Methyl nicotinate
- Iupac Name：methyl pyridine-3-carboxylate
- CAS No.: 93-60-7
- Molecular Weight：137.13598
- Modify Date.: 2022-11-29 05:46
- Introduction: Methyl nicotinate has a fresh, sweet, caramellic nutty odor.
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1. Names and Identifiers
- 1.1 Name
- Methyl nicotinate
- 1.2 Synonyms
3-methoxycarbonylpyridine 3-pyridinecarboxylic acid methyl ester 3-Pyridinecarboxylic acid, methyl ester EINECS 202-261-8 FEMA 3709 methyl 3-nicotinate methyl 3-pyridinecarboxylate METHYL NICOTINATE DAC Methyl nictinate METHYL PYRIDINE-3-CARBOXYLATE methylnicotinicacid Methylpyridin-3-carboxylat MFCD00006388 NIACIN METHYL ESTER Nicometh NICONACID METHYL ESTER NICOTINIC ACID METHYL ESTER Nikomet PELLAGRA PREVENTIVE FACTOR METHYL ESTER PYRIDINE-3-CARBOXYLIC ACID METHYL ESTER RARECHEM AL BF 0185
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- 1.3 CAS No.
- 93-60-7
- 1.4 CID
- 7151
- 1.5 EINECS(EC#)
- 202-261-8
- 1.6 Molecular Formula
- C7H7NO2 (isomer)
- 1.7 Inchi
- InChI=1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3
- 1.8 InChIkey
- YNBADRVTZLEFNH-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- COC(=O)C1=CN=CC=C1
- 1.10 Isomers Smiles
- COC(=O)C1=CN=CC=C1
2. Properties
- 2.1 Density
- 1.137
- 2.1 Melting point
- 38-43℃
- 2.1 Boiling point
- 209℃
- 2.1 Refractive index
- 1.5323 (estimate)
- 2.1 Flash Point
- 95℃
- 2.1 Precise Quality
- 137.04800
- 2.1 PSA
- 39.19000
- 2.1 logP
- 0.86820
- 2.1 Solubility
- H2O: 0.1?g/mL, clear
- 2.2 Appearance
- White to brownish Crystals or Crystalline Powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- Methyl nicotinate has a fresh, caramellic, nutty and mild tobacco odor.
- 2.5 Color/Form
- White to brownish
- 2.6 pKa
- pKa 3.1 (Uncertain)
- 2.7 Water Solubility
- H2O: negligible soluble
- 2.8 Stability
- Stable under normal temperatures and pressures.
- 2.9 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Usage
- Vasodilator. Methyl nicotinate Preparation Products And Raw materials Preparation Products
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/38
- 4.1 Safety Statements
- S26;S37/39
- 4.1 Hazard Declaration
- H315-H319-H335
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- QT1925000
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Moderately toxic by parenteral route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:?
Xi
Risk Statements: 36/37/38-36/38
36/37/38: Irritating to eyes, respiratory system and skin?
36/38: Irritating to eyes and skin?
Safety Statements: 26-36-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36: Wear suitable protective clothing?
37/39: Wear suitable gloves and eye/face protection?
WGK Germany: 3
RTECS: QT1925000
- 4.3 Specification
-
? Methyl nicotinate (CAS NO.93-60-7), its Synonyms are 3-(Carbomethoxy)pyridine ; 3-(Methoxycarbonyl)pyridine ; 3-Pyridinecarboxylic acid, methyl ester ; Methyl 3-pyridinecarboxylate ; Methyl-nicotinate ; Nicometh ; Nicotinic acid, methyl ester ; Nikomet ; m-(Methoxycarbonyl)pyridine .
- 4.4 Toxicity
- LD50 orally in Rabbit: > 2000 mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
93-60-7Total: 28 Synthesis Route
9. Other Information
- 9.0 Usage
- Used as a rubefacient, topical vasodilator used to test the efficacy of skin protection compounds (i.e. products designed to provide barriers to chemical warfare agents) and used as a flavoring agent. It is a useful synthetic intermediate. It can be used to prepare biarylcarboxamide inhibitors of phosphodiesterase IV and tumor necrosis factor-α in treatment of rheumatoid arthritis.
- 9.1 Absorption
- The presence of methyl group facilitates the penetration of methyl nicotinate through the skin with good lipophilicity, allowing rapid absorption following topical administration. _In vitro_, about 80-90% of the polar compounds methyl nicotinate rapidly penetrated the skin. It was demonstrated in excised skin of hairless mice that methyl nicotinate can effectively bypass the stratum corneum layer of the skin. In humans, nicotinic acid and nicotinamide were shown to be rapidly absorbed from the stomach and intestine via a sodium carrier-mediated mechanism at low concentrations.|Following epicutaneous administration of small radiolabelled dose of methyl nicotinate in human volunteers, approximately 15% of the dose was recovered in the urine within 108 hours after treatment. The excretion of nicotinic acid mainly takes place in the kidneys.|According to the animal studies, nicotinic acid is mainly concentrated in the liver, kidneys, and adipose tissue.|No pharmacokinetic data available.
- 9.2 Metabolism
- Methyl nicotinate undergoes ester hydrolysis to form nicotinic acid and methanol. The hydrolysis is thought to be mediated by nonspecific α-naphthylacetate-esterase at the dermis layer of the skin.
- 9.3 Biological Half Life
- _In vitro_, the half-life of methyl nicotinate in the dermis was 3 to 10 minutes.
- 9.4 Mesh Entry Terms
- methyl nicotinate
- 9.5 Manufacturing Info
- 3-Pyridinecarboxylic acid, methyl ester: ACTIVE
- 9.6 Use Classification
- Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Soothing; Tonic
- 9.7 Merck
- 14,6100
- 9.8 BRN
- 113951
- 9.9 Description
- Methyl nicotinate has a fresh, sweet, caramellic nutty odor.
- 9.10 Chemical Properties
- Methyl nicotinate has a fresh, caramellic, nutty and mild tobacco odor.
- 9.11 Chemical Properties
- white to brownish crystals or crystalline powder
- 9.12 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.
- 9.13 Uses
-
Methyl nicotinate can be employed as a precursor in the synthesis:
- Di-3-pyridyl ketone ligand, which is used in the preparation of silver(I) complexes for the derivation of coordination polymeric chains.
- 5-arylnicotinates , ±-sesbanine , and 1,4-dihydropyridine derivatives.
10. Computational chemical data
- Molecular Weight: 137.13598g/mol
- Molecular Formula: C7H7NO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 137.047678466
- Monoisotopic Mass: 137.047678466
- Complexity: 125
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 39.2
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBiMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgAAAAAADADBmgY+iJIIFACoAjD3TACCgCA1AiAI2CE4bNgIJvrAtZmEMYhmwAHI6caYEQIMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
Features Methyl Nicotinate, a derivative of Vitamin B3, is a white crystalline substance commonly used in nutritional supplements and cosmetics. It helps maintain and improve skin health, promotes blo..
-
2-Amino Methyl Nicotinate, also known as Methyl 2-aminonicotinate, is a white solid at room temperature and pressure. It is a pyridine derivative with important applications in medicinal chemistry, su..
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