428566

2,6-Dimethoxy-1,4-benzoquinone

97%

• Synonym(s): DMBQ
• Empirical Formula (Hill Notation): C₈H₈O₄
• CAS Number: 530-55-2
• Molecular Weight: 168.15
• EC Number: 208-484-7
• MDL number: MFCD00016368
• UNSPSC Code: 12352100
• PubChem Substance ID: 24866499
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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