METHYLHYDROQUINONE

CAS NO:95-71-6
EC NO:202-443-7

Methylhydroquinone is a natural product found in Hydropisphaera erubescens, Pyrola rotundifolia, and other organisms with data available.

Methylhydroquinone is a member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group. 
Methylhydroquinone has a role as an angiogenesis inhibitor, an anti-inflammatory agent and a Penicillium metabolite.

Industry Uses:
-Inhibitor

Consumer Uses:
-Inhibitor

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.

Physicochemical Information:
Flash point:    172 °C
Ignition temperature:    468 °C
Melting Point:    128 - 130 °C
Solubility:    77 g/l

Methylhydroquinone is used as a stabilizer in acrylics and as an antioxidant for fatty esters,linseed oil and other inedible fats and oils. Further research may identify additional product or industrial usages of this chemical.

Chemical Properties
white solid

Uses
Antioxidant, polymerization inhibitor.

Methylhydroquinone is used as stabilizer and antioxidant in aerylic monomers to prevent polymerization.

Methylhydroquinone is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway. Allows for screening of novel inhibitors of angiogenesis.

Definition
ChEBI: A member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group.

Methylhydroquinone is a reactive oxygen species (ROS) that can bind to DNA, forming covalent adducts. 
Methylhydroquinone has been shown to have an optimum concentration of 10 μM, and the hydroxyl group on its phenolic ring enables it to form hydrogen bonding interactions with nucleic acids. 
Methylhydroquinone has been shown to inhibit angiogenic process in vitro and in vivo, as well as inhibiting the growth of tumor cells by binding to DNA. 
Methylhydroquinone also inhibits the transfer of methyl groups from methyl donors such as S-adenosylhomocysteine and methionine to acceptor molecules such as p-hydroxybenzoic acid.

Technical Information:
Appearance :Powder
Physical State :Solid

About Methylhydroquinone
Helpful information
Methylhydroquinone is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.

Methylhydroquinone is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Consumer Uses
Methylhydroquinone is used in the following products: coating products.
Other release to the environment of Methylhydroquinone is likely to occur from: indoor use and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).
Article service life
ECHA has no public registered data on the routes by which Methylhydroquinone is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.

Widespread uses by professional workers
Methylhydroquinone is used in the following products: coating products, fillers, putties, plasters, modelling clay and polymers.
Methylhydroquinone is used in the following areas: building & construction work.
Methylhydroquinone is used for the manufacture of: plastic products.
Other release to the environment of Methylhydroquinone is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).

Formulation or re-packing
Methylhydroquinone is used in the following products: polymers, coating products, fillers, putties, plasters, modelling clay, adhesives and sealants and laboratory chemicals.
Release to the environment of Methylhydroquinone can occur from industrial use: formulation of mixtures and formulation in materials.

Uses at industrial sites
Methylhydroquinone is used in the following products: coating products, laboratory chemicals, polymers, fillers, putties, plasters, modelling clay and adhesives and sealants.
Methylhydroquinone is used for the manufacture of: chemicals and plastic products.
Release to the environment of Methylhydroquinone can occur from industrial use: as processing aid, as processing aid, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and for thermoplastic manufacture.

Manufacture
ECHA has no public registered data on the routes by which Methylhydroquinone is most likely to be released to the environment.

Methylhydroquinone is produced by the oxidation of o-cresol by the mutants G103S.
Methylhydroquinone used as a stabilizer for unsaturated polyesters and as an antioxidant for fatty esters, linseed oil.

Methylhydroquinone is a versatile compound. 
Methylhydroquinone finds many applications in the field of polymer science due to its good binding properties as well as its strength. 
Methylhydroquinone is an off-white crystalline solid with a molecular weight of 124.137 g/mol. 
Methylhydroquinone has a characteristic odor and its melting point is 262.4°F.

Methylhydroquinone is a member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group. 
Methylhydroquinone has a role as an angiogenesis inhibitor, an anti-inflammatory agent and a Penicillium metabolite.

Methylhydroquinone can be analyzed by this reverse phase (RP) HPLC method with simple conditions. The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 µm particles columns available for fast UPLC applications. This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation. 
Methylhydroquinone also suitable for pharmacokinetics.

Methylhydroquinone is used as medicine, dye, pigment intermediates, antioxidants, is also a new type of polymerization inhibitor.

ChEBI: A member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group.

FUNCTIONS
-Intermediates
-Polymerization Inhibitor  

IUPAC names:
2-METHYL HYDROQUINONE
2-Methyl-1,4-benzenediol
2-methylbenzene-1,4-diol
2-Methylhydroquinone
2-methylhydroquinone
Methylhydroquinone
methylhydroquinone

SYNONYMS:
2-Methyl-p-hydroquinone
1,4-Benzenediol, 2-methyl- [ACD/Index Name]
202-443-7 [EINECS]
2041489 [Beilstein]
2-Methyl-1,4-benzenediol [ACD/IUPAC Name]
2-Méthyl-1,4-benzènediol [French] [ACD/IUPAC Name]
2-Methyl-1,4-benzoldiol [German] [ACD/IUPAC Name]
2-Methylbenzene-1,4-diol [ACD/IUPAC Name]
2-Methylhydroquinone [ACD/IUPAC Name]
95-71-6 [RN]
Methylhydroquinone
MFCD00002345 [MDL number]
MX6700000
QR DQ B1 [WLN]
"1,4-BENZENEDIOL, 2-METHYL-"
"1,4-BENZENEDIOL, 2-METHYL-"|"2-METHYLBENZENE-1,4-DIOL"
"2-METHYLBENZENE-1,4-DIOL"
p-toluquinol
1-(3,4-Dihydroxyphenyl)-2-propanone
1,4-Dihydroxy-2-methylbenzene
135648-79-2 [RN]
140627-29-8 [RN]
2,4-DCT
2,5-DHTOP
2,5-Dihydroxytoluene
2,5-Dihydroxytoluene, Toluhydroquinone
2,5-Toluenediol
202-443-7MFCD00002345