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ethyl (E)-3-hexenoate
Ethyl (E)-3-hexenoate is a fruity ester compound with applications in flavors and fragrances, naturally found in muskmelon and passion fruit.
General Material Description
Ethyl (E)-3-hexenoate is an organic ester characterized by the molecular formula C8H14O2. It appears as a liquid with a distinctive fruity odour profile reminiscent of green fruit notes such as passion fruit, guava, and pineapple. This compound, also known by several synonyms including ethyl (3E)-hex-3-enoate and trans-3-hexenoic acid ethyl ester, is included in the controlled-vocabulary classification of esters linked at CHEBI:87560. It is naturally sourced from various fruits, including muskmelon and strawberry guava, and is widely synthesized for use in flavor and fragrance industries.
Occurrence, Applicability & Potential Uses
Ethyl (E)-3-hexenoate occurs naturally in fruits such as muskmelon, passion fruit, and strawberry guava, contributing to their characteristic aromas. Its fruity scent, described as sweet green with notes of passion fruit, pineapple, and honey, makes it valuable for flavoring applications. It is employed as a flavor and fragrance agent in various products to impart fruity and brandy-like notes, particularly in formulations resembling apple brandy, apricot brandy, and other fruit brandies. Cosmetic industries also utilize this ester as a perfuming agent. The compound's uses comply with standards such as FEMA (US Flavor and Extract Manufacturers Association), which regulates flavoring substances for safety and usage levels.
Physico-Chemical Properties Summary
Ethyl (E)-3-hexenoate exhibits a molecular weight of approximately 142.2 g/mol and a formula of C8H14O2. It has a boiling point ranging from 169 to 170 °C at standard atmospheric pressure (760 mm Hg), reflecting moderate volatility suitable for both flavor and fragrance applications. The compound has a specific gravity of 0.896 at 25 °C and a vapor pressure of about 1.553 mmHg at the same temperature, indicating moderate evaporation rate. Its estimated logP is 2.59, suggesting lipophilicity compatible with formulation in oils and alcohols; it is readily soluble in alcohol but has limited water solubility (approximately 480 mg/L at 25 °C). The flash point is reported as 139 °F (approximately 59.4 °C), underscoring considerations for safe handling and storage during manufacturing.
FAQ
What is ethyl (E)-3-hexenoate and what are its main characteristics?
Ethyl (E)-3-hexenoate is an organic ester known for its fruity aroma, resembling passion fruit, guava, and pineapple notes. It is a liquid with the molecular formula C8H14O2 and is naturally present in some fruits such as muskmelon and passion fruit. This compound is used primarily in flavor and fragrance applications where its sweet, green, fruity qualities are desired.
Where does ethyl (E)-3-hexenoate occur naturally and how is it used in industry?
Ethyl (E)-3-hexenoate is found naturally in fruits including muskmelon, passion fruit, and strawberry guava. Industrially, it is used as a flavoring agent to provide fruity and apple brandy-like notes in foods and beverages. Additionally, it serves as a perfuming agent in cosmetic products. The compound's fruity and slightly rummy characteristics make it suitable for adding complexity to various flavor and fragrance formulations.
What regulatory standards apply to ethyl (E)-3-hexenoate and how is it sourced?
Ethyl (E)-3-hexenoate is regulated under FEMA (US), which supervises the use of flavoring substances to ensure safety and appropriate usage levels in food products. The compound is recognized as generally safe for flavoring purposes within defined limits. It can be sourced naturally from fruit extracts or produced synthetically for commercial applications. Safety data indicates no significant hazards according to OSHA HCS, and it is commonly assessed by organizations such as RIFM and included in IFRA guidelines for fragrance 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 |
Literature & References
| ethyl (E)-hex-3-enoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 26553-46-8 |
| Pubchem (cid): | 5362622 |
| Pubchem (sid): | 135017587 |
| Publications by PubMed | |
| Characteristic aroma compounds from different pineapple parts. | |
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 |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | HMDB32266 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | ethyl (E)-3-hexenoate |
| Trivial Name | Ethyl (E)-3-hexenoate |
| Short Description | ethyl trans-3-hexenoate |
| Formula | C8 H14 O2 |
| CAS Number | 26553-46-8 |
| FEMA Number | 3342 |
| ECHA Number | 247-798-9 |
| FDA UNII | U53D99S694 |
| Nikkaji Number | J126.495H |
| MDL | MFCD00036524 |
| xLogP3-AA | 1.90 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
Suppliers
| BOC Sciences | EGNO Chimie |
| FCI SAS | Jiangyin Healthway |
| Kingchem Laboratories | Lluch Essence |
| Santa Cruz Biotechnology | Sigma-Aldrich: Aldrich |
| Synerzine | Jiangyin Healthway International Trade Co., Ltd |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 142.19798278809 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Boiling Point | 169 to 170°C @ 760 mm Hg |
| Boiling Point | 63 to 64°C @ 12 mm Hg |
| Vapor Pressure | 1.553 mmHg @ 25 °C |
| Flash Point TCC Value | 59.44 °C TCC |
| logP (o/w) | 2.59 est |
| Solubility | |
| alcohol | Yes |
| water, 480.5 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fruity | |
| green, fruity, passion fruit, guava, pineapple, papaya, weedy, honey | |
| Luebke, William tgsc, (2017) | At 100.00 %. sweet green fruity passion fruit guava pineapple papaya weedy honey |
| Flavor Type: Fruity | |
| fruity, green, passion fruit, pineapple, rummy, honey, papaya, weedy | |
| Luebke, William tgsc, (2017) | Sweet fruity green passion fruit pineapple rummy honey papaya weedy |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apple green apple , Fig , Guava |
| Flavoring purposes | Brandy apple brandy , Brandy , Brandy apricot brandy , Brandy cherry brandy , Brandy grape brandy , Brandy pear brandy , Brandy plum brandy |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| 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 | |||
| 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: 6 | |||
| Click here to view publication 6 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 4.00000 | |
| beverages(nonalcoholic): | - | 2.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 2.00000 | |
| fruit ices: | - | 2.00000 | |
| gelatins / puddings: | - | 2.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 4.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 2.00000 | |
| 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
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):26553-46-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5362622 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| ethyl (E)-hex-3-enoate |
| Chemidplus:0026553468 |