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59-67-6 Usage

Description

Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin that plays a crucial role in various biological processes. It is an essential nutrient for the formation of coenzymes NAD and NADP, which are involved in numerous cellular redox reactions. Nicotinic acid is widely distributed in nature and can be found in liver, fish, yeast, and cereal grains. It is an odorless white crystalline powder with a slightly acidic taste and is amphoteric, forming salts with both acids and bases.

Uses

1. Used in Pharmaceutical Applications:
Nicotinic acid is used as a precursor of the coenzymes NAD and NADP, which are essential for various cellular redox reactions. It is also used as an antidote, an antilipemic drug, a vasodilator agent, and an inhibitor of EC 3.5.1.19 (nicotinamidase).
2. Used in Nutritional Supplements:
Nicotinic acid is used as a nutrient and dietary supplement to prevent pellagra, a disease caused by niacin deficiency. It is also used to treat and prevent high cholesterol levels, as it can help reduce VLDL synthesis and lower cholesterol levels.
3. Used in Food Fortification:
Niacin USP granular is used for food fortification, as a dietary supplement, and as an intermediate in the production of pharmaceuticals.
4. Used in Animal Feed:
Nicotinic acid feed grade is used as a vitamin for poultry, swines, ruminants, fish, dogs, and cats. It is also used as an intermediate for nicotinic acid derivatives and technical applications.
5. Used in Skin Care and Hair Care:
Nicotinic acid, in the form of niacinamide, is used in the formulation of skin care products to improve the appearance of dry or damaged skin by reducing flaking and restoring suppleness. It also enhances the appearance and feel of hair by increasing body, suppleness, or sheen, or by improving the texture of hair that has been damaged physically or by chemical treatment.
6. Used in Chemical Synthesis:
Nicotinic acid is used as a starting material for the synthesis of various nicotinic acid derivatives, which have applications in different industries.

Preparation

Nicotinic acid exists naturally in grain germs, meats and peanuts. It can also be synthesized artificially through the liquid phase method (potassium permanganate oxidation and nitric acid oxidation) and gas phase method (ozone oxidation, ammonia oxidation and air oxidation). 3-methyl pyridine method In the gas phase ammonia oxidation process, add 3-methyl pyridine, air and ammonia into the fluidized bed reactor and catalyze the reaction at 290~360℃,V2O5 to produce nicotinonitrile; then hydrolyze in sodium hydroxide aqueous solution at 160℃ to produce sodium nicotinate; finally, add hydrochloric acid to acidify, creating nicotinic acid. In the potassium permanganate oxidation method, add potassium permanganate gradually at 80℃ to a mixture of 3-methyl pyridine and water, and then continue to mix for 30min at 85~90℃. Distill to collect and reuse the unreacted 3-methyl pyridine and filter away the produced manganese dioxide. Adjust the PH of the resulting nicotinic acid solution to 3.8~4.0 using hydrochloric acid, cool to 30℃ crystals, and filter to obtain crude nicotinic acid. Dissolve the crude nicotinic acid in hot water, add activated charcoal to eliminate the color, filter, cool, and obtain the crystalline end product. Yield is approximately 86%. 6- hydroxyquinoline method Add sulfuric acid and quinoline into a reaction kettle and mix while maintaining heat at 150~160℃ for 5h. Then with the temperature maintained at 180~220℃, slowly drop in nitric acid and the sulfuric acid mixture over the course of 36~40h. While maintaining the temperature, mix for 2~3h to obtain a nicotinic acid solution and add water to dilute the solution. Use 30%~33% NaOH solution to neutralize the PH to 8~9. Cool and filter away the sodium sulfate and sodium nitrate crystals, add copper sulfate solution to the filtered liquid, and mix and heat to yield copper nicotinate precipitation. Cool, filter and add the copper nicotinate to an adequate amount of water, drop in NaOH solution until PH>9 and the liquid is no longer blue, and filter away the produced cupric oxide. Add a small amount of sodium sulfide solution to remove traces of copper and iron until the solution no longer produces black precipitate, and then filter. Use hydrochloric acid to adjust the PH of the filtered liquid to 3.5~3.9, filter to yield crystals as crude nicotinic acid. Dissolve the crude product in 12 times the amount of distilled water, add activated charcoal to eliminate the color, filter, cool, and obtain the crystalline end product. Yield is 35%~39%. 2-methyl-5-ethyl pyridine method With 2-methyl-5-ethyl pyridine as the raw ingredient, oxidize with nitic acid under high pressure and high temperatures, then decarboxylate to yield nicotinic acid.

Identifying tests

Add 2 portions of 2, 4-Dinitrochlorobenzene to the sample and process into powder. Place 10mg of the powder in a test tube, gently heat until melted, and continue to heat for a couple of seconds. Cool and add 3ml potassium hydroxide ethanol solution (TS-190). The solution should be dark red. Dissolve 50mg of the sample solution in 20ml water, use 0.1mol/L sodium hydroxide to neutralize until a litmus paper reads neutral, and add 3ml copper sulfate solution (TS-78). Blue precipitate should begin forming slowly. Dry the sample for 1h at 105℃ and collect its mineral oil dispersions. The peak wavelength of its infrared absorption spectrum should resemble the standard reference sample formulated using the same method. Prepare an aqueous solution of the sample with a density of 20μg/ml, measure its absorbance at the wavelengths 237nm and 262nm in a 1cm pool, using water as a blank control. A237/A262 should be 0.35~0.39.

Content analysis

Precisely take a sample of 300mg and dissolve in 50ml water. Add a couple drops of phenolphthalein solution (TS-167) and titrate using 0.1mol/L sodium hydroxide. Conduct a control experiment at the same time. Every Ml0.1mol/L sodium hydroxide is equivalent to 12.31mg nicotinic acid (C6H5NO2).

Toxicity

LD50 7.0g/kg (Large mice, oral). GRAS(FDA,§182.5530,2000)。 ADI has no special regulations (EEC, 1990).

History

Huber first synthesized nicotinic acid in 1867. In 1914, Funk isolated nicotinic acid from rice polishings. Goldberger, in 1915, demonstrated that pellagra is a nutritional deficiency. In 1917, Chittenden and Underhill demonstrated that canine blacktongue is similar to pellagra. In 1935, Warburg and Christian showed that niacinamide is essential in hydrogen transport as diphosphopyridine nucleotide (DPN). In the following year, Euler et al. isolated DPN and determined its structure. In 1937, Elvhehjem et al. cured blacktongue by administration of niacinamide derived from liver. In the same year, Fouts et al. cured pellagra with niacinamide. In 1947, Handley and Bond established conversion of tryptophan to niacin by animal tissues.

Air & Water Reactions

Water soluble.

Reactivity Profile

Nicotinic acid is incompatible with strong oxidizers. Nicotinic acid is also incompatible with sodium nitrite.

Fire Hazard

Flash point data for Nicotinic acid are not available; however, Nicotinic acid is probably combustible.

Biological Activity

Nicotinic acid can be converted to nicotinamide in the animal body and, in this form, is found as a component of two oxidation-reduction coenzymes, NAD and NADP.The nicotinamide portion of the coenzyme transfers hydrogens by alternating between an oxidized quaternary nitrogen and a reduced tertiary nitrogen. Enzymes that contain NAD or NADP are usually called dehydrogenases. They participate in many biochemical reactions of lipid, carbohydrate, and protein metabolism. An example of an NAD-requiring system is lactic dehydrogenase which catalyzes the conversion of lactic acid to pyruvic acid.

Biochem/physiol Actions

Nicotinic is an antioxidant and acts as a coenzyme in the form of nicotinamide adenine nucleotides(NAD). It modulates lipid metabolism and may be useful in treating dyslipidemia. Nicotinic acid reduces the low-density lipoprotein (LDL) synthesis and improves high-density lipoprotein (HDL) levels. Deficiency of niacin leads to enhanced lipid peroxidation and is implicated in Crohn′s disease Deficiency also impacts DNA repair and also leads to skin and gastrointestinal disorder pellagra.

Mechanism of action

Nicotinic acid decreases formation and secretion of VLDL by the liver.This action appears secondary to its ability to inhibit fatty acid mobilization from adipose tissue. Circulating free fatty acids provide the main source of fatty acids for hepatic triglyceride synthesis, and lowering triglyceride synthesis lowers VLDL formation and secretion by the liver. Since plasma VLDL is the source of LDL, lowering VLDL can ultimately lower LDL. In addition, nicotinic acid shifts LDL particles to larger (more buoyant) sizes. The larger LDL particles are thought to be less atherogenic. Nicotinic acid can also significantly increase plasma HDL levels; the mechanism is unknown.

Pharmacokinetics

Nicotinic acid is readily absorbed. Peripheral vasodilation is seen within 20 minutes, and peak plasma concentrations occur within 45 minutes. The half-life of the compound is approximately one hour, thus necessitating frequent dosing or an extended-release formulation. Extended release tablets produce peripheral vasodilation within 1 hour, reach peak plasma concentrations within 4 to 5 hours, and have a duration of 8 to 10 hours. Dosing of nicotinic acid should be titrated to minimize adverse effects. An initial dose of 50 to 100 mg t.i.d. often is used with immediaterelease tablets. The dose then is gradually increased by 50 to 100 mg every 3 to 14 days, up to a maximum of 6 g/day, as tolerated. Therapeutic monitoring to assess efficacy and prevent toxicity is essential until a stable and effective dose is reached. Similar dosing escalations are available for extended-release products, with doses normally starting at 500 mg once daily at bedtime..

Clinical Use

Nicotinic acid has been esterified to prolong itshypolipidemic effect. Pentaerythritol tetranicotinate hasbeen more effective experimentally than niacin in reducingcholesterol levels in rabbits. Sorbitol and myo-inositolhexanicotinate polyesters have been used in the treatment ofpatients with atherosclerosis obliterans.The usual maintenance dose of niacin is 3 to 6 g/daygiven in three divided doses. The drug is usually given atmealtimes to reduce the gastric irritation that often accompanieslarge doses.

Side effects

Compliance with nicotinic acid therapy can be poor because the drug can produce an intense cutaneous flush. This can be reduced by beginning the drug in stepped doses of 250 mg twice daily and increasing the dose monthly by 500 to 1000 mg per day to a maximum of 3000 mg per day.Taking nicotinic acid on a full stomach (end of meal) and taking aspirin before dosage can reduce the severity of flushing. Time-release forms of nicotinic acid may also decrease cutaneous flushing. Nicotinic acid can cause gastrointestinal (GI) distress,liver dysfunction (especially at high doses), decreased glucose tolerance, hyperglycemia, and hyperuricemia. Thus, it is contraindicated in patients with hepatic dysfunction, peptic ulcer, hyperuricemia, or diabetes mellitus. A paradox associated with nicotinic acid is that it is the most widely available hypolipidemic drug (it is sold over the counter), yet its use requires the closest management by the physician.

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.

Synthesis

Nicotinic acid, pyridine-3-carboxylic acid (20.2.9) is synthesized industrially by heating a paraldehyde trimer of acetaldehyde, under pressure with ammonia, which leads to the formation of 2-methyl-5-ethylpyridine, followed by oxidation with nitric acid which gives the desired product.

Metabolism

Nicotinic acid is a B-complex vitamin that is converted to nicotinamide, NAD+ , and NADP+ .The latter two compounds are coenzymes and are required for oxidation/reduction reactions in a variety of biochemical pathways. Additionally, nicotinic acid is metabolized to a number of inactive compounds, including nicotinuric acid and N-methylated derivatives. Normal biochemical regulation and feedback prevent large doses of nicotinic acid from producing excess quantities of NAD+ and NADP+ .Thus, small doses of nicotinic acid, such as those used for dietary supplementation, will be primarily excreted as metabolites, whereas large doses, such as those used for the treatment of hyperlipoproteinemia, will be primarily excreted unchanged by the kidney.

Purification Methods

Crystallise the acid from *benzene, EtOH or H2O. It sublimes without decomposition. [McElvain Org Synth Coll Vol I 385 1941, Beilstein 22 III/IV 439, 22/2 V 57.]

Check Digit Verification of cas no

The CAS Registry Mumber 59-67-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 59-67:
(4*5)+(3*9)+(2*6)+(1*7)=66
66 % 10 = 6
So 59-67-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

59-67-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (N0082)  Nicotinic Acid  >99.0%(HPLC)(T)

  • 59-67-6

  • 25g

  • 105.00CNY

  • Detail
  • TCI America

  • (N0082)  Nicotinic Acid  >99.0%(HPLC)(T)

  • 59-67-6

  • 500g

  • 410.00CNY

  • Detail
  • Alfa Aesar

  • (A12683)  Nicotinic acid, 99%   

  • 59-67-6

  • 250g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (A12683)  Nicotinic acid, 99%   

  • 59-67-6

  • 1000g

  • 607.0CNY

  • Detail
  • Alfa Aesar

  • (A12683)  Nicotinic acid, 99%   

  • 59-67-6

  • 5000g

  • 2804.0CNY

  • Detail
  • Fluka

  • (72311)  Nicotinicacid  matrix substance for MALDI-MS, ≥99.5% (HPLC)

  • 59-67-6

  • 72311-250MG

  • 586.17CNY

  • Detail
  • Fluka

  • (72311)  Nicotinicacid  matrix substance for MALDI-MS, ≥99.5% (HPLC)

  • 59-67-6

  • 72311-1G

  • 1,889.55CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1276)  Niacin(NicotinicAcid)  pharmaceutical secondary standard; traceability to USP and BP

  • 59-67-6

  • PHR1276-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (N0700000)  Nicotinicacid  European Pharmacopoeia (EP) Reference Standard

  • 59-67-6

  • N0700000

  • 1,880.19CNY

  • Detail
  • USP

  • (1461003)  Niacin  United States Pharmacopeia (USP) Reference Standard

  • 59-67-6

  • 1461003-200MG

  • 4,662.45CNY

  • Detail
  • Supelco

  • (47864)  Nicotinicacid  analytical standard

  • 59-67-6

  • 000000000000047864

  • 207.09CNY

  • Detail
  • Cerilliant

  • (V-017)  Nicotinic acid (Vitamin B3) solution  1.0 mg/mL in methanol, ampule of 1 mL, certified reference material

  • 59-67-6

  • V-017-1ML

  • 716.04CNY

  • Detail

59-67-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Nicotinic acid

1.2 Other means of identification

Product number -
Other names Pyridine-3-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59-67-6 SDS

59-67-6Synthetic route

Pyridine-2,5-dicarboxylic acid
100-26-5

Pyridine-2,5-dicarboxylic acid

nicotinic 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;
3-Methylpyridine
108-99-6

3-Methylpyridine

nicotinic acid
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%
ETOFIBRATE
31637-97-5

ETOFIBRATE

A

nicotinic acid
59-67-6

nicotinic acid

B

Clofibric acid
882-09-7

Clofibric acid

C

ethylene glycol
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
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

nicotinic acid
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%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

nicotinic acid
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%
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

nicotinic acid
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;
methyl-3-oxo-3-(pyridin-3-yl)propanedithioate
1312414-21-3

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

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 100℃; for 10h; Reflux; chemoselective reaction;98%
quinoline-5-sulfonic acid
23261-58-7

quinoline-5-sulfonic acid

nicotinic 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

C8H6Cl3NO2

nicotinic acid
59-67-6

nicotinic acid

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

3-iodopyridine

diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

nicotinic 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%
3-Methylpyridine
108-99-6

3-Methylpyridine

A

nicotinic acid
59-67-6

nicotinic acid

B

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
With water; oxygen at 310℃; Product distribution / selectivity;A 93.13%
B 5.56%
With water; oxygen at 300℃; Product distribution / selectivity;A 93.16%
B 6.39%
With water; oxygen at 285℃; Product distribution / selectivity;A 92.22%
B 7.11%
nicotinamide
98-92-0

nicotinamide

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With tert.-butylnitrite; acetic acid at 75℃; for 2.5h; Inert atmosphere;92%
With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere;83%
With barium dihydroxide In water for 1h; Heating;
With recombinant Borrelia burgdorferi nicotinamidase at 25℃; pH=7.3; Kinetics; Reagent/catalyst; Concentration; aq. phosphate buffer; Enzymatic reaction;
With water In aq. phosphate buffer at 30℃; for 6h; pH=7; Time; Enzymatic reaction;41.66 mmol
1-(4-methoxyphenyl)-2-(pyridin-3-yl)-ethanone
52700-25-1

1-(4-methoxyphenyl)-2-(pyridin-3-yl)-ethanone

A

nicotinic acid
59-67-6

nicotinic acid

B

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction;A 92%
B 92%
pyridine-3-ylglyoxal
63464-84-6

pyridine-3-ylglyoxal

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide at 180℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;91%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

A

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

B

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With sodium hypochlorite; C8H18NPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity;A 90.1%
B 3.4%
With sodium hypochlorite; C13H26N2OPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity;A 87.7%
B 3.5%
With sodium hypochlorite; C16H28N2O5Pol; sodium hydrogencarbonate In water; 1,2-dichloro-ethane at 15 - 20℃; for 4.5h; Product distribution / selectivity;A 85.3%
B 5.3%
8-quinolinesulfonic acid
85-48-3

8-quinolinesulfonic acid

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With sulfuric acid; selenium at 240 - 300℃; for 1h; Product distribution; reaction time; SeO2 as catal.;90%
methyl-3-pyridylketone
350-03-8

methyl-3-pyridylketone

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry;90%
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 12h;68%
1,2-di(pyridin-3-yl)ethan-1-one
6339-93-1

1,2-di(pyridin-3-yl)ethan-1-one

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction;90%
3-Methylpyridine
108-99-6

3-Methylpyridine

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

C

nicotinic acid
59-67-6

nicotinic acid

D

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
at 140℃; for 14h; Product distribution;A 5%
B 18%
C 60%
D 88%
at 140℃; for 14h; Further byproducts given;A 5%
B 18%
C 60%
D 88%
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

C

nicotinic acid
59-67-6

nicotinic acid

D

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
With 3-Methylpyridine at 140℃; for 14h; Further byproducts given;A 5%
B 18%
C 60%
D 88%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

A

nicotinic acid
59-67-6

nicotinic acid

B

1,2-di(pyridine-3-yl)ethane-1,2-dione
35779-39-6

1,2-di(pyridine-3-yl)ethane-1,2-dione

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 8h; pH=11.5; Electrolysis;A 86%
B 6%
Nicotinic acid N-oxide
2398-81-4

Nicotinic acid N-oxide

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With pyridine for 30h; Heating; other temperature, other reactant ratio, sealed tube;85%
With 2,3-dimethyl-2,3-butane diol; bis(N,N-dimethylformamide)dichloridodioxidomolybdenum(VI) In N,N-dimethyl acetamide at 130℃; Microwave irradiation; Sealed tube; Green chemistry; chemoselective reaction;84%
With molybdenum(V) chloride; sodium iodide In acetonitrile at 20℃; for 2h;83%
3-picolyl bromide
69966-55-8

3-picolyl bromide

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With 5,10,15,20-tetra(4-nitrophenyl) porphyrinato iron chloride; [bis(acetoxy)iodo]benzene; water In methanol at 50℃; for 12h;85%
Myosmine
532-12-7

Myosmine

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With D-glucose at 200℃; for 1h; pH=7.5; Temperature; pH-value;84%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With TEA; magnesium bromide In dichloromethane at 20℃; for 48h; Cannizzaro reaction;A 82%
B n/a
With N,N,N',N'-tetramethylguanidine In water at 20℃; for 7h; Cannizzaro reaction;A 44%
B 41%
With barium dihydroxide; formaldehyd at 100 - 110℃; for 0.0333333h; Irradiation;A 97 % Chromat.
B 3 % Chromat.
With aluminum oxide; sodium hydroxide; water for 0.00416667h; Irradiation; Yield given; Yields of byproduct given;
3-Bromopyridine
626-55-1

3-Bromopyridine

potassium formate
590-29-4

potassium formate

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;82%
3-iodopyridine
1120-90-7

3-iodopyridine

molybdenum hexacarbonyl
13939-06-5, 199620-15-0

molybdenum hexacarbonyl

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); water; N-ethyl-N,N-diisopropylamine at 130℃; for 0.333333h; Microwave irradiation;81%
6-iodo-nicotinic acid
13054-02-9

6-iodo-nicotinic acid

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With hydrogenchloride; indium In water for 2h; Reflux;80%
With indium In water for 5h; Heating;57%
nicotinic acid
59-67-6

nicotinic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl nicotinate
94-44-0

benzyl nicotinate

Conditions
ConditionsYield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride In dichloromethane for 1h; Ambient temperature;100%
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;81%
With boric acid; glycerol Entfernen des entstehenden H2O;
nicotinic acid
59-67-6

nicotinic acid

pyridine-3-carbonyl chloride hydrochloride
20260-53-1

pyridine-3-carbonyl chloride hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 4h; Heating;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Inert atmosphere;100%
With thionyl chloride In toluene at 100℃; for 24h;100%
nicotinic acid
59-67-6

nicotinic acid

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

nicotinic acid succinimidyl ester
78348-28-4

nicotinic acid succinimidyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 48h;85%
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;80%
nicotinic acid
59-67-6

nicotinic acid

3-pyridinecarbonyl chloride
10400-19-8

3-pyridinecarbonyl chloride

Conditions
ConditionsYield
With thionyl chloride for 5h; Reflux;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Cooling with ice;100%
With oxalyl dichloride at 20℃; for 0.5h;100%
nicotinic acid
59-67-6

nicotinic acid

(3R,4R)-4-[4-(2-Hydroxy-ethoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

(3R,4R)-4-[4-(2-Hydroxy-ethoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester

Nicotinic acid 2-{4-[(3R,4R)-1-tert-butoxycarbonyl-3-(naphthalen-2-ylmethoxy)-piperidin-4-yl]-phenoxy}-ethyl ester

Nicotinic acid 2-{4-[(3R,4R)-1-tert-butoxycarbonyl-3-(naphthalen-2-ylmethoxy)-piperidin-4-yl]-phenoxy}-ethyl ester

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane Ambient temperature;100%
nicotinic acid
59-67-6

nicotinic acid

4-(5-nitro-1H-indol-1-yl)-1-butanol
578725-98-1

4-(5-nitro-1H-indol-1-yl)-1-butanol

nicotinic acid 4-(5-nitro-indol-1-yl)-butyl ester
578726-03-1

nicotinic acid 4-(5-nitro-indol-1-yl)-butyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
nicotinic acid
59-67-6

nicotinic acid

N-((piperidin-4-yl)methyl)-N'-(adamant-1-yl)urea hydrochloride

N-((piperidin-4-yl)methyl)-N'-(adamant-1-yl)urea hydrochloride

N-((1-(pyridine-3-carbonyl)piperidin-4-yl)methyl)-N'-(adamant-1-yl)urea

N-((1-(pyridine-3-carbonyl)piperidin-4-yl)methyl)-N'-(adamant-1-yl)urea

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 0 - 20℃; for 20h;100%
(1-S)-{4-[(5-tert-butoxycarbonylamino-1-hydroxymethyl-pentyl)-isobutyl-sulfamoyl]-phenyl}-carbamic acid tert-butyl ester
900187-22-6

(1-S)-{4-[(5-tert-butoxycarbonylamino-1-hydroxymethyl-pentyl)-isobutyl-sulfamoyl]-phenyl}-carbamic acid tert-butyl ester

nicotinic acid
59-67-6

nicotinic acid

(2S)-nicotinic acid 6-tert-butoxycarbonylamino-2-[(4-tert-butoxycarbonylamino-benzenesulfonyl)-isobutyl-amino]-hexyl ester
874339-83-0

(2S)-nicotinic acid 6-tert-butoxycarbonylamino-2-[(4-tert-butoxycarbonylamino-benzenesulfonyl)-isobutyl-amino]-hexyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethylformamide) at 20℃;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;100%
nicotinic acid
59-67-6

nicotinic acid

4-bromo-N2-methylbenzene-1,2-diamine
337915-79-4

4-bromo-N2-methylbenzene-1,2-diamine

C13H12BrN3O
1038408-42-2

C13H12BrN3O

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU; dmap In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h;100%
nicotinic acid
59-67-6

nicotinic acid

nicotinic acid sulfate
64030-04-2

nicotinic acid sulfate

Conditions
ConditionsYield
With sulfuric acid In dichloromethane at 20℃; Cooling with ice;100%
With sulfuric acid In dichloromethane at 20℃; for 0.5h;100%
nicotinic acid
59-67-6

nicotinic acid

methyl pyrrolidine-2-carboxylate
43041-12-9, 52183-82-1, 2577-48-2

methyl pyrrolidine-2-carboxylate

1-(pyridine-3-carbonyl)pyrrolidine-2-carboxylic acid methyl ester
955038-97-8

1-(pyridine-3-carbonyl)pyrrolidine-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 0 - 25℃;100%
nicotinic acid
59-67-6

nicotinic acid

C21H33N3O
1619984-56-3

C21H33N3O

N-(((1S,2S,3R,8aS)-2,5,5,8a-tetramethyl-3-(nicotinamido)decahydronaphthalen-1-yl)methyl)nicotinamide
1619983-87-7

N-(((1S,2S,3R,8aS)-2,5,5,8a-tetramethyl-3-(nicotinamido)decahydronaphthalen-1-yl)methyl)nicotinamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere;100%
nicotinic acid
59-67-6

nicotinic acid

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

trimethylsilyl 3-pyridinecarboxylate
25436-37-7

trimethylsilyl 3-pyridinecarboxylate

Conditions
ConditionsYield
With ammonium bisulphate for 24h; Reflux; Inert atmosphere;100%
With ammonium sulfate In toluene at 95 - 110℃; Inert atmosphere;92%
With iodine In neat (no solvent) at 20℃; for 19h; Green chemistry;61%
nicotinic acid
59-67-6

nicotinic acid

cholin hydroxide
123-41-1

cholin hydroxide

2-hydroxy-N,N,N-trimethylethanaminium nicotinate
49719-80-4

2-hydroxy-N,N,N-trimethylethanaminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 9; Cooling with ice;100%
In water pH=7.66;
nicotinic acid
59-67-6

nicotinic acid

L-arginine
74-79-3

L-arginine

L-arginine nicotinate

L-arginine nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 6 - 6.2; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-histidine
71-00-1

L-histidine

(S)-1-carboxy-2-(1H-imidazol-4-yl)ethanaminium nicotinate

(S)-1-carboxy-2-(1H-imidazol-4-yl)ethanaminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 5.5 - 5.8; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-proline
147-85-3

L-proline

(S)-2-carboxypyrrolidin-1-ium nicotinate

(S)-2-carboxypyrrolidin-1-ium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-valine
72-18-4

L-valine

(S)-1-carboxy-2-methylpropan-1-aminium nicotinate

(S)-1-carboxy-2-methylpropan-1-aminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-Tryptophan
73-22-3

L-Tryptophan

(S)-1-carboxy-2-(1H-indol-3-yl)ethanaminium nicotinate

(S)-1-carboxy-2-(1H-indol-3-yl)ethanaminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice; Heating;100%
nicotinic acid
59-67-6

nicotinic acid

L-carnitine
541-15-1

L-carnitine

(R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium nicotinate

(R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-methionine
63-68-3

L-methionine

(S)-1-carboxy-3-(methylthio)propan-1-aminium nicotinate

(S)-1-carboxy-3-(methylthio)propan-1-aminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 2.8 - 3.3; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-isoleucine
73-32-5

L-isoleucine

(1S,2S)-1-carboxy-2-methylbutan-1-aminium nicotinate

(1S,2S)-1-carboxy-2-methylbutan-1-aminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 2.3 - 3.3; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

D-Val-OH
640-68-6

D-Val-OH

(R)-1-carboxy-2-methylpropan-1-aminium nicotinate

(R)-1-carboxy-2-methylpropan-1-aminium nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

N-butylamine
109-73-9

N-butylamine

C6H5NO2*C4H11N

C6H5NO2*C4H11N

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 7 - 7.2; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

ascorbic acid
50-81-7

ascorbic acid

niacin, ascorbic acid

niacin, ascorbic acid

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 2.8 - 3; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

L-glutamic acid
56-86-0

L-glutamic acid

L-glutamic acid nicotinate

L-glutamic acid nicotinate

Conditions
ConditionsYield
In water for 0.166667h; pH=Ca. 2.8 - 3.3; Cooling with ice;100%
nicotinic acid
59-67-6

nicotinic acid

oxalic acid
144-62-7

oxalic acid

nicotinic acid ; hydrogenoxalate
117883-08-6

nicotinic acid ; hydrogenoxalate

Conditions
ConditionsYield
at 120℃; under 0.450045 Torr; for 7h; Temperature;100%
nicotinic acid
59-67-6

nicotinic acid

Nicotinic acid N-oxide
2398-81-4

Nicotinic acid N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; molybdic acid In water at 92 - 95℃; for 3h; Green chemistry;99.6%
With dihydrogen peroxide In tetrahydrofuran; water for 5h; Reflux;91%
With hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid In methanol; N,N-dimethyl-formamide at 25℃; for 3h;87%

59-67-6Relevant articles and documents

Analysis of simultaneous transport and metabolism of ethyl nicotinate in hairless rat skin

Sugibayashi, Kenji,Hayashi, Teruaki,Hatanaka, Tomio,Ogihara, Masahiko,Morimoto, Yasunori

, p. 855 - 860 (1996)

Purpose. Simultaneous skin transport and metabolism of ethyl nicotinate (EN), a model drug, were measured and theoretically analyzed. Methods. Several studies of EN or its metabolite nicotinic acid (NA) were done on full-thickness skin or stripped skin with and without an esterase inhibitor. Permeation parameters such as partion coefficient of EN from the donor solution to the stratum corneum and diffusion coefficients of EN and NA in the stratum corneum and the viable epidermis and dermis were determined by these studies. Enzymatic parameters (Michaelis constant K(m) and maximum metabolism rate V(max)) were obtained from the production rate of NA from different concentrations of EN in the skin homogenate. Obtained permeation data were then analyzed by numerical method based on differential equations showing Fick's second law of diffusion in the stratum corneum and the law with Michaelis-Menten metabolism in the viable epidermis and dermis. Results. Fairly good steady-state fluxes of EN and NA through the skin were obtained after a short lag time for all the concentrations of EN applied. These steady-state fluxes were not proportional to the initital donor concentration of EN: EN and NA curves were concave and convex, respectively, which suggests that metabolic saturation from EN to NA takes place in the viable skin at higher EN application. The steady-state fluxes of EN and NA calculated by the differential equations with resulting permeation and enzymatic parameters were very close to the obtained data. Conclusions. The present method is a useful tool to analyze simultaneous transport and metabolism of many drugs and prodrugs, especially those showing Michaelis-Menten type-metabolic saturation in skin.

Mechanism of the oxygen involvement in nicotinic acid formation under β-picoline oxidation on V-Ti-O catalyst

Chesalov, Yu. A.,Ovchinnikova,Chernobay,Popova, G.Ya.,Andrushkevich

, p. 39 - 43 (2010)

Mechanism of the oxygen involvement in nicotinic acid formation under β-picoline oxidation on vanadia-titania catalyst was studied by in situ FTIR spectroscopy and kinetic method in temperature range of 120-300 °C. The formation of nicotinic acid proceeds via a consecutive transformation of the surface carbonil-like and carboxylate complexes stabilized at reduced vanadium. Catalyst oxygen includes in formation of these complexes. Carboxylate is a direct precursor of nicotinic acid, it turns into nicotinic acid in the presence of the gas-phase oxygen in joint step of catalyst reoxidation-acid desorption. Significant concentration ratio of oxygen to β-picoline (C O2:CβP > 16:1) is necessary to effective running reaction. This factor can be explained by the reaction mechanism. The variety of oxygen functions and of oxygen species require the maximum oxidized state of the catalyst and explain the necessity of a high oxygen excess in the reaction mixture.

-

Rohrlich

, p. 122,126 (1950)

-

-

Rayburn et al.

, p. 115 (1941)

-

Oxidation of heterocyclic aldehydes by quinolinium dichromate: A kinetic study

Chaubey, Girija S.,Das, Simi,Mahanti, Mahendra K.

, p. 497 - 500 (2002)

Quinolinium dichromate in sulfuric acid, in 50% (v/v) acetic acid - water medium, oxidized heterocyclic aldehydes to the corresponding acids. The kinetic results supported a mechanistic pathway proceeding via a rate - determining oxidative decomposition of the chromate ester of the aldehyde hydrate.

-

Leete,Siegfried

, p. 4529 (1957)

-

THERMAL DECOMPOSITION OF AMMONIUM NICOTONATE

Guseinov, E. M.,Sokolovskii, A. A.,Kondrat'eva, N. M.,Zarutskii, V. V.,Oslyakov, G. V.

, p. 749 - 752 (1981)

-

Structural insights into the function of the nicotinate mononucleotide:phenol/p-cresol phosphoribosyltransferase (ArsAB) enzyme from Sporomusa ovata

Newmister, Sean A.,Chan, Chi Ho,Escalante-Semerena, Jorge C.,Rayment, Ivan

, p. 8571 - 8582 (2012)

Cobamides (Cbas) are cobalt (Co) containing tetrapyrrole-derivatives involved in enzyme-catalyzed carbon skeleton rearrangements, methyl-group transfers, and reductive dehalogenation. The biosynthesis of cobamides is complex and is only performed by some

Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions

Sharifi, Sina,Sharifi, Hannah,Koza, Darrell,Aminkhani, Ali

, p. 803 - 808 (2021/07/20)

Disproportionation of aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions often requires the application of high temperatures, equimolar or excess quantities of strong bases, and is mostly limited to the aldehydes with no CH2 or CH3 adjacent to the carbonyl group. Herein, we developed an efficient, mild, and multifunctional catalytic system consisting AlCl3/Et3N in CH2Cl2, that can selectively convert a wide range of not only aliphatic, but also aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature, and in high yields, without formation of the side products that are generally observed. We have also shown that higher AlCl3 content favors the reaction towards Cannizzaro reaction, yet lower content favors Tishchenko reaction. Moreover, the presence of hydride donor alcohols in the reaction mixture completely directs the reaction towards the Meerwein–Ponndorf–Verley reaction. Graphic abstract: [Figure not available: see fulltext.].

A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light

Qiu, Wenting,Shi, Shuai,Li, Ruining,Lin, Xianfeng,Rao, Liangming,Sun, Zhankui

supporting information, p. 1255 - 1258 (2021/05/05)

A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.

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