Hydroxycotinine

Base Information

• Chemical Name: Hydroxycotinine
• CAS No.: 34834-67-8
• Deprecated CAS: 27323-64-4,108450-02-8
• Molecular Formula: C10H12 N2 O2
• Molecular Weight: 192.217
• Hs Code.: 2933990090
• European Community (EC) Number: 803-421-5
• UNII: H7LH47Y29A
• DSSTox Substance ID: DTXSID30873224
• Nikkaji Number: J109.375D
• Wikidata: Q27139424
• Metabolomics Workbench ID: 65498
• ChEMBL ID: CHEMBL1614639
• Mol file: 34834-67-8.mol

Synonyms:1-methyl-3-hydroxy-5-(3-pyridyl)-2-pyrrolidinone;3'-hydroxycotinine;3-hydroxycotinine;hydroxycotinine;trans-3'-hydroxycotinine

Chemical Property of Hydroxycotinine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 107-109°C
• Boiling Point: 416.5°Cat760mmHg
• PKA: 13.02±0.40(Predicted)
• Flash Point: 205.7°C
• PSA: 53.43000
• Density: 1.275g/cm³
• LogP: 0.28360
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 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%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45

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
• Description: trans-3’-Hydroxycotinine (3HC) is a product of CYP2A6 metabolism of the primary nicotine metabolite, cotinine . Cotinine has a longer metabolic half-life compared to 3HC (16 hours vs. 5 hours). The ratio of 3HC to cotinine, termed the nicotine metabolite ratio, correlates with nicotine clearance from the body and is used as a biomarker of CYP2A6 activity. This measure of nicotine metabolism has been used to study tobacco and secondhand smoke exposure as well as to develop pharmacological intervention strategies for smoking cessation.
• Uses: A metabolite of Nicotine. Carcinogen. trans-3''-Hydroxy Cotinine is a metabolite of Nicotine (N412450, (S)-(-)-Nicotine).

Technology Process of Hydroxycotinine

There total 15 articles about 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: 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:

(3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one (146275-16-3) → trans-3'-Hydroxycotinine (34834-67-8,108450-02-8,27323-64-4,223655-46-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2004.08.023

Reference yield:

3-pyridinecarboxaldehyde (500-22-1) → trans-3'-Hydroxycotinine (34834-67-8,108450-02-8,27323-64-4,223655-46-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / toluene / 20 h / Heating

2: 80 percent / CH₂Cl₂ / 168 h / Heating

3: 76 percent / aq. HCl / ethanol / 5 h / 20 °C

4: H₂O / 2 h / 20 °C

5: 9.3 mg / Et₃SiH; CF₃CO₂H / CH₂Cl₂ / 0.5 h / Heating

6: 54 percent / H₂ / Pd/C / aq. ethanol / 1.5 h

7: DEAD; PPh₃ / toluene / 0.08 h / 20 °C

8: 6.0 mg / NaOH / methanol / 0.25 h / 20 °C

With hydrogenchloride; triethylsilane; sodium hydroxide; hydrogen; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; toluene; 7: Mitsunobu reaction;

DOI:10.1016/j.tet.2004.08.023

upstream raw materials:

(3'R,5'S)-trans-3'-hydroxycotininyl hexanoate

cotinine

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

3-pyridinecarboxaldehyde

Refernces

• 1、 Lin, Nan-Horng,Carrera, George M.,Anderson, David J.. "Synthesis and Evaluation of Nicotine Analogs as Neuronal Nicotinic Acetylcholine Receptor Ligands". . p. 3542 - 3553. Retrieved 2007/10/02.
• 2、 Chauncey, M. A.,Ninomiya, Shin-ichi. "METABOLIC STUDIES WITH MODEL CYTOCHROME p-450 SYSTEMS". . p. 5901 - 5904. Retrieved 2007/10/02.