Methyl nicotinate

Base Information

• Chemical Name: Methyl nicotinate
• CAS No.: 93-60-7
• Deprecated CAS: 123574-61-8
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 2933.39
• European Community (EC) Number: 202-261-8
• NSC Number: 403799,13126
• UNII: 7B1AVU9DJN
• DSSTox Substance ID: DTXSID7044471
• Nikkaji Number: J39.098D
• Wikidata: Q3341206
• NCI Thesaurus Code: C80889
• Metabolomics Workbench ID: 44063
• ChEMBL ID: CHEMBL379845
• Mol file: 93-60-7.mol

Synonyms:methyl nicotinate;methylnicotinate

Chemical Property of Methyl nicotinate

Chemical Property:

• Appearance/Colour: white to brownish crystals or crystalline powder
• Vapor Pressure: 0.0018mmHg at 25°C
• Melting Point: 42-44 °C(lit.)
• Refractive Index: 1.5323 (estimate)
• Boiling Point: 209 °C at 760 mmHg
• PKA: pKa 3.1 (Uncertain)
• Flash Point: 95.6 °C
• PSA: 39.19000
• Density: 1.137 g/cm³
• LogP: 0.86820
• Storage Temp.: Store below +30°C.
• Solubility.: H2O: 0.1 g/mL, clear
• Water Solubility.: NEGLIGIBLE
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

98% Min ^*data from raw suppliers

Methyl Nicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: COC(=O)C1=CN=CC=C1
• Recent EU Clinical Trials: Double-blind, randomised, multi-centre, placebo-controlled clinical trail to investigate the efficacy and safety of a combination of comfrey root extract plus methyl nicotinate versus a preparation containing methyl nicotinate alone or placebo in patients with conditions of acute upper or low back pain.
• Description: Methyl nicotinate is a skin irritant in man, in particular producing vasodilatation, which is used on purpose in “rubefacient”, to produce a redness or inflammation for a short period of time, often in lip plumper or other lip products. Methyl nicotinate is also an active ingredient of a number of veterinary preparations intended for topical application as a rubefacient for the treatment of a variety of diseases, such as respiratory diseases, vascular disorders (oedema, haematoma), and rheumatoid disorders in cattle and horses (doses not stated; the concentration in the formulated veterinary medicinal product is 2%).
• Uses: Methyl nicotinate (MN) is the methyl ester of nicotinic acid that is used as an active ingredient, a rubefacient and counter-irritant in over-the-counter topical preparations indicated for the temporary relief of aches and pains in muscles,tendons, and joints. The action of methyl nicotinate as a rubefacient is thought to involve peripheral vasodilation.For veterinary purposes，methyl nicotinate is used to treat respiratory diseases, vascular disorders, rheumatoid arthritis, and muscle and joint pains.Methyl nicotinate can be found in in guava fruit, papaya, strawberry, soursop(Annona muricata), beer, grape brandy, coffee, roasted filbert, roasted peanut and Bourbon vanilla.

Technology Process of Methyl nicotinate

There total 57 articles about Methyl nicotinate 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: 99.0%

nicotinic acid (59-67-6) + methanol (67-56-1) → methyl 3-pyridinecarboxylate (93-60-7)

Guidance literature:

With N-iodo-succinimide; potassium carbonate; at 20 ℃; for 2h; Inert atmosphere; Darkness;

DOI:10.1002/adsc.202101195

Reference yield: 98.0%

1-oxy-nicotinic acid methyl ester (15905-18-7) → methyl 3-pyridinecarboxylate (93-60-7)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.0166667h; Ambient temperature;

DOI:10.1055/s-1989-27349

Reference yield: 95.0%

3-hydroxymethylpyridin (100-55-0) + methanol (67-56-1) → methyl 3-pyridinecarboxylate (93-60-7)

Guidance literature:

With oxygen; potassium carbonate; at 60 ℃; for 20h; under 750.075 Torr;

DOI:10.1039/c6ra27073e

upstream raw materials:

diazomethane

nicotinic acid

quinoline

methanol

Downstream raw materials:

2-(2-pyridinyl)-1-(3-pyridinyl)ethanone

2-(3-pyridinyl)-2-propanol

N,N-Dimethylaminoethyl nicotinate

2,2-dimethyl-5-(3-pyridyl)pentane-3,5-dione

Refernces

• 1、 Winterfeld,Nonn. "-". . p. 2274. Retrieved 1967.
• 2、 Habtemariam, Abraha,Garino, Claudio,Ruggiero, Emmanuel,Castro, Silvia Alonso-De,Mareque-Rivas, Juan C.,Salassa, Luca. "Photorelease of pyridyl esters in organometallic Ru(II) arene complexes". . p. 7276 - 7291. Retrieved 2015.
• 3、 Wang, Congcong,Zhang, Yu-Fang,Guo, Shimeng,Zhao, Quan,Zeng, Yanping,Xie, Zhicheng,Xie, Xin,Lu, Boxun,Hu, Youhong. "GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington's Disease-Related Phenotypes". . p. 941 - 957. Retrieved 2020/11/30.
• 4、 Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee. "Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions". supporting information. p. 3735 - 3742. Retrieved 2021/05/04.