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112968

Sigma-Aldrich

Methylhydroquinone

99%

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Synonym(s):
Toluhydroquinone
Linear Formula:
CH3C6H3-1,4-(OH)2
CAS Number:
Molecular Weight:
124.14
Beilstein:
2041489
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

solid

autoignition temp.

851 °F

mp

128-130 °C (lit.)

SMILES string

Cc1cc(O)ccc1O

InChI

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

InChI key

CNHDIAIOKMXOLK-UHFFFAOYSA-N

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1 of 4

This Item
W23860054306D131350
Methylhydroquinone 99%

Sigma-Aldrich

112968

Methylhydroquinone

1,4-Dimethoxybenzene 99%, FG

Sigma-Aldrich

W238600

1,4-Dimethoxybenzene

1,4-Dimethoxybenzene analytical standard

Supelco

54306

1,4-Dimethoxybenzene

1,4-Dimethoxybenzene ReagentPlus®, 99%

Sigma-Aldrich

D131350

1,4-Dimethoxybenzene

form

solid

form

-

form

-

form

crystals

mp

128-130 °C (lit.)

mp

54-56 °C (lit.)

mp

54-56 °C (lit.)

mp

54-56 °C (lit.)

autoignition temp.

851 °F

autoignition temp.

1463 °F

autoignition temp.

1463 °F

autoignition temp.

1463 °F

General description

Methylhydroquinone is produced by the oxidation of o-cresol by the mutants G103S, G103S/A107G, and G103S/A107T.

Application

Methylhydroquinone can be used as a reactant to prepare:
  • A semiflexible thermotropic polyester via polycondensation reaction with 4,4′-sebacoyldioxydibenzoyl chloride.
  • A sesquiterpene (±)-helibisabonol A.
  • poly{hexakis[(methyl)(4-hydroxyphenoxy)]cyclotriphosphazene} by reacting with hexachlorocyclotriphosphazene.
  • 6-Hydroxy-4,7-dimethyl-2H-1-benzopyran-2-one by treating with ethyl acetoacetate in the presence of H2SO4 as a catalyst.

Biochem/physiol Actions

Methylhydroquinone (Toluquinol) inhibits the growth of endothelial and tumor cells in culture in the micromolar range and is a promising drug candidate in the treatment of cancer and other angiogenesis-related pathologies.

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First total synthesis of ?-helibisabonol A
Macias F A, et al.
Tetrahedron Letters, 43(36), 6417-6420 (2002)
Synthesis and mesomorphic properties of a semiflexible polyester based on 4, 4?-sebacoyldioxydibenzoyl chloride and methylhydroquinone
Costa Giovanna, et al.
Macromolecular Chemistry and Physics, 191(4), 791-800 (1990)
Ying Tao et al.
Journal of bacteriology, 186(14), 4705-4713 (2004-07-03)
Wild-type toluene 4-monooxygenase (T4MO) of Pseudomonas mendocina KR1 oxidizes toluene to p-cresol (96%) and oxidizes benzene sequentially to phenol, to catechol, and to 1,2,3-trihydroxybenzene. In this study T4MO was found to oxidize o-cresol to 3-methylcatechol (91%) and methylhydroquinone (9%), to
Synthesis and characterization of poly {hexakis [(methyl)(4-hydroxyphenoxy)] cyclotriphosphazene}
Luther T A, et al.
Journal of Applied Polymer Science, 82(14), 3439-3446 (2001)
Solvent-Free Synthesis and Insecticidal Activities of C6-Esterified Coumarins
Xie Ying, et al.
Letters in Drug Design & Discovery, 11(9), 1124-1132 (2014)

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