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Merck

428566

Sigma-Aldrich

2,6-Dimethoxy-1,4-benzoquinone

97%

Sinónimos:

DMBQ

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About This Item

Fórmula empírica (notación de Hill):
C8H8O4
Número de CAS:
Peso molecular:
168.15
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

253-257 °C (dec.) (lit.)

solubility

DMSO: soluble(lit.)

functional group

ether
ketone

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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
T Estlander et al.
Contact dermatitis, 44(4), 213-217 (2001-03-22)
Exposure to wood dusts may cause various skin and mucosal symptoms. Allergic dermatoses, caused by wood dusts, diagnosed at the Finnish Institute of Occupational Health during 1976-1999 are reported here. 16 had allergic contact dermatitis and, 2 had contact urticaria.
Gennady Ananyev et al.
Biochimica et biophysica acta, 1858(11), 873-883 (2017-07-25)
The desert microalga Chlorella ohadii was reported to grow at extreme light intensities with minimal photoinhibition, tolerate frequent de/re-hydrations, yet minimally employs antenna-based non-photochemical quenching for photoprotection. Here we investigate the molecular mechanisms by measuring Photosystem II charge separation yield

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