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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

Análisis

97%

mp

253-257 °C (dec.) (lit.)

solubilidad

DMSO: soluble(lit.)

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


Certificados de análisis (COA)

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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
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
Anomalous behavior in the two-step reduction of quinones in acetonitrile.
Lehmann MW and Evans DH.
Journal of Electroanalytical Chemistry, 500(1), 12-20 (2001)
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

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