41301-27-3

Basic information

• Product Name: 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one
• Synonyms: 4-HYDROXY-3-METHYL-2-(2-PROPYNYL)-2-CYCLOPENTEN-1-ONE (R,S);4-HYDROXY-3-METHYL-2-(2-PROPYNYL)-2-CYCLOPENTENE-1-ONE;S-Prallethrolone;4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one;Propargylone;4-hydroxy-3-Methyl-2-(prop-2-yn-1-yl)cyclopent-2-enone
• CAS NO: 41301-27-3
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Mol File: 41301-27-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 284.639 °C at 760 mmHg
• Flash Point: 119.424 °C
• Appearance: /
• Density: 1.161 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.545
• PKA: 12.76±0.60(Predicted)
• CAS DataBase Reference: 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one(41301-27-3)
• EPA Substance Registry System: 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one(41301-27-3)

Safety Data

• Hazardous Substances Data: 41301-27-3(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one, also known as carvomenthene, is a chemical compound with a molecular formula C10H12O2. It is a white, crystalline solid that is commonly used in the fragrance and flavor industry. Carvomenthene is found in various plants, including the essential oils of caraway and dill, and is known for its minty, woody, and slightly floral aroma. It is often used as a fragrance in cosmetic and personal care products, as well as in the manufacturing of food and beverages. Additionally, carvomenthene has been studied for its potential medicinal properties, including its antioxidant and antimicrobial properties.

InChI:InChI=1/C9H10O2/c1-3-4-7-6(2)8(10)5-9(7)11/h1,8,10H,4-5H2,2H3

Upstream product

• 77087-32-2 Dimethyl 2-(2-propynyl)-3-oxoglutarate 
• 90428-64-1 3-acetoxy-2-propargyl-3-methyl-4-cyclopentenone 
• 77806-76-9 2-propargyl-3-hydroxy-3-methyl-4-cyclopentenone 
• 77087-22-0 3-Hydroxy-8-nonyne-2,5-dione 

Downstream Products

• 51388-35-3 2-Propargyl-3-methyl-2-cyclopenten-1-on-4-yl-2',2',3',3'-tetramethylcyclopropancarbonsaeureester 
• 51629-00-6 2-(3-Methoxy-phenyl)-3-methyl-butyric acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester 
• 51629-83-5 2-(4-Fluoro-phenyl)-3-methyl-butyric acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester 
• 51630-94-5 2-Cyclohex-1-enyl-3-methyl-butyric acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester 
• 51630-18-3 2-(4-Chloro-phenyl)-butyric acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester 
• 51630-17-2 2-p-Tolyl-butyric acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester 
• 551-45-1 allethrolone 

Relevant articles and documents

A modified synthesis of (Z)-pyrethrolone

An accessible, efficient, and reliable synthesis for the production of (Z)-pyrethrolone remains necessary as previous syntheses suffer from drawbacks including the use of toxic reagents, expensive starting materials and lack of regioselectivity in the production of key intermediates. This work attempts to alleviate the issues of prior syntheses by making use of well-known and regioselective transformations for the efficient synthesis of (Z)-pyrethrolone. Ultimately, (Z)-pyrethrolone is generated in an overall 20% yield over five steps from a cheap, easily accessible starting material using reliable, optimised transformations.

Process for preparing 4-hydroxy-2-cyclopentenones

A process for producing a compound of the formula: STR1 wherein R1 is a hydrogen atom, an alkyl group or an alkenyl group and R2 is an alkyl group, an alkenyl group or an alkynyl group, which comprises treating a compound of the formula: STR2 wherein R1 and R2 are each as defined above and R is a hydrogen atom or a lower alkyl group in the presence of an acidic substance and water.

Process for preparing cyclopentenolones

A process for preparing cyclopentenolones of the formula STR1 wherein R1 is an alkyl group having not more than 6 carbon atoms, an alkenyl or alkynyl group having not more than 6 carbon atoms or a group of the formula: STR2 in which R2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: STR3 wherein R1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.