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Sigma-Aldrich

Methylhydroquinone

99%

Synonym(s):

Toluhydroquinone

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About This Item

Linear Formula:
CH3C6H3-1,4-(OH)2
CAS Number:
95-71-6
Molecular Weight:
124.14
Beilstein:
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.

Signal Word

Danger

Hazard Statements

H314,H317,H335,H410

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 Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

341.6 °F - closed cup

Flash Point(C)

172 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
First total synthesis of ?-helibisabonol A
Macias F A, et al.
Tetrahedron Letters, 43(36), 6417-6420 (2002)
J W Priest et al.
Biochemistry, 28(23), 9192-9200 (1989-11-14)
A crude extract that catalyzes the epoxidation of toluquinol and gentisyl alcohol was isolated from cultures of Penicillium patulum. About 60% of the activity sedimented from crude extract upon centrifugation at 105,000g for 2 h, and at 30,000g for 30
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