54653-25-7

Usage

Uses

Used in Flavor and Fragrance Industry:
Ethyl-5-hexenoate is used as a flavoring agent for its sweet, fruity, and pineapple-like aroma. Its taste threshold values range from 5 to 10 ppm, making it a suitable addition to the flavor industry to enhance the taste and aroma of various products.
Used in Aromatherapy:
Due to its pleasant and fruity scent, Ethyl-5-hexenoate can be used as an aromatherapy agent. Its odor characteristics at 10,000 ppm include a sharp estery, sweet with ripe fruity notes of pineapple, apple, and strawberry, along with winy and acidic depth notes. This makes it a potential candidate for creating a relaxing and uplifting atmosphere in aromatherapy applications.
Used in Perfumery:
Ethyl-5-hexenoate's unique and fruity aroma also makes it suitable for use in the perfumery industry. It can be used as a base note or blended with other fragrance components to create complex and long-lasting scents for perfumes and colognes.
Used in the Food and Beverage Industry:
The fruity and sweet characteristics of Ethyl-5-hexenoate make it an ideal additive for the food and beverage industry. It can be used to enhance the flavor and aroma of various products, such as fruit juices, candies, and baked goods, providing a more enjoyable and appetizing experience for consumers.

InChI:InChI=1/C8H14O2/c1-3-5-6-7-8(9)10-4-2/h3H,1,4-7H2,2H3

Upstream product

• 64-17-5 ethanol 
• 1577-22-6 5-hexenoic acid 
• 31696-00-1 diethyl 2-(3-butenyl)malonate 
• 104089-16-9 2-ethoxycarbonyethylzinc iodide 
• 107-18-6 allyl alcohol 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 106-95-6 allyl bromide 
• 92085-71-7 1-allyl-2,8,9-trioxa-5-aza-1-silabicyclo<3.3.3>undecane 
• 140-88-5 ethyl acrylate 
• 3066-75-9 allyl diethyl phosphate 
• 42216-96-6 triethyl orthoacrylate 
• 821-41-0 5-Hexen-1-ol 
• 105-60-2 caprolactam 
• 1073930-92-3 5-(ethoxycarbonyl)pentyl 1-naphthyl selenide 

Downstream Products

• 22668-36-6 ethyl 5-oxopentanoate 
• 821-41-0 5-Hexen-1-ol 
• 946485-28-5 C₁₅H₁₉F₂IO₄S 
• 58019-68-4 Ethyl 6-Methyl-2-oxo-cyclohexanecarboxylate 
• 144192-31-4 Ethyl 2-oxo-6-phenylcyclohexanecarboxylate 
• 144192-34-7 Ethyl 1,6-Dimethyl-2-oxocyclohexanecarboxylate 
• 144192-39-2 (1R^*,6S^*)-Ethyl 1-methyl-2-oxo-6-phenylcyclohexanecarboxylate 
• 122130-95-4 2-(4-phenylthio-but-1-yl)-3-methoxymaleic anhydride 
• 13984-57-1 ethyl 5-oxohexanoate 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 
• 1332896-03-3 ethyl 3-(3-trifluoromethylphenyl)hexanoate 
• 1332896-01-1 ethyl 3-(4-chlorophenyl)hexanoate 
• 1332895-99-4 ethyl 3-(4-toluyl)hexanoate 
• 72277-16-8 ethyl 3-phenylhexanoate 

Relevant academic research and scientific papers

Microbiological transformations. Part 51: The first example of a dynamic kinetic resolution process applied to a microbiological Baeyer-Villiger oxidation

The dynamic resolution of racemic 2-benzyloxymethylcyclopentanone 1 upon microbiologically mediated Baeyer-Villiger oxidation allowed the corresponding (R)-lactone 2 to be prepared in 85% yield and 96% ee.

Enantioselective allylic hydroxylation of w-alkenoic acids and esters by P450 BM3 monooxygenase

Chiral allylic alcohols of w-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. The direct enantioselective C-H oxidation of linear terminal olefins offers the shortest route toward these compounds, but known synthetic methods are limited and suffer from low selectivities. Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo- and enantioselectivities providing the desirable secondary alcohols.

Sunlight oxidation of alkyl aryl tellurides to the corresponding carbonyl compounds: A new carbonyl precursor

Alkyl aryl tellurides were efficiently transformed to the corresponding carbonyl compounds by photo-oxidation with sunlight without affecting various functional groups in the alkyl moiety. The tellurides can be used as a new carbonyl precursor, and the photolysis can be conducted without special equipment for light sources.

Facile photochemical transformation of alkyl aryl selenides to the corresponding carbonyl compounds by molecular oxygen: Use of selenides as masked carbonyl groups

(Chemical Equation Presented) Alkyl aryl selenides with and without functional groups on the alkyl group were transformed efficiently into the corresponding carbonyl compounds, particulary primary alkyl aryl selenides in good yields, by a simple photolysis in the presence of air or oxygen. This transformation can be conducted without protection of functional groups. The yield of carbonyl compounds was much affected by the solvent viscosity, reaction temperature, concentration of dissolved oxygen in the solvents, wavelength of light, and structure of the aryl substituents. The present study indicates that aryl selenides can be considered as a masked carbonyl group that can be easily converted to a carbonyl group by very mild reaction conditions even in the presence of various unprotected functional groups. Therefore, this functional group transformation can be used as an important tool in organic synthesis due to its simplicity and mild reaction condition.

Synthesis of unsaturated dibasic acid esters from five-, six-, and seven-membered cycloalkanones

A new route to diesters of symmetrical octene-, decene-, and dodecenedioic acids was proposed. The ratio of the cis/trans-isomers was 1:4. The synthesis involved oxidative splitting of five-, six-, and seven-membered cycloalkanones with hydrogen peroxide into the corresponding ω-alkenoic acids followed by esterification and metathesis over Re2O7/B 2O3-Al2O3-SnMe4.

Highly regioselective coupling reactions of allylic and propargylic alcohol derivatives with γ,γ-dialkoxyallylic zirconium species via Zr-to-Cu transmetalation

(Chemical Equation Presented) In the presence of CuCN, reaction of γ,γ-dialkoxyallylic zirconium species 4, generated in situ by treating triethyl orthoacrylate with zirconocene-butene complex, with allylic and propargylic phosphates proceeded at the α-po

Synthesis of C3-C9-alkenyl 2,3-unsaturated glucosides from glucose and some alkenols

C3-C9-Alkenyl 2,3-unsaturated glucosides have been synthesized from glucose and C3-C9-alkenols by using Ferrier reaction with boron trifluoride etherate (BF3·Et2O) as Lewis acid catalyst in key step.

Cu(I)-assisted carbon-carbon bond forming reactions of γ,γ-dialkoxyallylic zirconium species: A new versatile homoenolate equivalent of propionate

In the presence of CuCN, reaction of γ,γ-dialkoxyallylic zirconium species 1 with acyl chloride or allylic phosphates proceeded at the α-position of 1 to give alkanoates 3 after aqueous work-up. The ketene dialkylacetal moiety in the coupling products 2 can be used for further bond forming reaction with electrophiles such as nitrosobenzene, nitrostyrene or trichloroacetylisocyanate. (C) 2000 Elsevier Science Ltd.

Stannyl radical-mediated cleavage of π-deficient heterocyclic sulfones. Synthesis of α-fluoro esters

Treatment of ethyl 2-(pyridin-2-ylsulfonyl)hexanoate with tributylstannane and azobis(2-methyl-2-propanitrile) (AIBN) in benzene at reflux for 36 h resulted in hydrogenolysis to give ethyl hexanoate (60%), whereas no reaction was observed after 48 h at reflux with ethyl 2-(phenylsulfonyl)-hexanoate. Ethyl 2-(pyrimidin-2-ylsulfonyl)hexanoate underwent quantitative hydrogenolysis within 1 h under these conditions. This represents a mild new methodology for removal of the synthetically useful sulfone moiety. Substitution of Bu3SnD for Bu3SnH gave access to α-deuterium-labeled esters. Treatment of the α-(pyrimidin-2-ylsulfonyl) enolates derived from several esters with Selectfluor gave high yields of the 2-fluoro-2-(pyrimidin-2-ylsulfonyl)alkanoates, which were smoothly desulfonylated [Bu3SnH (2 equiv)/AIBN/benzene/Δ] to give 2-fluoroalkanoates. "Catalytic" tin hydride, generated from tribuytltin chloride (0.15 equiv) and excess polymethylhydrosiloxane in the presence of potassium fluoride, also effected removal of the π-deficient α-(pyrimidin-2-ylsulfonyl) moiety from acid derivatives in high yields. Desulfonylation is suggested to proceed via alkoxy ketyl-type radicals and tin enolates.

Single Electron Transfer Mechanism in the Reaction of 1,3-Dithianyllithium and Alkyl Iodides

The reaction between 2-lithio-1,3-dithiane and optically active (R)-2-iodooctane was found to proceed with complete inversion of configuration.This result suggests that the SN2 (rather than single electron transfer (SET)) mechanism is the preferred pathway for reaction between dithianyllithium and unhindered alkyl halides.When the neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene was used as the substrate halide, 6-11percent cyclized alkylated product was obtained.This result suggests that when the SN2 pathway is blocked, SET mechanisms become operative to some extent, at least with iodide as the halogen.The reaction of dithianyllithium and (R)-2-iodooctane and 5,5-dimethyl-6-iodo-1-hexene, with hexane as the solvent, proceeds under heterogeneous conditions to bring about complete racemization of the respective iodide.These results demonstrate for the first time that 2-lithio-1,3-dithiane can act as electron donor in reactions initiated by electron transfer to alkyl iodides.