Digallic acid

Digallic acid
Names
meta-depside bond digalloyl ester
Preferred IUPAC name 3,4-Dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoic acid
Other names Digallate 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate m-digallic acid Digalloyl ester
Identifiers
CAS Number	536-08-3^Y
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL366356^N
ChemSpider	334^N
ECHA InfoCard	100.007.842
PubChem	341
InChI InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)^N Key: COVFEVWNJUOYRL-UHFFFAOYSA-N^N InChI=1/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21) Key: COVFEVWNJUOYRL-UHFFFAOYAG
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)[O-] O=C(O)c2cc(O)c(O)c(OC(=O)c1cc(O)c(O)c(O)c1)c2
Properties
Chemical formula	C₁₄H₁₀O₉
Molar mass	322.22 g/mol
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

Digallic acid is a polyphenolic compound found in Pistacia lentiscus.^[1] Digallic acid is also present in the molecule of tannic acid.^[2] Digalloyl esters involve either -meta or -para depside bonds.^[3]

Tannase is an enzyme that uses digallate to produce gallic acid. This enzyme can also be used to produce digallic acid from gallotannins.^[4]

References

↑ Bhouri, W.; Derbel, S.; Skandrani, I.; Boubaker, J.; Bouhlel, I.; Sghaier, M. B.; Kilani, S.; Mariotte, A. M.; Dijoux-Franca, M. G.; Ghedira, K.; Chekir-Ghedira, L. (2010). "Study of genotoxic, antigenotoxic and antioxidant activities of the digallic acid isolated from Pistacia lentiscus fruits". Toxicology in Vitro. 24 (2): 509–515. doi:10.1016/j.tiv.2009.06.024. PMID 19563883.
↑ Delahaye, P.; Verzele, M. (1983). "Analysis of gallic, digallic and trigallic acids in tannic acids by high-performance liquid chromatography". Journal of Chromatography A. 265: 363–367. doi:10.1016/S0021-9673(01)96734-2.
↑ Tannin chemistry, by Ann E. Hagerman
↑ Nierenstein, M. (1932). "A biological synthesis of m-digallic acid". The Biochemical Journal. 26 (4): 1093–1094. doi:10.1042/bj0261093. PMC 1261008. PMID 16744910.

Types of gallotannins

Aglycones

Galloyl glucoses

1-Galloyl glucose Glucogallin

Digalloyl glucoses:	1,6-Digalloyl glucose 2,6-Digalloyl glucose 3,6-digalloyl glucose

Trigalloyl glucoses:	1,2,3-Trigalloyl glucose 1,2,3-tri-O-galloyl-β-D-glucose 1,2,6-Trigalloyl glucose / 1,3,6-Trigalloyl glucose

Tetragalloyl glucoses:	1,2,3,6-tetragalloylglucose 1,2,3,6-tetra-O-galloyl-β-D-glucose 1,2,4,6-Tetragalloyl glucose 1,2,4,6-tetra-O-galloyl-β-D-glucose

Pentagalloyl glucose:	1,2,3,4,6-Pentagalloyl-glucose 6-digalloyl-1,2,3-trigalloyl-glucose

other	Hexagalloyl glucose Heptagalloyl glucose Octagalloyl glucose Nonagalloyl glucose Decagalloyl glucose

Galloyl quinic acids

Galloyl quinic acids:	3-O-Galloylquinic acid theogallin 4-O-Galloylquinic acid 5-O-Galloylquinic acid

Digalloyl quinic acids:	1,4-Di-O-galloylquinic acid 3,4-di-O-Galloylquinic acid 3,5-di-O-Galloylquinic acid 4,5-di-O-Galloylquinic acid

Trigalloyl quinic acids:	1,3,4-Tri-O-galloylquinic acid 3,4,5-Tri-O-galloylquinic acid

Galloyl shikimic acids

4-O-Galloyl shikimic acid
5-O-Galloyl shikimic acid
3,5-di-O-galloyl-shikimic acid
3,4,5-tri-O-galloylshikimic acid

others

1,2,6-trigalloyl alloside
1,3,6-trigalloyl alloside
1,2,3,6-tetragalloyl alloside
1-O-galloyl proto-quercitol
1,4-di-O-galloyl proto-quercitol

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