Glucogallin

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) ^[1] and Amla fruit (Phyllanthus emblica).^[2]

Glucogallin

Names
IUPAC name [(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]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 Y
3D model (JSmol)	Interactive image
ChemSpider	26333268 N
ECHA InfoCard	100.242.331
PubChem CID	124021
UNII	4X7JGS9BFY Y
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/s1 N Key: KGHSLXLLBHRMML-VKISENBKSA-N 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/s1 Key: KGHSLXLLBHRMML-VKISENBKBE
SMILES CO[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)c2cc(c(c(c2)O)O)O)O)O)O
Properties
Chemical formula	C13H16O10
Molar mass	332.261 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[3]

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.