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Merck
CN

72420

Methyl nicotinate

puriss., ≥99.0% (GC)

Synonym(s):

Nicotinic acid methyl ester

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About This Item

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

Key Documents

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InChI key

YNBADRVTZLEFNH-UHFFFAOYSA-N

InChI

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

SMILES string

COC(=O)c1cccnc1

biological source

synthetic

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

functional group

ester

Quality Level

100

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6975
SDBB3633
SDBB0592
STBL2268
STBL1524

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Topical antirheumatic agents as hydroxyl radical scavengers
Billany MR, et al.
International Journal of Pharmaceutics, 124(2), 279-283 (1995)
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)
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)
Mona Syhre et al.
Tuberculosis (Edinburgh, Scotland), 89(4), 263-266 (2009-06-02)
Recent figures show that tuberculosis (TB) is advancing and killing more than two million people annually, yet no breakthrough in rapid diagnostics is in sight. Volatile metabolites of Mycobacterium tuberculosis (MTB) may provide just that. It is well established that
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)
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