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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
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

97%

mp

253-257 °C (dec.) (lit.)

solubilidad

DMSO: soluble(lit.)

grupo funcional

ether
ketone

cadena SMILES

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

Clave InChI

OLBNOBQOQZRLMP-UHFFFAOYSA-N

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Descripción general

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.

Aplicación

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.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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)
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
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
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

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