Skip to Content
Merck
All Photos(4)

Key Documents

View All Documentation

428566

Sigma-Aldrich

2,6-Dimethoxy-1,4-benzoquinone

97%

Synonym(s):

DMBQ

Sign Into View Organizational & Contract Pricing
All Photos(4)

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

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

Looking for similar products? Visit Product Comparison Guide

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

S P Wolff et al.
Experimental eye research, 45(6), 791-803 (1987-12-01)
The ability of 2,6-dimethoxyquinone (DMQ) to impair 86Rb uptake by bovine lens epithelial cells was found to be independent of exogenous ascorbate in contrast to the impairment induced by Fe/Cu or riboflavin plus light. The cytotoxicity was associated with an
Phenolic derivatives related to lignin metabolism as substrates for Azospirillum laccase activity.
Faure D, et al.
Phytochemistry, 42(2), 357-359 (1996)
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service