428566
2,6-Dimethoxy-1,4-benzoquinone
97%
Synonym(s):
DMBQ
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About This Item
Empirical Formula (Hill Notation):
C8H8O4
CAS Number:
Molecular Weight:
168.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
208-484-7
MDL number:
Assay:
97%
InChI key
OLBNOBQOQZRLMP-UHFFFAOYSA-N
InChI
1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3
SMILES string
COC1=CC(=O)C=C(OC)C1=O
assay
97%
mp
253-257 °C (dec.) (lit.)
solubility
DMSO: soluble(lit.)
functional group
ether, ketone
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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
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
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
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