72002-30-3

Basic information

• Product Name: D-6-OXO-PIPECOLINIC ACID
• Synonyms: 2-Piperidinecarboxylic acid, 6-oxo-, (2R)-;R-2-Piperidinone-6-carboxylic acid
• CAS NO: 72002-30-3
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.14
• Mol File: 72002-30-3.mol

Chemical Properties

• Boiling Point: 437°C at 760 mmHg
• Flash Point: 218.1°C
• Appearance: /
• Density: 1.286g/cm³
• Vapor Pressure: 7.39E-09mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.59±0.20(Predicted)
• CAS DataBase Reference: D-6-OXO-PIPECOLINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: D-6-OXO-PIPECOLINIC ACID(72002-30-3)
• EPA Substance Registry System: D-6-OXO-PIPECOLINIC ACID(72002-30-3)

Safety Data

• Hazardous Substances Data: 72002-30-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-6-OXO-PIPECOLINIC ACID is used as an anti-inflammatory agent for its potential to reduce inflammation, which can be beneficial in treating various inflammatory conditions.
Used in Neuroprotection:
D-6-OXO-PIPECOLINIC ACID is used as a neuroprotective agent for its potential to protect neurons and support brain health, which may be particularly relevant in conditions involving neurodegeneration.
Used in Immune Regulation:
D-6-OXO-PIPECOLINIC ACID is used in immune regulation applications for its potential role in modulating the immune system, which could have implications for treating autoimmune diseases or enhancing immune responses.
Used in Diagnostics:
D-6-OXO-PIPECOLINIC ACID is used as a diagnostic marker for its potential to indicate the presence of certain diseases, providing valuable information for medical diagnosis and treatment planning.

InChI:InChI=1/C6H9NO3/c8-5-3-1-2-4(7-5)6(9)10/h4H,1-3H2,(H,7,8)(H,9,10)/t4-/m1/s1

Upstream product

• 7620-28-2 D-2-aminoadipic acid 
• 7732-18-5 water 
• 24325-12-0 (+/-)-2-chloroacetaminohexanedioic acid 
• 542-32-5 (R,S)-2-aminoadipic acid 

Downstream Products

• 1050394-42-7 (2R,6S)-2-hydroxymethyl-(3,4,5-trifluorophenyl)piperidine-1-carboxylic acid benzyl ester 
• 937399-85-4 (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylic acid methyl ester 
• 937399-86-5 [(2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-yl]methanol 
• 213532-95-7 (R)-6-hydroxymethyl-piperidin-2-one 
• 183890-34-8 methyl (R)-6-oxopiperidine-2-carboxylate 

Relevant articles and documents

Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists

2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the 1-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be ≥95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K i 5-130 nM) at EP4 and subtype selectivity.

Synthesis of a new dual metalloprotease inhibitor. I. Diastereoselective alkylation of protected 6-oxopipecolic acid esters

Diastereoselective methylation of the enolate generated from various protected 6-oxopipecolic acid esters (3aa-3cd) was studied. The protecting groups on the carboxylic acid and amino groups significantly influenced the trans/cis selectivity in the methylation reaction. The optimal substrate (3ca), bearing benzhydryl ester and carbobenzyloxy moieties gave a trans/cis isomer ratio of ca. 4:1. Investigation of the reaction conditions revealed that the reaction solvent, alkylating reagent, and base employed to generate the enolate, were decisive factors for diastereoselectivity. Further optimization of reaction conditions, including the amounts of the reagents and their addition sequence enabled maximization of reaction conversion and minimization of by-products to produce the trans rich 5-methyl-6-oxopipecolic acid ester (4ca) on a large scale.