83680-83-5

Basic information

• Product Name: L-Pipecolicacid
• Synonyms: S-2-Pipecolinic acid
• CAS NO: 83680-83-5
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.16
• Mol File: 83680-83-5.mol
• Article Data: 117

Chemical Properties

• Boiling Point: 265.8 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.125 g/cm³
• CAS DataBase Reference: L-Pipecolicacid(CAS DataBase Reference)
• NIST Chemistry Reference: L-Pipecolicacid(83680-83-5)
• EPA Substance Registry System: L-Pipecolicacid(83680-83-5)

Safety Data

• Hazardous Substances Data: 83680-83-5(Hazardous Substances Data)

Usage

Description

L-Pipecolic acid, a naturally occurring organic compound and a derivative of the amino acid lysine, is found in various plant and animal tissues. It plays a crucial role in the biosynthesis of the neurotransmitter gamma-aminobutyric acid (GABA) and is known for its potential therapeutic applications in treating metabolic disorders and neurological conditions. L-Pipecolic acid has also been studied for its antioxidant and anti-inflammatory properties, as well as its ability to modulate immune function. Its diverse biological activities and potential health benefits have garnered interest in the fields of medicine, biochemistry, and nutrition.

Uses

Used in Pharmaceutical Industry:
L-Pipecolic acid is used as a therapeutic agent for the treatment of metabolic disorders and neurological conditions due to its involvement in the biosynthesis of gamma-aminobutyric acid (GABA) and its potential health benefits.
Used in Nutraceutical Industry:
L-Pipecolic acid is used as a dietary supplement to support overall health and well-being, owing to its antioxidant, anti-inflammatory, and immune-modulating properties.
Used in Research and Development:
L-Pipecolic acid is utilized in scientific research to study its potential applications in medicine, biochemistry, and nutrition, as well as to explore its diverse biological activities and health benefits.

Upstream product

• 4043-87-2 pipecolic Acid 
• 31456-71-0 (2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid 
• 98-98-6 2-Picolinic acid 
• 692-04-6 H-Lys(acetyl)-OH 
• 156-86-5 L-homoarginine 
• 1190-49-4 N-6-(aminocarbonyl)-L-lysine 
• 19889-77-1 (RS)-piperidine-2-carboxamide 
• 147-71-7 D-tartaric acid 
• 87-69-4 L-Tartaric acid 
• 158221-57-9 (4R,9aS)-4-Phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 56-87-1 L-lysine 
• 32559-18-5 methyl piperidine-2-carboxylate hydrochloride 
• 15912-30-8 (R)-(+)-2-piperidinecarboxylic acid (+)-tartrate 
• 849758-49-2 N-acetyl-D-2-amino-6-bromohexanoic acid 

Downstream Products

• 117614-95-6 (S)-2-Phenyl-3-thioxo-hexahydro-imidazo[1,5-a]pyridin-1-one 
• 56099-72-0 Ethyl-N-tosyl-L-pipecolenat 
• 47285-65-4 (S)-1-(2-Benzyloxycarbonylamino-acetyl)-piperidine-2-carboxylic acid 
• 74408-01-8 (R)-1-(Toluene-4-sulfonyl)-piperidine-2-carboxylic acid ethyl ester 
• 69973-86-0 3-methyl-9,10-dibenzoyl-5,6,7,8-tetrahydro-3,8a-etheno-oxazolo[3,4-a]pyridin-1-one 
• 77034-33-4 ethyl piperidine-2-carboxylate hydrochloride 
• 87281-43-4 methyl 5,6,7,8-tetrahydro-1-indolizinylcarboxylate 
• 87281-44-5 methyl 5,6,7,8-tetrahydroindolizine-2-carboxylate 
• 1118-90-7 L-homoglutamic acid 
• 427882-96-0 N-(5-methyl-2-furoyl)pipecolinic acid 
• 1070657-03-2 2-[p-(hydroxymethyl)benzenesulfonyl]-3-methyl-1-phenyl-5,6,7,8-tetrahydroindolizine 
• 178162-69-1 1-(4-bromobenzyl)piperidine 
• 15923-61-2 (R)-α,α-diphenyl-2-piperidine methanol 
• 74408-04-1 Toluene-4-sulfonic acid (R)-1-[(R)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester 

Relevant articles and documents

A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics

A novel and enantioselective synthesis of (S)-2-pipecolic acid (5) has been achieved from Oppolzer’s sultam (1) and ethyl N-(diphenylmethylene)glycinate (2) as readily available starting materials. The highly stereoselective alkylation of chiral glycine intermediate (3) with 1,4-dibromobutane afforded the key backbone of (S)-2-pipecolic acid (5) in one-step that was utilized into the preparation of the local anesthetics mepivacaine, ropivacaine and bupivacaine.

Preparation method of bupivacaine and intermediate (S)-2-piperidinecarboxylic acid thereof

The invention discloses bupivacaine and a preparation method of an intermediate (S)-2-piperidinecarboxylic acid of the bupivacaine; wherein the intermediate (S)-2-piperidinecarboxylic acid is prepared by taking (R)-4-benzyl-2-oxazolidinone as a chiral auxiliary agent through amidation, asymmetric alkylation, hydrolysis, cyclization and auxiliary group removal; wherein the prepared (S)-2-piperidinecarboxylic acid is used as a raw material to prepare the local anesthetic (S)-bupivacaine. The method utilizes cheap and easily available organic raw materials, and has the advantages of simple operation, mild reaction conditions, good stereoselectivity, high yield and the like.

Cell-free biocatalytic syntheses of l-pipecolic acid: A dual strategy approach and process intensification in flow

As an alternative to the traditional chemical synthesis or in vivo production of l-pipecolic acid, we have developed two ex vivo strategies using purified and immobilised enzymes for the production of this key building block. Firstly, a transaminase capable of lysine ?-deamination was coupled with a novel pyrroline-5-carboxylate reductase, yielding 60% conversion at the 50 mM scale with free enzymes and in situ recycling of the cofactor. A second, simpler, redox neutral system was then constructed by combining the pyrroline-5-carboxylate reductase with a lysine-6-dehydrogenase. This bienzymatic system, with catalytic amount of free cofactor yielded >99% of pipecolic acid in batch and, following co-immobilisation of both enzymes, it was applied as a packed-bed reactor in continuous flow achieving again a molar conversion of >99% with 30 min residence time, and a space-time yield up to 2.5 g L-1 h-1. The sustainability of the system was further improved by a catch-and-release strategy to purify the product, and recovery and recycling of the cofactor.