90111-36-7

Basic information

• Product Name: 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• Synonyms: 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS NO: 90111-36-7
• Molecular Weight: 168.149
• Mol File: 90111-36-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione(90111-36-7)
• EPA Substance Registry System: 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione(90111-36-7)

Safety Data

• Hazardous Substances Data: 90111-36-7(Hazardous Substances Data)

Upstream product

• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 213831-88-0 2-acetoxy-5-methoxy-3-methyl-[1,4]benzoquinone 
• 54812-43-0 1,2,4,5-tetramethoxy-3-methylbenzene 
• 2441-46-5 1,2,4,5-tetramethoxybenzene 
• 213831-72-2 acetic acid 4-acetoxy-2-methyl-3,6-dioxo-cyclohexa-1,4-dienyl ester 
• 2207-58-1 2,5-dihydroxy-6-methylbenzoquinone 
• 67-56-1 methanol 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 6485-17-2 2,3,6-triacetoxy-5-methoxy-toluene 

Downstream Products

• 1760-82-3 2,5-dimethoxy-3-methyl-[1,4]benzoquinone 
• 854629-31-5 6-hydroxy-5-methyl-3-(methylamino)cyclohexa-2,5-diene-1,4-dione 

Relevant articles and documents

Phytotoxic potential of secondary metabolites and semisynthetic compounds from endophytic fungus xylaria feejeensis strain SM3e-1b isolated from sapium macrocarpum

Bioactivity-directed fractionation of the combined culture medium and mycelium extract of the endophytic fungus Xylaria feejeensis strain SM3e-1b, isolated from Sapium macrocarpum, led to the isolation of three known natural products: (4S,5S,6S)-4-hydroxy-3-methoxy-5-methyl-5,6-epoxycyclohex-2-enone or coriloxine, 1; 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 2; and 2,6-dihydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione or fumiquinone B, 3. This is the first report of compound 3 being isolated from this species. Additionally, four new derivatives of coriloxine were prepared: (4R,5S,6R)-6-chloro-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-enone, 4; 6-hydroxy-5-methyl-3-(methylamino)cyclohexa-2,5- diene-1,4-dione, 5; (4R,5R,6R)-4,5-dihydroxy-3-methoxy-5-methyl-6-(phenylamino)cyclohex-2-enone, 6; and 2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 7. X-ray analysis allowed us to unambiguously determine the structures and absolute configuration of semisynthetic derivatives 4, 5, and 6. The phytotoxic activity of the three isolated natural products and the coriloxine derivatives is reported. Germination of the seed, root growth, and oxygen uptake of the seedlings of Trifolium pratense, Medicago sativa, Panicum miliaceum, and Amaranthus hypochondriacus were significantly inhibited by all of the tested compounds. In general, they were more effective inhibiting root elongation than suppressing the germination and seedling oxygen uptake processes as shown by their IC50 values.

Preparation and structure-activity relationships of novel asterriquinone derivatives

Asterriquinone (ARQ, la) is an antitumor metabolite of Aspergillus terreus IFO 6123. To gain insight into the structure-activity relationships of ARQ, a series of chemically modified derivatives (1 - 6), the ARQ analogues (b - e) and the 2,5-dihydroxy-p-benzoquinone analogues (f - h), were prepared, and cytotoxic activity against mouse leukemia P388 cells investigated. Results indicated that: 1) at least one hydroxy group or acetoxy group in the p-benzoquinone moiety is important to exhibit cytotoxicity; 2) in the p-benzoquinone moiety, a single methoxy group and/or one acetoxy group substitution showed more potent cytotoxicity than when two hydroxy groups are substituted (1); 3) the indole ring is important for the cytotoxicity of ARQ analogues; 4) the 1,1-dimethyl-2-propenyl group in the indole ring is not important for the cytotoxic activity of ARQ.

The acid-catalyzed oxidation of methoxybenzenes to p-benzoquinones by dimethyldioxirane

Methoxybenzenes 1 were oxidized to phenols and/or p-benzoquinones by dimethyldioxirane; in the presence of strong acids, the intermediate phenols were effectively converted to the p-benzoquinones 3.