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Glucogallin

Names
IUPAC name 3,4,5-trihydroxybenzoate
Other names β-Glucogallin 1-Galloylglucose 1-Galloyl-β-glucose 1-O-Galloyl-β-D-glucose beta-Glucogallin Monogalloyl glucose
Identifiers
CAS Number	13405-60-2
3D model (JSmol)	Interactive image
ChemSpider	26333268
ECHA InfoCard	100.242.331
PubChem CID	124021
UNII	4X7JGS9BFY
CompTox Dashboard (EPA)	DTXSID00928396
InChI InChI=1S/C13H16O10/c1-21-12-9(18)8(17)10(19)13(23-12)22-11(20)4-2-5(14)7(16)6(15)3-4/h2-3,8-10,12-19H,1H3/t8-,9-,10+,12-,13+/m0/s1Key: KGHSLXLLBHRMML-VKISENBKSA-N InChI=1/C13H16O10/c1-21-12-9(18)8(17)10(19)13(23-12)22-11(20)4-2-5(14)7(16)6(15)3-4/h2-3,8-10,12-19H,1H3/t8-,9-,10+,12-,13+/m0/s1Key: KGHSLXLLBHRMML-VKISENBKBE
SMILES CO1((((O1)OC(=O)c2cc(c(c(c2)O)O)O)O)O)O
Properties
Chemical formula	C13H16O10
Molar mass	332.261 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Glucogallin is chemical compound formed from gallic acid and β-D-glucose. It can be found in oaks species like the North American white oak (Quercus alba), European red oak (Quercus robur) and Amla fruit (Phyllanthus emblica).

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 glucogallin. This enzyme can be found in oak leaf preparations.

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

β-Glucogallin is aldose reductase inhibitor.

Half-life of β-Glucogallin in human body seems to be unknown.

References

1. Mämmelä, Pirjo; Savolainen, Heikki; Lindroos, Lasse; Kangas, Juhani; Vartiainen, Terttu (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A. 891 (1): 75–83. doi:10.1016/S0021-9673(00)00624-5. PMID 10999626.
2. Puppala, M; Ponder, J; Suryanarayana, P; Reddy, GB; Petrash, JM; LaBarbera, DV (2012). "The isolation and characterization of β-glucogallin as a novel aldose reductase inhibitor from Emblica officinalis". PLOS ONE. 7 (4): e31399. Bibcode:2012PLoSO...731399P. doi:10.1371/journal.pone.0031399. PMC 3317655. PMID 22485126.
3. Gross, G.G. (1982). "Synthesis of β-glucogallin from UDP-glucose and gallic acid by an enzyme preparation from oak leaves". FEBS Letters. 148: 67–70. doi:10.1016/0014-5793(82)81244-1. S2CID 86402007.

• Gallotannins