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59-67-6

Basic Information
CAS No.: 59-67-6
Name: Nicotinic acid
Article Data: 301
Cas Database
Molecular Structure:
Molecular Structure of 59-67-6 (Nicotinic acid)
Formula: C6H5NO2
Molecular Weight: 123.111
Synonyms: Nicocidin;Efacin;Nicocap;Niacor;Niac;Nicamin;Nicotinipca;Daskil;Nicotene;Nicosan 3;Nicodon;Nicobid;Davitamon PP;pyridine-3-carboxylate;NICO;Peviton;Nicovasan;Nicotamin;Pellagrin;Niconat;Enduracin;Nicangin;Nicodelmine;Niacin (vitamin B3);Nicotinic acid(Medicine used);Nikotinsaeure;Niacin;
EINECS: 200-441-0
Density: 1.293 g/cm3
Melting Point: 236-239 °C(lit.)
Boiling Point: 292.467 °C at 760 mmHg
Flash Point: 130.68 °C
Solubility: 1-5 g/100 mL at 17 °C in water
Appearance: White powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25
Transport Information: N/A
PSA: 50.19000
LogP: 0.77980
Synthetic route
100-26-5

Pyridine-2,5-dicarboxylic acid

59-67-6

nicotinic acid

Conditions
ConditionsYield
With water at 230℃; for 2h;99.9%
With water at 205℃;
With water at 175 - 180℃; under 22065.2 Torr;
108-99-6

3-Methylpyridine

59-67-6

nicotinic acid

Conditions
ConditionsYield
With oxygen; V2O5/Sb2O3-TiO2 In water at 260 - 280℃; Industry scale; Inert atmosphere; Gas phase;99.58%
With oxygen; V2O5/Sb2O3-TiO2 In water at 260 - 280℃; Product distribution / selectivity; Inert atmosphere; Gas phase; Industry scale;99.58%
With water; oxygen Product distribution / selectivity;97.3%
31637-97-5

ETOFIBRATE

A

59-67-6

nicotinic acid

B

882-09-7

Clofibric acid

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With hydrogenchloride; [RuCl2(CO)2(Ph2P-3-C6H4COOH)2] In methanol; water at 75℃; for 0.333333h;A 99.1%
B n/a
C n/a
500-22-1

3-pyridinecarboxaldehyde

59-67-6

nicotinic acid

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water at 30℃; for 24h; Enzymatic reaction;99%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
100-55-0

3-hydroxymethylpyridin

59-67-6

nicotinic acid

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride In methanol; water at 20℃; for 0.5h; Reagent/catalyst; Green chemistry;99%
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 12h; pH=9.8 - 10.1; Electrolysis;96%
With ferrous(II) sulfate heptahydrate; Oxone In water at 20℃; for 0.5h; Sonication; Green chemistry;94%
614-18-6

3-pyridinecarboxylic acid ethyl ester

59-67-6

nicotinic acid

Conditions
ConditionsYield
With PPA at 155℃; for 4.5h;98%
With alkaline H2O In dimethyl sulfoxide at 30℃; Rate constant; other solvent (EtOH); variation of water concentrations;
esterase in WBN; IL-Ht rat abdominal skin homogenate at 37℃; Enzyme kinetics;
1312414-21-3

methyl-3-oxo-3-(pyridin-3-yl)propanedithioate

59-67-6

nicotinic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 100℃; for 10h; Reflux; chemoselective reaction;98%
23261-58-7

quinoline-5-sulfonic acid

59-67-6

nicotinic acid

Conditions
ConditionsYield
With sulfuric acid; selenium at 240 - 300℃; for 1h; Product distribution; reaction time; SeO2 as catal.;95%

C8H6Cl3NO2

59-67-6

nicotinic acid

Conditions
ConditionsYield
With indium; ammonium chloride In tetrahydrofuran for 11h; Heating;95%
1120-90-7

3-iodopyridine

18414-58-9

diphenylmethylsilanecarboxylic acid

59-67-6

nicotinic acid

Conditions
ConditionsYield
With potassium trimethylsilonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h;95%
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Chemistry


IUPAC Name: Pyridine-3-carboxylic acid
Molecular Formula: C6H5NO2
Molecular Weight: 123.11 g/mol
Canonical SMILES: C1=CC(=CN=C1)C(=O)O
InChI: InChI=1/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
EINECS: 200-441-0
Classification Code: Antihyperlipidemic; Antilipemic Agents; Antimetabolites; Cardiovascular Agents; Drug / Therapeutic Agent; Growth Substances; Human Data; Micronutrients; Tumor data; Vasodilator Agents; Vitamin B Complex; Vitamin; Vitamins
H-Bond Donor: 1
H-Bond Acceptor: 3
Density: 1.293 g/cm3
Flash Point: 130.7 °C
Enthalpy of Vaporization: 56.18 kJ/mol
Boiling Point: 292.5 °C at 760 mmHg
Melting Point: 236-239 °C(lit.)
Storage temperature: 0-6°C
Water Solubility: 1.80E+04 mg/L at 25 °C
Henry's Law Constant: 5.11E-11 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 1.72E-13 cm3/molecule-sec at 25 °C
Vapour Pressure of Niacin (CAS NO.59-67-6): 5.70E-06 mm Hg at 25 °C

History

In 1873, Niacin was first described by Hugo Weidel in his studies of nicotine.Niacin was extracted from livers by Conrad Elvehjem who later identified the active ingredient, then referred to as the "pellagra-preventing factor" and the "anti-blacktongue factor." When the biological significance of nicotinic acid was realized, it was thought appropriate to choose a name to dissociate it from nicotine, in order to avoid the perception that vitamins or niacin-rich food contains nicotine, or that cigarettes contain vitamins. The resulting name 'niacin' was derived from nicotinic acid + vitamin.
 Niacin is referred to as Vitamin B3 because it was the third of the B vitamins to be discovered. It has historically been referred to as "vitamin PP."

Uses

 Niacin (CAS NO.59-67-6) feed grade is used as vitamin for poultry, swines, ruminants, fish, dogs and cats, etc. It is also used as intermediate for nicotinic acid derivatives and technical applications. Niacin USP is used for food fortification, as dietary supplement and as an intermediate of pharmaceuticals,as dietary supplement and as an intermediate of pharmaceuticals. It is a brand name for a sustained release Niacin tablet, which is used to reduce cholesterol.

Production

 Niacin (CAS NO.59-67-6) can be selectively isolated from the hydrolysis by varying the hydrolysis time and nitrite concentration. A higher hydrolysis temperature favors production of niacin.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 3500mg/kg (3500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Proceedings of the Society for Experimental Biology and Medicine. Vol. 38, Pg. 241, 1938.
man TDLo intravenous 357ug/kg (0.357mg/kg) CARDIAC: CARDIAC OUTPUT
LUNGS, THORAX, OR RESPIRATION: CYANOSIS
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Annals of Internal Medicine. Vol. 29, Pg. 558, 1948.
man TDLo oral 2571mg/kg/90D (2571mg/kg) BLOOD: CHANGE IN CLOTTING FACTORS
BLOOD: CHANGES IN PLATELET COUNT
Archives of Internal Medicine. Vol. 152, Pg. 861, 1992.
man TDLo oral 9713mg/kg/58W (9713mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING
SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Southern Medical Journal. Vol. 84, Pg. 496, 1991.
man TDLo oral 31200mg/kg/78 (31200mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE
SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
JAMA, Journal of the American Medical Association. Vol. 279, Pg. 1702, 1998.
mouse LD50 intraperitoneal 358mg/kg (358mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977.
mouse LD50 intravenous 5gm/kg (5000mg/kg)   Therapie. Vol. 26, Pg. 831, 1971.
mouse LD50 oral 3720mg/kg (3720mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 149, 1973.
mouse LD50 subcutaneous 3500mg/kg (3500mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977.
mouse LD50 unreported 4gm/kg (4000mg/kg)   British UK Patent Application. Vol. #2041937,
rabbit LD50 oral 4550mg/kg (4550mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977.
rat LD50 intraperitoneal 730mg/kg (730mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977.
rat LD50 oral 7gm/kg (7000mg/kg)   Drugs in Japan Vol. 6, Pg. 544, 1982.
rat LD50 subcutaneous 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 544, 1982.
rat LD50 unreported 4gm/kg (4000mg/kg)   United States Patent Document. Vol. #4412998,
rat LDLo intravenous 3500mg/kg (3500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Proceedings of the Society for Experimental Biology and Medicine. Vol. 38, Pg. 241, 1938.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion, intravenous, and subcutaneous routes. Human systemic effects: change in clotting factors, changes in platelet count. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing. 
S24/25: Avoid contact with skin and eyes.
WGK Germany of Niacin (CAS NO.59-67-6): 1

Specification

 Niacin (CAS NO.59-67-6), its Synonyms are Nicotinic acid ; 3-Pyridinecarboxylic acid ; 3-Carboxypyridine ; Acide nicotinique ; Acido nicotinico ; Acidum nicotinicum ; Akotin ; Apelagrin ; Kyselina nikotinova ; Enduracin ; Daskil ; Davitamon PP ; Diacin ; Direktan ; Niaspan Titration Starter Pack ; Nicacid ; Nicagin ; Nicamin ; Nicangin ; Pyridine-3-carboxylic acid ; Pyridine-beta-carboxylic acid ; Pyridine-carboxylique-3 ; Pyridinecarboxylic acid, 3- . It is odorless white crystalline powder with a feebly acid taste.