2363-88-4

Usage

Uses

Used in Flavor Industry:
TRANS,TRANS-2,4-DECADIENAL is used as a flavoring agent for its rich oily fatty, aldehydic, green, chicken meat with tropical fruit and cilantro nuances. It is added to various food products to enhance their taste and aroma.
Used in Fragrance Industry:
TRANS,TRANS-2,4-DECADIENAL is used as a fragrance ingredient for its citrus odor at lower concentrations. It is used in the production of perfumes, colognes, and other scented products.
Used in Food Industry:
TRANS,TRANS-2,4-DECADIENAL is used as a natural flavoring agent in the food industry. It is added to various food products such as fried potatoes, tomato, citrus peel oils, orange juice, tangerine juice, guava fruit, strawberry fruit, cabbage, carrot, raw potato, bell pepper, butter, cooked chicken, beer, rum, tea, peanut oil, popcorn, potato chips, corn tortilla, oatmeal, Brazil nut, roasted almonds, roasted peanuts and pecans, soybeans, cassava, caviar, cooked beef, lamb, mutton, and fish to enhance their taste and aroma.
Used in Chemical Industry:
TRANS,TRANS-2,4-DECADIENAL is used as a chemical intermediate in the synthesis of various compounds. Its powerful, oily, chicken fat odor and sweet, orange-like odor at high concentration make it a valuable component in the chemical industry.

Preparation

By autooxidation of methyl (trans, trans)-linolate hydroperoxide.

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

• 54306-01-3 1,1-diethoxy-oct-2-ene 
• 109-92-2 ethyl vinyl ether 
• 110905-37-8 (E)-(4-Oxo-2-butenyl)phosphonsaeure-diethylester 
• 66-25-1 hexanal 
• 3658-93-3 1,1-diethoxyhexane 
• 2548-87-0 2-octen-1-al 
• 54305-98-5 1,1,3-triethoxy-octane 
• 63-91-2 L-phenylalanine 
• 14606-80-5 methyl 13-hydroperoxyoctadeca-9,11-dienoate 
• 14606-84-9 methyl 13-hydroperoxyoctadeca-9,11,15-trienoate 
• 95285-77-1 ethyl arachidonate 

Downstream Products

• 16356-11-9 1,3,5,8-unidecatriene 
• 2548-87-0 2-octen-1-al 
• 75-07-0 acetaldehyde 
• 66-25-1 hexanal 
• 1279108-70-1 C₃₁H₃₅NO₅ 
• 73528-44-6 4,5-epoxy-2-decenal 

Relevant academic research and scientific papers

Highly efficient oxidation of alcohols catalyzed by a porphyrin-inspired manganese complex

A novel strategy for catalytic oxidation of a variety of benzylic, allylic, propargylic, and aliphatic alcohols to the corresponding aldehydes or ketones by an in situ formed porphyrin-inspired manganese complex in excellent yields (up to 99%) has been successfully developed.

Effect of oxidized arachidonic acid and hexanal on the mouse taste perception of bitterness and umami

The oxidization of fatty acids generates many volatile compounds forming an aroma, but little is known whether mammals use gustatory sense to detect the oxidized products as a taste or only use olfactory sense to detect as an aroma. We examined in this study the effect of aqueous extracts of the compounds from autoxidized arachidonic acid (AA) ethyl ester or hexanal which is the predominant component generated from oxidized AA by the anosmic mouse licking performance to a tastant. The addition of the water extract from oxidized AA or hexanal to a quinine hydrochloride (QHC1) solution decreased the anosmic mice licking frequency at several concentrations of QHC1. Hexanal also reduced the licking frequency of anosmic mice conditioned to avoid MSG at several concentrations of monosodium glutamate (MSG). These results suggest that hexanal would affect mouse taste perception to QHC1 and MSG via the gustatory sensation.

Model studies on the degradation of phenylalanine initiated by lipid hydroperoxides and their secondary and tertiary oxidation products

The reaction of methyl 13-hydroperoxyoctadeca-9,11-dienoate (MeLOOH), methyl 13-hydroperoxyoctadeca-9,11,15-trienoate (MeLnOOH), methyl 13-hydroxyoctadeca-9,11-dienoate (MeLOH), methyl 13-oxooctadeca-9,11-dienoate (MeLCO), methyl 9,10-epoxy-13-hydroxy-11-octadecenoate (Me-LEPOH), and methyl 9,10-epoxy-13-oxo-11-octadecenoate (MeLEPCO) with phenylalanine was studied to determine the comparative reactivity of primary, secondary, and tertiary lipid oxidation products in the Strecker degradation of amino acids. All assayed lipids were able to degrade the amino acid to a high extent, although the lipid reactivity decreased slightly in the following order: MeLEPCO ≥ MeLCO > MeLEPOH ≥ MeLOH > MeLOOH ≈ MeLnOOH. These data confirmed the ability of many lipid oxidation products to degrade amino acids by a Strecker-type mechanism and suggested that, once the lipid oxidation is produced, a significant Strecker degradation of surrounding amino acids should be expected. The contribution of different competitive mechanisms to this degradation is proposed, among which the conversion of the different lipid oxidation products assayed into the most reactive MeLEPCO and the fractionation of long-chain primary and secondary lipid oxidation products into short-chain aldehydes are likely to play a major role.

New Functionalized Horner-Wadsworth-Emmons Reagents: Useful Building Blocks in the Synthesis of Polyunsaturated Aldehydes. A Short Synthesis of (+/-)-(E,E)-Coriolic Acid

The new Horner-Wadsworth-Emmons reagents 4 and 5 transform carbonyl compounds into 2,4-pentadienals and 3-methyl-2,4-pentadienals, respectively.Reagent 4 gives good yields of the desired products with a variety of aldehydes and ketones; reagent 5 generally gives good yields with aldehydes, but gives lower yields with ketones.The reactions proceed under mild conditions and give the products as predominantly 2E,4E isomers, with moderate to good stereoselectivity.In general, pure samples of the 2E,4E-dienals can be obtained after chromatography.Reagents 4 have been used in the key step in a short synthesis of (+/-)-13-hydroxy-9(E),11(E)-octadecanoic acid ((E,E)-coriolic aicd, 45).