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Merck

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6975
SDBB3633
SDBB0592
STBL2268
STBL1524

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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)
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)
Daniel B Yarosh et al.
Journal of dermatological science, 42(1), 13-21 (2006-01-21)
Wu-Zhu-Yu, is an extract prepared from the small berry fruit of Evodia rutaecarpa and is reported to have anti-inflammatory and anti-nociceptic activity. Methyl nicotinate (MN) is known to induce the release of PGD(2) resulting in localized erythema within 30 min
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