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72420

Sigma-Aldrich

Methyl nicotinate

puriss., ≥99.0% (GC)

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Synonym(s):
Nicotinic acid methyl ester
Empirical Formula (Hill Notation):
C7H7NO2
CAS Number:
93-60-7
Molecular Weight:
137.14
Beilstein:
113951
EC Number:
202-261-8
MDL number:
MFCD00006388
UNSPSC Code:
12352100
PubChem Substance ID:
329764069
NACRES:
NA.22

biological source

synthetic

Quality Level

100

grade

puriss.

Assay

≥99.0% (GC)

form

powder or crystals (possibly with chunks)

color

white to faint yellow

bp

204 °C (lit.)

mp

39-42 °C
42-44 °C (lit.)

solubility

H2O: 0.1 g/mL, clear

SMILES string

COC(=O)c1cccnc1

InChI

1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3

InChI key

YNBADRVTZLEFNH-UHFFFAOYSA-N

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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.

Application

Methyl nicotinate can be used as a precursor:
  • In the asymmetric synthesis of 1-azasugars (glycosidase inhibitors) for biomedical applications.
  • In the total synthesis of ±-sesbanine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Selective fowler reductions: asymmetric total syntheses of isofagomine and other 1-azasugars from methyl nicotinate
Zhao G, et al.
Organic Letters, 3(2), 201-203 (2001)
A facile synthesis of ? -sesbanine via γ-addition of ketene silyl acetal with quaternized methyl nicotinate
Wada M, et al.
Tetrahedron Letters, 26(27), 3267-3270 (1985)
Topical antirheumatic agents as hydroxyl radical scavengers
Billany MR, et al.
International Journal of Pharmaceutics, 124(2), 279-283 (1995)
Stability of methylnicotinate in aqueous solution as utilized in the'niacin patch test'
Ross BM and Katzman M
BMC Research Notes, 1(1), 89-89 (2008)
Identification and quantification of methyl nicotinate in rice (Oryza sativa L.) by gas chromatography-mass spectrometry
RB Muralidhara, et al.
Food Chemistry, 105(2), 736-741 (2007)
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