3,5-Dimethoxyphenol

Fatal Taxus baccata ingestion with perimortem serum taxine B quantification.[Pubmed:27436403]

Clin Toxicol (Phila). 2016 Nov;54(9):878-880.

INTRODUCTION: Common yew (Taxus baccata) is a common decorative evergreen shrub with potentially fatal toxicity hallmarked by seizure, arrhythmia and cardiovascular collapse if ingested. Taxine B has been identified as one of the most cardiotoxic taxine alkaloids in Taxus spp, and another alkaloid, 3,5-Dimethoxyphenol (3,5-DMP), is used as a marker of ingestion. We present a fatal case of ingestion of yew with perimortem serum and gastric taxine B, and 3,5-DMP concentrations. CASE PRESENTATION: A 22-year-old woman was brought to the emergency department (ED) from a nearby botanical garden after she was found apneic and pulseless after a witnessed generalized tonic clonic seizure. The patient was found to have a wide complex rhythm with persistent cardiovascular collapse and expired despite maximal supportive care in the ED. A baggie of plant material was found on the patient, identified as Taxus baccata. Perimortem serum and gastric samples were analyzed to quantify serum and gastric taxine B and 3,5-DMP concentrations. RESULTS: Perimortem serum showed a 3,5-DMP concentration of 86.9 ng/mL, and taxine B of 80.9 ug/mL. CONCLUSION: We report a perimortem serum and gastric taxine B and 3,5-DMP concentrations in a fatal case of T. baccata toxicity.

New phenolic glycosides from Pilea cavaleriei.[Pubmed:24911100]

J Asian Nat Prod Res. 2014;16(6):565-73.

Five new phenolic glycosides, 2-hydroxy-(2'E)-prenyl benzoate-2,4'-di-O-beta-D-glucopyranoside (1), 2-hydroxy-(2'E)-prenyl benzoate-2-O-alpha-L-arabinopyranosyl-(1 --> 6)-beta-D-glucopyranoside (2), 4-methylphenol-1-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (3), 4-methylphenol-1-O-alpha-L-arabinopyranosyl-(1 --> 6)-beta-D-glucopyranoside (4), and 3,5-Dimethoxyphenol-1-O-beta-D-apiofuranosyl-(1 --> 2)-beta-D-glucopyranoside (5), together with six known glycosides (6-11), were isolated from the n-BuOH fraction of the EtOH extract of Pilea cavaleriei Levl subsp. cavaleriei. Their structures were elucidated by extensive spectroscopic analysis, including 1D and 2D NMR spectroscopy as well as HR-ESI-MS, and chemical evidences. All these compounds were isolated from the genus Pilea for the first time.

An efficient Friedel-Crafts/oxa-Michael/aromatic annulation: rapid access to substituted naphtho[2,1-b]furan, naphtho[1,2-b]furan, and benzofuran derivatives.[Pubmed:23386481]

Chemistry. 2013 Mar 25;19(13):4344-51.

Substituted naphthofurans and benzofurans are easily accessible by treatment of naphthols/substituted phenols with nitroallylic acetates through a substitution-elimination process promoted by cesium carbonate. Reactions between naphthols and aromatic/heteroaromatic-substituted nitroallylic acetates gave the desired functionalized naphthofurans in high to excellent chemical yields (14-97%). On the other hand, treatment of phenol derivatives (i.e., 3-dimethylamino-, 3-methoxy-, and 3,5-Dimethoxyphenol) with various nitroallylic acetates afforded the corresponding benzofurans in moderate to good chemical yields (24-91%). The reaction proceeded through an interesting Friedel-Crafts S(N)2' process followed by intramolecular oxa-Michael cyclization and subsequent aromatization. A plot of log (k/kH) against Hammett constants sigma(p) showed satisfactory linearity with a positive rho value, indicating that the initial Friedel-Crafts-type S(N)2' process constituted the rate-determining step. This methodology has been applied to the synthesis of various novel C2 and C3 symmetric bis- and trisfurans by using catechol and phloroglucinol as the nucleophilic partners. The reactivity decreased when alkyl-substituted nitroallylic acetate systems were used. This might be related to the decreased electrophilic character of these substrates.