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54050

Sigma-Aldrich

4-Methoxyphenol

purum, ≥98.0% (HPLC)

Synonym(s):

4-Hydroxyanisole, 4-MP, HQMME, Hydroquinone monomethyl ether, MEHQ, p-Guaiacol

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100 G
$37.80
500 G
$76.30

About This Item

Linear Formula:
CH3OC6H4OH
CAS Number:
Molecular Weight:
124.14
Beilstein/REAXYS Number:
507924
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

$37.80


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vapor density

4.3 (vs air)

Quality Level

vapor pressure

<0.01 mmHg ( 20 °C)

grade

purum

assay

≥98.0% (HPLC)

autoignition temp.

789 °F

impurities

≤2% hydroquinone dimethyl ether

bp

243 °C (lit.)

mp

54-56 °C
55-57 °C (lit.)

SMILES string

COc1ccc(O)cc1

InChI

1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

InChI key

NWVVVBRKAWDGAB-UHFFFAOYSA-N

Gene Information

human ... TYR(7299)

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General description

4-Methoxyphenol, a 4-alkoxyphenol, can be synthesized from hydroquinone.[1] It undergoes polymerization in the presence of horseradish peroxidase (enzymatic catalyst) and sodium dodecyl sulfate (surfactant) to afford poly(4-methoxyphenol).[2]

Application

4-Methoxyphenol may be used in to synthesize chiral building blocks such as 1,2-diols.[3] It also has various industrial applications, such as an antioxidant, an inhibitor for the polymerization reactions and a stabilizing agent.[1]

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Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Synthesis of poly (4-methoxyphenol) by enzyme-catalyzed polymerization and evaluation of its antioxidant activity.
Zheng K, et al.
New. J. Chem., 37(12), 4185-4191 (2013)
Paolo Ruzza et al.
Journal of medicinal chemistry, 52(15), 4973-4976 (2009-07-16)
We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activatable phenolic moiety and a GSH-reactive alpha,beta-unsaturated carbonyl group. Both the E (1) and Z (2)
Enantioselective ring opening of epoxides with 4-methoxyphenol catalyzed by gallium heterobimetallic complexes: An efficient method for the synthesis of optically active 1, 2-diol monoethers.
Iida T, et al.
Angewandte Chemie (International Edition in English), 37(16), 2223-2226 (1998)
Simple synthesis of non-symmetric 1, 4-dialkoxybenzenes via 4-alkoxyphenols.
Radoslaw M, et al.
Organic Communications, 9(1) (2016)
Majid Y Moridani
Cancer letters, 243(2), 235-245 (2006-01-24)
In the current work we investigated for the first time the biochemical basis of 4-hydroxyanisole (4-HA) induced toxicity in B16-F0 melanoma cells. It was found that dicoumarol, a diaphorase inhibitor, and 1-bromoheptane, a GSH depleting agent, increased 4-HA induced toxicity

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