Glucogallin

Glucogallin

IUPAC name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]3,4,5-trihydroxybenzoate
Other names beta-Glucogallin 1-Galloylglucose 1-Galloyl-beta-glucose 1-O-Galloyl-beta-D-glucose β-glucogallin
Identifiers
CAS number	13405-60-2
PubChem	124021
Jmol-3D images	Image 1
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OC2C(C(C(C(O2)CO)O)O)O
Properties
Molecular formula	C₁₃H₁₆O₁₀
Molar mass	332.26 g/mol
Exact mass	332.074347 u
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glucogallin is chemical compound formed from gallic acid and β-D-glucose. It is formed by a gallate 1-beta-glucosyltransferase (UDP-glucose: gallate glucosyltransferase), an enzyme performing the esterification of two substrates, UDP-glucose and gallate to yield two products, UDP and 1-galloyl-beta-D-glucose (glucogallin). This enzyme can be found in oak leaves preparations^[1]

This the first step in the biosynthesis of gallotannins. The molecule is then used by enzymes in the gallotannins synthetis pathway like beta-glucogallin O-galloyltransferase or beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase.

References

^ Synthesis of β-glucogallin from UDP-glucose and gallic acid by an enzyme preparation from oak leaves. G.G. Gross, FEBS Letters, Volume 148, Issue 1, 1 November 1982, pp. 67-70, doi:10.1016/0014-5793(82)81244-1

Types of gallotannins

Aglycones	Digallic acid \| Gallic acid \| Vanillic acid

Examples	Burkinabin A \| B \| C \| Galloyl glucose \| Digalloyl glucose \| Trigalloyl glucose: 1,2,6-Trigalloyl glucose / 1,3,6,-Trigalloyl glucose (Corilagin) \| Tetragalloyl glucose: 1,2,3,6-tetragalloylglucose \| Pentagalloyl glucose: 1,2,3,4,6-pentagalloyl-glucose and 6-digalloyl-1,2,3-trigalloyl-glucose \| Hexagalloyl glucose \| Heptagalloyl glucose \| Octagalloyl glucose \| Nonagalloyl glucose \| Decagalloyl glucose \| 1,3,4-Tri-O-galloylquinic acid \| 3,4,5-Tri-O-galloylquinic acid \| 3,5-di-O-galloyl-shikimic acid \| 3,4,5-tri-O-galloylshikimic acid \| 1,2,6-trigalloyl alloside \| 1,3,6-trigalloyl alloside \| 1,2,3,6-tetragalloyl alloside