1,6-Digalloylglucose

1,6-Digalloylglucose
Names
	IUPAC name β-D-Glucopyranose 1,6-bis(3,4,5-trihydroxybenzoate)
	Systematic IUPAC name (2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-{[(3,4,5-trihydroxybenzoyl)oxy]methyl}oxan-2-yl 3,4,5-trihydroxybenzoate
	Other names Digalloyl glucose
Identifiers
CAS Number	23363-08-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15723;
ChEMBL	ChEMBL522251;
ChemSpider	389206;
KEGG	C04101;
PubChem CID	440221;
CompTox Dashboard (EPA)	DTXSID301045329 ;
	InChI InChI=1S/C20H20O14/c21-8-1-6(2-9(22)13(8)25)18(30)32-5-12-15(27)16(28)17(29)20(33-12)34-19(31)7-3-10(23)14(26)11(24)4-7/h1-4,12,15-17,20-29H,5H2/t12-,15-,16+,17-,20+/m1/s1 Key: LYGRISUQIZNHGM-IVABAYMNSA-N; InChI=1/C20H20O14/c21-8-1-6(2-9(22)13(8)25)18(30)32-5-12-15(27)16(28)17(29)20(33-12)34-19(31)7-3-10(23)14(26)11(24)4-7/h1-4,12,15-17,20-29H,5H2/t12-,15-,16+,17-,20+/m1/s1 Key: LYGRISUQIZNHGM-IVABAYMNBE;
	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)O)O)O;
Properties
Chemical formula	C20H20O14
Molar mass	484.366 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,6-Digalloylglucose, or more specifically 1,6-di-O-galloyl-β-D-glucose, is a gallotannin. It can be found in some oak species.^[1]

Biosynthesis

The enzyme beta-glucogallin O-galloyltransferase, characterised from oak, produces 1,6-digalloylglucose from two units of glucogallin:^[2]

2

+

1,6-digalloylglucose can then be converted into 1,2,6-trigalloylglucose, another gallotannin.^[3]

↑ 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.
↑ Gross, GG (1983). "Synthesis of mono-galloyl-beta-D-glucose di-galloyl-beta-D-glucose and trigalloyl-beta-D-glucose by beta-glucogallin-dependent galloyltransferases from oak leaves". Z. Naturforsch. C. 38: 519–523. doi:10.1515/znc-1983-7-804.
↑ Denzel K, Schilling G, Gross GG (1988). "Biosynthesis of gallotannins - enzymatic conversion of 1,6-digalloylglucose to 1,2,6-trigalloylglucose". Planta. 176 (1): 135–137. Bibcode:1988Plant.176..135D. doi:10.1007/BF00392489. PMID 24220744.