Nicotinic acid

Base Information

• Chemical Name: Nicotinic acid
• CAS No.: 59-67-6
• Deprecated CAS: 123574-58-3,1580002-26-1
• Molecular Formula: C6H5NO2
• Molecular Weight: 123.111
• Hs Code.: 2936.29 Oral rat LD50: 7,000 mg/kg
• European Community (EC) Number: 200-441-0
• ICSC Number: 1702
• NSC Number: 757241,169454
• UNII: 2679MF687A
• DSSTox Substance ID: DTXSID1020932
• Nikkaji Number: J2.809F
• Wikipedia: Niacin
• Wikidata: Q134658
• NCI Thesaurus Code: C689
• RXCUI: 7393
• Pharos Ligand ID: KMQTZ53B948L,KMR1XXHPFJH1
• Metabolomics Workbench ID: 37821
• ChEMBL ID: CHEMBL573
• Mol file: 59-67-6.mol

Synonyms:3 Pyridinecarboxylic Acid;3-Pyridinecarboxylic Acid;Aluminum Salt, Niacin;Enduracin;Hydrochloride, Niacin;Induracin;Lithium Nicotinate;Niacin;Niacin Aluminum Salt;Niacin Ammonium Salt;Niacin Calcium Salt;Niacin Cobalt (2+) Salt;Niacin Copper (2+) Salt;Niacin Hydrochloride;Niacin Iron (2+) Salt;Niacin Lithium Salt;Niacin Lithium Salt, Hemihydrate;Niacin Magnesium Salt;Niacin Manganese (2+) Salt;Niacin Potassium Salt;Niacin Sodium Salt;Niacin Tartrate;Niacin Tosylate;Niacin Zinc Salt;Nicamin;Nico 400;Nico-400;Nico400;Nicobid;Nicocap;Nicolar;Nicotinate;Nicotinate, Lithium;Nicotinic Acid;Potassium Salt, Niacin;Sodium Salt, Niacin;Tartrate, Niacin;Tosylate, Niacin;Wampocap

Chemical Property of Nicotinic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0.000836mmHg at 25°C
• Melting Point: 236-239 °C(lit.)
• Refractive Index: 1.57
• Boiling Point: 292.467 °C at 760 mmHg
• PKA: 4.85(at 25℃)
• Flash Point: 130.68 °C
• PSA: 50.19000
• Density: 1.293 g/cm³
• LogP: 0.77980
• Storage Temp.: 0-6°C
• Solubility.: 18g/l
• Water Solubility.: 1-5 g/100 mL at 17 ºC
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 123.032028402
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

Niacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-36-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Drug Classes: Antilipemic Agents; Vitamins
• Canonical SMILES: C1=CC(=CN=C1)C(=O)O
• Recent ClinicalTrials: Investigation of Radium-223 Dichloride (Xofigo), a Treatment That Gives Off Radiation That Helps Kill Cancer Cells, Compared to a Treatment That Inactivates Hormones (New Antihormonal Therapy, NAH) in Patients With Prostate Cancer That Has Spread to the Bone Getting Worse on or After Earlier NAH
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• Recent NIPH Clinical Trials: Efficacy of the nutrients supplement 'AMP01' for the fatigue of the hemodialysis patients
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes.
• Applications and Importance: Biological, Nutritional, and Food Safety Applications: Nicotinic acid (NA) serves as a basic vitamin B3.
• Antiatherosclerotic Activity: Prevention and Treatment of Atherosclerosis: Nicotinic acid (niacin) has been utilized for decades for this purpose.; Antidyslipidemic Effects: Its antiatherogenic activity is believed to result from these effects.
• Dual Potency: Vitamin Potency: Effective in milligram doses as a vitamin.; Lipid Drug Potency: Potent in gram doses as a broad-spectrum lipid drug.
• Historical Background: Discovery: In the 20th century, Rudolf Altschul discovered the cholesterol-lowering effects of nicotinic acid.; Vitamin Effects: Demonstrated in the early 20th century.; Lipid Effects: Altschul's studies showed lipid-lowering effects, including inhibition of lipid deposits and atheromatosis.
• Mechanism of Action: Inhibition of Lipolysis: Nicotinic acid inhibits fat-mobilizing lipolysis in adipose tissue, leading to a decrease in plasma-free fatty acids (FFA).; Coenzyme Precursor: Nicotinic acid and nicotinamide are precursors to the coenzyme nicotinamide adenine dinucleotide (NAD+), crucial in fuel metabolite oxidation.
• Pharmacological Effects: Lipid and Lipoprotein Modulation: Pharmacological doses induce significant changes in plasma lipid and lipoprotein levels.; HDL Cholesterol Increase: Nicotinic acid strongly increases plasma high-density lipoprotein (HDL) cholesterol levels.
• Cardiovascular Benefits: Atherosclerosis Progression Reduction: Nicotinic acid alone or in combination with LDL cholesterol-lowering drugs can reduce atherosclerosis progression and cardiovascular event risk.; Receptor Discovery: The identification of the G protein鈥揷oupled receptor GPR109A has enhanced our understanding of nicotinic acid's effects.

Technology Process of Nicotinic acid

There total 214 articles about Nicotinic acid 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: 99.1%

ETOFIBRATE (31637-97-5) → nicotinic acid (59-67-6) + Clofibric acid (882-09-7) + ethylene glycol (107-21-1)

Guidance literature:

With hydrogenchloride; [RuCl₂(CO)2(Ph₂P-3-C₆H₄COOH)2]; In methanol; water; at 75 ℃; for 0.333333h;

DOI:10.1016/j.saa.2007.11.001

Reference yield: 92.0%

1-(4-methoxyphenyl)-2-(pyridin-3-yl)-ethanone (52700-25-1) → nicotinic acid (59-67-6) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With oxygen; potassium hydroxide; at 20 ℃; chemoselective reaction; Schlenk technique;

DOI:10.1021/acs.joc.5b02506

Reference yield: 82.0%

3-pyridinecarboxaldehyde (500-22-1) → 3-hydroxymethylpyridin (100-55-0) + nicotinic acid (59-67-6)

Guidance literature:

With TEA; magnesium bromide; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/ol052506y

upstream raw materials:

3-pyridinecarboxaldehyde

3-ethylpyridine

quinoline

3,4-pyridinecarboxylic acid

Downstream raw materials:

nicopholine

Tetrahydrofurfuryl nicotinate

2-Cyan-6-methoxycarbonyl-7-<(1-phenyl-2-methoxycarbonyl-vinyl)-amino>-hepta-2,4,6-trien-saeure-methylester

2-(3-methyl-but-2-enyl)-4-phenyl-2-pyridin-3-yl-2H-oxazol-5-one

Refernces

• 1、 Adams, Richard D.,Chen, Mingwei,Elpitiya, Gaya,Potter, Matthew E.,Raja, Robert. "Iridium-bismuth cluster complexes yield bimetallic nano-catalysts for the direct oxidation of 3-picoline to niacin". . p. 3106 - 3110. Retrieved 2013.
• 2、 Li, He,Dong, Weiliang,Zhang, Yue,Liu, Kuan,Zhang, Wenming,Zhang, Min,Ma, Jiangfeng,Jiang, Min. "Enhanced catalytic efficiency of nitrilase from Acidovorax facilis 72W and application in bioconversion of 3-cyanopyridine to nicotinic acid". . p. S459 - S467. Retrieved 2016.
• 3、 Kulka. "-". . p. 2472. Retrieved 1946.
• 4、 Huang, Rong,Zhang, Xian-Dong,Wu, Xing,Liu, Ji-Kai. "β-Carboline-Based pH Fluorescent Probe and Its Application for Monitoring Enzymatic Ester Hydrolysis". . . Retrieved 2021.
• 5、 Tabanelli, Tommaso,Mari, Massimiliano,Folco, Federico,Tanganelli, Federico,Puzzo, Francesco,Setti, Laura,Cavani, Fabrizio. "Reactivity of vanadyl pyrophosphate catalyst in ethanol ammoxidation and β-picoline oxidation: Advantages and limitations of bi-functionality". . . Retrieved 2021.
• 6、 Jordan. "-". . p. 332. Retrieved 1952.
• 7、 Ryzhakov, A. V.,Elaev, N. R.. "Transfer of Oxygen from Nicotinic Acid N-Oxide to Pyridine". . p. 859 - 861. Retrieved 1987.
• 8、 ?etinkaya, S?d?ka,Yurdakal, Sedat. "Partial photocatalytic oxidations of 3-pyridinemethanol and 3-picoline by TiO2 prepared in HCl, HNO3 and H2SO4 at different temperatures". . p. 237 - 247. Retrieved 2020/12/13.
• 9、 Kim, Hun Young,Oh, Kyungsoo,Si, Tengda. "One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence". . p. 18150 - 18155. Retrieved 2021/12/09.