25152-84-5

Basic information

• Product Name: trans,trans-2,4-Decadien-1-al
• Synonyms: (2E,4E)-Deca-2,4-dienal;Trans, trans-2,4-decadienal, 95%, tech.;(2E,4E)-2,4-Decanedienal;Trans,Trans-2,4-Decadienal, Remainder Mainly Trans,Cis Isomer;2,4-Decadiena(Trans,Trans);trans,trans-2,4-Decadienal;trans,trans-2,4-Decadienal technical grade, 85%;DDA
• CAS NO: 25152-84-5
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 246-668-9
• Product Categories: aldehyde Flavor;Alphabetical Listings;C-D;Flavors and Fragrances;Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 25152-84-5.mol

Chemical Properties

• Boiling Point: 114-116 °C10 mm Hg(lit.)
• Flash Point: 214 °F
• Appearance: Clear yellow/Liquid
• Density: 0.872 g/mL at 20 °C(lit.)
• Vapor Density: >1 (vs air)
• Refractive Index: n20/D 1.515(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 1704897
• CAS DataBase Reference: trans,trans-2,4-Decadien-1-al(CAS DataBase Reference)
• NIST Chemistry Reference: trans,trans-2,4-Decadien-1-al(25152-84-5)
• EPA Substance Registry System: trans,trans-2,4-Decadien-1-al(25152-84-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: HD3000000
• F: 10-23
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 25152-84-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
trans,trans-2,4-Decadien-1-al is used as a flavoring agent for its characteristic chicken-like aroma, enhancing the taste and appeal of various food products. It is particularly useful in the creation of meat-flavored seasonings and additives.
Used in Perfumery:
Due to its citrus odor at lower concentrations, trans,trans-2,4-Decadien-1-al is also utilized as a fragrance ingredient in the perfumery industry, contributing to the development of unique and pleasant scents.
Used in the Food Industry:
trans,trans-2,4-Decadien-1-al is used as a natural flavor enhancer in the food industry, adding depth and complexity to the taste of various dishes, particularly those involving meat or meat substitutes.
Used in the Cosmetic Industry:
In the cosmetic industry, trans,trans-2,4-Decadien-1-al may be used as a component in the formulation of certain products due to its unique aroma, potentially contributing to the sensory experience of the product.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 4223, 1995 DOI: 10.1016/0040-4039(95)00704-G

InChI:InChI=1/C10H16O/c1-2-3-4-5-6-7-8-9-10-11/h6-10H,2-5H2,1H3/b7-6+,9-8+

Upstream product

• 66-25-1 hexanal 
• 25073-24-9 3t-oxiranyl-propenal 
• 4762-26-9 hexyltriphenylphosphonium bromide 
• 3391-86-4 1-octen-3-ol 
• 6228-98-4 phenylthioacetylene 
• 4885-02-3 Dichloromethyl methyl ether 
• 70960-90-6 trimethyl-nona-1,3t-dien-t-yl-silane 
• 16195-71-4 (2E,4Z)-2,4-decadien-1-ol 
• 129422-73-7 (5-aza-5-cyclohexylpenta-2,4-dienyl)diethoxyphosphin-1-one 
• 2548-87-0 (E)-2-Octenal 
• 927-80-0 1-ethoxyacetylene 
• 103698-50-6 triphenylarsonium salt of bromoacetaldehyde 
• 177600-18-9 4-acetoxy-2(E)-decenenitrile 
• 168295-35-0 (2E,4E)-5-iodopenta-2,4-dienal 

Downstream Products

• 7328-34-9 ethyl 2E,4E-decadienoate 
• 16356-11-9 (3E,5E)-1,3,5-undecatriene 
• 18409-21-7 (2E,4E)-2,4-decadien-1-ol 
• 7328-33-8 methyl (2E,4E)-decadienoate 
• 112-31-2 caprinaldehyde 
• 1802-20-6 3-pentyl-pyridine 
• 2294-76-0 2-pentylpyridine 
• 372937-60-5 (S)-(+)-N-(2,4-decaylidene)-p-toluenesulfinamide 
• 613676-99-6 (E,E)-1-phenyl-undeca-3,5-dien-2-ol 
• 720682-27-9 4-Methyl-benzenesulfinic acid (R)-[(2E,4E)-deca-2,4-dien-(E)-ylidene]amide 
• 30361-33-2 (2E,4E)-deca-2,4-dienoic acid 
• 134454-31-2 (2E,4RS,5RS)-(±)-4,5-epoxy-(E)-2-decenal 
• 145178-65-0 6E,8E,10E,12E-octadecatetraenoic acid 
• 97134-11-7 (9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid 

Relevant articles and documents

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Anaerobic nitroxide-catalyzed oxidation of alcohols using the NO +/NO· redox pair

A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3·OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO· pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization and no formation of nonvolatile byproducts.

A detailed identification study on high-temperature degradation products of oleic and linoleic acid methyl esters by GC-MS and GC-FTIR

GC-MS and GC-FTIR were complementarily applied to identify oxidation compounds formed under frying conditions in methyl oleate and linoleate heated at 180 °C. The study was focused on the compounds that originated through hydroperoxide scission that remain attached to the glyceridic backbone in fats and oils and form part of non-volatile molecules. Twenty-one short-chain esterified compounds, consisting of 8 aldehydes, 3 methyl ketones, 4 primary alcohols, 5 alkanes and 1 furan, were identified. In addition, twenty non-esterified volatile compounds, consisting of alcohols, aldehydes and acids, were also identified as major non-esterified components. Furanoid compounds of 18 carbon atoms formed by a different route were also identified in this study. Overall, the composition of the small fraction originated from hydroperoxide scission provides a clear idea of the complexity of the new compounds formed during thermoxidation and frying.

Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z,3Z)-butyltelluro-4-methoxy-1,3-butadiene

(1Z,3Z)-Butyltelluro-4-methoxy-1,3-butadiene 2 was obtained by the hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a-d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α,β,γ,δ-unsaturated aldehydes of (E,E) configuration, which are precursors of trienes obtained from natural sources. The products of this reaction were employed in the synthesis of methyl-(2E,4E)-decadienoate 7, which is a component of the flavor principles of ripe Bartlett pears. Performing the Wittig reaction of the methyl triphenylphosphorane with the deca-(2E,4E)-dienal 5a, we were able to synthesize the undeca-(1,3E,5E)-triene 6a. This compound is a sex-pheromone component of the marine brown algae Fucus serratus, Dictyopteris plagiograma, and Dictyopteris australis. Performing the Wittig reaction of methyl triphenylphosphorane with the octa-(2E,4E)-dienal 5c, the nona-(1,3E,5E)-triene 6b was synthesized. The compound obtained is a sex-pheromone component of the marine brown alga Sargassum horneri. The octa-(1,3E,5E)-triene 6c was easily obtained from hepta-(2E,4E)-dienal 5d by the Wittig reaction with methyl triphenylphophorane. This compound is a sex-pheromone component of the marine brown alga Fucus serratus.

Catalytic enantioselective allylation of dienals through the intermediacy of unsaturated π-allyl complexes

(Chemical Equation Presented) The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester [allylB(pin)] to >,β,γ,δ-unsaturated aldehydes is described. This reaction results in a remarkable inversion of substrate olefin geometry, providing the Z,E-configured reaction product in good enantioselectivity and olefin stereoselectivity. The reaction appears to proceed by conversion of the dienal to an unsaturated B-allyl complex followed by reductive elimination via transition state II. Enantioselectivities range from 73-94% ee for a range of δ-substituted dienals when chiral ligand L3 is employed.

Aggregation behavior of tetraenoic fatty acids in aqueous solution

(Chemical Equation Presented) Why so blue? Unique blue-shifted UV absorptions were used to follow the aggregation of C24 tetraene fatty acids in aqueous solution. Aggregation takes place through three distinct states (i.e. K→T1→T2; see picture). It is suggested that all of these aggregates are lamellar-type in a local sense but differ in the packing mode of the fatty acid backbone.

2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata

Marine green alga Ulva conglobata was investigated for the biogeneration of oxygenated products from exogenously added arachidonic acid (ARA). A crude enzyme from the alga afforded the detectable amount of a hydroperoxyicosatetraenoic acid (HPITE), which was identified as (R)-11-HPITE by HPLC and GC-MS. Headspace-SPME method indicated that ARA was selectively used to form 2,4-decadienals. These results showed that 2,4-decadienals are produced via (R)-11-HPITE from ARA exclusively.

Palladium catalyzed cross-coupling reaction of functional organozinc reagents with (2E,4E)- and (2E,4Z)-5-bromopenta-2,4-dienals: Easy access to functional conjugated dienic aldehydes

Functional zinc reagents can be applied to palladium catalyzed cross-coupling reaction with (2E,4E)- and (2E,4Z)-5-bromopenta-2,4-dienal. The corresponding functional dienic aldehydes were obtained in goods yields. From the (2E,4E) isomer, the (2E,4E) dienals were isolated as single isomer according to a total stereoselective reaction. But, from the (2E,4Z) isomer the coupling reaction has lead to a mixture of (2E,4E) and (2E,4Z) isomers. A mechanism for the loss of stereoselectivity in the last case is proposed.

Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms

α,β,γ,δ-Unsaturated aldehydes have gained increasing attention since 2,4-decadienal and 2,4,7-decatrienal were isolated from the diatom Thalassiosira rotula and characterized as cell antiproliferative metabolites. Structurally related α,β,γ,δ-unsaturated aldehydes were found in this alga as well as in other diatom species. We present a short and universal synthesis of this compound class along with a structure-activity study of the potential to inhibit sea urchin egg cleavage. Pd0- or CoII-mediated cross coupling of 5-iodo-penta-2,4-dienal with organo-zincates allows the fast and flexible synthesis of numerous aldehydes from this universal precursor. The stereochemistry of the double bond system of the precursor was preserved during the coupling. Bioassays showed that the polarity of the side chain is important for antiproliferative activity with 2,4-decadienal as the most active compound tested compared to the shorter-chain aliphatic homologues and to ω-oxo acids with conjugated double systems. In contrast, the double bond geometry has no influence on biological activity. The α,β-unsaturated 2E-decenal was also highly active, while activity diminished in the case of saturated aldehydes of similar chain length. 1-Decanol, 2-decanone and decanoic acid were not active.