15118-53-3

Basic information

• Product Name: 2,2-Dimethyl-4-oxohexanoic acid
• Synonyms: 2,2-Dimethyl-4-oxohexanoic acid
• CAS NO: 15118-53-3
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19496
• Mol File: 15118-53-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 87-88℃
• Boiling Point: 268℃
• Flash Point: 130℃
• Appearance: /
• Density: 1.038
• CAS DataBase Reference: 2,2-Dimethyl-4-oxohexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-4-oxohexanoic acid(15118-53-3)
• EPA Substance Registry System: 2,2-Dimethyl-4-oxohexanoic acid(15118-53-3)

Safety Data

• Hazardous Substances Data: 15118-53-3(Hazardous Substances Data)

Usage

General Description

2,2-Dimethyl-4-oxohexanoic acid, also known as 2,2-dimethyl-4-ketohexanoic acid, is a chemical compound with the molecular formula C8H14O3. It is a colorless liquid that is slightly soluble in water and is often used in the synthesis of pharmaceuticals and other organic compounds. The compound is a carboxylic acid with a ketone functional group, and it is commonly used as an intermediate in the production of various drugs and other organic chemicals. Its chemical properties make it a valuable building block for the synthesis of a wide range of compounds in the pharmaceutical and chemical industries.

Upstream product

• 17347-61-4 2,2-dimethylsuccinic anhydride 
• 557-20-0 diethylzinc 
• 597-43-3 2,2-dimethylsuccinic acid 
• 54491-23-5 2,2-dimethyl-4-hydroxyhexanoic acid γ-lactone 
• 14307-98-3 5-ethyl-2,2-dimethoxy-3,3-dimethyl-2,3-dihydro-furan 
• 89509-76-2 ethyl 2,2-dimethyl-4-oxohexanoate 

Downstream Products

• 103253-35-6 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid 
• 125687-06-1 3-(1-(4-chlorobenzyl)-3-methyl-1H-indol-2-yl)-2,2-dimethylpropanoic acid 
• 125687-07-2 3-[1-(4-Chloro-benzyl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester 
• 1427215-02-8 C₂₂H₂₂ClNO₄ 
• 103253-15-2 3-[1-(4-chlorophenylmethyl)-5-fluoro-3-methylindol-2-yl]-2,2-dimethylpropanoic acid 
• 862555-24-6 3-[1-(4-chloro-benzyl)-5-(2-fluoro-2'-methyl-biphenyl-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester 

Relevant articles and documents

Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer

Castrate-resistant prostate cancer (CRPC) is a fatal, metastatic form of prostate cancer. CRPC is characterized by reactivation of the androgen axis due to changes in androgen receptor signaling and/or adaptive intratumoral androgen biosynthesis. AKR1C3 is upregulated in CRPC where it catalyzes the formation of potent androgens. This makes AKR1C3 a target for the treatment of CRPC. AKR1C3 inhibitors should not inhibit AKR1C1/AKR1C2, which inactivate 5α-dihydrotestosterone. Indomethacin, used to inhibit cyclooxygenase, also inhibits AKR1C3 and displays selectivity over AKR1C1/AKR1C2. Parallel synthetic strategies were used to generate libraries of indomethacin analogues, which exhibit reduced cyclooxygenase inhibitory activity but retain AKR1C3 inhibitory potency and selectivity. The lead compounds inhibited AKR1C3 with nanomolar potency, displayed >100-fold selectivity over AKR1C1/AKR1C2, and blocked testosterone formation in LNCaP-AKR1C3 cells. The AKR1C3·NADP +·2′-des-methyl-indomethacin crystal structure was determined, and it revealed a unique inhibitor binding mode. The compounds reported are promising agents for the development of therapeutics for CRPC.

An Unusual Fischer Indole Synthesis with 4-Keto Acids: An Indole Incorporating the Terminal Hydrazine Nitrogen

During preparation of a pharmaceutically active, N-benzylated indole derivative from 4-keto acid and N1-benzylated phenylhydrazine precursors, the N-unsubstituted indole analogue arose as a significant byproduct.The proportion of debenzylated indole was greater with α-alkylated rather than straight-chain keto acids and the byproduct was fully suppressed when a keto ester was substituted for the keto acid.The benzylic group was shown to have eliminated as the amine and 15N label incorporation demonstrated terminal phenylhydrazine nitrogen incorporation in the indole byproduct only, an exception to the usual course of the Fischer indolization reaction.A ring-chain equilibration in the ketimino acid intermediate is proposed to account for the competing pathway.