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(E)-2-dodecenal
(E)-2-dodecenal is a natural aliphatic aldehyde notable for its citrus, herbal, and waxy odor notes, utilized mainly in flavor and fragrance industries.
General Material Description
(E)-2-dodecenal is a member of the aliphatic aldehyde class characterized by a trans double bond at the second carbon of a dodecyl chain. This compound appears as a clear to slightly yellow liquid with a molecular formula of C12H22O and a molecular weight near 182.3 g/mol. Sensory evaluation identifies it with citrus, mandarin, and herbal nuances combined with waxy and fatty undertones. Also known by many synonyms such as trans-2-dodecenal and aldehyde mandarin 10%, it features prominently in flavor and fragrance formulations. Naturally sourced from botanical materials including coriander leaf oil, mandarin oil, carrot, and orange peel oil, it is linked by its PubChem CID 5283361. Its utility rests on its distinctive aromatic profile derived from naturally occurring precursors.
Occurrence, Applicability & Potential Uses
(E)-2-dodecenal naturally occurs in various plant-derived materials, notably coriander leaf oil where it constitutes approximately 15.6 to 21.6%, as well as in mandarin oil, carrot, ginger, and certain flower oils like Eschweilera coriacea. Its biological presence extends to foods and spices such as bitter orange and roasted peanut. This compound is principally applied as a flavoring and fragrance agent due to its citrus and herbal aromatic qualities. In formulations, it is used to impart notes of mandarin, coriander, green and spice nuances, as well as fatty and waxy elements contributing complexity to citrus and herbal flavor profiles. Regulatory frameworks including FEMA (US) govern its use levels, and IFRA (Global) provides guidelines on maximum concentrations in cosmetics and perfumery to ensure safe application.
Physico-Chemical Properties Summary
(E)-2-dodecenal is moderately lipophilic with an estimated logP of approximately 4.5, indicating significant affinity for oils and alcohols compared to water, where its solubility is low but measurable. It exhibits a refractive index between 1.455 and 1.459 at 20 °C and a specific gravity around 0.841 to 0.849 at 25 °C. The compound is volatile, boiling near 125 to 128 °C at standard atmospheric pressure and displays a low vapor pressure (approximately 0.01 mmHg at 25 °C), factors important for its performance in formulations. Its flash point exceeds 100 °C (212 °F), suggesting moderate flammability. Stability data demonstrate compatibility with various product types including detergents and fine fragrances at low concentrations. Storage recommendations emphasize protection from heat and light in sealed containers to maintain integrity over a shelf life of at least six months.
FAQ
What is (E)-2-dodecenal and what are its primary characteristics?
(E)-2-dodecenal is an aliphatic aldehyde featuring a trans double bond at the second carbon position. It is recognized for its distinct citrus mandarin, herbal, and waxy odor notes, combined with a fatty, aldehydic flavor profile. The compound exists as a clear liquid and is known by synonyms such as trans-2-dodecenal or aldehyde mandarin 10%. It is sourced naturally from various plants including coriander leaf oil, mandarin oil, and carrot.
Where does (E)-2-dodecenal occur naturally and how is it used in industry?
(E)-2-dodecenal naturally occurs in essential oils of coriander leaf (15.6–21.6%), mandarin, carrot, ginger, and bitter orange, as well as in some flower oils and roasted peanut. Industrially, it serves primarily as a flavor and fragrance ingredient in products aiming to evoke citrus, green, and herbal notes along with fatty and spicy accents. Standards such as FEMA (US) guide its usage levels, ensuring consistency and safety in food flavorings and perfumery.
What regulations apply to (E)-2-dodecenal regarding its safety and usage?
(E)-2-dodecenal is regulated by agencies including FEMA (US) and is subject to safety assessments by IFRA (Global) for use in fragrance products. Usage limits, often up to 1.0% in fragrance concentrates, are established to mitigate irritation potential. Toxicological data indicate low acute toxicity with no significant sensitization at typical use concentrations. The compound is classified as an irritant for skin contact under European regulations and should be handled with appropriate protective measures. Comprehensive evaluations by EFSA provide guidance on maximum permitted levels for food flavoring applications.
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
| (E)-dodec-2-enal | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 20407-84-5 |
| Pubchem (cid): | 5283361 |
| Pubchem (sid): | 134984196 |
| Flavornet: | 20407-84-5 |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB31020 |
| FooDB: | FDB003014 |
| Export Tariff Code: | 2912.19.5000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | (E)-2-dodecenal |
| Trivial Name | (E)-2-Dodecenal |
| Short Description | trans-2-dodecenal |
| Formula | C12 H22 O |
| CAS Number | 20407-84-5 |
| FEMA Number | 2402 |
| Flavis Number | 5.144 |
| ECHA Number | 243-797-2 |
| FDA UNII | 1D55O81P4E |
| Nikkaji Number | J280.586C |
| Beilstein Number | 2434537 |
| MDL | MFCD00014674 |
| COE Number | 124 |
| xLogP3-AA | 4.80 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 182.30653381348 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 6.998 to 7.065 |
| Refractive Index | 1.455 to 1.459 @ 20 °C |
| Boiling Point | 73 to 74°C @ 0.5 mm Hg |
| Boiling Point | 125 to 128°C @ 760 mm Hg |
| Vapor Pressure | 0.01 mmHg @ 25 °C |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 4.51 |
| Shelf life | 6 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| fixed oils | Yes |
| water, 7.259 mg/L @ 25 °C (est) | Yes |
| Stability | |
| APC: traces - 1% | Unspecified |
| candle: traces - 1% | Unspecified |
| detergent: traces - 1% | Unspecified |
| fine fragrances: traces - 0.5% | Unspecified |
| shampoo: traces - 0.5% | Unspecified |
| shower gel: traces - 0.5% | Unspecified |
| soap: traces - 0.5% | Unspecified |
| softener: traces - 1% | Unspecified |
Organoleptic Properties
| Odor Type: Herbal | |
| citrus, metallic, mandarin, orange, waxy, aldehydic | |
| Odor strength | high , recommend smelling in a 1.00 % solution or less |
| Substantivity | 72 hour(s) at 10.00 % in dipropylene glycol |
| Luebke, William tgsc, (1986) | At 1.00 % in dipropylene glycol. citrus metallic mandarin orange waxy aldehydic |
| Flavor Type: Waxy | |
| waxy, citrus peel, aldehydic, orange bitter orange, mandarin, cilantro, fatty, herbal | |
| Luebke, William tgsc, (1986) | Waxy citrus peel aldehydic bitter orange mandarin cilantro fatty herbal |
| Citrus flavors, specifically orange and tangerine. Excellent for cilantro and similar herbal type flavors. Can be used to impart fatty notes of melon & cucumber. | Fatty, waxy, citrus peel notes with cilantro and similar types of herbal notes |
| General comment | Sulphurous, meaty, aspects of roasted coffee; meaty, roasted, savory, beef and popcorn |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Citrus , Cologne , Coriander , Fern , Green , Mandarin , Orange , Orange bitter orange peel , Spice , Tangerine |
| Flavoring purposes | Coriander , Orange bitter orange peel |
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 36 - Wear suitable protective clothing. | |
| 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. | |
| Human Experience: | |
| 1 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 > 5000 mg/kg | |
| Dermal Toxicity: | |
| skin-rabbit LD50 5000 mg/kg | |
| 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 (E)-2-dodecenal usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.75 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 2000 (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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 2.80000 | |
| beverages(nonalcoholic): | - | 2.90000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 3.10000 | |
| fruit ices: | - | 3.10000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 2.80000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| 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: | - | - | |
| 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): | 5.70000 | 12.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 1.50000 | 14.25000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.90000 | 2.98000 | |
| Processed fruit (04.1): | - | - | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 5.00000 | 5.03000 | |
| Confectionery (05.0): | 5.50000 | 14.46000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 4.80000 | 11.55000 | |
| Bakery wares (07.0): | 8.00000 | 19.07000 | |
| Meat and meat products, including poultry and game (08.0): | 0.90000 | 2.98000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.90000 | 2.98000 | |
| Eggs and egg products (10.0): | 0.90000 | 2.98000 | |
| Sweeteners, including honey (11.0): | 0.90000 | 2.98000 | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 2.00000 | 5.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 2.00000 | 4.43000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 2.00000 | |
| Ready-to-eat savouries (15.0): | 2.50000 | 4.50000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.90000 | 2.98000 | |
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): |
| EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 200, Revision 1 (FGE.200 Rev.1): 74 a,ß-unsaturated aliphatic aldehydes and precursors from chemical subgroup 1.1.1 of FGE.19 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 5, Revision 3 (FGE.05Rev3): Branched- and straight-chain unsaturated aldehydes, dienals, unsaturated and saturated carboxylic acids and related esters with saturated and unsaturated aliphatic alcohols and a phenylacetic acid related ester from chemical groups 1, 2, 3, 5 and 15 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):20407-84-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5283361 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1760 |
| WGK Germany:2 |
| (E)-dodec-2-enal |
| Chemidplus:0020407845 |
| RTECS:JR5150000 for cas# 20407-84-5 |