3572-64-3

Basic information

• Product Name: 3-oxo-2-pentylcyclopentaneacetic acid
• Synonyms: 2-Pentyl-3-oxocyclopentane-1-acetic acid;(±)-9,10-DIHYDROJASMONIC ACID (DJA);Cyclopentaneacetic acid, 3-oxo-2-pentyl-;Einecs 222-687-8;2-Amyl-3-(carboxymethyl)cyclopentanone 2-Amyl-3-oxocyclopentaneacetic Acid 3-(Carboxymethyl)-2-pentylcyclopentanone 3-Oxo-2-pentylcyclopentaneacetic Acid
• CAS NO: 3572-64-3
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.2854
• EINECS: 222-687-8
• Mol File: 3572-64-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 361.9°C at 760 mmHg
• Flash Point: 186.8°C
• Appearance: /
• Density: 1.038g/cm³
• Vapor Pressure: 3.21E-06mmHg at 25°C
• Refractive Index: 1.4700-1.4750
• Storage Temp.: <0°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.52±0.10(Predicted)
• CAS DataBase Reference: 3-oxo-2-pentylcyclopentaneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxo-2-pentylcyclopentaneacetic acid(3572-64-3)
• EPA Substance Registry System: 3-oxo-2-pentylcyclopentaneacetic acid(3572-64-3)

Safety Data

• Hazardous Substances Data: 3572-64-3(Hazardous Substances Data)

Usage

Description

3-Oxo-2-pentylcyclopentaneacetic acid is a chemical compound with the molecular formula C11H18O3. It is a derivative of cyclopentaneacetic acid, featuring a pentyl group and a ketone functional group. This organic compound has potential applications in various fields due to its unique structural properties.

Uses

Used in Analytical Chemistry:
3-Oxo-2-pentylcyclopentaneacetic acid is used as an analyte in biological and analytical studies for UHPLC-MS/MS (Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry) based target profiling. It is particularly useful for the identification and quantification of stress-induced phytohormones, including jasmonic acid and its precursors, as well as amino acid conjugates. 3-Oxo-2-pentylcyclopentaneacetic acid's unique structure allows for accurate detection and analysis in complex biological samples, making it a valuable tool in the study of plant stress responses and hormone regulation.
Used in Pharmaceutical Research:
3-Oxo-2-pentylcyclopentaneacetic acid may also have potential applications in the pharmaceutical industry, particularly in the development of new drugs targeting various diseases. Its unique structural features could be exploited to design novel molecules with specific biological activities, such as modulating cellular signaling pathways or interacting with specific protein targets. Further research and development would be required to explore these potential applications fully.
Used in Chemical Synthesis:
As a versatile organic compound, 3-Oxo-2-pentylcyclopentaneacetic acid can be used as a building block or intermediate in the synthesis of more complex molecules. Its ketone and carboxylic acid functional groups can be modified through various chemical reactions, allowing for the creation of a wide range of derivatives with different properties and potential applications. This makes it a valuable starting material for the development of new compounds in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)

Upstream product

• 51806-23-6 methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate 
• 42607-76-1 3-(2-oxoethyl)-2-pentylcyclopentanone 
• 25564-22-1 2-pentyl-2-cyclopenten-1-one 
• 110-53-2 1-Bromopentane 
• 75351-26-7 2-Pentyl-3-vinyl-cyclopentanone 
• 75351-23-4 2-Oxo-1-pentyl-5-vinyl-cyclopentanecarboxylic acid methyl ester 
• 82259-82-3 methyl 2-pentyl-3-oxo-8-phenoxy-6-octenoate 
• 75983-90-3 methyl (E)-3-oxo-8-phenoxy-6-octenoate 
• 24851-93-2 2-pentylcyclopent-1-en-1-yl acetate 
• 4819-67-4 2-pentyl-cyclopentanone 
• 24852-03-7 2-Ethoxycarbonyl-2-pentyl-1-cyclopentanone 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 24851-98-7 methyl 3-oxo-2-pentylcyclopentaneacetate 

Downstream Products

• 24851-98-7 methyl 3-oxo-2-pentylcyclopentaneacetate 
• 2570-03-8 (+/-)-methyl dihydroepijasmonate 
• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 

Relevant articles and documents

SALTS OF DIHYDROJASMONIC ACID AND USE THEREOF IN AGRICULTURE

A compound comprising a water soluble salt of formula (I) wherein R1 is a C1-10alkyl group; or a C2-10a1kenyl group; M is a cation of valency n, provided that when R1 is a pent-2-enyl group, Mn+ is other than sodium or potassium. These salts are particularly suitable for use in agricultural formulations. The formulations may further comprise benzoic acid derivatives and/or antioxidants.

Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation

The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.

New synthesis in dihydrojasmone series

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