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
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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.
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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M Matvienko et al.
Plant physiology, 127(1), 272-282 (2001-09-13)
Parasitic plants in the Scrophulariaceae use chemicals released by host plant roots to signal developmental processes critical for heterotrophy. Haustoria, parasitic plant structures that attach to and invade host roots, develop on roots of the hemiparasitic plant Triphysaria versicolor within
Hikaru Sano et al.
ChemSusChem, 13(9), 2354-2363 (2020-03-29)
Organic compounds as electrode materials can contribute to sustainability because they are nontoxic and environmentally abundant. The working mechanism during charge-discharge for reported organic compounds as electrode materials is yet to be completely understood. In this study, the structural behavior
Wei-Yu Lin et al.
Planta medica, 69(8), 757-764 (2003-10-08)
A novel quinonoid terpenoid, (-)- alpha-tocospirone, a new chromanone, (-)-gynuraone, as well as three new steroids, (22 E,24 S)-7 alpha-hydroperoxystigmasta-5,22-dien-3 beta-ol, (22 E,24 S)-stigmasta-1,4,22-trien-3-one, and (24 R)-stigmasta-1,4-dien-3-one, together with 15 known components, were isolated from the rhizome of Formosan Gynura
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)
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