Basic information
- CAS
26547-64-8- Standard SMILES
COC1=CC(=O)C=C(OC)C1=O- InChIKey
OLBNOBQOQZRLMP-UHFFFAOYSA-N- Molecular formula
- C8H8O4
- Average molar mass
- 168.15 g/mol
- Monoisotopic mass
- 168.04225873
Overview
2,6-dimethoxyquinone has been reported in Iris milesii, Diospyros eriantha, and other organisms with data available.
Names & identifiers
- Preferred name
- 2,6-Dimethoxy-1,4-Benzoquinone
- IUPAC
- 2,6-dimethoxycyclohexa-2,5-diene-1,4-dione
- English name
- 2,6-DIMETHOXY-1,4-BENZOQUINONE
- Molecular formula
- C8H8O4
- Molecular weight
- 168.15
Names & synonyms
2,6-Dimethoxy-1,4-benzoquinone530-55-22,6-Dimethoxyquinone2,6-Dimethoxy-p-benzoquinone2,6-dimethoxycyclohexa-2,5-diene-1,4-dione2,6-Dimethoxy-p-quinone2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy-p-Benzoquinone, 2,6-dimethoxy-DTXSID80862128NSC-24500NSC-563361Z701W789S
Show more names
dmbq56336LABOTEST-BB LT00159337Sitagliptin Impurity 1622，6-dimethoxy-1，4-benzeneDimethoxybenzoquinone,2,6-Phloroglucinol Impurity 43
RefChem:25890DTXCID30810937208-484-72,6-DimethoxybenzoquinoneMFCD000163682,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione2,6-Dimethoxysemiquinone anions2,6-Dimethoxybenzo-1,4-quinone
Database identifiers
- CAS
26547-64-8、530-55-2- PubChem CID
- 68262
- DTXSID
DTXSID80862128
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 259
Experimental & physicochemical properties
LogP
-0.06
-0.05
Melting Point252 °C
Physical DescriptionSolid
Collision Cross Section
129.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
125.18 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 253 · 253-257 °C (dec.) (lit.)
- Boiling point
- 257.07 °C · 257.07°C (rough estimate)
- Density
- 1.3037 · 1.3037 (rough estimate)
- refractive index
- 1.509 · 1.5090 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO: soluble(lit.)
- form
- Crystalline Powder
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- DK4750000
- hs_code
- 29146990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
Description2,6-DimethoXY-1A-benzoquinone is an allergen in more than 50 different plants and wood species, e.g., mahogany, macore~, sipo, wenge, oak, beech, elms, and poplar. With acamelin, it is one of the allergens of Acacia melanoxylon. Sensitization can occur in woodworkers such as carpenters, joiners and sawyers.
Uses2,6-Dimethoxy-1,4-benzoquinone may be used in the synthesis of 2-aryl-3,5-dimethoxy-1,4-benzoquinone derivatives.
General Description2,6-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.
Upstream & downstream products
Downstream products
Related reactions
1 records
Compound notes
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