75950-52-6

Upstream product

• 127-19-5 N,N-dimethyl acetamide 
• 75950-51-5 methyl 4-methyl-3,5-dioxohexanoate 
• 31581-32-5 ethyl 2,4-dihydroxy-3,6-dimethylbenzoate 
• 71-36-3 butan-1-ol 
• 4707-47-5 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester 

Downstream Products

• 261174-81-6 C₃₀H₃₄O₇ 
• 261174-62-3 n-butyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate 

Relevant academic research and scientific papers

Activity-guided isolation of an antiandrogenic compound of Pygeum africanum

Inactivation of the androgen receptor (AR) through androgen ablation and treatment with antiandrogens is a major goal in the therapy for prostate hyperplasia and prostate cancer. Bioactivity-directed fractionation of a selective dichloromethane extract from the stem bark of Pygeum africanum led to the isolation of the antiandrogenic compound atraric acid. Its activity was examined by an androgen receptor responsive reporter gene assay. For lead structure optimization we transformed the natural occurring compound atraric acid into its ethyl, n-propyl and n-butyl esters and their antiandrogenic activities were examined as well. In addition, benzoic acid was isolated. The structures of all compounds were determined and characterized by means of 1H- and 13C-NMR, HR-EI-mass, IR and UV spectroscopy. Georg Thieme Verlag KG Stuttgart.

Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid

A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range.

Convenient Syntheses of Alkyl β-Resorcylate Derivatives

Syntheses of methyl 2,4-dihydroxy-6-methyl- (1a) and -3,6-dimethylbenzoates (1b) and methyl 2,4-dihydroxy-6-pentylbenzoate (1c) are described.Condensation reactions of dimethyl sodiomalonate with the dianion derived from pentane-2,4-dione or the dimerisation of the methyl acetoacetate dianion or the acetylation of the trianion derived from methyl 3,5,7-trioxo-octanoate gave (1a) (78percent) after work-up at pH 9.Analogous convenient, short, optimised syntheses of (1b and c) are given in detail.