33224-01-0

Basic information

• Product Name: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE
• Synonyms: trans-4-Cotininecarboxylic acid 97%;trans-1-Methyl-4-carboxy-5-(3-pyridyl)-2-pyrrolidinone;TIMTEC-BB SBB003355;TRANS-1-METHYL-2-(3-PYRIDYL)PYRROLIDIN-5-ONE-3-CARBOXYLIC ACID;TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE;TRANS-4-COTININECARBOXYLIC ACID;TRANS-4'-CARBOXYCOTININE;CARBOXY COTININE
• CAS NO: 33224-01-0
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.22
• Product Categories: Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks;Nicotine Derivatives;C9 to C46;Heterocyclic Building Blocks;Pyridines
• Mol File: 33224-01-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 194-195 °C(lit.)
• Boiling Point: 483.8°Cat760mmHg
• Flash Point: 246.4°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 3.6E-10mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.94±0.40(Predicted)
• CAS DataBase Reference: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE(33224-01-0)
• EPA Substance Registry System: TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE(33224-01-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 33224-01-0(Hazardous Substances Data)

Usage

Description

TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE, also known as trans-4-Cotininecarboxylic acid, is a major metabolite of nicotine in humans. It is a chemical compound with a unique structure that features a pyrrolidinone ring, a methyl group, a carboxylic acid group, and a pyridine ring. TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE has been found to have various applications in different fields, particularly in the development of analytical methods and coordination chemistry.
Used in Pharmaceutical Industry:
TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE is used as a metabolite marker for monitoring nicotine exposure and assessing the effectiveness of smoking cessation therapies. Its presence in biological samples can be detected and quantified using various analytical techniques, providing valuable information on an individual's nicotine consumption and the success of their smoking cessation efforts.
Used in Analytical Chemistry:
TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE is used as an analyte in the development and validation of analytical methods for the detection and quantification of nicotine and its metabolites in biological samples. These methods can be employed in clinical, forensic, and research settings to study the pharmacokinetics, pharmacodynamics, and potential health effects of nicotine and its metabolites.
Used in Immunoblot Analysis:
TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE is used as a component in the preparation of cotinine-conjugated horseradish peroxidase during immunoblot analysis. This technique allows for the detection and quantification of specific proteins in complex biological samples, providing valuable insights into the molecular mechanisms underlying various biological processes and diseases.
Used in Coordination Chemistry:
The anion of TRANS-1-METHYL-4-CARBOXY-5-(3-PYRIDYL)-2-PYRROLIDINONE has been employed as a pyridyl-carboxylate ligand in the preparation of polymeric copper(II) complexes. These complexes exhibit unique structural and electronic properties, making them promising candidates for various applications in materials science, catalysis, and other fields.

InChI:InChI=1/C11H12N2O3/c1-13-9(14)5-8(11(15)16)10(13)7-3-2-4-12-6-7/h2-4,6,8,10H,5H2,1H3,(H,15,16)/t8-,10+/m1/s1

Synthetic route

rac trans-4-cotinine carboxylic acid → (2R,3R)-cotinine carboxylic acid + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0)

Conditions	Yield
With ammonium formate In methanol at 20℃; Reagent/catalyst; Solvent; Resolution of racemate;

2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanamine (474082-35-4) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) → (2S,3S)-N-(29-amino-3,6,9,12,15,18,21,24,27-nonaoxanonacosyl)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxamide

Conditions	Yield
Stage #1: (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 0.25h; Sonication; Stage #2: 2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanamine In dimethyl sulfoxide for 0.25h; Sonication;	28.9%

diazomethane (186581-53-3, 908094-01-9) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) → trans-4'-carboxycotinine methyl ester (33224-03-2)

Conditions	Yield
In acetone at 20℃; for 0.333333h;	39 mg

Fmoc-Val-OH (68858-20-8) + C39H59NO15 + Fmoc-Tyr(tBu)-OH (71989-38-3) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1, 144701-23-5, 112883-40-6) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6) → W peptide

Conditions

Yield

Stage #1: Nα-fluorenyl-9-methoxycarbonyl-D-Met With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; MBHA link amide resin; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.166667h; MBHA link amide resin; Automated synthesizer; Stage #3: Fmoc-Val-OH; C39H59NO15; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester Further stages;

...Expand

C39H59NO15 + Fmoc-D-Lys(BOC)-OH (92122-45-7) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1, 144701-23-5, 112883-40-6) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) + Fmoc-D-Tyr(O-tBu)-OH + 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan → wkymvm-NH2

Conditions

Yield

Stage #1: Nα-fluorenyl-9-methoxycarbonyl-D-Met With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; MBHA link amide resin; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.166667h; MBHA link amide resin; Automated synthesizer; Stage #3: C39H59NO15; Fmoc-D-Lys(BOC)-OH; Nα-fluorenyl-9-methoxycarbonyl-D-Met; N-(9-fluorenylmethoxycarbonyl)-D-valine; (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid; Fmoc-D-Tyr(O-tBu)-OH; 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan Further stages;

2-(2-(2-(2-(2-(2-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethanamine (474082-35-4) + (2S,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylic acid (33224-01-0) → (2S,3S)-N-(1-(4-((3-(((S)-4-(3,4-dichlorobenzyl)morpholin-2-yl)methyl)ureido)methyl)phenyl)-1-oxo-5,8,11,14,17,20,23,26,29-nonaoxa-2-azahentriacontan-31-yl)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxamide trifluoroacetic acid salt

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dimethyl sulfoxide / 0.25 h / Sonication 1.2: 0.25 h / Sonication 2.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dimethyl sulfoxide / 0.5 h / Sonication 2.2: 0.5 h / Sonication View Scheme

Downstream Products

• 33224-03-2 trans-1-Methyl-4-methoxycarbonyl-5-(3-pyridyl)-2-pyrrolidinon 
• 187986-11-4 wkymvm-NH₂ 
• 187986-11-4 W peptide 

Relevant articles and documents

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.