Abstract
We describe the synthesis of some 3-tert-butyl-4-hydroxyphenyl D-glycopyranosides by reaction of tert-butylhydroquinone with beta-D-pentaacetyl-glucose, beta-D-pentaacetyl-galactose, 2-acetamido- and 3,4,6-tri-O-acetyl-2-butanamido-2-deoxy-beta-D-glucopyranosyl chlorides as well as the formation of anomeric 3-tert-butyl-4-hydroxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-eno-pyranosides by reaction between tert-butylhydroquinone and 3,4,6-tri-O-acetyl-D-glucal. All compounds, except 3-tert-butyl-4-hydroxyphenyl alpha- and beta-D-glucopyranosides, inhibited lipid peroxidation with a degree of potency comparable to that of tert-butyl hydroxyanisole.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylation
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Animals
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Antioxidants / chemical synthesis*
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Antioxidants / pharmacology
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Ascorbic Acid / metabolism
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Benzenesulfonates / metabolism
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Glucose / analogs & derivatives*
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Glucose / metabolism
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Glycosides / chemical synthesis*
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Glycosides / pharmacology
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Hydroquinones / chemistry*
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Iron / metabolism
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Linoleic Acid / metabolism
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Lipid Peroxidation / drug effects*
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Microsomes, Liver / metabolism
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Rats
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Structure-Activity Relationship
Substances
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Antioxidants
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Benzenesulfonates
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Glycosides
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Hydroquinones
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glucose pentaacetate
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Linoleic Acid
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2-tert-butylhydroquinone
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Iron
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Glucose
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Ascorbic Acid
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4-toluenesulfonic acid