4165-99-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Isopropylglutaric acid is used as a key intermediate in the synthesis of the neurotransmitter glutamate, which plays a crucial role in the proper functioning of the nervous system. Its involvement in the biosynthesis of glutamate makes it a potential target for the development of drugs aimed at treating neurodegenerative disorders.
Used in Neurological Research:
3-Isopropylglutaric acid is used as a biomarker for certain neurological diseases, as its elevated levels have been found in the cerebrospinal fluid of patients with specific neurodegenerative disorders. This makes it a valuable tool for researchers studying the pathophysiology of these conditions and for the development of diagnostic tests.
Used in Metabolic Research:
3-Isopropylglutaric acid is used as a potential biomarker for certain metabolic disorders, given its role in the body's metabolic processes. This application aids researchers in understanding the underlying mechanisms of these disorders and in developing targeted therapies for their treatment.

InChI:InChI=1/C8H14O4/c1-5(2)6(3-7(9)10)4-8(11)12/h5-6H,3-4H2,1-2H3,(H,9,10)(H,11,12)

Upstream product

• 854654-10-7 2-isopropyl-propane-1,1,3-tricarboxylic acid 
• 49538-78-5 3-isopropylsuccinic anhydride 
• 116-51-8 terpenylic acid 
• 18424-76-5 dimethyl malonate sodium salt 
• 78-84-2 isobutyraldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 85608-24-8 2-isopropyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester 
• 996-82-7 sodium diethylmalonate 
• 7647-01-0 hydrogenchloride 
• 92188-14-2 2,4-dicyano-3-isopropyl-glutaric acid diamide 
• 110846-99-6 3-isopropyl-6-oxo-heptanenitrile 
• 104036-46-6 3-isopropyl-hept-5-enoic acid 
• 847997-46-0 3-isopropyl-5-oxo-hexanoic acid 
• 18456-87-6 5-isopropyl-1,3-cyclohexanedione 

Downstream Products

• 116-51-8 terpenylic acid 

Relevant academic research and scientific papers

Divergent Synthesis of γ-Amino Acid and γ-Lactam Derivatives from meso-Glutaric Anhydrides

The first divergent synthesis of both γ-amino acid and γ-lactam derivatives from meso-glutaric anhydrides is described. The organocatalytic desymmetrisation with TMSN3 relies on controlled generation of a nucleophilic ammonium azide species mediated by a polystyrene-bound base to promote efficient silylazidation. After Curtius rearrangement of the acyl azide intermediate to access the corresponding isocyanate, hydrolysis/alcoholysis provided uniformly high yields of γ-amino acids and their N-protected counterparts. The same intermediates were shown to undergo an unprecedented decarboxylation–cyclisation cascade in situ to provide synthetically useful yields of γ-lactam derivatives without using any further activating agents. Mechanistic insights invoke the intermediacy of an unconventional γ-N-carboxyanhydride (γ-NCA) in the latter process. Among the examples prepared using this transformation are 8 APIs/molecules of considerable medicinal interest.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.

Prochiral Recognition in the Reaction of 3-Substituted Glutaric Anhydrides with Chiral Secondary Alcohols

The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated.Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtaine the corresponding diesters 16-20.The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, which the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively.The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.

Tobacco smoke chemistry. 1. A chemical and mass spectrometric study of tobacco smoke alkyl 2-hydroxy-2-cyclopentenones.

A series of alkyl 2-hydroxy-2-cyclopentenones, which comprise biologically and organoleptically active compounds, have been synthesized and subjected to high resolution mass spectrometric studies to clarify structurally significant fragmentation pathways. On the basis of these results, 26 alkyl 2-hydroxy-2-cyclopentenones were identified in the weakly acidic fraction of smoke condensate from American blend type cigarettes, eighteen of which had not been detected in tobacco smoke previously. The utility for identification purposes of the corresponding quinoxaline derivatives, obtained through condensation with o-phenylenediamine, is discussed.