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2,4-decadienal

Chemical Structure

General Material Information

Preferred name 2,4-decadienal
Trivial Name 2,4-Decadienal
Short Description deca-2,4-dienal
Formula C10 H16 O
CAS Number 2363-88-4
Flavis Number 5.081
ECHA Number 219-114-9
FDA UNII Search
Beilstein Number 1704897
COE Number 2120
xLogP3-AA 3.20 (est)
NMR Predictor External link
Synonyms
  • deca-2,4-dienal
  • 2,4-decadianal natural
  • 2,4-decadien-1-al
  • 2,4-decadien-1-al FCC, no antioxidant
  • 2,4-decadienal 10% in ETOH natural
  • 2,4-decadienal nat
  • 2,4-decadienal natural
  • 2,4-decadienal synthetic
  • 2,4-Decadien-1-al

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Literature & References

deca-2,4-dienal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:2363-88-4
Pubchem (cid):16899
Pubchem (sid):134983663
Publications by PubMed
Prevalence and mechanism of polyunsaturated aldehydes production in the green tide forming macroalgal genus Ulva (Ulvales, Chlorophyta).
Analysis of particle-borne odorants emitted from concentrated animal feeding operations.
Methods to create thermally-oxidized lipids and comparison of analytical procedures to characterize peroxidation.
A fishy odor episode in a north China reservoir: occurrence, origin, and possible odor causing compounds.
Exocrine secretions of wheel bugs (Heteroptera: Reduviidae: Arilus spp.): clarification and chemistry.
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.
Chemometric resolution approaches in characterisation of volatile constituents in Plantago ovata seeds using gas chromatography-mass spectrometry: methodology and performance assessment.
The effect of feed solids concentration and inlet temperature on the flavor of spray dried whey protein concentrate.
Ultrahigh performance liquid chromatography analysis of volatile carbonyl compounds in virgin olive oils.
Antimicrobial activity of untypical lipid compounds in the cuticular and internal lipids of four fly species.
Identification of volatiles from oxidised phosphatidylcholine molecular species using headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS).
Akt and ERK/Nrf2 activation by PUFA oxidation-derived aldehydes upregulates FABP4 expression in human macrophages.
Cooked carrot volatiles. AEDA and odor activity comparisons. Identification of linden ether as an important aroma component.
Aroma-active components of yeast extract pastes with a basic and characteristic meaty flavour.
Impact of flavour solvent (propylene glycol or triacetin) on vanillin, 5-(hydroxymethyl)furfural, 2,4-decadienal, 2,4-heptadienal, structural parameters and sensory perception of shortcake biscuits over accelerated shelf life testing.
Determination of compounds responsible for tempeh aroma.
Investigation of heat induced reactions between lipid oxidation products and amino acids in lipid rich model systems and hazelnuts.
Identification of aroma active compounds of cereal coffee brew and its roasted ingredients.
Simulated restaurant cook exposure to emissions of PAHs, mutagenic aldehydes, and particles from frying bacon.
Identification of characteristic flavour precursors from enzymatic hydrolysis-mild thermal oxidation tallow by descriptive sensory analysis and gas chromatography-olfactometry and partial least squares regression.
Influence of endogenous ferulic acid in whole wheat flour on bread crust aroma.
Impact of different distribution scenarios and recommended storage conditions on flavor related quality attributes in ripening fresh tomatoes.
Differences in the volatile compositions of ginseng species (Panax sp.).
In depth study of acrylamide formation in coffee during roasting: role of sucrose decomposition and lipid oxidation.
Identification and quantification of aroma compounds of tartary buckwheat (Fagopyrum tataricum Gaertn.) and some of its milling fractions.
Chemical conversion of phenylethylamine into phenylacetaldehyde by carbonyl-amine reactions in model systems.
Treatment with algae extracts promotes flocculation, and enhances growth and neutral lipid content in Nannochloropsis oculata--a candidate for biofuel production.
Male-produced pheromone in the European woodwasp, Sirex noctilio.
Nematicidal activity of (E,E)-2,4-decadienal and (E)-2-decenal from Ailanthus altissima against Meloidogyne javanica.
Quality evaluation of olive oil by statistical analysis of multicomponent stable isotope dilution assay data of aroma active compounds.
Evaluation of the key aroma compounds in beef and pork vegetable gravies a la chef by stable isotope dilution assays and aroma recombination experiments.
Studies on the key aroma compounds in soy milk made from three different soybean cultivars.
Dynamics of dissolved and particulate polyunsaturated aldehydes in mesocosms inoculated with different densities of the diatom Skeletonema marinoi.
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.
Chemical characterization of commercial Sherry vinegar aroma by headspace solid-phase microextraction and gas chromatography-olfactometry.
A new method for the determination of carbonyl compounds in wines by headspace solid-phase microextraction coupled to gas chromatography-ion trap mass spectrometry.
Asparagine decarboxylation by lipid oxidation products in model systems.
Rheological properties, oxidative stability, and tocopherol content during storage of fried dough made with Silky fowl egg: comparison with hen egg.
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.
Differentiation of chocolates according to the cocoa's geographical origin using chemometrics.
Biochemical analysis of a recombinant glutathione transferase from the cestode Echinococcus granulosus.
Characterization of the key aroma compounds in beef and pork vegetable gravies á la chef by application of the aroma extract dilution analysis.
Pulmonary changes induced by trans,trans-2,4-decadienal, a component of cooking oil fumes.
Conversion of 3-aminopropionamide and 3-alkylaminopropionamides into acrylamide in model systems.
Degradation of sulfide linkages between isoprenes by lipid peroxidation catalyzed by manganese peroxidase.
[Ozonation of odorous organic compounds in eutrophic water].
Volatile composition of Catharanthus roseus (L.) G. Don using solid-phase microextraction and gas chromatography/mass spectrometry.
Thermal processing of paper sludge and characterisation of its pyrolysis products.
[Chemical constituents from the seed of Chimonanthus praecox extracted by supercritical carbon dioxide].
Comparison of the key aroma compounds in organically grown, raw West-African peanuts (Arachis hypogaea) and in ground, pan-roasted meal produced thereof.
Proteomic analysis of proteins associated with tt-DDE induced toxicity in BEAS-2B cells.
Contribution of lipid oxidation products to acrylamide formation in model systems.
[Characterization of chemical components of essential oil from cupitulum of Chrysanthemum morifolium cultivated in Tongxiang city].
Characterization of the key aroma compounds in an american bourbon whisky by quantitative measurements, aroma recombination, and omission studies.
Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.
Hydroxy radical, hexanal, and decadienal generation by autocatalysts in autoxidation of linoleate alone and with eleostearate.
Studies on the aroma of five fresh tomato cultivars and the precursors of cis- and trans-4,5-epoxy-(E)-2-decenals and methional.
Characterization of odor-active compounds in extracts obtained by simultaneous extraction/distillation from moroccan black olives.
Influence of lipids in the generation of phenylacetaldehyde in wort-related model systems.
trans,trans-2,4-decadienal induces mitochondrial dysfunction and oxidative stress.
Comparison of odor-active compounds from six distinctly different rice flavor types.
Antennal and behavioral responses of Cis boleti to fungal odor of Trametes gibbosa.
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.
Re-evaluation of peroxide value as an indicator of the quality of edible oils.
Inter- and intraspecific variation in defensive compounds produced by five neotropical stink bug species (Hemiptera: Pentatomidae).
Odourous algal-derived alkenes: differences in stability and treatment responses in drinking water.
Conversion of phenylalanine into styrene by 2,4-decadienal in model systems.
Identification of volatile degradants in formulations containing sesame oil using SPME/GC/MS.
Instrumental and sensory characterization of heat-induced odorants in aseptically packaged soy milk.
Strecker degradation of phenylalanine initiated by 2,4-decadienal or methyl 13-oxooctadeca-9,11-dienoate in model systems.
Association of cooking oil fumes exposure with lung cancer: involvement of inhibitor of apoptosis proteins in cell survival and proliferation in vitro.
Chemical nature of stochastic generation of protein-based carbonyls: metal-catalyzed oxidation versus modification by products of lipid oxidation.
An evaluation of the allelopathic potential of selected perennial groundcovers: foliar volatiles of catmint (Nepeta x faassenii) inhibit seedling growth.
Stability of linseed oil and antioxidants containing dry fermented sausages: A study of the lipid fraction during different storage conditions.
A stress surveillance system based on calcium and nitric oxide in marine diatoms.
Characterization of dried whey protein concentrate and isolate flavor.
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.
Chemical composition of the volatile oil from Cynanchum stauntonii and its activities of anti-influenza virus.
Structural characterization of an etheno-2'-deoxyguanosine adduct modified by tetrahydrofuran.
Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis.
Exposure to 2,4-decadienal negatively impacts upon marine invertebrate larval fitness.
Effects of cooking oil fumes on the genotoxicity and oxidative stress in human lung carcinoma (A-549) cells.
Isolation and characterisation of a cytotoxic polyunsaturated aldehyde from the marine phytoplankter Phaeocystis pouchetii (Hariot) Lagerheim.
Structural characterization of diastereoisomeric ethano adducts derived from the reaction of 2'-deoxyguanosine with trans,trans-2,4-decadienal.
Formation of volatile compounds in model experiments with crude leek (Allium ampeloprasum Var. Lancelot) enzyme extract and linoleic acid or linolenic acid.
A new insight into the formation of odor active carbonyls by thermally-induced degradation of phospholipids in self-assembly structures.
Identification and sensory evaluation of volatile compounds in oxidized porcine liver.
Flavoring components of raw monsooned arabica coffee and their changes during radiation processing.
Aldehydes mediate tissue factor induction: a possible mechanism linking lipid peroxidation to thrombotic events.
Semiochemicals from the predatory stink bug Eocanthecona furcellata (Wolff): components of metathoracic gland, dorsal abdominal gland, and sternal gland secretions.
The use of a brine shrimp (Artemia salina) bioassay to assess the toxicity of diatom extracts and short chain aldehydes.
A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos.
Cytotoxic effects of the lipid peroxidation product 2,4-decadienal in vascular smooth muscle cells.
2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata.
Odorants generated by thermally induced degradation of phospholipids.
Formation of aroma compounds and lipoxygenase (EC 1.13.11.12) activity in unblanched leek (Allium ampeloprasum Var. Bulga) slices during long-term frozen storage.
Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl-metabolizing enzymes. I. Aliphatic alkenals.
Determination of stale-flavor carbonyl compounds in beer by stir bar sorptive extraction with in-situ derivatization and thermal desorption-gas chromatography-mass spectrometry.
Gas chromatographic-olfactometric characterization of aroma compounds in two types of cashew apple nectar.
Differential effects of tomato (Lycopersicon esculentum mill) matrix on the volatility of important aroma compounds.
Important aroma compounds in freshly ground wholemeal and white wheat flour-identification and quantitative changes during sourdough fermentation.
Study on the mechanisms of the antibacterial action of some plant alpha,beta-unsaturated aldehydes.
Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays.
Inhibition of embryonic development and fertilization in broadcast spawning marine invertebrates by water soluble diatom extracts and the diatom toxin 2-trans,4-trans decadienal.
Unsaturated fatty acids and their oxidation products stimulate CD36 gene expression in human macrophages.
Phospholipase A2 activity triggers the wound-activated chemical defense in the diatom Thalassiosira rotula.
4,5-Epoxy-2(E)-decenal-induced formation of 1,N(6)-etheno-2'-deoxyadenosine and 1,N(2)-etheno-2'-deoxyguanosine adducts.
Volatile flavor components of stored nonfat dry milk.
1,N6-etheno-2'-deoxyadenosine adducts from trans, trans-2,4-decadienal and trans-2-octenal.
Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable isotope dilution assays and sensory studies.
Aroma components of an oil-based grill flavoring by direct thermal desorption-gas chromatography-olfactometry and sample dilution analysis.
Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay.
2,4-Decadienal downregulates TNF-alpha gene expression in THP-1 human macrophages.
Identification of potent odorants formed by autoxidation of arachidonic acid: structure elucidation and synthesis of (E,Z,Z)-2,4,7-tridecatrienal.
Aldehydic lipid peroxidation products derived from linoleic acid.
In vitro antibacterial activity of some aliphatic aldehydes from Olea europaea L.
Characterization of the glutathione binding site of aldose reductase.
Mutagenicity and identification of mutagenic compounds of fumes obtained from heating peanut oil.
Effect of oleic and linoleic acids on the production of deep-fried odor in heated triolein and trilinolein.
Formation of Pentylpyridines in an Oil Medium.
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.
Volatile compounds from potato-like model systems.
Kinetic and structural characterization of the glutathione-binding site of aldose reductase.
Identification of Toxic 2,4-Decadienal in Oxidized, Low-Density Lipoprotein by Solid-Phase Microextraction.
Purine DNA adducts of 4,5-dioxovaleric acid and 2,4-decadienal.
Identification of potent odorants in Japanese green tea (Sen-cha).
Identification of character impact odorants of different soybean lecithins.
Synthesis of deuterated volatile lipid degradation products to be used as internal standards in isotope dilution assays. 1. Aldehydes.
Influence of variety and growing location on the development of off-flavor in precooked vacuum-packed potatoes.
Volatile flavor components of rice cakes.
Identification and quantitation of volatile compounds in two heated model compounds, trilinolein and linoleic acid esterified propoxylated glycerol.
Hepatic production of apolar aldehydes in rats with carbon tetrachloride-induced cirrhosis.
Simvastatin decreases aldehyde production derived from lipoprotein oxidation.
Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses.
Formation of 1,N6-etheno-2'-deoxyadenosine adducts by trans,trans-2, 4-Decadienal.
Oxidized lipoproteins including HDL and their lipid peroxidation products inhibit TNF-alpha secretion by THP-1 human macrophages.
trans,trans-2,4-decadienal: cytotoxicity and effect on glutathione level in human erythroleukemia (HEL) cells.
Biochemical analysis of recombinant glutathione S-transferase of Fasciola hepatica.
Multiple lipid oxidation products in low density lipoproteins induce interleukin-1 beta release from human blood mononuclear cells.
Oxodiene formation during the Vicia sativa lipoxygenase-catalyzed reaction: occurrence of dioxygenase and fatty acid lyase activities associated in a single protein.
Formation of fluorescent substances from degradation products of methyl linoleate hydroperoxides with amino compound.
Characterization of fluorescent products from reaction of methyl linoleate hydroperoxides with adenine in the presence of Fe2+ and ascorbic acid.
Antimutagenic effect of volatile decomposition products from thermally oxidized linoleate.
Cytotoxicities of a linoleic acid hydroperoxide and its related aliphatic aldehydes toward cultured human umbilical vein endothelial cells.
Lethal effects of a linoleic acid hydroperoxide and its autoxidation products, unsaturated aliphatic aldehydes, on human diploid fibroblasts.
[Co-oxydation of linoleic acid to volatile compounds by lipoxygenase isoenzymes from soya beans (author's transl)].

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
FooDB:FDB015510
Export Tariff Code:2912.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon 7.206 to 7.289
Refractive Index 1.512 to 1.517 @ 20 °C
Acid Value 5 max KOH/g
Vapor Pressure 0.03 mmHg @ 25 °C
Flash Point TCC Value 107.22 °C TCC
logP (o/w) 3.419 est
Solubility
alcohol Yes
propylene glycol Yes
water, 105.7 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Fatty
orange, sweet, fresh, citrus, fatty, green, oily, chicken
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity > 24 hour(s) at 100.00 %
General comment At 1.00 % in dipropylene glycol. orange sweet fresh citrus fatty green
Mosciano, Gerard P&F 17, No. 6, 41, (1992) At 10.00 % in ethyl alcohol. Fatty, oily, green, chicken skin-like
Flavor Type: Fatty
fatty, oily, chicken, fried, rancid, tallow
Mosciano, Gerard P&F 17, No. 6, 41, (1992) At 10.00 ppm. Fatty, oily, chicken, fried, with a slight rancid tallow nuance
Chicken flavors, fatty notes in various nut flavors, specifically peanut and peanut butter. Useful in savory and dairy flavors, and at low levels in various citrus and other fruit flavors. Blends well with other dienals. Fatty, oily, chicken fat, fried potatoes. Bitter orange character in high diution
2,4-DECADIENAL adds at higher dosages nice chicken fat and fried notes. In dilution it can be used for cucumber, melon, peach, plum, orange, tangerine and mandarin tonalities. Very powerful fatty, oily and citrus-like notes

Occurrences

Potential Uses

Applications
Odor purposes Aldehydic
Flavoring purposes Citrus, Cucumber, Mandarin, Melon, Orange, Peach, Plum, Tangerine
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 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 2,4-decadienal usage levels up to:
PROHIBITED: Should not be used as a fragrance ingredient.
Maximised Survey-derived Daily Intakes (MSDI-EU): 27.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 560 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
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): 1.50000-
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.500005.00000
Edible ices, including sherbet and sorbet (03.0): 0.500001.50000
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): 1.000005.00000
Confectionery (05.0): 1.000005.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 1.000005.00000
Bakery wares (07.0): 1.000005.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
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): 2.500007.50000
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 3.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.060001.00000
Ready-to-eat savouries (15.0): 5.0000020.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.500001.50000

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 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
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EPA Substance Registry Services (TSCA):2363-88-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :16899
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
deca-2,4-dienal
Chemidplus:0002363884