2,4-Decadienal

2,4-Decadienal
Compound Structure:
Synonyms: (2E,4E)-deca-2,4-dienal;trans,trans-2,4-Decadienal;2,4-DECADIENAL; 2,4-Decadienal, (2E,4E)-;trans,trans-2,4-Decadien-1-al;(E,E)-2,4-Decadienal;(2E,4E)-2,4-Decadienal;(2E,4E)-Decadienal;2,4-Decadienal, (E,E)-;decadienal;2-trans-4-trans-Decadiena
Compound ID: NMPC-052
PubChem ID:

5283349

Molecular Formula: C10H16O
Canonical SMILES: CCCCCC=CC=CC=O
InChIKey: JZQKTMZYLHNFPL-BLHCBFLLSA-N
About the compound:

(2E,4E)-deca-2,4-dienal is a polyunsaturated fatty aldehyde derived from decanal that has undergone formal dehydrogenation, resulting in the introduction of trans-double bonds at the 2-3 and 4-5 positions. It is a product of lipid peroxidation in cell membranes and is also found in cooking oil fumes. This compound serves various roles, including being a nematicide (used to kill plant-parasitic nematodes) and an apoptosis inducer. 2,4-Decadienal is a natural product found in organisms such as Vaccinium vitis-idaea and Streptomyces. Additionally, trans,trans-2,4-decadienal is a metabolite found in or produced by Saccharomyces cerevisiae. (E,E)-2,4-Decadienal is an aromatic substance present in various food items, including butter, cooked beef, fish, potato chips, roasted peanuts, buckwheat, and wheat bread crumbs. In its isolated form, it has a deep fat flavor, reminiscent of a chicken aroma (at 10 ppm concentration). At lower concentrations, it exhibits the odor of citrus, resembling notes of orange or grapefruit. It is worth noting that (E,E)-2,4-decadienal has raised concerns about its potential carcinogenicity. While it has been used as an aroma in the European Union, there are restrictions on its use until the required data regarding its safety have been submitted. This compound has diverse sensory properties and is found in a range of food products, contributing to their characteristic aromas and flavors, but its safety for consumption is subject to regulatory scrutiny.

https://en.wikipedia.org/wiki/(E,E)-2,4-Decadienal

GHS Hazard Statements

H312 (81.93%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (99.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (15.26%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

152.23 g/mol

XLogP3-AA

3.2

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

6

Exact Mass

152.120115130 g/mol

Monoisotopic Mass

152.120115130 g/mol

Topological Polar Surface Area

17.1Ų

Heavy Atom Count

11

Formal Charge

0

Complexity

134

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

2

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Pale yellow to dark brown liquid with a buttery, fatty, orange odor; [Advanced BioTech MSDS] Strong green odor; Odor like sweet oranges at high concentrations; [Citrus and Allied Essences MSDS]

Density

0.866-0.876

Solubility 

soluble in fixed oils; Insoluble in water

Source: PubChem

Source Species: Bryophyllum pinnatum
Lagenaria siceraria
Hirsute Palisota
Brachystegia eurycoma
Plumeria alba
Pyrenacantha staudtii
Tecoma stans
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