Basic information
- CAS
4192-31-8- Standard SMILES
O=C(O)CCC(=O)c1cccnc1- InChIKey
JGSUNMCABQUBOY-UHFFFAOYSA-N- Molecular formula
- C9H9NO3
- Average molar mass
- 179.17 g/mol
- Monoisotopic mass
- 179.05824315
Overview
4-oxo-4-(pyridin-3-yl)butanoic acid is a monocarboxylic acid that is succinic acid in which the hydroxy group of one of the carboxy groups is replaced by a pyridin-3-yl group. A byproduct of tobacco-specific N-nitrosamines generated by cytochrome P-450 which catalyzes methylnitrosaminopyridylbutanone hydroxylation, this nicotine metabolite is commonly found in the urine of smokers. It is a monocarboxylic acid, a member of pyridines and an aromatic ketone. It is functionally related to a 4-oxo-4-(pyridin-3-yl)butanal. It is a conjugate acid of a 4-oxo-4-(pyridin-3-yl)butanoate.
Names & identifiers
- Preferred name
- 4-Oxo-4-(3-pyridyl)butyric acid
- IUPAC
- 4-oxo-4-pyridin-3-ylbutanoic acid
- English name
- 4-(Pyrid-3-yl)-4-oxo-butyric acid hydrochloride
- Molecular formula
- C9H9NO3
- Molecular weight
- 179.17
Names & synonyms
4192-31-84-oxo-4-(pyridin-3-yl)butanoic acid4-Oxo-4-(3-pyridyl)butyric acid4-oxo-4-(3-pyridyl)butanoic acidgamma-oxo-3-pyridinebutanoic acid8Y4EX5XJ5B4-oxo-4-(3-pyridyl)-butanoic acidCHEBI:66951DTXSID608633354-OPC4ARefChem:100261DTXCID30811969
Show more names
OPBACotinine Impurity 1-Oxo-3-pyridinebutyric Acidγ-Oxo-3-pyridinebutyric Acidγ-Oxo-3-pyridinebutanoic Acid3-Pyridinebutanoic acid, γ-oxo-3-Pyridinebutanoic acid, g-oxo-4-(3-Pyridyl)-4-oxobutyric Acid4-keto-4-(3-pyridyl)butyric acid
675-338-03-succinoylpyridine4-Oxo-4-pyridin-3-yl-butyric acid4-oxo-4-pyridin-3-ylbutanoic acidgamma-oxo-3-pyridinebutyric acidMFCD008707371-(3-pyridyl)-1-butanone-4-carboxylic acid3-pyridinebutanoic acid, gamma-oxo-
Database identifiers
- CAS
4192-31-8
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 67.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 203
Experimental & physicochemical properties
LogP-1.06
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 129 · 129-130°C
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO, Methanol
- form
- Solid
- color
- Off-White to Light Beige
- FDA UNII
- 8 Y4EX5XJ5B · 8Y4EX5XJ5B
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 233 · P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites4-Oxo-4-(3-pyridyl)-butanoic acid (OPBA) is a known thirdhand smoke metabolite of N'-Nitrosonornicotine (NNN), Nicotine, 4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone (NNK), and 4-(Methylnitrosamino)-4-(3-pyridyl)butanal (NNA).
Applications
UsesA metabloite of NNK (Cat. # M325750)
UsesA metabolite of NNK (M325750).
Usesγ-Oxo-3-pyridinebutyric Acid (cas# 4192-31-8) is a compound useful in organic synthesis.
Upstream & downstream products
Downstream products
Suppliers27 total
艾吉析科技（上海）有限公司17717235263 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海皓竹医药科技有限公司18912729622 · [email protected]
Hangzhou Sage Chemical Co., Ltd.+86057186818502 13588463833 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
烟台盛凯伦生物制品有限公司
Related reactions
4 records
Compound notes
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