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129658

Sigma-Aldrich

m-Anisaldehyde

97%

Synonym(s):

3-Methoxybenzaldehyde

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About This Item

Linear Formula:
CH3OC6H4CHO
CAS Number:
Molecular Weight:
136.15
Beilstein:
606013
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

refractive index

n20/D 1.553 (lit.)

bp

143 °C/50 mmHg (lit.)

density

1.117 g/mL at 20 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1cccc(OC)c1

InChI

1S/C8H8O2/c1-10-8-4-2-3-7(5-8)6-9/h2-6H,1H3

InChI key

WMPDAIZRQDCGFH-UHFFFAOYSA-N

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General description

m-Anisaldehyde has significant antifungal activity against Candida sp., including the azole-resistant strains.

m-Anisaldehyde is a class of benzaldehyde, used as a potent antifungal agent and as the starting material for complex aromatic compounds.

Application

m-Anisaldehyde was used as an eluent for mono-13C isotopomers of vanillin in normal phase silica gel chromatography. It was also used as an inhibitor of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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M A Morse et al.
Cancer letters, 97(2), 255-261 (1995-11-06)
As part of a routine screening assay, benzaldehyde was found to inhibit 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism. Consequently, the effects of benzaldehyde and several structurally related compounds on NNK metabolism were examined in murine hepatic and pulmonary microsomes. All test compounds inhibited
Sheikh Shreaz et al.
Microbial pathogenesis, 51(4), 277-284 (2011-06-15)
Attention has been drawn to evaluate the antifungal activity of p-anisaldehyde (1), o-anisaldehyde (2) and m-anisaldehyde (3). To put forward this approach, antifungal activity has been assessed in thirty six fluconazole-sensitive and eleven fluconazole-resistant Candida isolates. Growth and sensitivity of
Eliot P Botosoa et al.
Journal of chromatography. A, 1216(42), 7043-7048 (2009-09-15)
Quantitative isotopic (13)C NMR at natural abundance has been used to determine the site-by-site (13)C/(12)C ratios in vanillin and a number of related compounds eluted from silica gel chromatography columns under similar conditions. Head-to-tail isotope fractionation is observed in all
Chao-Bin Xue et al.
Bioorganic & medicinal chemistry, 15(5), 2006-2015 (2007-01-30)
Phenoloxidase (PO), also known as tyrosinase, is a key enzyme in insect development, responsible for catalyzing the hydroxylation of tyrosine into o-diphenols and the oxidation of o-diphenols into o-quinones. Inhibition of PO may provide a basis for novel environmentally friendly

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