Isonicotinsure
INA · PYRIDINE-4-CARBOXYLIC ACID · 4-PICOLINIC ACID · 4-PYRIDINECARBOXYLIC ACID · PYRIDINE-3-CARBOXYLIC ACID · Isonicotinic · Isonicotic acid · 4-Carboxypyridine
Identifikatoren & physikalische Daten
| CAS No. | 163751-04-0 |
|---|---|
| Summenformel | C6H5NO2 |
| Durchschnittliche Molmasse | 123,11 g/mol |
| Monoisotopische Masse | 123,0320284 g/mol |
| SMILES | O=C(O)c1ccncc1 |
| InChIKey | TWBYWOBDOCUKOW-UHFFFAOYSA-N |
| PubChem CID | 5922 |
| ChEMBL | CHEMBL1203 |
| ChEBI | CHEBI:6032 |
| EC No. | 200-228-2 |
| DTXSID | DTXSID8020757 |
| Lokaler Name | Isonicotinsure |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 50,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 108 |
| Stoffklassen | Nitrogen Compounds -> Pyridines |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | -0.57 |
| Dampfdruck | 0.00789 [mmHg] |
| Physical Description | Solid[Merck Index] Beige powder[Sigma-Aldrich MSDS] |
| Dissociation Constants | 1.77 |
| Schmelzpunkt | ≥300 °C (lit.) |
| Siedepunkt | 260 °C (15 mmHg) |
| Dichte | 1,47g/cm |
| Brechungsindex | 1.5423 (estimate) |
| Flammpunkt | 260°C/15mm |
| Lagerbedingungen | no restrictions. |
| Löslichkeit | 6g/l5.2 g/L (20 ºC) |
| pKa (Säurekonstante) | 4.96(at 25℃) |
| Aggregatzustand | powder |
| Farbe | yellow to tan |
| pH | 3-4 (6g/l, H2O, 20℃)(saturated solution) |
| Biologische Quelle | rabbit |
| Merck | 14,5187 |
| BRN | 109599 |
| Henry-Konstante | 1.6×104 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - MISCELLANEOUS |
| InChI | 1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9) |
| InChIKey | TWBYWOBDOCUKOW-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccncc1 |
| CAS Datenbank | 55-22-1(CAS DataBase Reference) |
| NIST chemische Informationen | Isonicotinic acid(55-22-1) |
| EPA chemische Informationen | Isonicotinic acid (55-22-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 35.8% (34 of 95) of reports.WarningH315 (57.9%): 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 95 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 4-Pyridinecarboxylic acidStatus: Active Update: 16-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/225234-Pyridinecarboxylic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| Gefahrenübersicht | Causes somnolence, ataxia, and changes in motor activity in oral lethal-dose studies of ratsCauses other liver changes and multiple enzyme effects in 40-day intermittent oral studies of rats[RTECS] A skin and strong eye irritant[Sigma-Aldrich MSDS] See Nicotinic acid. |
| Hazard Classes and Categories | Skin Irrit. 2 (57.9%) |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29333999 |
| RTECS-Nr. | NS1103000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: 5000 mg/kg |
Anwendungen & Verwendung
Verwenden
Isonicotinic acid is a metabolite of isoniazid. It is an isomer of nicotinic acid. The chronic toxicity of isonicotinic acid is slightly higher than that of isonicotinic acid hydrazide ( INH ) .Isonicotinic acid is a moderately basic compound (based on its pKa). Isonicotinic acid is an organic compound with a carboxyl group on a pyridine ring. The carboxyl group for isonicotinic acid is on the 4-position instead of the 3-position for nicotinic acid. It is an isomer of nicotinic acid. Isonicotinic acid is a metabolite of isoniazid.Isonicotinic acid considered to be inactive isomer of nicotinic acid. Isonicotinic acid is a metabolite of pyridine-4-carboxy hydrazide (isonicotinyl hydrazide; isoniazid) a front-line weapon in the battle against tuberculosis. Isonicotinic acid and its derivatives are used in manufacturing pharmaceuticals and agrochemicals.Used in the biological study of differentiation induced by nicotinic acid, nicotinamide and isonicotinic acid in human leukemia cell lines
Herstellung & Synthese
synthetische
Isonicotinic acid is synthesized by continuous oxidation with 4-methylpyridine as raw material and vanadium pentoxide as catalyst. The purity of the industrial product isonicotinic acid is more than 95%, and the yield of the above method is 70-75%. The consumption of 4-methylpyridine per ton of product is 1070kg.