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2,4-heptadienal

2,4-Heptadienal is an aldehyde used as a flavoring agent, notable for its green, citrus, and creamy sensory characteristics.
Chemical Structure

General Material Description

2,4-Heptadienal is a volatile aldehyde with the molecular formula C7H10O, recognized for its distinct green, fruity, and citrus-flavored odor profile. It is an aliphatic unsaturated aldehyde featuring conjugated double bonds that contribute to its sensory properties. Also known by several synonyms including hepta-2,4-dienal and 2,4-heptadien-1-al, this compound is identified in natural sources such as fish flesh and laurel leaf oil. It serves primarily as a flavoring agent enhancing citrus and creamy notes in formulations. The compound’s chemical identity is cataloged under CAS number 5910-85-0 and can be referenced through established chemical databases such as PubChem. Its sourcing typically involves extraction from natural oils or chemical synthesis for use in the flavor industry.

Occurrence, Applicability & Potential Uses

2,4-Heptadienal naturally occurs in various biological sources, including fish species and the stems of kohlrabi. Trace amounts are also present in laurel leaf oil, which derives from sweet bay leaves. These occurrences associate the compound with fresh and green sensory notes in natural products. The compound’s primary application lies in the flavor industry, where it functions as a flavoring agent to impart green, citrus, and creamy characteristics, particularly in citrus and dairy-type flavor profiles. Its use and safety are governed by flavoring regulatory standards such as FEMA (US), ensuring controlled application in food and beverage formulations. The characteristic odor and flavor contributions make it valuable for enhancing natural and formulated flavor profiles.

Physico-Chemical Properties Summary

2,4-Heptadienal exhibits physical and chemical properties relevant to its formulation and use as a flavor compound. It has a molecular weight of approximately 110.16 g/mol and features moderate volatility, boiling between 177 and 178°C at standard atmospheric pressure. The compound displays a log P value of about 1.89 (estimated), indicating moderate hydrophobicity, and a vapor pressure of 1.044 mmHg at 25°C, which influences its aroma release profile. Solubility characteristics include good miscibility with alcohol and limited aqueous solubility estimated at 2805 mg/L at 25°C. Its flash point is reported as 74°C (163°F), relevant for handling and safety assessments. These properties ensure its functional performance in flavor preparations that require stable, yet perceptible volatile components.

FAQ

What is 2,4-heptadienal and what are its main sensory characteristics?
2,4-Heptadienal is an unsaturated aldehyde used primarily as a flavoring agent in the food industry. It is recognized for its distinctive green and fresh aroma with citrus overtones, particularly reminiscent of orange and tangerine. Additionally, it contributes creamy and fatty notes to flavor compositions, enhancing mouthfeel in dairy-type flavors. These organoleptic features make it a valuable component in flavor formulations that aim to replicate or enhance natural citrus and green aromas.
Where does 2,4-heptadienal naturally occur and how is it commonly used?
This compound naturally occurs in fish, the stems of kohlrabi, and in trace amounts within laurel leaf oil obtained from sweet bay. Its natural presence associates it with green and fresh sensory profiles in these biological materials. In commercial applications, 2,4-heptadienal is utilized as a flavoring ingredient to impart green, citrus, and creamy characteristics. It is often included in flavor formulations for beverages, dairy products, and other foods where such sensory effects are desired.
What regulatory standards apply to 2,4-heptadienal in flavoring applications?
2,4-Heptadienal is regulated under flavoring safety standards including the FEMA (US) guidelines, which assess its safe use levels in food. According to IFRA (Global) standards, it is prohibited as a fragrance ingredient, highlighting its specific usage restrictions outside the flavoring domain. Toxicological data indicate moderate oral and dermal toxicity, emphasizing the importance of compliance with recommended use concentrations. Safety assessments and registrations with agencies like the European Chemicals Agency (ECHA) and the U.S. FDA facilitate its controlled application in flavorings.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

hepta-2,4-dienal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:5910-85-0
Pubchem (cid):20307
Pubchem (sid):134987452
Publications by PubMed
A fishy odor episode in a north China reservoir: occurrence, origin, and possible odor causing compounds.
Simultaneous determination of ten taste and odor compounds in drinking water by solid-phase microextraction combined with gas chromatography-mass spectrometry.
Aroma chemistry of African Oryza glaberrima and Oryza sativa rice and their interspecific hybrids.
Pro-oxidant/antioxidant behaviours of ascorbic acid, tocopherol, and plant extracts in n-3 highly unsaturated fatty acid rich oil-in-water emulsions.
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.
Essential oil composition of Prasium majus from Croatia.
Iron-lactoferrin complex reduces iron-catalyzed off-flavor formation in powdered milk with added fish oil.
In depth study of acrylamide formation in coffee during roasting: role of sucrose decomposition and lipid oxidation.
Gas chromatographic-olfactometric aroma profile and quantitative analysis of volatile carbonyls of grilled beef from different finishing feed systems.
Change of volatile compounds in fresh fish meat during ice storage.
Oxidative Stability of Polyunsaturated Edible Oils Mixed With Microcrystalline Cellulose.
The volatile compounds in lamb fat are affected by the time of grazing.
Dynamics of dissolved and particulate polyunsaturated aldehydes in mesocosms inoculated with different densities of the diatom Skeletonema marinoi.
Determination of the volatile profile of stoned table olives from different varieties by using HS-SPME and GC/IT-MS.
Biotechnological process for obtaining new fermented products from cashew apple fruit by Saccharomyces cerevisiae strains.
Rapid fingerprinting and classification of extra virgin olive oil by microjet sampling and extractive electrospray ionization mass spectrometry.
Atmospheric carbon dioxide changes photochemical activity, soluble sugars and volatile levels in broccoli (Brassica oleracea var. italica).
Modeling the formation and reactions of benzene metabolites.
Iron is an essential cause of fishy aftertaste formation in wine and seafood pairing.
Characterization of volatile substances in apples from Rosaceae family by headspace solid-phase microextraction followed by GC-qMS.
Monitoring of autoxidation in LCPUFA-enriched lipid microparticles by electronic nose and SPME-GCMS.
Antioxidant activity of oregano, parsley, and olive mill wastewaters in bulk oils and oil-in-water emulsions enriched in fish oil.
Analysis of volatile compounds of Iberian dry-cured loins with different intramuscular fat contents using SPME-DED.
Differential effect of three polyunsaturated aldehydes on marine bacterial isolates.
Growth inhibition of cultured marine phytoplankton by toxic algal-derived polyunsaturated aldehydes.
1,3-diene probes for detection of triplet carbonyls in biological systems.
Studies on the aroma of maté (Ilex paraguariensis St. Hil.) using headspace solid-phase microextraction.
Age and nutrient limitation enhance polyunsaturated aldehyde production in marine diatoms.
Odourous algal-derived alkenes: differences in stability and treatment responses in drinking water.
The aggregation pheromone of Diorhabda elongata, a biological control agent of saltcedar (Tamarix spp.): identification of two behaviorally active components.
Comparison of volatile aldehydes present in the cooking fumes of extra virgin olive, olive, and canola oils.
Formation of volatile compounds in model experiments with crude leek (Allium ampeloprasum Var. Lancelot) enzyme extract and linoleic acid or linolenic acid.
Modeling the sensory impact of defined combinations of volatile lipid oxidation products on fishy and metallic off-flavors.
Volatile constituents from the leaves of Callicarpa japonica Thunb. and their antibacterial activities.
Chemical and olfactometric characterization of volatile flavor compounds in a fish oil enriched milk emulsion.
Identification of odoriferous compounds from adults of a swallowtail butterfly, Papilio machaon (Lepidoptera: Papilionidae).
Aroma profiles of vegetable oils varying in fatty acid composition vs. concentrations of primary and secondary lipid oxidation products.
Dynamic headspace gas chromatography/mass spectrometry characterization of volatiles produced in fish oil enriched mayonnaise during storage.
Response of urinary lipophilic aldehydes and related carbonyl compounds to factors that stimulate lipid peroxidation in vivo.
Hepatic production of apolar aldehydes in rats with carbon tetrachloride-induced cirrhosis.
Lipophilic aldehydes and related carbonyl compounds in rat and human urine.
Oxidized lipoproteins including HDL and their lipid peroxidation products inhibit TNF-alpha secretion by THP-1 human macrophages.
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.
Generation, characterization, and histochemical application of monoclonal antibodies selectively recognizing oxidatively modified apoB-containing serum lipoproteins.
Multiple lipid oxidation products in low density lipoproteins induce interleukin-1 beta release from human blood mononuclear cells.
Studies on epitopes on low-density lipoprotein modified by 4-hydroxynonenal. Biochemical characterization and determination.
Detection of new epitopes formed upon oxidation of low-density lipoprotein, lipoprotein (a) and very-low-density lipoprotein. Use of an antiserum against 4-hydroxynonenal-modified low-density lipoprotein.
Autoxidation of human low density lipoprotein: loss of polyunsaturated fatty acids and vitamin E and generation of aldehydes.
Detection of Lipid Degradation Products in the Water of a Reservoir During a Bloom of Synura uvella.
Autoxidation of tissue lipids. II. Monocarbonyl compounds formed by the autoxidation of methyl eicosapentaenoate, methyl docosahexaenoate, and cod-liver oil.
Multiple roles of plant volatiles in jasmonate-induced defense response in rice.

General Material Information

Preferred name 2,4-heptadienal
Trivial Name 2,4-Heptadienal
Short Description 2,4-heptadienal
Formula C7 H10 O
CAS Number 5910-85-0
ECHA Number 227-627-4
FDA UNII Search
Beilstein Number 1699244
xLogP3-AA 1.60 (est)
NMR Predictor External link
Synonyms
  • hepta-2,4-dienal
  • 2,4-heptadien-1-al
  • 2,4-heptadien-1-al FCC
  • 2,4-heptadien-1-al FCC, no antioxidant
  • 2,4-heptadiene-1-al
  • 2,4-Heptadien-1-al

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 110.15589904785
Boiling Point 177 to 178°C @ 760 mm Hg
Vapor Pressure 1.044 mmHg @ 25 °C
Flash Point TCC Value 72.6 °C TCC
logP (o/w) 1.891 est
Solubility
alcohol Yes
water, 2805 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
green, pungent, fruity, spicy
General comment Citrus flavors, especially orange and tangerine. Can also be used for mouth feel in a variety of dairy type flavors. green pungent fruity spicy
Flavor Type: Creamy
sweet, creamy, fatty, citrus peel
General comment Sweet creamy fatty citrus peel
Citrus flavors, especially orange and tangerine. Can also be used for mouth feel in a variety of dairy type flavors. Sweet, creamy, fatty, citrus peel

Occurrences

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:
oral-rat LD50 1150 mg/kg
Food and Chemical Toxicology. Vol. 21, Pg. 855, 1983.

Dermal Toxicity:
skin-rabbit LD50 313 mg/kg
Food and Chemical Toxicology. Vol. 21, Pg. 855, 1983.

skin-guinea pig LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 21, Pg. 855, 1983.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
IFRA Critical Effect:
Insufficient data
View the IFRA Standard
Recommendation for 2,4-heptadienal usage levels up to:
PROHIBITED: Should not be used as a fragrance ingredient.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):5910-85-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :20307
National Institute of Allergy and Infectious Diseases:Data
hepta-2,4-dienal
Chemidplus:0005910850