMEO:hazardous materials |