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428566

Sigma-Aldrich

2,6-Dimethoxy-1,4-benzoquinone

97%

Synonym(s):

DMBQ

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About This Item

Empirical Formula (Hill Notation):
C8H8O4
CAS Number:
530-55-2
Molecular Weight:
168.15
EC Number:
208-484-7
MDL number:
MFCD00016368
UNSPSC Code:
12352100
PubChem Substance ID:
24866499
NACRES:
NA.22

Quality Level

100

assay

97%

mp

253-257 °C (dec.) (lit.)

solubility

DMSO: soluble(lit.)

SMILES string

COC1=CC(=O)C=C(OC)C1=O

InChI

1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3

InChI key

OLBNOBQOQZRLMP-UHFFFAOYSA-N

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General description

2,6-Dimethoxy-1,4-benzoquinone (DBQ, 2,6-DMBQ, DMOBQ) is a 1,4-benzoquinone derivative. It is a wood allergen, has been reported to cause various skin and mucosal symptoms on exposure to wood dusts. It is formed as a product due to the activity of bacterial Azospirillum lipoferum laccase on phenolic compounds of the syringic type. DBQ is one of the components isolated from the rhizome of Gynura japonica with a potential to show anti-platelet aggregation activity in vitro. It is an anticancer agent, whose kinetics of cyclic redox transformation induced by ascorbate (AscH-) has been studied using the Clark electrode and ESR techniques. Its electrochemical reduction in acetonitrile has been studied.

Application

2,6-Dimethoxy-1,4-benzoquinone may be used in the synthesis of 2-aryl-3,5-dimethoxy-1,4-benzoquinone derivatives.
Known haustorial inducing factor.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Fang-Rong Chang et al.
Journal of natural products, 65(3), 255-258 (2002-03-23)
Three new eudesmanolide sesquiterpenes, neolitacumone A-C (1-3), and one new benzylisoquinoline alkaloid, neolitacumonine (5), along with 27 known compounds were isolated from the stem bark of Neolitsea acuminatissima. The structures of compounds 1-3 and 5 were established on the basis
Lelde Krumina et al.
Environmental science & technology, 51(16), 9053-9061 (2017-07-12)
Hydroquinones are important mediators of electron transfer reactions in soils with a capability to reduce Fe(III) minerals and molecular oxygen, and thereby generating Fenton chemistry reagents. This study focused on 2,6-dimethoxy hydroquinone (2,6-DMHQ), an analogue to a common fungal metabolite
V A Roginsky et al.
Biochemistry. Biokhimiia, 63(2), 200-206 (1998-06-02)
The kinetics of cyclic redox transformation of 2,6-dimethoxy-1, 4-benzoquinone (DMOBQ)--the well-known effective anticancer agent--induced by ascorbate (AscH-) were studied in phosphate buffer, pH 7.40, at 37 degreesC using the Clark electrode and ESR techniques. The process is due to the
Anomalous behavior in the two-step reduction of quinones in acetonitrile.
Lehmann MW and Evans DH.
Journal of Electroanalytical Chemistry, 500(1), 12-20 (2001)
Quy A Ngo et al.
BMC plant biology, 13, 28-28 (2013-02-20)
Plant parasitism represents an extraordinary interaction among flowering plants: parasitic plants use a specialized organ, the haustorium, to invade the host vascular system to deprive host plants of water and nutrients. Various compounds present in exudates of host plants trigger
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