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39579

Sigma-Aldrich

2,5-Dimethyl-1,4-benzoquinone

≥98.0%

Synonym(s):

2,5-Dimethyl-2,5-cyclohexadiene-1,4-dione, 2,5-Dimethyl-p-benzoquinone, 2,5-Dimethyl-p-quinone, 2,5-Dimethylbenzoquinone, 2,5-Xyloquinone, 3,6-Dimethyl-p-benzoquinone

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About This Item

Empirical Formula (Hill Notation):
C8H8O2
CAS Number:
137-18-8
Molecular Weight:
136.15
Beilstein:
2041348
EC Number:
205-283-6
MDL number:
MFCD00041737
UNSPSC Code:
12352100
PubChem Substance ID:
57649863
NACRES:
NA.22

Assay

≥98.0%

mp

123-125 °C

solubility

toluene: soluble 0.5 g/10 mL, clear to faintly turbid, yellow to brown

SMILES string

CC1=CC(=O)C(C)=CC1=O

InChI

1S/C8H8O2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3

InChI key

MYKLQMNSFPAPLZ-UHFFFAOYSA-N

General description

2,5-Dimethyl-1,4-benzoquinone is a quinone derivative. Its reaction with jack bean urease in phosphate buffer, pH 7.8 has been studied. It is present as one of the component of defensive secretion of opilionid Acanthopachylus aculeatus. It has been investigated as inhibitor of jack bean urease in 50mM phosphate buffer, pH 7.0.

Application

2,5-Dimethyl-1,4-benzoquinone may be used in a key step involved in the total synthesis of (−)-cyathin A3.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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P Mäenpää et al.
Plant molecular biology, 38(6), 1191-1200 (1998-12-30)
Ala-251 in the membrane-parallel helix in the D-E loop of the D1 polypeptide close to the Q(B) pocket of photosystem II (PS II), was mutated to aspartate (D), lysine (K), leucine (L) or serine (S) in Synechocystis 6803. O2 evolution
Wiesława Zaborska et al.
Journal of enzyme inhibition and medicinal chemistry, 17(4), 247-253 (2003-01-18)
1,4-benzoquinone (BQ) and 2,5-dimethyl-1,4-benzoquinone (DMBQ) were studied as inhibitors of jack bean urease in 50 mM phosphate buffer, pH 7.0. The mechanisms of inhibition were evaluated by progress curves studies and steady-state approach to data achieved by preincubation of the
Wiesława Zaborska et al.
Bioorganic chemistry, 35(3), 233-242 (2006-12-16)
In this work we studied the reaction of four quinones, 1,4-benzoquinone (1,4-BQ), 2,5-dimethyl-1,4-benzoquinone (2,5-DM-1,4-BQ), tetrachloro-1,4-benzoquinone (TC-1,4-BQ) and 1,4-naphthoquinone (1,4-NQ) with jack bean urease in phosphate buffer, pH 7.8. The enzyme was allowed to react with different concentrations of the quinones
Catherine E Sansom et al.
Journal of natural products, 70(12), 2042-2044 (2007-12-07)
Bioactivity-directed isolation work on the endemic New Zealand brown alga Perithalia capillaris, seeking anti-inflammatory compounds, led to a new bis-prenylated quinone ( 4). This compound inhibited superoxide production by human neutrophils in vitro (IC 50 2.1 microM), but was more
J Cao et al.
Biochimica et biophysica acta, 1015(2), 180-188 (1990-02-02)
Upon illumination, a dark-adapted photosynthetic sample shows time-dependent changes in chlorophyll (Chl) a fluorescence yield, known as the Kautsky phenomenon or the OIDPS transient. Based on the differential effects of electron acceptors such as 2,5-dimethyl-p-benzoquinone (DMQ) and 2,6-dichloro-p-benzoquinone (DCBQ) on
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