90111-36-7

Upstream product

• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 67-56-1 methanol 
• 2207-58-1 2,5-dihydroxy-6-methylbenzoquinone 
• 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 
• 4463-33-6 1,2-dimethoxy-3-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 academic research and scientific papers

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.

Phytotoxic activity of quinones and resorcinolic lipid derivatives

On the basis of the reported phytotoxic activity of sorgoleone and resorcinolic lipids identified from the root extracts of Sorghum bicolor, 8 resorcinolic lipid derivatives and 10 quinones with various side chain sizes were synthesized. The phytotoxicity of the compounds was tested against a monocot and a dicot species. The quinones were phytotoxic, whereas the resorcinolic lipids were not. Of the quinones, 2-hydroxy-5-methoxy-3- pentylcyclohexa-2,5-diene-1,4-dione, having a five-carbon side chain, showed phytotoxic activity similar to that of natural compound sorgoleone. This article not subject to U.S. Copyright. Published 2010 by the American Chemical Society.

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.

Dimerization of 2,5-Dihydroxybenzoquinones in Water

2,5-Dihydroxybenzoquinones, when heated in water, react to form different types of compounds through dimerization. The features of this unique reaction were clarified using a model compund, 2,5-dihydroxy-3-methyl-benzoquinone. The structures of the products were established by X-ray analysis and spectroscopic means. - Key words: 2,5-dihydroxybenzoquinone; dimerization; furanylidene benzofuranone; 1,4-dibenzofurandione; X-ray analysis

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.

Oxidation of Methoxy- and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H2O2 in HCOOH

The oxidation of a number of arenes (methoxybenzenes, methylbenzenes, and naphthalenes) to quinones and phenols by H2O2 in HCOOH has been examined.Methoxybenzenes were much more easily oxidized to p-benzoquinones than methylbenzenes (e.g., 1,3,5-trimethoxybenzene was oxidized to 2,6-dimethoxy-p-benzoquinone in a 75percent yield and 1,2,4-trimethylbenzene to 2,3,5-trimethyl-p-benzoquinone in a 16percent yield).Electron-withdrawing substituents, such as nitro, cyano, and chloro groups, lowered the conversion of reactants and changed the product selectivity from quinones to phenols.Methoxybenzonitriles were oxidized to corresponding phenols in a moder ate yield (e.g., 2,6-dimethoxybenzonitrile to 3-hydroxy-2,6-dimethoxybenzonitrile in a 39percent yield and a 64percent selectivity).