pentagalloylglucose

Also known as beta-D-glucopyranose pentakis(3,4,5-trihydroxybenzoate), 1,2,3,4,6-Pgg

Pentagalloylglucose, or more specifically '1,2,3,4,6-penta-O-galloyl-β-D-glucose', is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

Chemical data

Formula: C41H32O26
Molecular weight: 940.7 g/mol
IUPAC name: [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

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Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 940.118181

Show 5 more facts

chemical formula: C₄₁H₃₂O₂₆
isomeric SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
found in taxon: Eucalyptus cornuta
has characteristic: bitterness

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Encyclopedic overview

6 sections

Contents

Natural occurrence
Biosynthesis
Metabolism
Chemistry
Research
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477199709 | Name = Pentagalloylglucose | ImageFile = Beta-penta-O-galloyl-glucose.svg | ImageSize = 250px | ImageName = Chemical structure of pentagalloylglucose | IUPACName = β-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate) | SystematicName = (2S,3R,4S,5R,6R)-6-{[(3,4,5-Trihydroxybenzoyl)oxy]methyl}oxane-2,3,4,5-tetrayl tetrakis(3,4,5-trihydroxybenzoate) | OtherNames = 1,2,3,4,6-Penta-O-galloyl-β-D-glucose1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucosebeta-Penta-O-galloyl-glucosePGG1,2,3,4,6-Penta-O-galloyl-beta-D-glucose |Section1= |Section2= }} Pentagalloylglucose, or more specifically '1,2,3,4,6-penta-O-galloyl-β-D-glucose', is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

Pentagalloylglucose can precipitate proteins, including human salivary α-amylase.

Excerpted from Wikipedia’s “pentagalloylglucose” article, available under the CC BY-SA 4.0 licence.

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