cis-3'-Hydroxycotinine

Base Information

• Chemical Name: cis-3'-Hydroxycotinine
• CAS No.: 37096-14-3
• Molecular Formula: C10H12 N2 O2
• Molecular Weight: 192.217
• Hs Code.: 2933990090
• UNII: WML2ZJK52E
• DSSTox Substance ID: DTXSID30891867
• Nikkaji Number: J355.910F
• Wikidata: Q63395909
• Mol file: 37096-14-3.mol

Synonyms:cis-3'-Hydroxy Cotinine;37096-14-3;cis-3'-Hydroxycotinine;3'-Hydroxycotinine, cis-;WML2ZJK52E;(3S,5S)-3-hydroxy-1-methyl-5-pyridin-3-ylpyrrolidin-2-one;276799-61-2;(3S,5S)-3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone;2-Pyrrolidinone, 3-hydroxy-1-methyl-5-(3-pyridinyl)-, (3S,5S)-;2-Pyrrolidinone,3-hydroxy-1-methyl-5-(3-pyridinyl)-, (3R,5R)-rel-;(3S,5S)-3-Hydroxycotinine;UNII-WML2ZJK52E;SCHEMBL10890289;DTXSID30891867;CHEBI:177590;AKOS006275998;Q63395909;2-Pyrrolidinone,3-hydroxy-1-methyl-5-(3-pyridinyl)-,(3S,5S)-;(3S,5S)-3-HYDROXY-1-METHYL-5-(PYRIDIN-3-YL)PYRROLIDIN-2-ONE

Chemical Property of cis-3'-Hydroxycotinine

Chemical Property:

• Vapor Pressure: 1.11E-07mmHg at 25°C
• Melting Point: 128-130°C
• Boiling Point: 416.5°Cat760mmHg
• Flash Point: 205.7°C
• PSA: 53.43000
• Density: 1.275g/cm³
• LogP: 0.28360
• Storage Temp.: -20°C Freezer
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 192.089877630
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

98%Min ^*data from raw suppliers

cis-3''-HydroxyCotinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(CC(C1=O)O)C2=CN=CC=C2
• Isomeric SMILES: CN1[C@@H](C[C@@H](C1=O)O)C2=CN=CC=C2

Technology Process of cis-3'-Hydroxycotinine

There total 10 articles about cis-3'-Hydroxycotinine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

(2S)-N-[[(3S,5S)-2-methyl-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam (796843-65-7) → cis-(3'S,5'S)-3'-hydroxycotinine (37096-14-3,108450-02-8,27323-64-4,223655-46-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1.5h;

DOI:10.1016/j.tet.2004.08.023

Reference yield: 7.0%

cotinine (15569-85-4) → 5-hydroxy-1-methyl-5-(3-pyridyl)-2-pyrrolidinone (61192-50-5,75919-05-0) + trans-3'-hydroxycotinine (34834-67-8,37096-14-3,61192-46-9,79581-34-3,108450-02-8,27323-64-4,223655-46-7)

Guidance literature:

With iodosylbenzene; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)97989-9

Reference yield:

cotinine (486-56-6) → trans-3'-Hydroxycotinine (34834-67-8,108450-02-8,27323-64-4,223655-46-7) + cis-(3'S,5'S)-3'-hydroxycotinine (37096-14-3,108450-02-8,27323-64-4,223655-46-7)

Guidance literature:

With MoO₅*pyridine*HMPA; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, hexane, -78 deg C, 2.) a) from -78 to 0 deg C, 15 min, b) from 0 to 10 deg C, 15 min;

DOI:10.1021/jm00169a009

upstream raw materials:

cotinine

(2S)-N-[[(3S,5S)-2-methyl-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam

3-pyridinecarboxaldehyde

(2S)-N-[[(3S,5S)-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam

Downstream raw materials:

trans-3'-Hydroxycotinine

(3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one

Refernces

• 1、 Jacob III,Shulgin,Benowitz. "Synthesis of (3'R,5'S)-trans-3'-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3'-hydroxycotinine in humans is highly stereoselective". . p. 1888 - 1891. Retrieved 2007/10/02.