We have found 46587 results matching your criteria.
Please wait while we search...

General Material Information

Preferred name (E,E)-2,4-undecadienal
Trivial Name 2,4-Undecadienal, (2E,4E)-
Short Description trans,trans-2,4-undecadienal
Formula C11 H18 O
CAS Number 30361-29-6
FEMA Number 3422
ECHA Number 250-148-7
FDA UNII 7L26S7BW06
Nikkaji Number J126.515F
MDL MFCD00014677
COE Number 10385
xLogP3-AA 3.80 (est)
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • (2E,4E)- undeca-2,4-dienal
  • (E,E)- undeca-2,4-dienal
  • (E)-2,(E)-4-undeca-2,4-dienal
  • (E,E)-2,4-undecadien-1-al
  • (E)-2,(E)-4-undecadien-1-al
  • (E2,E4)- undecadien-1-al
  • trans,trans-2,4-undecadien-1-al
  • 2,4-undecadien-1-al, no antioxidant
  • (2E,4E)-2,4-undecadienal
  • 2,4-trans,trans- undecadienal
  • trans, trans-2,4-undecadienal
  • trans,trans-2,4-undecadienal
  • 2,4-undecadienal, (2E,4E)-
  • 2,4-undecadienal, (E,E)-
  • (2E,4E)-undeca-2,4-dienal
  • 2,4-Undecadienal, (2E,4E)-
  • 2,4-Undecadienal, (E,E)-
  • (2E,4E)-2,4-Undecadienal
  • Undeca-trans-2,trans-4-dienal
  • 2,4-trans,trans-Undecadienal
  • (E,E)-2,4-Undecadien-1-al
  • trans,trans-2,4-Undecadienal

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

(2E,4E)-undeca-2,4-dienal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:30361-29-6
Pubchem (cid):5367531
Pubchem (sid):135019036
Publications by PubMed
Diunsaturated Aldehyde, trans,trans-2,4-Decadienal in the Intestinal Lumen Suppresses Gastric Emptying through Serotonin Signaling in Rats.
Powdered activated carbon adsorption of two fishy odorants in water: Trans,trans-2,4-heptadienal and trans,trans-2,4-decadienal.
3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar.
Identification of trans,trans-2,4-decadienal metabolites in mouse and human cells using liquid chromatography-mass spectrometry.
A quantitative quantum-chemical analysis tool for the distribution of mechanical force in molecules.
Metabolomic profiling of mice urine and serum associated with trans-trans 2, 4-decadienal induced lung lesions by liquid chromatography-mass spectrometry.
Evaluation of the non-catalytic binding function of Ts26GST a glutathione transferase isoform of Taenia solium.
Simultaneous determination of ten taste and odor compounds in drinking water by solid-phase microextraction combined with gas chromatography-mass spectrometry.
Pro-oxidant/antioxidant behaviours of ascorbic acid, tocopherol, and plant extracts in n-3 highly unsaturated fatty acid rich oil-in-water emulsions.
A pilot study of the effect of (e, e)-2, 4-undecadienal on the offensive odour of trimethylamine.
Oxetane ring enlargement through nucleophilic trapping of radical cations by acetonitrile.
Chemical composition and antibacterial activity of Indian seagrasses against urinary tract pathogens.
Treatment with algae extracts promotes flocculation, and enhances growth and neutral lipid content in Nannochloropsis oculata--a candidate for biofuel production.
trans,trans-2,4-Hexadiene incorporation on enzymes for site-specific immobilization and fluorescent labeling.
NTP toxicity studies of toxicity studies of 2,4-decadienal (CAS No. 25152-84-5) administered by gavage to F344/N Rats and B6C3F1 mice.
Identification of (E,E)-2,4-undecadienal from coriander (Coriandrum sativum L.) as a highly effective deodorant compound against the offensive odor of porcine large intestine.
Rapid fingerprinting and classification of extra virgin olive oil by microjet sampling and extractive electrospray ionization mass spectrometry.
Exposure to polycyclic aromatic hydrocarbons (PAHs), mutagenic aldehydes and particulate matter during pan frying of beefsteak.
DNA damages induced by trans, trans-2,4-decadienal (tt-DDE), a component of cooking oil fume, in human bronchial epithelial cells.
The fate of benzene-oxide.
Biochemical analysis of a recombinant glutathione transferase from the cestode Echinococcus granulosus.
Pulmonary changes induced by trans,trans-2,4-decadienal, a component of cooking oil fumes.
trans,trans-2,4-decadienal induces mitochondrial dysfunction and oxidative stress.
Trans, trans-2,4-decadienal induced cell proliferation via p27 pathway in human bronchial epithelial cells.
Covalent modification of cytochrome c exposed to trans,trans-2,4-decadienal.
Complete 1H and 13C NMR assignment of trans,trans-2,3-divinylfuran derivatives.
Microwave-assisted three-component synthesis of 7-aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and their selective reduction.
Addition of cyclopropyl alkynes to a Brook silene: definitive evidence for a biradical intermediate.
Genotoxicity and oxidative stress of the mutagenic compounds formed in fumes of heated soybean oil, sunflower oil and lard.
Trans, trans-2,4-decadienal, a product found in cooking oil fumes, induces cell proliferation and cytokine production due to reactive oxygen species in human bronchial epithelial cells.
Cyclopropyl alkynes as mechanistic probes to distinguish between vinyl radical and ionic intermediates.
Structural characterization of an etheno-2'-deoxyguanosine adduct modified by tetrahydrofuran.
Effects of cooking oil fumes on the genotoxicity and oxidative stress in human lung carcinoma (A-549) cells.
The weak acid preservative sorbic acid inhibits conidial germination and mycelial growth of Aspergillus niger through intracellular acidification.
Structural characterization of diastereoisomeric ethano adducts derived from the reaction of 2'-deoxyguanosine with trans,trans-2,4-decadienal.
NTP toxicology and carcinogensis Studies of 2,4-hexadienal (89% trans,trans isomer, CAS No. 142-83-6; 11% cis,trans isomer) (Gavage Studies).
Flavoring components of raw monsooned arabica coffee and their changes during radiation processing.
Mechanistic studies of the addition of carbonyl compounds to tetramesityldigermene.
Photosensitiser-controlled regioselectivity in the electron-transfer cycloreversion of 2,3-diphenyloxetanes.
Inhibition of vertebrate telomerases by the triphosphate derivatives of carbocyclic oxetanocin analogs.
Conformational restraint in thermal rearrangements of a cyclobutane: 3,4-dicyanotricyclo[4.2.2.0(2,5)]decane.
The stereochemistry of the thermal cheletropic decarbonylation of 3-cyclopentenone as determined by multiphoton infrared photolysis/thermolysis.
Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl-metabolizing enzymes. I. Aliphatic alkenals.
Reactive-state spin-dependent diastereoselective photoisomerization of trans,trans-2,3-diphenylcyclopropane-1- carboxylic acid derivatives included in zeolites.
Stereochemistry of the [4 + 2] cycloadditions of trans,trans- and cis,trans-2,4-hexadiene to C(60).
4,5-Epoxy-2(E)-decenal-induced formation of 1,N(6)-etheno-2'-deoxyadenosine and 1,N(2)-etheno-2'-deoxyguanosine adducts.
1,N6-etheno-2'-deoxyadenosine adducts from trans, trans-2,4-decadienal and trans-2-octenal.
Interaction of 3,4-dienoyl-CoA thioesters with medium chain acyl-CoA dehydrogenase: stereochemistry of inactivation of a flavoenzyme.
Mutagenicity and identification of mutagenic compounds of fumes obtained from heating peanut oil.
Enantioselective Michael reactions of chiral secondary enaminoesters with 2-substituted nitroethylenes. Syntheses of trans, trans-2,4-disubstituted pyrrolidine-3-carboxylates
Structure-activity relationships in the induction of DNA-protein cross-links by hematotoxic ring-opened benzene metabolites and related compounds in HL60 cells.
trans,trans-2,4-decadienal-induced 1,N(2)-etheno-2'-deoxyguanosine adduct formation.
Novel 1,N(6)-etheno-2'-deoxyadenosine adducts from lipid peroxidation products.
Kinetic and structural characterization of the glutathione-binding site of aldose reductase.
In vitro toxicity of spiroorthocarbonate monomers designed for non-shrinking dental restoratives.
trans,trans-2-cyano-5-(4-methoxyphenyl)penta-2,4-dienethioamide
The Rotational Spectrum of Tricarbonyl(trans,trans-2,4-hexadiene) Iron.
Formation of 1,N6-etheno-2'-deoxyadenosine adducts by trans,trans-2, 4-Decadienal.
Development of a highly sensitive enzyme-linked immunosorbent assay based on polyclonal antibodies for the detection of polychlorinated dibenzo-p-dioxins.
Induction of a wide range of C(2-12) aldehydes and C(7-12) acyloins in the kidney of Wistar rats after treatment with a renal carcinogen, ferric nitrilotriacetate.
Monoamine Oxidase-Catalyzed Oxidative Rearrangement of trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane.
Reactive ring-opened aldehyde metabolites in benzene hematotoxicity.
Synthesis and Aza-[2,3]-Wittig Rearrangements of Vinylaziridines: Scope and Limitations.
Molecular cloning, expression and characterization of a recombinant glutathione S-transferase from Echinococcus multilocularis.
2,4-Diarylpyrrolidine-3-carboxylic acids--potent ETA selective endothelin receptor antagonists. 1. Discovery of A-127722.
trans,trans-2,4-decadienal: cytotoxicity and effect on glutathione level in human erythroleukemia (HEL) cells.
Iron-stimulated ring-opening of benzene in a mouse liver microsomal system. Mechanistic studies and formation of a new metabolite.
Galactose-containing amphiphiles prepared with a lipophilic radical initiator: association processes between liposomes triggered by enzymatic reaction.
The hematotoxic effects of 6-hydroxy-trans,trans-2,4-hexadienal, a reactive metabolite of trans,trans-muconaldehyde, in CD-1 mice.
Biochemical analysis of recombinant glutathione S-transferase of Fasciola hepatica.
Mutagenicity of trans,trans-muconaldehyde and its metabolites in V79 cells.
Identification of 6-hydroxy-trans,trans-2,4-hexadienoic acid, a novel ring-opened urinary metabolite of benzene.
Synthesis and antiviral activity of carbocyclic oxetanocin analogues (C-OXT-A, C-OXT-G) and related compounds. II.
Pathways of trans,trans-muconaldehyde metabolism in mouse liver cytosol: reversibility of monoreductive metabolism and formation of end products.
Synthesis and polymerization of new expanding dental monomers.
Aliphatic molecules (C-6 to C-8) containing double or triple bonds as potential penicillin side-chain precursors.
Purification by affinity chromatography of 2,4-dienoyl-CoA reductases from bovine liver and Escherichia coli.
Total synthesis of the racemic form of the second juvenile hormone (methyl 12-homojuvenate) from the cecropia silk moth.
The metabolism of cis- and trans-decalin.
Trans,trans-2,8-trans-bicyclo[8.4.0]tetradecadiene.

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
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2912.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 166.26365661621
Specific gravity @ 25 °C
Pounds per Gallon 7.456 to 7.539
Refractive Index 1.5 to 1.505 @ 20 °C
Acid Value 5 max KOH/g
Vapor Pressure 0.015 mmHg @ 25 °C
Flash Point TCC Value 107.22 °C TCC
logP (o/w) 3.929 est
Solubility
alcohol Yes
essential oils Yes
water, 34.73 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
oily, caramellic, spicy, citrus, buttery, baked, fatty, waxy, chicken, sweet
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity > 168 hour(s) at 100.00 %
General comment At 1.00 % in dipropylene glycol. oily caramellic spicy citrus buttery baked
Mosciano, Gerard P&F 15, No. 1, 19, (1990) Fatty, waxy, chicken with sweet nuances
Flavor Type: Fatty
fatty, waxy, green, chicken
Mosciano, Gerard P&F 15, No. 1, 19, (1990) At 10.00 ppm. Fatty, waxy green, with chicken nuances
Fatty, nut flavors, especially hazelnut. Also useful in melon, cucumber, and citrus at lower levels. Sweet chicken fat, with some citrus notes

Occurrences

Potential Uses

Applications
Odor purposes Melon
Flavoring purposes Butter, Citrus, Coconut, Cucumber, Lard, Peanut, Spice
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 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.
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 (E,E)-2,4-undecadienal usage levels up to:
PROHIBITED: Should not be used as a fragrance ingredient.
Maximised Survey-derived Daily Intakes (MSDI-EU): 3.20 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 89 (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: 7
Click here to view publication 7
average usual ppmaverage maximum ppm
baked goods: -1.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: -1.00000
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: -1.00000
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -1.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -1.00000
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/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.100001.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.500005.00000
Edible ices, including sherbet and sorbet (03.0): 0.010001.00000
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): 0.010001.00000
Confectionery (05.0): 0.100001.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.030001.00000
Bakery wares (07.0): 0.500001.00000
Meat and meat products, including poultry and game (08.0): 0.500005.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.500003.00000
Eggs and egg products (10.0): 0.010001.00000
Sweeteners, including honey (11.0): 0.010001.00000
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.300001.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.010001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.020001.00000
Ready-to-eat savouries (15.0): 0.500003.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.100001.00000

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 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):30361-29-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5367531
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2E,4E)-undeca-2,4-dienal
Chemidplus:0030361296