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4-penten-1-yl acetate
4-penten-1-yl acetate is an acetate ester notable for its green, fruity aroma and use primarily as a flavoring agent in foods and beverages.
General Material Description
4-penten-1-yl acetate is a synthetic acetate ester with the molecular formula C7H12O2. It appears as a colorless to pale liquid and possesses a distinct green, fruity odor reminiscent of fresh vegetables and ripe mango. Also known by synonyms such as acetic acid pent-4-en-1-yl ester and pent-4-enyl acetate, this compound features a pentene chain esterified with acetic acid. The compound is registered under CAS number 1576-85-8 and included in the chemical database CHEBI (Chemical Entities of Biological Interest). Typically sourced through chemical synthesis, 4-penten-1-yl acetate can also be found naturally in some fruits, such as mangaba. Its pleasant green and fruity sensory profile makes it valuable in flavor formulations.
Occurrence, Applicability & Potential Uses
4-penten-1-yl acetate occurs naturally in certain tropical fruits including mangaba, contributing to their characteristic aroma. Its green vegetable and fruity odor profile is utilized by the flavor industry chiefly as a flavoring agent in products such as coffee, caramel, cappuccino, and certain fruit-flavored beverages. The compound imparts notes of green grass, mango, and vegetable freshness, enhancing complex food flavors. Recognized under FEMA number 4011, 4-penten-1-yl acetate is evaluated for safety and usage according to FEMA (US) guidelines. Usage levels are carefully controlled to comply with regulatory standards, ensuring its function as a flavor additive without adverse effects.
Physico-Chemical Properties Summary
4-penten-1-yl acetate is a moderately volatile liquid with a boiling point range of 144 to 146°C at standard atmospheric pressure. Its vapor pressure at 25°C is approximately 4.96 mmHg, indicating moderate evaporation tendency at room temperature. The estimated logP value of about 1.89 suggests moderate lipophilicity, favoring solubility in organic solvents such as alcohols and propylene glycol, with limited water solubility reported around 1233 mg/L at 25°C. The flash point is reported near 45°C (converted from 113°F), signifying flammable characteristics. These physicochemical parameters influence its handling, formulation, and stability within food and flavor products.
FAQ
What is 4-penten-1-yl acetate and what are its primary sensory characteristics?
4-penten-1-yl acetate is an acetate ester with the molecular formula C7H12O2, used predominantly as a flavoring agent. It exhibits a strong green odor described as fresh, plastic, and weedy with fruity and vegetable undertones. In flavor applications, it contributes green, sweet, and mango-like notes, often enhancing the aroma profiles of foods and beverages.
Where does 4-penten-1-yl acetate occur naturally and how is it applied in flavor formulations?
This compound naturally occurs in certain fruits such as mangaba and is responsible for some of their distinctive aromas. Industrially, it is synthesized for use in flavor formulations, especially in coffee, caramel, cappuccino flavors, and fruit-related products. Its pleasant green and fruity scent properties make it suitable for enhancing complex flavor blends.
What safety regulations and usage guidelines apply to 4-penten-1-yl acetate in flavor applications?
4-penten-1-yl acetate is regulated under FEMA (US) with FEMA number 4011 and evaluated by JECFA for use as a flavoring agent. Usage levels are limited and monitored to ensure safety, with maximum recommended concentrations provided for various food categories such as baked goods and beverages. Safety assessments do not indicate significant toxicological hazards at regulated use levels, but the compound is classified as flammable and harmful to aquatic organisms, requiring caution during handling and environmental release.
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): | HMDB32460 |
| FooDB: | FDB010037 |
| Export Tariff Code: | 2915.39.4550 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 4-penten-1-yl acetate |
| Trivial Name | 4-Penten-1-yl acetate |
| Short Description | 4-pentenyl acetate |
| Formula | C7 H12 O2 |
| CAS Number | 1576-85-8 |
| FEMA Number | 4011 |
| Flavis Number | 9.917 |
| ECHA Number | 216-413-6 |
| FDA UNII | V4SIF0MABV |
| Nikkaji Number | J118.111D |
| Beilstein Number | 1747236 |
| MDL | MFCD00008723 |
| xLogP3-AA | 1.60 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1270 4-pentenyl acetate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 1576-85-8 ; 4-PENTENYL ACETATE |
| Synonyms |
|
Suppliers
| BOC Sciences | Endeavour Specialty Chemicals |
| Penta International | Robinson Brothers |
| Santa Cruz Biotechnology | TCI AMERICA |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 128.1710357666 |
| Boiling Point | 144 to 146°C @ 760 mm Hg |
| Vapor Pressure | 4.96 mmHg @ 25 °C |
| Flash Point TCC Value | 45 °C TCC |
| logP (o/w) | 1.892 est |
| Solubility | |
| alcohol | Yes |
| propylene glycol | Yes |
| water, 1233 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Green | |
| green, plastic, weedy, acrylate, vegetable, metallic, cooked, meaty, sulfurous | |
| Odor strength | high , recommend smelling in a 1.00 % solution or less |
| Substantivity | < 1 hour(s) at 100.00 % |
| Luebke, William tgsc, (2006) | At 1.00 % in dipropylene glycol. green plastic weedy acrylate vegetable metallic cooked meat sulfide |
| Flavor Type: Green | |
| sweet, green, vegetable, weedy, plastic, grassy, hay | |
| Luebke, William tgsc, (2006) | At 10.00 ppm in water. sweet green vegetable weedy plastic grassy hay |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Floral , Green grass , Green grass |
| Flavoring purposes | Cappuccino , Caramel , Coffee , Green , Mango , Vegetable |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn N - Harmful, Dangerous for the environment. | |
| R 10 - Flammable. R 22 - Harmful if swallowed. R 41 - Risk of serious damage to eyes. R 50 - Very toxic to aquatic organisms. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 39 - Wear eye/face protection. S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet. | |
| 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 4-penten-1-yl acetate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 3.40 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 4.00 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | ND (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: 20 | |||
| Click here to view publication 20 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 20.00000 | 40.00000 | |
| beverages(nonalcoholic): | 8.00000 | 16.00000 | |
| beverages(alcoholic): | 8.00000 | 16.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 100.00000 | 200.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 16.00000 | 32.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 20.00000 | 50.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | 10.00000 | 20.00000 | |
| 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): |
| 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 |
| Flavouring Group Evaluation 62 Rev1 (FGE.62 Rev1): Consideration of of linear and branched-chain aliphatic unsaturated, unconjugated alcohols, aldehydes, acids, and related esters evaluated by JECFA (61st and 68th meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids and esters of these with aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010) and to straight- and branched-chain aliphatic unsaturated primary alcohols, aldehydes, carboxylic acids, and esters evaluated by EFSA in FGE.06Rev1 (2008) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :74096 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3272 |
| WGK Germany:3 |
| pent-4-enyl acetate |
| Chemidplus:0001576858 |