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(E)-3-hexen-1-yl crotonate
(E)-3-hexen-1-yl crotonate is an ester compound known for its green, fresh odor and application as a flavoring agent in various food products.
General Material Description
(E)-3-hexen-1-yl crotonate is an ester compound featuring the molecular formula C10H16O2. It is also known by several synonyms including (3E)-3-Hexen-1-yl (2E)-2-butenoate and trans-3-hexenyl crotonate. This compound exhibits a green, fresh, and slightly metallic odor profile at 100% concentration. Classified as a flavoring ester, it is used predominantly to impart a fresh green note in flavor formulations. Its chemical structure can be found in controlled-vocabulary databases such as PubChem. Typically, this compound is sourced or synthesized for use in food flavoring industries, contributing characteristic herbaceous attributes.
Occurrence, Applicability & Potential Uses
(E)-3-hexen-1-yl crotonate naturally occurs as a volatile compound contributing to the aroma profile in various plants and fruits. It finds primary application as a flavoring agent, recognized by standard bodies including FEMA (US) which governs flavor additive use. The compound delivers green and fresh sensory notes, making it valuable in food flavor formulations such as beverages, confectionery, and savory products. Its inclusion adheres to regulatory frameworks that guide safe and effective use levels in flavor applications.
Physico-Chemical Properties Summary
(E)-3-hexen-1-yl crotonate is a moderately lipophilic ester with an estimated log P of approximately 3.6, indicating substantial affinity for organic phases. It exhibits a boiling point near 223–224°C at atmospheric pressure and has a refractive index ranging from 1.427 to 1.437 at 20°C. The specific gravity lies between 0.894 and 0.904 at 25°C. The compound’s vapor pressure is low, measured around 0.085 mmHg at 25°C, suggesting limited volatility under ambient conditions. Its solubility profile shows compatibility with alcohols and a modest estimated water solubility at 81.27 mg/L at 25°C, influencing its formulation behavior. The flash point is 96°C (205°F) by Tag closed cup, requiring attention during handling and processing.
FAQ
What is (E)-3-hexen-1-yl crotonate?
(E)-3-hexen-1-yl crotonate is an organic ester compound recognized for its green, fresh odor. It is chemically classified as an ester of crotonic acid and (E)-3-hexen-1-ol. This compound features a molecular formula of C10H16O2, with multiple synonyms including trans-3-hexenyl crotonate. It is utilized primarily as a flavoring agent to impart fresh, herbaceous notes in food products.
How is (E)-3-hexen-1-yl crotonate used and where is it found?
(E)-3-hexen-1-yl crotonate naturally occurs in plants contributing to their characteristic green aroma. It is commonly used in flavor formulations within the food industry to add green, fresh sensory attributes. Recognized under flavoring agent applications, it is important in beverages, confections, and savory flavors. Its use is generally limited to flavorings and not indicated for fragrance applications.
What regulations and safety information apply to (E)-3-hexen-1-yl crotonate?
This ester is evaluated under regulatory frameworks such as FEMA (US) for flavoring agents. It poses no significant hazard classification under OSHA HCS standards, and no specific precautionary statements are listed. Toxicological data including oral, dermal, and inhalation toxicity remain undetermined. Its usage levels for flavor purposes are defined, with recommendations explicitly excluding fragrance use. Referencing EFSA evaluations provides additional context for its safe application in food flavorings.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| [(E)-hex-3-enyl] (E)-but-2-enoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 6436990 |
| Pubchem (sid): | 135061834 |
| Publications by US Patents | |
| 8,183,200 - Organoleptic compound | |
| Organoleptic compound | |
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 |
| ChemSpider: | View |
General Material Information
| Preferred name | (E)-3-hexen-1-yl crotonate |
| Trivial Name | (3E)-3-Hexen-1-yl (2E)-2-butenoate |
| Short Description | trans-3-hexenyl crotonate |
| Formula | C10 H16 O2 |
| CAS Number | 68938-58-9 |
| ECHA Number | 273-131-6 |
| FDA UNII | Search |
| Nikkaji Number | J332.767A |
| xLogP3-AA | 2.70 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.2359161377 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.439 to 7.522 |
| Refractive Index | 1.427 to 1.437 @ 20 °C |
| Boiling Point | 223 to 224°C @ 760 mm Hg |
| Vapor Pressure | 0.085 mmHg @ 25 °C |
| Flash Point TCC Value | 96.11 °C TCC |
| logP (o/w) | 3.647 est |
| Solubility | |
| alcohol | Yes |
| water, 81.27 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Green | |
| green, fresh, dirty, chemical, metallic | |
| General comment | At 100.00 %. green, fresh, slightly dirty, chemical, and metallic |
Safety Information
Safety information
| 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: | |||
| flavoring agents | |||
| Recommendation for (E)-3-hexen-1-yl crotonate usage levels up to: | |||
| not for fragrance use. | |||
Safety references
| 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) on a request from the Commission related to Flavouring Group Evaluation 5: Esters of 23 branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and 24 branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 View page or View pdf |
| Flavouring Group Evaluation 5, Revision 1 (FGE.05Rev1):Esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - 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 62 (FGE.62) Consideration of linear and branched-chain aliphatic unsaturated, unconjugated alcohols, aldehydes, acids, and related esters evaluated by JECFA (61st 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.05 (2005) and to straight- and branched-chain aliphatic unsaturated primary alcohols, aldehydes, carboxylic acids, and esters evaluated by EFSA in FGE.06 (2004) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
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| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):68938-58-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6436990 |
| National Institute of Allergy and Infectious Diseases:Data |
| [(E)-hex-3-enyl] (E)-but-2-enoate |
| Chemidplus:0065405803 |