54972-10-0

Basic information

• Product Name: ethyl 2-hydroxycyclopentane-1-carboxylate
• CAS NO: 54972-10-0
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol File: 54972-10-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ethyl 2-hydroxycyclopentane-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-hydroxycyclopentane-1-carboxylate(54972-10-0)
• EPA Substance Registry System: ethyl 2-hydroxycyclopentane-1-carboxylate(54972-10-0)

Safety Data

• Hazardous Substances Data: 54972-10-0(Hazardous Substances Data)

Usage

Description

Ethyl 2-hydroxycyclopentane-1-carboxylate is a chemical compound with the molecular formula C8H14O3, characterized by its fruity and floral odor. It is commonly found in natural sources such as fruits and flowers and is widely used as a flavor and fragrance agent in various consumer products.

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

• 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 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 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 
• 5299-60-5 6-hydroxy-hexanoic acid ethyl ester 
• 294212-80-9 2-bromo-6-triethylsilanyloxy-hexanoic acid ethyl ester 
• 294212-79-6 ethyl 6-triethylsilyloxyhexanoate 
• 294212-81-0 ethyl 2-bromo-6-hydroxyhexanoate 
• 294212-87-6 ethyl 2-bromo-6-oxohexanoate 

Downstream Products

• 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 
• 61586-79-6 ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate 
• 122331-03-7 ethyl (1S,2S)-2-hydroxycyclopentanecarboxylate 
• 1421957-11-0 2-(ethoxycarbonyl)cyclopentyl 4-bromobenzoate 
• 110611-68-2 ethyl syn-(1S,2R)-2-hydroxycyclopentanecarboxylate 
• 169868-13-7 (1S,2R)-2-hydroxycyclopentane-1-carboxylic acid 
• 124150-23-8 (1R,2S)-2-methoxycarbonylcyclopentan-1-ol 
• 110611-67-1 ethyl (1R,2R)-2-hydroxycyclopentanecarboxylate 

Relevant articles and documents

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.

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.

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.