Methyl Nicotinate
NICOTINIC ACID METHYL ESTER · FEMA 3709 · METHYL PYRIDINE-3-CARBOXYLATE · Nicometh · METHYL 3-PYRIDINECARBOXYLATE · Nikomet · Methyl niacin · Methyl nicotite
Identifiers & Physical Properties
| CAS No. | 93-60-7 |
|---|---|
| Molecular formula | C7H7NO2 |
| Average molar mass | 137.14 g/mol |
| Monoisotopic mass | 137.04767847 g/mol |
| SMILES | COC(=O)c1cccnc1 |
| InChIKey | YNBADRVTZLEFNH-UHFFFAOYSA-N |
| PubChem CID | 7151 |
| ChEMBL | CHEMBL379845 |
| ChEBI | CHEBI:134761 |
| EC No. | 202-261-8 |
| DTXSID | DTXSID7044471 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 39.2 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 2 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 125 |
| LogP (partition coefficient) | 0.80.83 |
| Solubility | Soluble47.6 mg/mL at 20 °CSoluble in fatSlightly soluble in waterSoluble (in ethanol)H2O: 0.1 g/mL, clearNEGLIGIBLE |
| Boiling point | 209209.00 °C. @ 760.00 mm Hg204 °C (lit.) |
| Melting point | 38-4338 °C42-44 °C (lit.) |
| Vapor pressure | 0.27 [mmHg]0.4 hPa (25 °C) |
| Physical Description | Solid[Merck Index]White crystalline solidFresh caramelic nutty, mild tobacco aroma |
| Kovats Retention Index | 1100111610981127.11141.21152.21137.41139.21140.11145113611491136.61743177917391767.717931773.5 |
| Collision Cross Section | 126.6 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID7044471] |
| Density | 1.2528 (rough estimate) |
| Bulk density | 600kg/m3 |
| FEMA | 3709 | METHYL NICOTINATE |
| Refractive index | 1.5323 (estimate) |
| FLAVIS Number | 14.071 | Methyl nicotinate |
| Flash point | 204 °F |
| Storage conditions | Store below +30°C. |
| Physical state | Crystals or Crystalline Powder |
| pKa (acidity coefficient) | pKa 3.1 (Uncertain) |
| Color | White to brownish |
| Odor | at 10.00 % in dipropylene glycol. warm herbal tobacco |
| Odor type | herbal |
| Biological source | synthetic |
| JECFA Number | 1320 |
| Merck | 14,6100 |
| BRN | 113951 |
| Cosmetics Ingredients Functions | SOOTHINGTONIC |
| InChI | 1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3 |
| InChIKey | YNBADRVTZLEFNH-UHFFFAOYSA-N |
| SMILES | COC(=O)c1cccnc1 |
| LogP (partition coefficient) | 0.68 at 25℃ |
| CAS DataBase Reference | 93-60-7(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | METHYL NICOTINATE |
| FDA 21 CFR | 310.545 |
| EWG's Food Scores | 1 |
| FDA UNII | 7B1AVU9DJN |
| NIST Chemistry Reference | Methyl nicotinate(93-60-7) |
| EPA Substance Registry System | Methyl nicotinate (93-60-7) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38-36/38 |
| Safety statements (S) | 26-36-37/39 |
| Water hazard class (WGK) | 3 |
| RTECS number | QT1925000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29333999 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.8% (13 of 1623) of reports.WarningH315 (98.6%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (99.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 1623 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 13 of 1623 reports by companies.There are 12 notifications provided by 1610 of 1623 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: 3-Pyridinecarboxylic acid, methyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Cease Manufacture Update: 08-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/19335Status: Active Update: 28-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20643Methyl nicotinate: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| Hazards summary | Erythema provoked is basis of a methylnicotinate test of anti-inflammatories. [ChemIDplus] Contact irritant that causes non-immunologic contact reactions[ToxPlanet: DOD] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritant[Sigma-Aldrich MSDS] See Ethyl nicotinate and Methyl isonicotinate. |
| Hazard Classes and Categories | Skin Irrit. 2 (98.6%)Eye Irrit. 2 (99.1%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | QT1925000 |
| Customs code | 29333999 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| Risk statements (R) | 36/37/38-36/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36-37/39 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Applications & Uses
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%).
Occurrence
Reported found in ground coffee, roasted filberts, guanabana (Annona muicata L.), roasted peanuts, wild strawberries, vanilla bean, papaya, guava, plum, beer cognac, soursop, malt, wort, Bourbon vanilla and mountain papaya.
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.
General Description
Methyl nicotinate (or nicotinic acid methyl ester) is used as a rubefacient for the relief of pains in muscles, tendons, and joints. It is also used in food as a flavoring agent.
Preparation & Synthesis
Preparation
Methyl nicotinate was prepared by esterification of nicotinic acid by refluxing with methanol in the presence of concentrated sulphuric acid, esterification product obtained was extracted into organic solvent (chloroform) after neutralization of the reaction mixture with 10% sodium bicarbonate.Synthesis and antinociceptive activity of methyl nicotinateDOI:10.4314/jpb.v12i1.8