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3-nonen-4-olide
3-nonen-4-olide is a lactone compound employed as a flavor and fragrance agent known for its tropical fruity and milky dairy odor characteristics.
General Material Description
3-nonen-4-olide, also known by its trivial name 5-pentyl-3H-furan-2-one, is a lactone compound characterized by the molecular formula C9H14O2. This chemical is a heterocyclic gamma-lactone that appears as a colorless liquid with a tropical fruity odor complemented by milky dairy nuances at dilute concentrations, such as 10% in dipropylene glycol. Synonyms include 5-amyl-3H-furan-2-one and 4-hydroxy-3-nonenoic acid lactone. 3-nonen-4-olide can be found naturally in aquatic plants like Ceratophyllum demersum and Vallisneria spiralis. This compound is commercially sourced either by extraction from natural origins or chemical synthesis. Detailed chemical and spectral data are available through the PubChem database for reference and identification purposes.
Occurrence, Applicability & Potential Uses
3-nonen-4-olide occurs naturally in aquatic plants such as Ceratophyllum demersum and Vallisneria spiralis, contributing to their characteristic scent profiles. This compound finds specialized application as a flavor and fragrance agent due to its distinctive tropical, fruity, and creamy odor characteristics. Its use is documented across various product categories including baked goods, beverages, confectionery, and other foodstuffs. Regulatory frameworks like FEMA (US) recognize 3-nonen-4-olide with FEMA number 4323 as generally accepted for flavor use, and it is also subject to standards set by IFRA (Global) for fragrance concentration limits. Typical usage levels in fragrance concentrates are recommended not to exceed 0.2% according to the IFRA Code of Practice (Global). Its functional role primarily enhances tropical and creamy notes in formulations.
Physico-Chemical Properties Summary
3-nonen-4-olide is a moderately lipophilic lactone with an estimated logP value near 2.3, reflecting a balance between aqueous solubility and oil affinity that guides its behavior in formulations. It is a colorless liquid at room temperature, with specific gravity ranging from approximately 0.97 to 0.98 g/cm3 at 25 °C. The refractive index lies between 1.447 and 1.459 measured at 20 °C. Its boiling point is relatively high, about 288 to 289 °C at atmospheric pressure (760 mm Hg), while under reduced pressure (1.2 mm Hg), it boils between 73 and 74 °C. Vapor pressure is low at 0.002 mm Hg at 25 °C, indicating low volatility at standard conditions. Solubility is slight in water (estimated ~1450 mg/L at 25 °C) and alcohols, supporting compatibility with both aqueous and organic media. The flash point is reported at 243 °F (~117 °C), suggesting moderate flammability. These characteristics influence its handling, storage, and blending in diverse applications.
FAQ
What is 3-nonen-4-olide and what are its main characteristics?
3-nonen-4-olide is a lactone organic compound with the molecular formula C9H14O2. It is known for its tropical fruity and milky dairy odor and is often used in flavor and fragrance formulations. Also referred to as 5-pentyl-3H-furan-2-one, it naturally occurs in certain aquatic plants. The compound is a colorless liquid that exhibits moderate solubility in water and alcohol, and it has physical properties, such as a boiling point near 288 °C at atmospheric pressure and a low vapor pressure, that are important for formulation scientists.
How is 3-nonen-4-olide used and where does it commonly occur?
3-nonen-4-olide is primarily used as a flavor and fragrance agent to impart tropical, fruity, and creamy notes in a variety of consumer products. It naturally occurs in aquatic plants like Ceratophyllum demersum and Vallisneria spiralis. The compound's applications span across baked goods, beverages, confectionery, perfumes, and personal care formulations. Its physicochemical properties allow it to blend well in both aqueous and oil-based systems, which facilitates its versatility in product development.
What regulations or safety standards apply to 3-nonen-4-olide in flavor and fragrance use?
3-nonen-4-olide is recognized by the FEMA Expert Panel in the US with FEMA number 4323 as a flavoring substance generally regarded as safe (GRAS) at specified levels. The International Fragrance Association (IFRA) (Global) provides guidelines limiting its concentration in fragrance concentrates to 0.2% to ensure safe use. The compound has not been assigned specific hazard classifications under OSHA's Hazard Communication Standard, and toxicity data for oral, dermal, and inhalation routes remain limited or undetermined. Regulatory assessments by EFSA (EU) have also reviewed its safety profile in food applications. Use in food products follows limits detailed in various food categories to comply with safety and quality standards.
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 |
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 |
| HMDB (The Human Metabolome Database): | HMDB32463 |
| FooDB: | FDB010041 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
| FAO: | 5-Pentyl-3H-furan-2-one |
General Material Information
| Preferred name | 3-nonen-4-olide |
| Trivial Name | 5-Pentyl-2(3H)-furanone |
| Short Description | 5-pentyl-3H-furan-2-one |
| Formula | C9 H14 O2 |
| CAS Number | 51352-68-2 |
| FEMA Number | 4323 |
| Flavis Number | 10.17 |
| FDA UNII | MDN0631PBW |
| Nikkaji Number | J1.653.745D |
| xLogP3-AA | 2.50 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1989 5-pentyl-3H-furan-2-one |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 51352-68-2 ; 5-PENTYL-3H-FURAN-2-ONE |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 154.208984375 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.071 to 8.155 |
| Refractive Index | 1.447 to 1.459 @ 20 °C |
| Boiling Point | 288 to 289°C @ 760 mm Hg |
| Boiling Point | 73 to 74°C @ 1.2 mm Hg |
| Vapor Pressure | 0.002 mmHg @ 25 °C |
| Flash Point TCC Value | 117.22 °C TCC |
| logP (o/w) | 2.274 est |
| Solubility | |
| alcohol, slightly | Yes |
| water, slightly | Yes |
| water, 1450 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Tropical | |
| tropical, fruity, milky, dairy | |
| General comment | At 10.00 % in dipropylene glycol. tropical fruity milky dairy |
Occurrences
| (data available) |
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: | |||
| 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 3-nonen-4-olide usage levels up to: | |||
| 0.2000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.20 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 3800 (μg/person/day) | ||
| Threshold of Concern: | 90 (μg/person/day) | ||
| Structure Class: | II | ||
| 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: 23 | |||
| Click here to view publication 23 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 2.00000 | 10.00000 | |
| beverages(nonalcoholic): | 1.00000 | 3.00000 | |
| beverages(alcoholic): | 2.00000 | 10.00000 | |
| breakfast cereal: | 2.00000 | 10.00000 | |
| cheese: | 2.00000 | 10.00000 | |
| chewing gum: | 2.00000 | 10.00000 | |
| condiments / relishes: | 2.00000 | 10.00000 | |
| confectionery froastings: | 1.00000 | 5.00000 | |
| egg products: | - | - | |
| fats / oils: | 2.00000 | 10.00000 | |
| fish products: | - | - | |
| frozen dairy: | 1.00000 | 5.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 1.00000 | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 2.00000 | 10.00000 | |
| imitation dairy: | 1.00000 | 5.00000 | |
| instant coffee / tea: | 2.00000 | 10.00000 | |
| jams / jellies: | 1.00000 | 5.00000 | |
| meat products: | - | - | |
| milk products: | 1.00000 | 5.00000 | |
| nut products: | 0.20000 | 0.20000 | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 100.00000 | 1000.00000 | |
| snack foods: | 1.00000 | 5.00000 | |
| soft candy: | 1.00000 | 5.00000 | |
| soups: | - | - | |
| sugar substitutes: | - | - | |
| sweet sauces: | 1.00000 | 5.00000 | |
| 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): | 5.00000 | 20.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 2.00000 | 10.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 1.00000 | 5.00000 | |
| Processed fruit (04.1): | 1.00000 | 5.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 1.00000 | 5.00000 | |
| Confectionery (05.0): | 4.00000 | 20.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 2.20000 | 10.00000 | |
| Bakery wares (07.0): | 3.00000 | 15.00000 | |
| Meat and meat products, including poultry and game (08.0): | - | - | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | - | - | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 101.00000 | 1005.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 3.00000 | 10.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 2.00000 | 10.00000 | |
| Ready-to-eat savouries (15.0): | 2.00000 | 10.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 2.00000 | 10.00000 | |
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 10, Revision 3 (FGE.10Rev3): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 217 Revision 2 (FGE.217Rev2), consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: lactones 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 :10725569 |
| National Institute of Allergy and Infectious Diseases:Data |
| 5-pentyl-3H-furan-2-one |
| Chemidplus:0051352682 |