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112968

Sigma-Aldrich

Methylhydroquinone

99%

Sinónimos:

Toluhydroquinone

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About This Item

Fórmula lineal:
CH3C6H3-1,4-(OH)2
Número de CAS:
95-71-6
Peso molecular:
124.14
Beilstein/REAXYS Number:
2041489
EC Number:
202-443-7
MDL number:
MFCD00002345
UNSPSC Code:
12352100
PubChem Substance ID:
24847123
NACRES:
NA.22

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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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.

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1A - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

341.6 °F - closed cup

flash_point_c

172 °C - closed cup

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
WXBD6402V
WXBD4338V
WXBD1930V
WXBD0306V
WXBC8810V

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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
Stefanie Töwe et al.
Molecular microbiology, 66(1), 40-54 (2007-08-30)
Catechol and 2-methylhydroquinone (2-MHQ) cause the induction of the thiol-specific stress response and four dioxygenases/glyoxalases in Bacillus subtilis. Using transcription factor arrays, the MarR-type regulator YkvE was identified as a repressor of the dioxygenase/glyoxalase-encoding mhqE gene. Transcriptional and proteome analyses
C Schewe et al.
Biomedica biochimica acta, 50(3), 299-305 (1991-01-01)
Various polymeric oxidation products of polyphenols strongly inhibited the purified lipoxygenase of rabbit reticulocytes, whereas the prostaglandin H synthase of sheep vesicular gland was only weakly inhibited. The oxidized polymeric preparations of caffeic acid, 2,5-dihydroxytoluene and 3,4-dihydroxytoluene were the most
Van Duy Nguyen et al.
Proteomics, 7(9), 1391-1408 (2007-04-05)
Bacillus subtilis is exposed to a variety of antimicrobial compounds in the soil. In this paper, we report on the response of B. subtilis to the fungal-related antimicrobials 6-brom-2-vinyl-chroman-4-on (chromanon) and 2-methylhydroquinone (2-MHQ) using proteome and transcriptome analyses. Chromanon, a
C Furihata et al.
Japanese journal of cancer research : Gann, 84(3), 223-229 (1993-03-01)
The possible tumor-promoting and tumor-initiating activities of p-methylcatechol and methylhydroquinone in the pyloric mucosa of male F344 rats were studied. Ornithine decarboxylase (ODC) and replicative DNA synthesis (RDS) were used as markers of tumor promotion and DNA single strand scission
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