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ethyl (E)-2-hexenoate
ethyl (E)-2-hexenoate is an ester compound with a green, fruity odor widely used as a flavor and fragrance agent in food and beverage applications.
General Material Description
ethyl (E)-2-hexenoate is an organic ester with the molecular formula C8H14O2, known for its clear liquid appearance and distinctive green, fruity aroma. Also referred to by synonyms such as ethyl trans-2-hexenoate and rum hexenoate, this compound exhibits sensory descriptors including sweet, tropical fruit notes reminiscent of papaya, guava, and passion fruit. It belongs to the class of aliphatic esters widely used in the flavor and fragrance industries. The compound is naturally present in various fruits, including blackberry, guava, and quince, and in alcoholic beverages such as brandy and wine. It can be sourced by extraction from natural materials or synthesized chemically. For detailed chemical information, see its ChEBI entry.
Occurrence, Applicability & Potential Uses
ethyl (E)-2-hexenoate naturally occurs in a range of fruits such as blackberry, guava, quince, passion fruit, and tropical fruit varieties, as well as in fermented beverages including brandy, red and white wines, and concord grape products. Its aroma and flavor profile, characterized by green, fruity, and tropical notes, render it useful in flavor and fragrance formulations. The compound is utilized predominantly to impart fruity and green nuances in beverage and confectionery flavorings, often in rum and alcoholic flavor blends. Usage levels and safety are governed under FEMA (US) flavoring regulations and the IFRA (Global) Code of Practice, which provide guidelines for safe inclusion rates in consumer products.
Physico-Chemical Properties Summary
ethyl (E)-2-hexenoate exhibits physicochemical attributes influencing its performance in formulations, including a molecular weight of approximately 142.2 g/mol and a moderate estimated logP of 2.8 indicating lipophilicity suitable for oil-based and alcoholic matrices. It has a boiling range of 182 to 183 B0C at atmospheric pressure and a vapor pressure of about 1.3 mmHg at 25 B0C, evidencing moderate volatility that supports its olfactory presence while maintaining persistence. Its specific gravity ranges from 0.894 to 0.9 at 25 B0C, and the refractive index lies between 1.431 and 1.438 at 20 B0C, which helps characterize purity and concentration. Solubility is good in alcohols and slight in water, facilitating incorporation in diverse flavor and fragrance formulations. The flash point is approximately 54 B0C (130 B0F), indicating moderate flammability precautions during handling.
FAQ
What is ethyl (E)-2-hexenoate and what are its main sensory characteristics?
ethyl (E)-2-hexenoate is a chemical ester widely used as a flavor and fragrance ingredient. It is characterized by a distinctive green, fruity odor profile with nuances of tropical fruits like papaya, guava, and passion fruit. Sensory evaluations describe it as sweet and juicy, offering a fresh and rummy aroma that contributes to various fruit and beverage flavors.
Where is ethyl (E)-2-hexenoate commonly found and how is it used in flavor formulations?
This compound occurs naturally in fruits such as blackberry, quince, guava, and passion fruit, as well as in alcoholic beverages including brandy and wines. Its fruity and green aroma makes it a valuable ingredient in flavor formulations, especially in rum and tropical fruit flavorings. It is used to enhance or recreate natural fruit notes in food, beverages, and fragrance products.
What regulatory standards apply to ethyl (E)-2-hexenoate and how is its safety assessed?
ethyl (E)-2-hexenoate is regulated under FEMA (US) guidelines as a generally recognized as safe (GRAS) flavoring substance. The International Fragrance Association (IFRA) also provides usage recommendations for this compound in fragrances, limiting concentrations to ensure consumer safety. Toxicological evaluations indicate low acute toxicity, though standard safety measures include avoiding skin and eye contact and handling under proper conditions due to its irritant and flammable properties.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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 |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | HMDB32268 |
| FooDB: | FDB017564 |
| Export Tariff Code: | 2916.19.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | ethyl (E)-2-hexenoate |
| Trivial Name | Ethyl trans-2-hexenoate |
| Short Description | ethyl trans-2-hexenoate |
| Formula | C8 H14 O2 |
| CAS Number | 27829-72-7 |
| FEMA Number | 3675 |
| Flavis Number | 9.85 |
| ECHA Number | 248-681-5 |
| FDA UNII | OL4EUZ6C13 |
| Nikkaji Number | J250.597E |
| COE Number | 631 |
| xLogP3-AA | 2.30 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1808 ethyl trans-2-hexenoate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 27829-72-7 ; ETHYL TRANS-2-HEXENOATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 142.19798278809 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.439 to 7.489 |
| Refractive Index | 1.431 to 1.438 @ 20 °C |
| Boiling Point | 110 to 111°C @ 10 mm Hg |
| Boiling Point | 182 to 183°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 1.322 mmHg @ 25 °C |
| Vapor Density | 4.8 |
| Flash Point TCC Value | 54.44 °C TCC |
| logP (o/w) | 2.825 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 480.5 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Green | |
| green, fruity, tropical, juicy, papaya, quince, winey, rummy, orange, vegetable, sweet | |
| Odor strength | medium |
| Substantivity | > 1 hour(s) at 100.00 % |
| Luebke, William tgsc, (2021) | At 100.00 %. green fruity tropical juicy papaya quince winey rummy orange vegetable |
| Mosciano, Gerard P&F 18, No. 1, 43, (1993) | Sweet, green, fruity with a vegetative nuance |
| Flavor Type: Fruity | |
| fruity, green, juicy, juicy fruit, tropical, papaya, kiwi, licorice, vegetable, sweet | |
| Luebke, William tgsc, (2021) | Fruity green juicy juicy fruit tropical papaya kiwi licorice vegetable |
| Mosciano, Gerard P&F 18, No. 1, 43, (1993) | At 10.00 ppm. Fruity, green, sweet, with a juicy fruity undernote |
| Mostly used in rum and alcoholic flavors, can also be used in other fruity applications | Fruity |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple , Banana , Grape , Green , Guava , Papaya , Passion fruit , Pineapple , Quince , Raspberry , Saffron , Strawberry |
| Flavoring purposes | Fruit tropical fruit |
| Other purposes | Grass |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 10 - Flammable. 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 36/37/39 - Wear suitable clothing, gloves and eye/face protection. | |
| 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: | |
| oral-mouse LD50 > 8000 mg/kg | |
| 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 (E)-2-hexenoate usage levels up to: | |||
| 5.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 21.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.02 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 3900 (μg/person/day) | ||
| Threshold of Concern: | 1800 (μg/person/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: 13 | |||
| Click here to view publication 13 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 12.00000 | |
| beverages(nonalcoholic): | - | 0.50000 | |
| beverages(alcoholic): | - | 1.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 10.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | 3.00000 | |
| gelatins / puddings: | - | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 5.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | 2.50000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 7.00000 | 35.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 5.00000 | 25.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 10.00000 | 50.00000 | |
| Processed fruit (04.1): | 7.00000 | 35.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 10.00000 | 50.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 5.00000 | 25.00000 | |
| Bakery wares (07.0): | 10.00000 | 50.00000 | |
| Meat and meat products, including poultry and game (08.0): | 2.00000 | 10.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 2.00000 | 10.00000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 25.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 10.00000 | 50.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 5.00000 | 25.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 10.00000 | 50.00000 | |
| Ready-to-eat savouries (15.0): | 20.00000 | 100.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 5.00000 | 25.00000 | |
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): |
| Scientific Opinion on Flavouring Group Evaluation 95 (FGE.95): Consideration of aliphatic, linear or branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (69th meeting) structurally related to esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids evaluated by EFSA in FGE.05Rev1 (2008) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):27829-72-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5364778 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3272 |
| WGK Germany:2 |
| ethyl (E)-hex-2-enoate |
| Chemidplus:0027829727 |