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2,4-nonadienal
2,4-nonadienal is an unsaturated aldehyde notable for its fatty, green, and cucumber flavor characteristics used primarily as a flavoring agent in food and fragrance applications.
General Material Description
2,4-nonadienal is a type of unsaturated aliphatic aldehyde with the molecular formula C9H14O. It appears as a colorless to pale yellow liquid and exhibits characteristic fatty and green odor notes reminiscent of cucumber and melon. This compound is also known under synonyms including nona-2,4-dienal, n-nona-2,4-dienal, and 2,4-nonadien-1-al. As a flavor and fragrance substance, it contributes green, fatty, and fruity nuances to various formulations. Its chemical structure and information can be cross-referenced via the PubChem database. Naturally, 2,4-nonadienal is found in coffee and mushroom aromas, making it integral to certain food flavor profiles. Industrially, it is typically derived by chemical synthesis for use in flavoring agents and, to a limited extent, fragrance perfuming compounds.
Occurrence, Applicability & Potential Uses
2,4-nonadienal occurs naturally in foods such as coffee and various mushrooms, where it contributes to their characteristic aroma. It is often applied as a flavoring agent to impart fatty, green, cucumber, and tropical fruit notes in food products. The compound is used in formulations requiring green and nutty nuances, such as baked goods, beverages, and savory items. Its usage is governed by standards including FEMA (US), where it is recognized with the FEMA Number 3212 for flavoring purposes. The International Fragrance Association (IFRA) (Global) restricts its use as a fragrance ingredient due to insufficient safety data. Regulatory frameworks assess its safety profile for human exposure, restricting its use to levels considered safe while highlighting the need for caution in perfuming applications.
Physico-Chemical Properties Summary
2,4-nonadienal is a lipophilic unsaturated aldehyde with a molecular weight of approximately 138.2 g/mol and an estimated logP of 2.91, indicating moderate hydrophobicity. It has a boiling point near 221–222°C at standard atmospheric pressure and a relatively low vapor pressure of 0.102 mmHg at 25°C, indicative of limited volatility. The specific gravity ranges between 0.85 and 0.87 at 25°C, and its refractive index is from 1.522 to 1.525 at 20°C. It exhibits limited solubility in water but dissolves well in alcohols. The flash point is approximately 199°F, marking it as a combustible liquid. These properties influence its formulation behavior, favoring incorporation into lipid-based or alcoholic matrices and requiring careful handling to avoid oxidation or skin irritation. The aldehyde functional group provides reactive chemical characteristics relevant to flavor stability and sensory impact.
FAQ
What is 2,4-nonadienal and what are its key properties?
2,4-nonadienal is an unsaturated aldehyde characterized by the molecular formula C9H14O. It is known for its distinct fatty, green, and cucumber odor and flavor notes. This compound appears as a colorless to pale yellow liquid with moderate hydrophobicity and limited water solubility. It naturally occurs in foods like coffee and mushrooms, contributing to their aroma. 2,4-nonadienal is used primarily as a flavoring agent and in limited perfume applications.
How is 2,4-nonadienal used, and where does it commonly occur?
2,4-nonadienal is primarily employed as a flavoring ingredient to provide green and fatty nuances, including cucumber and tropical fruit notes. It is found naturally in coffee and mushroom aromas. Due to its sensory profile, it is incorporated into food products such as baked goods, beverages, and savory foods. In perfumery, regulatory guidance prohibits its use as a fragrance ingredient because of insufficient safety data.
What regulations govern the use of 2,4-nonadienal and where can it be sourced?
The flavoring use of 2,4-nonadienal is regulated by authorities such as FEMA (US), which assigns it FEMA number 3212 and recognizes it under flavoring agents. The IFRA (Global) standards currently prohibit its use as a fragrance ingredient due to limited safety information. It is subject to usage limits in various food categories according to EU regulations and is listed in databases such as ECHA REACH (EU) with identifier 229-810-4. Industrial 2,4-nonadienal is typically sourced from chemical suppliers specializing in flavor and fragrance raw materials.
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
| nona-2,4-dienal | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 6750-03-4 |
| Pubchem (cid): | 23203 |
| Pubchem (sid): | 134987512 |
| Flavornet: | 6750-03-4 |
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): | HMDB31685 |
| FooDB: | FDB008348 |
| Export Tariff Code: | 2912.19.9000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2,4-nonadienal |
| Trivial Name | 2,4-Nonadienal |
| Short Description | nona-2,4-dienal |
| Formula | C9 H14 O |
| CAS Number | 6750-03-4 |
| FEMA Number | 3212 |
| Flavis Number | 5.071 |
| ECHA Number | 229-810-4 |
| FDA UNII | Search |
| COE Number | 732 |
| xLogP3-AA | 2.70 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1185 2,4-nonadienal |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 6750-03-4 ; 2,4-NONADIENAL |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 138.20977783203 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.073 to 7.239 |
| Refractive Index | 1.522 to 1.525 @ 20 °C |
| Boiling Point | 221 to 222°C @ 760 mm Hg |
| Acid Value | 5 max KOH/g |
| Vapor Pressure | 0.102 mmHg @ 25 °C |
| Flash Point TCC Value | 92.78 °C TCC |
| logP (o/w) | 2.91 est |
| Solubility | |
| alcohol | Yes |
| water, 318.8 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Green | |
| fatty, green, cucumber, fruit tropical fruit | |
| Odor strength | high , recommend smelling in a 0.10 % solution or less |
| Substantivity | > 24 hour(s) at 100.00 % |
| General comment | At 0.10 % in dipropylene glycol. fatty green cucumber |
| Flavor Type: Fatty | |
| chicken fat, citrus peel, waxy, melon, cucumber | |
| General comment | Chicken fat citrus peel waxy melon cucumber |
| Chicken flavors, citrus especially orange and tangerine. Also used to impart fatty notes for peanut butter, as well as back notes of melon and cucumber flavors. | Strong chicken fat notes, with citrus peel, waxy notes; melon and cucumber back notes |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Violet leaf |
| Flavoring purposes | Cucumber , Fruit tropical fruit , Green , Nut , Violet |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 38 - Irritating to 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 37/39 - Wear suitable 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: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| IFRA Critical Effect: | |||
| Insufficient data | |||
| View the IFRA Standard | |||
| Recommendation for 2,4-nonadienal usage levels up to: | |||
| PROHIBITED: Should not be used as a fragrance ingredient. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.94 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.70 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 560 (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: 4. Update in publication number(s): 29 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 2.00000 | 7.00000 | |
| beverages(nonalcoholic): | 0.90000 | 4.00000 | |
| beverages(alcoholic): | 0.01000 | 2.00000 | |
| breakfast cereal: | 0.20000 | 0.20000 | |
| cheese: | - | - | |
| chewing gum: | 5.00000 | 10.00000 | |
| condiments / relishes: | 1.00000 | 2.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 2.00000 | 7.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 1.00000 | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | 0.50000 | 2.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 3.00000 | 18.00000 | |
| milk products: | 0.20000 | 0.20000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | 2.00000 | 8.00000 | |
| soups: | 0.20000 | 0.20000 | |
| 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): | 0.50000 | 1.50000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.50000 | 5.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.01000 | 1.00000 | |
| Processed fruit (04.1): | - | - | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 0.01000 | 1.00000 | |
| Confectionery (05.0): | 1.00000 | 5.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.05100 | 1.00000 | |
| Bakery wares (07.0): | 1.00000 | 5.00000 | |
| Meat and meat products, including poultry and game (08.0): | 3.00000 | 5.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 2.00000 | 5.00000 | |
| Eggs and egg products (10.0): | 0.01000 | 1.00000 | |
| Sweeteners, including honey (11.0): | 0.01000 | 1.00000 | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 3.00000 | 10.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.05000 | 1.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.02000 | 1.00000 | |
| Ready-to-eat savouries (15.0): | 3.00000 | 5.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.01000 | 1.00000 | |
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): |
| Flavouring Group Evaluation 203: alpha,beta-Unsaturated aliphatic aldehydes and precursors from chemical subgroup 1.1.4 of FGE.19 with two or more conjugated double bonds and with or without additional non-conjugated double bonds View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 203, Revision 1 (FGE.203Rev1): a,ß-Unsaturated aliphatic aldehydes and precursors from chemical subgroup 1.1.4 of FGE.19 with two or more conjugated double-bonds and with or without additional non-conjugated double-bonds View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 203, Revision 2 (FGE.203Rev2): a,ß-unsaturated aliphatic aldehydes and precursors from chemical subgroup 1.1.4 of FGE.19 with two or more conjugated double-bonds and with or without additional non-conjugated double-bonds View page or View pdf |
| Safety and efficacy of 26 compounds belonging to chemical group 3 (a,ß-unsaturated straight-chain and branched-chain aliphatic primary alcohols, aldehydes, acids and esters) when used as flavourings for all animal species and categories View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 70, Revision 1 (FGE.70Rev1): consideration of aliphatic, linear, a,ß-unsaturated, di- and trienals and related alcohols, acids and esters evaluated by JECFA (61st-68th-69th meeting) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):6750-03-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :23203 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| nona-2,4-dienal |
| Chemidplus:0006750034 |