54972-10-0

Usage

Uses

Used in Perfumery and Cosmetics Industry:
Ethyl 2-hydroxycyclopentane-1-carboxylate is used as a flavor and fragrance agent for its pleasant fruity and floral aroma, enhancing the scent profiles of perfumes and cosmetics.
Used in Food and Beverage Industry:
In the food and beverage industry, ethyl 2-hydroxycyclopentane-1-carboxylate is used as a flavoring agent to impart a desirable aroma to food products, contributing to a more enjoyable sensory experience for consumers.
Used in Medicinal Applications:
Ethyl 2-hydroxycyclopentane-1-carboxylate has been studied for its potential medicinal properties, such as anti-inflammatory and antioxidant effects. It is being explored for its therapeutic benefits in various medical applications.
Used in Consumer Product Safety:
Due to its low toxicity and safety profile, ethyl 2-hydroxycyclopentane-1-carboxylate is approved for use in consumer products, ensuring that it does not pose significant health risks to users.

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 63578-04-1 (+/-)-cis-2-(3,5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 294212-87-6 ethyl 2-bromo-6-oxohexanoate 
• 294212-81-0 ethyl 2-bromo-6-hydroxyhexanoate 
• 294212-79-6 ethyl 6-triethylsilyloxyhexanoate 
• 294212-80-9 2-bromo-6-triethylsilanyloxy-hexanoic acid ethyl ester 
• 5299-60-5 6-hydroxy-hexanoic acid ethyl ester 
• 1092929-40-2 (Z)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 13038-15-8 (E)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 124668-80-0 (E)-ethyl 6-[(methylsulfonyl)oxy]hex-2-enoate 
• 63578-04-1 (+/-)-trans-2-(3.5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 

Downstream Products

• 90792-88-4 2-Methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 1421957-11-0 2-(ethoxycarbonyl)cyclopentyl 4-bromobenzoate 
• 1421956-83-3 2-(ethoxycarbonyl)cyclopentyl 4-hydroxybenzoate 
• 63578-04-1 (+/-)-trans-2-(3.5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 63578-04-1 (+/-)-cis-2-(3,5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 110611-68-2 ethyl syn-(1S,2R)-2-hydroxycyclopentanecarboxylate 
• 169868-13-7 (1S,2R)-2-hydroxycyclopentane-1-carboxylic acid 
• 61586-79-6 ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate 
• 124150-23-8 (1R,2S)-2-methoxycarbonylcyclopentan-1-ol 
• 5809-02-9 ethyl cyclopent-2-enyl carboxylate 

Relevant academic research and scientific papers

Investigation of Electrostatic Interactions towards Controlling Silylation-Based Kinetic Resolutions

Electrostatic interactions between a silylated isothiourea intermediate and an ester π system were explored by determining how variations in sterics and electronics affect the selectivity of a silylation-based kinetic resolution. Sterics on the π systems affect the selectivity factors of alkyl 2-hydroxycyclohexanecarboxylates, resulting in a strong correlation of selectivity factors to Charton values. Induction effects of electron-withdrawing substituents on phenyl esters significantly enhance selectivity supporting an edge to face π–π interaction. The linear free energy relationships that were uncovered will aid in future incorporation of intermolecular electrostatic interactions towards controlling asymmetric reactions.

Copper-catalyzed, stereoconvergent,: Cis -diastereoselective borylative cyclization of ω -mesylate- α, β -unsaturated esters and ketones

The Cu(i)-catalyzed stereoconvergent borylative cyclization of ω-mesylate-α,β-unsaturated compounds is facilitated by a simple Cu-bisphosphine catalyst. This reaction provides a novel route to cis-β-boron-substituted five- and six-membered carbocycle and heterocycle esters. Mechanistic studies indicate that stereoconvergence and cis-substitution likely stem from the rapid enolation of the borylcopper adduct with the substrate double bond and the formation of a five-membered intermediate, respectively.

Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis

The ester function of ethyl cis-(±)-2-hydroxycyclopentane-1- carboxylate [(±)-1] and ethyl (±)-5-hydroxycyclopent-1- enecarboxylate [(±)-2] was demonstrated to undergo hydrolysis, as a side-reaction, during asymmetric (E > 200) O-acylation with Candida antarctica lipase B (CAL-B) as catalyst and vinyl acetate as acyl donor in t-BuOMe at 30 C. This competition of acylation and undesirable hydrolysis draws attention to CAL-B-catalyzed non-hydrolytic resolutions where the substrates contain any hydrolysable functions. Enantiomerically enriched cis-2-hydroxycyclopentane-1-carboxylic acid (ee = 90%) and 5-hydroxycyclopent-1- enecarboxylic acid (ee = 47%) were prepared through de novo CAL-B-catalyzed hydrolysis of (±)-1 and (±)-2 with added H2O in t-BuOMe at 30 C.

Lipase-catalysed resolution of cyclic cis- and trans-β-hydroxy esters

Lipases A and B from Candida antarctica are shown to be highly efficient and complementary biocatalysts for the resolution of five- to seven-membered cyclic β-hydroxy esters by O-acylation. Using this procedure, all four stereoisomers of each one are obtained in enantiopure form and very high yields.

Rhodium-catalyzed reformatsky-type reaction

(equation presented) A novel Reformatsky-type reaction was developed using RhCl(PPh3)3 and diethylzinc. Inter- and intramolecular Reformatsky-type reactions were achieved efficiently under mild reaction conditions to give β-hydroxy esters.