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300756

Sigma-Aldrich

2,3-Dimethylhydroquinone

97%

Synonym(s):

1,4-Dihydroxy-2,3-dimethylbenzene, 2,3-Dimethyl-1,4-benzenediol

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About This Item

Linear Formula:
(CH3)2C6H2-1,4-(OH)2
CAS Number:
608-43-5
Molecular Weight:
138.16
Beilstein:
636976
MDL number:
MFCD00009997
UNSPSC Code:
12162002
PubChem Substance ID:
24857938
NACRES:
NA.23

Assay

97%

form

powder

mp

223-225 °C (lit.)

SMILES string

Cc1c(C)c(O)ccc1O

InChI

1S/C8H10O2/c1-5-6(2)8(10)4-3-7(5)9/h3-4,9-10H,1-2H3

InChI key

BXJGUBZTZWCMEX-UHFFFAOYSA-N

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General description

2,3-Dimethylhydroquinone is an alkyl p-hydroquinone that can be used as a chain breaking antioxidant and an electron donor for redox intermediates. It acts as an antioxidant due to its characteristic to terminate kinetic chains on reaction with peroxy radicals.

Application

2,3-Dimethylhydroquinone can be used as an antioxidant for lipid peroxidation. It is also used in the synthesis of benzofuran-5-ols which can further be utilized as antifungal agents in biological applications.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Substituted p-hydroquinones as inhibitors of lipid peroxidation
Roginsky V, et al.
Chemistry and Physics of Lipids, 125(1), 49-58 (2003)
Electrochemical oxidation of 2, 3-dimethylhydroquinone in the presence of 1, 3-dicarbonyl compounds
Hosseiny D, et al.
The Journal of Organic Chemistry, 71(5), 2139-2142 (2006)
Alnald Javier et al.
Dalton transactions (Cambridge, England : 2003), 43(39), 14798-14805 (2014-08-28)
Previous studies, based on thin-layer electrochemistry (TLE), in situ scanning tunneling microscopy (EC-STM), high-resolution electron energy loss spectroscopy (HREELS) and density functional theory (DFT) computations, on the chemical adsorption of hydroquinone from aqueous solutions onto atomically smooth Pd (and Pt)
Synthesis and antifungal activity of benzofuran-5-ols
Ryu C, et al.
Bioorganic & Medicinal Chemistry Letters, 20(22), 6777-6780 (2010)
Marco Persico et al.
Scientific reports, 7, 45485-45485 (2017-04-07)
In the present work we performed a combined experimental and computational study on the interaction of the natural antimalarial endoperoxide plakortin and its synthetic analogue 4a with heme. Obtained results indicate that the studied compounds produce reactive carbon radical species
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