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(E,Z,Z)-2,4,7-tridecatrienal
(E,Z,Z)-2,4,7-tridecatrienal is a conjugated aldehyde with fatty and bitter sensory properties used in flavor and fragrance formulations.
General Material Description
(E,Z,Z)-2,4,7-tridecatrienal is a polyunsaturated aldehyde featuring a molecular formula of C13H20O. It belongs to the chemical family of conjugated aliphatic aldehydes characterized by three conjugated double bonds at the 2-, 4-, and 7-positions with specified stereochemistry. The compound is a colorless to pale yellow liquid with a fatty, citrus peel-like odor and a flavor described as bitter, waxy, and sweet. Synonyms include (2E,4Z,7Z)-trideca-2,4,7-trienal and 2-trans-4-cis-7-cis-tridecatrienal. This substance occurs naturally in heated egg yolk and is sourced or synthesized for use primarily in flavor and fragrance industries. For authoritative chemical data, the compound is linked to its PubChem entry (CID 6421281), which provides extensive molecular and safety information.
Occurrence, Applicability & Potential Uses
(E,Z,Z)-2,4,7-tridecatrienal arises naturally as a volatile compound in heated egg yolk, indicating its biological origin from lipid oxidation or thermal degradation. In commercial settings, it is used as a flavor and fragrance agent to impart fatty, coconut, and tropical notes in various formulations. Flavor industry standards such as FEMA (US) recognize this aldehyde under FEMA number 3638, with established usage guidelines. Likewise, it appears on JECFA's (Global) flavoring agent list. Its fatty and citrus peel waxy odor lends to applications in perfumery and flavoring, particularly in products that benefit from complex, fatty aldehydic aroma facets.
Physico-Chemical Properties Summary
(E,Z,Z)-2,4,7-tridecatrienal has a molecular weight of approximately 192.3 g/mol and a molecular formula of C13H20O. It is a relatively hydrophobic compound with an estimated log P value of 4.26, indicating significant lipophilicity. The compound has a specific gravity between 0.801 and 0.809 at 25 °C and a refractive index ranging from 1.472 to 1.478 at 20 °C. It possesses a high boiling point of 307 to 308 °C at atmospheric pressure (760 mmHg) and a very low vapor pressure of 0.001 mmHg at 25 °C, contributing to moderate volatility. It is soluble in alcohol and slightly soluble in water (estimated 5.743 mg/L at 25 °C). Its flash point is approximately 300 °F (149 °C), which is relevant for handling and formulation safety. These properties influence its behavior in formulations, favoring incorporation in oils and solvents rather than aqueous systems.
FAQ
What is (E,Z,Z)-2,4,7-tridecatrienal and what are its main characteristics?
(E,Z,Z)-2,4,7-tridecatrienal is a polyunsaturated aldehyde with three conjugated double bonds configured as trans-cis-cis across positions 2, 4, and 7 in a 13-carbon chain. It is a colorless to pale yellow liquid noted for its fatty, bitter flavor and citrus peel-like, waxy aroma. The compound is chemically classified as an alpha,beta-unsaturated aldehyde and features prominently in flavor and fragrance applications due to its distinct sensory qualities.
Where does (E,Z,Z)-2,4,7-tridecatrienal naturally occur, and how is it used?
(E,Z,Z)-2,4,7-tridecatrienal naturally occurs in heated egg yolk as a flavor volatile produced during heating processes. Industrially, it is employed as a flavor and fragrance agent to impart fatty and tropical notes, including coconut-like aromas. Its applications span various flavor formulations requiring complex aldehydic characters. Usage levels conform to recommendations from regulatory bodies such as FEMA (US) and JECFA (Global) to ensure safe incorporation.
What safety and regulatory standards apply to (E,Z,Z)-2,4,7-tridecatrienal?
(E,Z,Z)-2,4,7-tridecatrienal is listed under FEMA number 3638 and is recognized by JECFA for use as a flavoring substance. Safety assessments indicate no significant hazard classifications under OSHA regulations, with no specific GHS hazard or precautionary statements. IFRA (Global) guidelines permit usage in fragrance concentrate up to 2.0%. Exposure limits established by various authorities are low, reflecting controlled use in consumables and fragrances. Regulatory compliance requires adherence to specified maximum usage concentrations in different product categories.
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): | HMDB33545 |
| FooDB: | FDB011608 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | (E,Z,Z)-2,4,7-tridecatrienal |
| Trivial Name | (E,Z,Z)-2,4,7-Tridecatrienal |
| Short Description | 2-trans-4-cis-7-cis-tridecatrienal |
| Formula | C13 H20 O |
| CAS Number | 13552-96-0 |
| FEMA Number | 3638 |
| Flavis Number | 5.064 |
| ECHA Number | 236-936-3 |
| FDA UNII | ITP9P36029 |
| COE Number | 685 |
| xLogP3-AA | 4.20 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1198 2-trans-4-cis-7-cis-tridecatrienal |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 13552-96-0 ; 2-TRANS,4-CIS,7-CIS-TRIDECATRIENAL |
| Synonyms |
|
Suppliers
| BOC Sciences | Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 192.30160522461 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 6.665 to 6.732 |
| Refractive Index | 1.472 to 1.478 @ 20 °C |
| Boiling Point | 307 to 308°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.001 mmHg @ 25 °C |
| Flash Point TCC Value | 148.89 °C TCC |
| logP (o/w) | 4.259 est |
| Solubility | |
| alcohol | Yes |
| water, 5.743 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Fatty | |
| citrus peel, waxy, fatty, oily, fruity | |
| General comment | At 1.00 % in dipropylene glycol. citrus peel waxy fatty oily fruity |
| Flavor Type: Bitter | |
| bitter, waxy, sweet | |
| General comment | Bitter waxy sweet |
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 (E,Z,Z)-2,4,7-tridecatrienal usage levels up to: | |||
| 2.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.18 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.009 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 1.20 (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: 12 | |||
| Click here to view publication 12 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | 0.01000 | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 0.01000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.05000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | 0.01000 | |
| snack foods: | - | 0.01000 | |
| soft candy: | - | - | |
| soups: | - | 0.10000 | |
| 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): | - | - | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.00100 | 1.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | - | - | |
| Processed fruit (04.1): | - | - | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | - | - | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | - | - | |
| Bakery wares (07.0): | - | - | |
| Meat and meat products, including poultry and game (08.0): | 0.00100 | 2.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.00100 | 1.00000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.00100 | 1.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | - | - | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | - | - | |
| Ready-to-eat savouries (15.0): | 0.05000 | 1.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | - | - | |
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 |
| 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 ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6421281 |
| National Institute of Allergy and Infectious Diseases:Data |
| (2E,4Z,7Z)-trideca-2,4,7-trienal |
| Chemidplus:0013552960 |