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

Uses

(±)-9,10-Dihydrojasmonic Acid can be used as analyte in biological and analytical study for UHPLC-MS/MS based target profiling of stress-induced phytohormones including jasmonic acid and its precursors and amino acid conjugates.

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

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

Downstream Products

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

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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