37096-14-3

Basic information

• Product Name: (3S,5S)-3'-HYDROXYCOTININE
• Synonyms: CIS-3-HYDROXYCOTININE;(3S,5S)-3'-HYDROXYCOTININE;(3S)-3β-Hydroxy-1-methyl-5β-(3-pyridinyl)-2-pyrrolizinone;(3S,5S)-3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolizinone;(3S,5S)-3-Hydroxy-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone;(3S-cis)-3-Hydroxycotinine
• CAS NO: 37096-14-3
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• Product Categories: Chiral Reagents;Heterocycles;Metabolites & Impurities;Mutagenesis Research Chemicals;Nicotine Derivatives
• Mol File: 37096-14-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 128-130°C
• Boiling Point: 416.5°Cat760mmHg
• Flash Point: 205.7°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 1.11E-07mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: (3S,5S)-3'-HYDROXYCOTININE(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S)-3'-HYDROXYCOTININE(37096-14-3)
• EPA Substance Registry System: (3S,5S)-3'-HYDROXYCOTININE(37096-14-3)

Safety Data

• Hazardous Substances Data: 37096-14-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9-/m0/s1

Upstream product

• 486-56-6 cotinine 
• 796843-65-7 (2S)-N-[[(3S,5S)-2-methyl-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam 
• 15569-85-4 cotinine 
• 796843-63-5 (2S)-N-[[(3S,5S)-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam 
• 500-22-1 3-pyridinecarboxaldehyde 
• 796843-64-6 (2S)-N-[[(3S,5S)-2-ethoxymethyl-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam 

Downstream Products

• 34834-67-8 trans-3'-Hydroxycotinine 
• 146275-16-3 (3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one 

Relevant articles and documents

Synthesis of (3′R,5′S)-3′-hydroxycotinine using 1,3-dipolar cycloaddition of a nitrone

To synthesize (3′R,5′S)-3′-hydroxycotinine [(+)-1], the main metabolite of nicotine (2), cycloaddition of C-(3-pyridyl)nitrones 3a, 3c, and 15 with (2R)- and (2S)-N-(acryloyl)bornane-10,2-sultam [(2R)- and (2S)-8] was examined. Among them, l-gulose-derived nitrone 15 underwent stereoselective cycloaddition with (2S)-8 to afford cycloadduct 16, which was elaborated to (+)-1. Graphical Abstract

Synthesis of (3'R,5'S)-trans-3'-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3'-hydroxycotinine in humans is highly stereoselective

A method for the synthesis of (3'R,5'S-trans-3'-hydroxycotinine, a major metabolite of nicotine in humans, is described. The method involves deprotonation of (S)-cotinine with lithium diisopropylamide (LDA) followed by oxidation with the transition metal peroxide oxodiperoxymolybdenum (pyridine)(hexamethylphosphoric triamide)(MoOPH) to give an 80:20 mixture of trans-/cis-3'-hydroxycotinine. The pure (>98%) trans isomer is obtained by conversion to the solid hexanoate ester, recrystallization, and cleavage of the ester by heating with n-butylamine. GC-MS analysis of urine extracts from several smokers indicated that in humans metabolic 3'-hydroxycotinine is 95-98% trans.